NPASS Compound

Natural Product: NPC49196

Natural Product ID	NPC49196
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Yohimbine
IUPAC Name	methyl (1S,15R,18S,19R,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
Synonyms	Yohimbine
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL15245
PubChem CID	8969
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0001786] Yohimbine alkaloids

The Chemical Classification was calculated by Classyfire, a software for chemical taxonomy calculation. Reference: DOI:10.1186/s13321-016-0174-y.

Chemical Representations

RDKit 3D 53 57 0 0 0 0 0 0 0 0999 V2000 -2.7343 3.5897 -1.9572 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8285 2.2370 -1.5037 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.9195 1.9547 -0.1528 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.9137 2.9444 0.6267 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0195 0.6105 0.4104 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.8587 -0.2824 0.0860 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.5179 0.3542 0.3360 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4832 -0.6700 -0.2329 C 0 0 1 0 0 0 0 0 0 0 0 0 1.8399 -0.0674 -0.3058 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7502 -0.4051 0.5896 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4276 -1.3783 1.6629 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5950 -2.4645 0.9713 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4139 -1.9135 0.4160 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.7262 -2.2734 1.1303 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9610 -1.4918 0.9712 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1382 -2.3099 0.4173 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3693 -1.4535 0.6191 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2775 -0.1232 -0.0744 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.1959 -0.3752 -1.4457 O 0 0 0 0 0 0 0 0 0 0 0 0 3.9592 0.3381 0.2624 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2323 0.4236 0.8048 C 0 0 0 0 0 0 0 0 0 0 0 0 6.2178 1.2323 0.2800 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9350 2.0018 -0.8438 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6548 1.9248 -1.4008 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6881 1.1096 -0.8580 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3648 0.8796 -1.2424 N 0 0 0 0 0 4 0 0 0 0 0 0 -2.6651 4.2581 -1.0644 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7865 3.7477 -2.5376 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6336 3.8721 -2.5527 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1128 0.6451 1.5138 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8929 -0.5999 -0.9687 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4506 1.2505 -0.3179 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3143 0.5745 1.3881 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0904 -0.8271 -1.2868 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8541 -0.9046 2.4825 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3252 -1.8939 2.0595 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2878 -2.9006 0.1973 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3540 -3.2703 1.6719 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9726 -3.3515 0.8814 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4554 -2.3331 2.2279 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3317 -1.1197 1.9668 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9690 -2.5919 -0.6211 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2407 -3.2040 1.0346 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2447 -2.0052 0.2262 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4414 -1.2655 1.7222 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.1614 0.4602 0.1848 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2480 -1.3404 -1.6597 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4588 -0.1690 1.6748 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2124 1.2616 0.7515 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6828 2.6391 -1.2723 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4901 2.5431 -2.2719 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2901 0.3998 -2.1891 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7733 1.7327 -1.3194 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 3 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 10 20 1 0 20 21 2 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 18 5 1 0 25 20 1 0 15 6 1 0 13 8 1 0 26 9 1 0 1 27 1 0 1 28 1 0 1 29 1 0 5 30 1 1 6 31 1 6 7 32 1 0 7 33 1 0 8 34 1 6 11 35 1 0 11 36 1 0 12 37 1 0 12 38 1 0 14 39 1 0 14 40 1 0 15 41 1 1 16 42 1 0 16 43 1 0 17 44 1 0 17 45 1 0 18 46 1 6 19 47 1 0 21 48 1 0 22 49 1 0 23 50 1 0 24 51 1 0 26 52 1 0 26 53 1 0 M CHG 1 26 1 M END

Standard InCHIKey	BLGXFZZNTVWLAY-SCYLSFHTSA-N
Standard InCHI	InChI=1S/C21H26N2O3/c1-26-21(25)19-15-10-17-20-14(13-4-2-3-5-16(13)22-20)8-9-23(17)11-12(15)6-7-18(19)24/h2-5,12,15,17-19,22,24H,6-11H2,1H3/p+1/t12-,15-,17-,18-,19+/m0/s1
SMILES	COC(=O)[C@@H]1[C@H]2C[C@H]3C4=C(CCN3C[C@@H]2CC[C@@H]1O)c1ccccc1[NH2+]4

Calculated Properties

Physi-Chem Properties

Molecular Weight:	354.19	Volume:	364.172 ? Van der Waals volume.
Dense:	0.973	LogP:	2.556 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.597 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.773 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	26.0
TPSA:	65.56 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	2.0	Rings:	5.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.773	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.875	Fsp³:	0.571
MCE-18:	95.333 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.316	Fluc inhibitor:	0.018 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.637 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.016 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.001	Promiscuous compounds:	0.821

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.453	MDCK Permeability:	-4.971
Pgp-inhibitor:	0.046	Pgp-substrate:	0.928
PAMPA:	0.281 ? The experimental data for Peff was logarithmically transformed (logPeff). Molecules with log Peff values below 2.0 were classified as low-permeability (Category 0), while those with log Peff values exceeding 2.5 were classified as high-permeability (Category 1).	Human Intestinal Absorption (HIA):	0.0
20% Bioavailability (F20%):	0.018	30% Bioavailability (F30%):	0.326
50% Bioavailability (F50%):	0.987

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.84	MRP1:	0.966
Plasma Protein Binding (PPB):	80.556%	Volume Distribution (VD):	0.102
Fu:	16.918% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.986
BSEP inhibitor:	0.906

ADMET: Metabolism

CYP1A2-inhibitor:	0.335	CYP1A2-substrate:	0.003
CYP2C19-inhibitor:	0.316	CYP2C19-substrate:	0.007
CYP2C9-inhibitor:	0.003	CYP2C9-substrate:	0.993
CYP2D6-inhibitor:	0.921	CYP2D6-substrate:	0.007
CYP3A4-inhibitor:	0.864	CYP3A4-substrate:	0.628
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.208
HLM stability:	0.618 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

9.144

Half-life (T1/2):

1.539

ADMET: Toxicity

hERG Blockers:	0.456	hERG Blockers (10um):	0.597
Human Hepatotoxicity (H-HT):	0.586	Drug-induced Liver Injury (DILI):	0.104
AMES Toxicity:	0.56	Rat Oral Acute Toxicity:	0.679
Maximum Recommended Daily Dose:	0.927	Skin Sensitization:	0.943
Carcinogencity:	0.694	Eye Corrosion:	0.0
Eye Irritation:	0.395	Respiratory Toxicity:	0.972
Drug-induced Neurotoxicity:	0.611	Ototoxicity:	0.552
Hematotoxicity:	0.107	Drug-induced Nephrotoxicity:	0.553
Genotoxicity:	0.561	RPMI-8226 Immunitoxicity:	0.057
A549 Cytotoxicity:	0.24	Hek293 Cytotoxicity:	0.477
BCF:	0.641 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	3.389 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.942 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.275 ? 96 hour fathead minnow LC50. The unit of LC50FM is -log10[(mg/L)/(1000*MW)].

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO32758	rauwolfia serpentina	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15974606]
NPO7282	Rauvolfia serpentina	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7282	Rauvolfia serpentina	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7282	Rauvolfia serpentina	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9519	Sonchus erzincanicus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7282	Rauvolfia serpentina	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Kd	40
Ratio	7
IC50	47
pC30	1
Selectivity index	2
Ki	99
ID50	4
Selectivity ratio	4
Selectivity	2
Relative potency	1
Inhibition	30
-Log KB	3
AD50	1
EC50	5
Potency	19
Ratio_Papp	1
Ratio_ATPase activity	1
% maximum response	1
pKb	1
AC50	135
FC	2
Kb	3
ED50	5
Activity	5

Activity Type	# Activity
Individual protein	240
Cell line	1
Protein family	112
Single protein	15
Organism	22
Protein complex group	2
Others	26
Protein complex	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1858	Individual protein	Dopamine D2 receptor	Rattus norvegicus	IC50	=	1125.0	nM	PMID[11020279]
NPT1788	Individual protein	Alpha-1a adrenergic receptor	Homo sapiens	Kd	=	398.11	nM	PMID[6142954]
NPT222	Individual protein	Alpha-2a adrenergic receptor	Homo sapiens	Ki	=	0.42	nM	PMID[10762040]
NPT223	Individual protein	Alpha-2b adrenergic receptor	Homo sapiens	Ki	=	2.01	nM	PMID[10762040]
NPT221	Individual protein	Alpha-1d adrenergic receptor	Homo sapiens	Ki	=	1.6	nM	PMID[7658428]
NPT3048	Individual protein	Alpha-1d adrenergic receptor	Rattus norvegicus	Ki	=	52.0	nM	PMID[7658428]
NPT1789	Individual protein	Alpha-1b adrenergic receptor	Homo sapiens	Ki	=	7.2	nM	PMID[7658428]
NPT1789	Individual protein	Alpha-1b adrenergic receptor	Homo sapiens	Ki	=	1.1	nM	PMID[7658428]
NPT3049	Individual protein	Alpha-2a adrenergic receptor	Sus scrofa	Ki	=	4.4	nM	PMID[7658428]
NPT3051	Individual protein	Alpha-1a adrenergic receptor	Bos taurus	Ki	=	3.6	nM	PMID[7658428]
NPT110	Individual protein	Cytochrome P450 2D6	Homo sapiens	Ki	=	180.0	nM	PMID[15481972]
NPT110	Individual protein	Cytochrome P450 2D6	Homo sapiens	Ki	=	230.0	nM	PMID[8487254]
NPT110	Individual protein	Cytochrome P450 2D6	Homo sapiens	Ki	=	520.0	nM	PMID[8487254]
NPT110	Individual protein	Cytochrome P450 2D6	Homo sapiens	Ki	=	140.0	nM	PMID[8487254]
NPT110	Individual protein	Cytochrome P450 2D6	Homo sapiens	Ki	=	190.0	nM	PMID[8487254]
NPT1788	Individual protein	Alpha-1a adrenergic receptor	Homo sapiens	Ki	=	1057.0	nM	PMID[7562902]
NPT1789	Individual protein	Alpha-1b adrenergic receptor	Homo sapiens	Ki	=	966.0	nM	PMID[7562902]
NPT221	Individual protein	Alpha-1d adrenergic receptor	Homo sapiens	Ki	=	289.0	nM	PMID[7562902]
NPT222	Individual protein	Alpha-2a adrenergic receptor	Homo sapiens	Ki	=	7.5	nM	PMID[7562902]
NPT223	Individual protein	Alpha-2b adrenergic receptor	Homo sapiens	Ki	=	4.6	nM	PMID[7562902]
NPT224	Individual protein	Alpha-2c adrenergic receptor	Homo sapiens	Ki	=	2.3	nM	PMID[7562902]
NPT2719	Individual protein	Voltage-gated L-type calcium channel alpha-1C subunit	Rattus norvegicus	Ki	=	45.0	nM	PMID[7562902]
NPT228	Individual protein	Norepinephrine transporter	Homo sapiens	IC50	>	20000.0	nM	PMID[8558529]
NPT3051	Individual protein	Alpha-1a adrenergic receptor	Bos taurus	Ki	=	200.0	nM	PMID[6088770]
NPT1779	Individual protein	Serotonin 2b (5-HT2b) receptor	Rattus norvegicus	-Log KB	=	6.92	n.a.	PMID[8709108]
NPT1778	Individual protein	Serotonin 2a (5-HT2a) receptor	Rattus norvegicus	Ki	=	1621.81	nM	PMID[8709108]
NPT3053	Individual protein	Serotonin 2c (5-HT2c) receptor	Mus musculus	Ki	>	10000.0	nM	PMID[8709108]
NPT1778	Individual protein	Serotonin 2a (5-HT2a) receptor	Rattus norvegicus	-Log KB	=	6.37	n.a.	PMID[8709108]
NPT3054	Individual protein	Adenosine A2b receptor	Rattus norvegicus	-Log KB	=	7.77	n.a.	PMID[8709108]
NPT3056	Individual protein	Dopamine D3 receptor	Rattus norvegicus	Ki	=	2430.0	nM	PMID[8098771]
NPT3057	Individual protein	Alpha-2a adrenergic receptor	Bos taurus	Ki	=	49.0	nM	PMID[2999400]
NPT3051	Individual protein	Alpha-1a adrenergic receptor	Bos taurus	Ki	=	220.0	nM	PMID[2999400]
NPT222	Individual protein	Alpha-2a adrenergic receptor	Homo sapiens	Ki	=	3.1	nM	PMID[23403082]
NPT3059	Individual protein	Alpha-2b adrenergic receptor	Rattus norvegicus	Ki	=	2.0	nM	PMID[10602703]
NPT110	Individual protein	Cytochrome P450 2D6	Homo sapiens	IC50	=	8.4	nM	PMID[15481972]
NPT224	Individual protein	Alpha-2c adrenergic receptor	Homo sapiens	Ki	=	0.88	nM	PMID[15911252]
NPT222	Individual protein	Alpha-2a adrenergic receptor	Homo sapiens	Ki	=	1.4	nM	PMID[15911252]
NPT223	Individual protein	Alpha-2b adrenergic receptor	Homo sapiens	Ki	=	7.1	nM	PMID[15911252]
NPT143	Individual protein	DNA topoisomerase I	Homo sapiens	IC50	=	30000.0	nM	PMID[15974606]
NPT222	Individual protein	Alpha-2a adrenergic receptor	Homo sapiens	EC50	=	8.5	nM	PMID[16562853]
NPT242	Individual protein	Dopamine D1 receptor	Homo sapiens	Potency	n.a.	17782.8	nM	PubChem BioAssay data set
NPT242	Individual protein	Dopamine D1 receptor	Homo sapiens	Potency	n.a.	2909.1	nM	PubChem BioAssay data set
NPT219	Individual protein	Alpha-1a adrenergic receptor	Rattus norvegicus	IC50	=	1235.0	nM	DrugMatrix in vitro pharmacology data
NPT219	Individual protein	Alpha-1a adrenergic receptor	Rattus norvegicus	Ki	=	500.0	nM	DrugMatrix in vitro pharmacology data
NPT220	Individual protein	Alpha-1b adrenergic receptor	Rattus norvegicus	IC50	=	1188.0	nM	DrugMatrix in vitro pharmacology data
NPT220	Individual protein	Alpha-1b adrenergic receptor	Rattus norvegicus	Ki	=	658.0	nM	DrugMatrix in vitro pharmacology data
NPT221	Individual protein	Alpha-1d adrenergic receptor	Homo sapiens	IC50	=	1013.0	nM	DrugMatrix in vitro pharmacology data
NPT221	Individual protein	Alpha-1d adrenergic receptor	Homo sapiens	Ki	=	498.0	nM	DrugMatrix in vitro pharmacology data
NPT222	Individual protein	Alpha-2a adrenergic receptor	Homo sapiens	IC50	=	6.151	nM	DrugMatrix in vitro pharmacology data
NPT222	Individual protein	Alpha-2a adrenergic receptor	Homo sapiens	Ki	=	2.307	nM	DrugMatrix in vitro pharmacology data
NPT223	Individual protein	Alpha-2b adrenergic receptor	Homo sapiens	IC50	=	17.0	nM	DrugMatrix in vitro pharmacology data
NPT223	Individual protein	Alpha-2b adrenergic receptor	Homo sapiens	Ki	=	7.947	nM	DrugMatrix in vitro pharmacology data
NPT224	Individual protein	Alpha-2c adrenergic receptor	Homo sapiens	IC50	=	36.0	nM	DrugMatrix in vitro pharmacology data
NPT224	Individual protein	Alpha-2c adrenergic receptor	Homo sapiens	Ki	=	5.162	nM	DrugMatrix in vitro pharmacology data
NPT110	Individual protein	Cytochrome P450 2D6	Homo sapiens	IC50	=	2031.7	nM	DrugMatrix in vitro pharmacology data
NPT243	Individual protein	Dopamine D2 receptor	Homo sapiens	IC50	=	2060.0	nM	DrugMatrix in vitro pharmacology data
NPT243	Individual protein	Dopamine D2 receptor	Homo sapiens	Ki	=	687.0	nM	DrugMatrix in vitro pharmacology data
NPT288	Individual protein	Serotonin 1a (5-HT1a) receptor	Rattus norvegicus	IC50	=	126.0	nM	DrugMatrix in vitro pharmacology data
NPT288	Individual protein	Serotonin 1a (5-HT1a) receptor	Rattus norvegicus	Ki	=	72.0	nM	DrugMatrix in vitro pharmacology data
NPT291	Individual protein	Serotonin 2b (5-HT2b) receptor	Homo sapiens	IC50	=	74.0	nM	DrugMatrix in vitro pharmacology data
NPT291	Individual protein	Serotonin 2b (5-HT2b) receptor	Homo sapiens	Ki	=	47.0	nM	DrugMatrix in vitro pharmacology data
NPT294	Individual protein	Serotonin 6 (5-HT6) receptor	Homo sapiens	IC50	=	1689.0	nM	DrugMatrix in vitro pharmacology data
NPT294	Individual protein	Serotonin 6 (5-HT6) receptor	Homo sapiens	Ki	=	784.0	nM	DrugMatrix in vitro pharmacology data
NPT1474	Individual protein	ATP-dependent Clp protease proteolytic subunit	Bacillus subtilis (strain 168)	Potency	n.a.	14125.4	nM	PubChem BioAssay data set
NPT3060	Individual protein	Dual specificity phosphatase Cdc25A	Homo sapiens	IC50	=	22300.0	nM	PMID[22537178]
NPT1779	Individual protein	Serotonin 2b (5-HT2b) receptor	Rattus norvegicus	pKb	=	7.74	n.a.	DOI[10.1007/s00044-005-0125-z]
NPT222	Individual protein	Alpha-2a adrenergic receptor	Homo sapiens	Inhibition	=	-5.0	%	PMID[23403082]
NPT222	Individual protein	Alpha-2a adrenergic receptor	Homo sapiens	IC50	=	8.4	nM	PMID[23403082]
NPT223	Individual protein	Alpha-2b adrenergic receptor	Homo sapiens	Ki	=	28.84	nM	PMID[24365159]
NPT223	Individual protein	Alpha-2b adrenergic receptor	Homo sapiens	Ki	=	3.2	nM	PMID[24365159]
NPT104	Individual protein	Cerebroside-sulfatase	Homo sapiens	Potency	n.a.	2393.4	nM	PubChem BioAssay data set
NPT224	Individual protein	Alpha-2c adrenergic receptor	Homo sapiens	Ki	=	0.5	nM	PMID[25557493]
NPT265	Individual protein	Muscarinic acetylcholine receptor M4	Homo sapiens	Inhibition	=	4.0	%	PMID[31913038]
NPT232	Individual protein	Cannabinoid CB1 receptor	Homo sapiens	Inhibition	=	35.0	%	PMID[31913038]
NPT1287	Individual protein	Cannabinoid CB2 receptor	Homo sapiens	Inhibition	=	20.0	%	PMID[31913038]
NPT243	Individual protein	Dopamine D2 receptor	Homo sapiens	Inhibition	=	102.0	%	PMID[31913038]
NPT251	Individual protein	Histamine H1 receptor	Homo sapiens	Inhibition	=	30.0	%	PMID[31913038]
NPT1416	Individual protein	Neuropeptide S receptor	Homo sapiens	Inhibition	=	-3.0	%	PMID[31913038]
NPT1015	Individual protein	Prostanoid IP receptor	Homo sapiens	Inhibition	=	8.0	%	PMID[31913038]
NPT222	Individual protein	Alpha-2a adrenergic receptor	Homo sapiens	Ki	=	3.13	nM	PMID[31834797]
NPT223	Individual protein	Alpha-2b adrenergic receptor	Homo sapiens	Ki	=	1.16	nM	PMID[31834797]
NPT224	Individual protein	Alpha-2c adrenergic receptor	Homo sapiens	Ki	=	0.8	nM	PMID[31834797]
NPT1789	Individual protein	Alpha-1b adrenergic receptor	Homo sapiens	Inhibition	=	90.0	%	PMID[32616180]
NPT223	Individual protein	Alpha-2b adrenergic receptor	Homo sapiens	Inhibition	=	107.0	%	PMID[32616180]
NPT1647	Individual protein	Vasopressin V2 receptor	Homo sapiens	Inhibition	=	-1.0	%	PMID[32616180]
NPT292	Individual protein	Serotonin 2c (5-HT2c) receptor	Homo sapiens	Inhibition	=	1.0	%	PMID[32616180]
NPT222	Individual protein	Alpha-2a adrenergic receptor	Homo sapiens	Inhibition	=	92.0	%	PMID[32616180]
NPT1464	Individual protein	Phosphodiesterase 4D	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT245	Individual protein	Dopamine D4 receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT1647	Individual protein	Vasopressin V2 receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT261	Individual protein	Monoamine oxidase A	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT291	Individual protein	Serotonin 2b (5-HT2b) receptor	Homo sapiens	AC50	>	300.0	nM	PMID[37468498]
NPT262	Individual protein	Muscarinic acetylcholine receptor M1	Homo sapiens	AC50	>	300.0	nM	PMID[37468498]
NPT1788	Individual protein	Alpha-1a adrenergic receptor	Homo sapiens	AC50	>	300.0	nM	PMID[37468498]
NPT244	Individual protein	Dopamine D3 receptor	Homo sapiens	AC50	>	300.0	nM	PMID[37468498]
NPT2879	Individual protein	Equilibrative nucleoside transporter 1	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT242	Individual protein	Dopamine D1 receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT263	Individual protein	Muscarinic acetylcholine receptor M2	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT271	Individual protein	Delta opioid receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT291	Individual protein	Serotonin 2b (5-HT2b) receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT246	Individual protein	Dopamine transporter	Homo sapiens	AC50	>	300.0	nM	PMID[37468498]
NPT228	Individual protein	Norepinephrine transporter	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT232	Individual protein	Cannabinoid CB1 receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT2769	Individual protein	Thromboxane A2 receptor	Homo sapiens	AC50	>	300.0	nM	PMID[37468498]
NPT292	Individual protein	Serotonin 2c (5-HT2c) receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT31	Individual protein	Cyclooxygenase-2	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT1410	Individual protein	GABA receptor alpha-1 subunit	Rattus norvegicus	AC50	>	10000.0	nM	PMID[37468498]
NPT252	Individual protein	Histamine H2 receptor	Homo sapiens	AC50	=	19404.4	nM	PMID[37468498]
NPT259	Individual protein	Melanocortin receptor 4	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT218	Individual protein	Adenosine A3 receptor	Homo sapiens	AC50	=	14050.1	nM	PMID[37468498]
NPT30	Individual protein	Cyclooxygenase-1	Homo sapiens	AC50	>	300.0	nM	PMID[37468498]
NPT242	Individual protein	Dopamine D1 receptor	Homo sapiens	AC50	=	2000.0	nM	PMID[37468498]
NPT251	Individual protein	Histamine H1 receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT2719	Individual protein	Voltage-gated L-type calcium channel alpha-1C subunit	Rattus norvegicus	AC50	>	10000.0	nM	PMID[37468498]
NPT222	Individual protein	Alpha-2a adrenergic receptor	Homo sapiens	AC50	=	5.9	nM	PMID[37468498]
NPT153	Individual protein	Androgen Receptor	Homo sapiens	AC50	>	300.0	nM	PMID[37468498]
NPT226	Individual protein	Beta-2 adrenergic receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT1788	Individual protein	Alpha-1a adrenergic receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT244	Individual protein	Dopamine D3 receptor	Homo sapiens	AC50	=	2000.0	nM	PMID[37468498]
NPT145	Individual protein	Mu opioid receptor	Homo sapiens	AC50	>	300.0	nM	PMID[37468498]
NPT248	Individual protein	Estrogen receptor beta	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT291	Individual protein	Serotonin 2b (5-HT2b) receptor	Homo sapiens	Ki	=	43.0	nM	PMID[37584406]
NPT290	Individual protein	Serotonin 2a (5-HT2a) receptor	Homo sapiens	AC50	=	6247.8	nM	PMID[37468498]
NPT262	Individual protein	Muscarinic acetylcholine receptor M1	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT222	Individual protein	Alpha-2a adrenergic receptor	Homo sapiens	AC50	=	3.7	nM	PMID[37468498]
NPT242	Individual protein	Dopamine D1 receptor	Homo sapiens	AC50	=	2200.0	nM	PMID[37468498]
NPT242	Individual protein	Dopamine D1 receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT108	Individual protein	Estrogen receptor alpha	Homo sapiens	AC50	>	300.0	nM	PMID[37468498]
NPT295	Individual protein	Serotonin transporter	Homo sapiens	AC50	>	300.0	nM	PMID[37468498]
NPT295	Individual protein	Serotonin transporter	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT244	Individual protein	Dopamine D3 receptor	Homo sapiens	AC50	=	20000.0	nM	PMID[37468498]
NPT145	Individual protein	Mu opioid receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT218	Individual protein	Adenosine A3 receptor	Homo sapiens	AC50	>	300.0	nM	PMID[37468498]
NPT2761	Individual protein	Phosphodiesterase 4A	Homo sapiens	AC50	>	300.0	nM	PMID[37468498]
NPT294	Individual protein	Serotonin 6 (5-HT6) receptor	Homo sapiens	AC50	=	691.8	nM	PMID[37468498]
NPT1788	Individual protein	Alpha-1a adrenergic receptor	Homo sapiens	AC50	=	2639.6	nM	PMID[37468498]
NPT226	Individual protein	Beta-2 adrenergic receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT232	Individual protein	Cannabinoid CB1 receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT246	Individual protein	Dopamine transporter	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT261	Individual protein	Monoamine oxidase A	Homo sapiens	AC50	>	300.0	nM	PMID[37468498]
NPT264	Individual protein	Muscarinic acetylcholine receptor M3	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT242	Individual protein	Dopamine D1 receptor	Homo sapiens	AC50	>	300.0	nM	PMID[37468498]
NPT290	Individual protein	Serotonin 2a (5-HT2a) receptor	Homo sapiens	AC50	=	2400.0	nM	PMID[37468498]
NPT243	Individual protein	Dopamine D2 receptor	Homo sapiens	AC50	=	188.9	nM	PMID[37468498]
NPT263	Individual protein	Muscarinic acetylcholine receptor M2	Homo sapiens	AC50	>	300.0	nM	PMID[37468498]
NPT299	Individual protein	Androgen Receptor	Rattus norvegicus	AC50	>	30000.0	nM	PMID[37468498]
NPT249	Individual protein	Glucocorticoid receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT1478	Individual protein	Vascular endothelial growth factor receptor 2	Homo sapiens	AC50	>	300.0	nM	PMID[37468498]
NPT225	Individual protein	Beta-1 adrenergic receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT291	Individual protein	Serotonin 2b (5-HT2b) receptor	Homo sapiens	AC50	=	86.2	nM	PMID[37468498]
NPT226	Individual protein	Beta-2 adrenergic receptor	Homo sapiens	Ki	=	0.04	nM	PMID[38516587]
NPT2769	Individual protein	Thromboxane A2 receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT216	Individual protein	Adenosine A1 receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT228	Individual protein	Norepinephrine transporter	Homo sapiens	AC50	>	300.0	nM	PMID[37468498]
NPT246	Individual protein	Dopamine transporter	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT227	Individual protein	Beta-3 adrenergic receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT272	Individual protein	Kappa opioid receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT1788	Individual protein	Alpha-1a adrenergic receptor	Homo sapiens	AC50	=	1202.3	nM	PMID[37468498]
NPT223	Individual protein	Alpha-2b adrenergic receptor	Homo sapiens	AC50	=	12.3	nM	PMID[37468498]
NPT1814	Individual protein	Glucagon receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT222	Individual protein	Alpha-2a adrenergic receptor	Homo sapiens	AC50	=	14.8	nM	PMID[37468498]
NPT230	Individual protein	Bradykinin B2 receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT303	Individual protein	Vasopressin V1a receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT224	Individual protein	Alpha-2c adrenergic receptor	Homo sapiens	AC50	=	3.4	nM	PMID[37468498]
NPT108	Individual protein	Estrogen receptor alpha	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT1163	Individual protein	Glutamate (NMDA) receptor subunit zeta 1	Rattus norvegicus	AC50	>	10000.0	nM	PMID[37468498]
NPT243	Individual protein	Dopamine D2 receptor	Homo sapiens	AC50	=	2545.6	nM	PMID[37468498]
NPT217	Individual protein	Adenosine A2a receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT204	Individual protein	Acetylcholinesterase	Homo sapiens	AC50	>	300.0	nM	PMID[37468498]
NPT247	Individual protein	Endothelin receptor ET-A	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT222	Individual protein	Alpha-2a adrenergic receptor	Homo sapiens	AC50	=	12.8	nM	PMID[37468498]
NPT267	Individual protein	Neuropeptide Y receptor type 1	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT239	Individual protein	Cholecystokinin A receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT1788	Individual protein	Alpha-1a adrenergic receptor	Homo sapiens	AC50	=	6200.0	nM	PMID[37468498]
NPT252	Individual protein	Histamine H2 receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT222	Individual protein	Alpha-2a adrenergic receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT291	Individual protein	Serotonin 2b (5-HT2b) receptor	Homo sapiens	AC50	=	260.0	nM	PMID[37468498]
NPT968	Protein family	Adrenergic receptor alpha-1	Rattus norvegicus	Kd	=	630.96	nM	PMID[7310808]
NPT968	Protein family	Adrenergic receptor alpha-1	Rattus norvegicus	Ratio	=	0.032	n.a.	PMID[7310808]
NPT968	Protein family	Adrenergic receptor alpha-1	Rattus norvegicus	IC50	=	1580.0	nM	PMID[11020279]
NPT968	Protein family	Adrenergic receptor alpha-1	Rattus norvegicus	Kd	=	1905.46	nM	PMID[6142954]
NPT968	Protein family	Adrenergic receptor alpha-1	Rattus norvegicus	IC50	=	1300.0	nM	PMID[6142954]
NPT968	Protein family	Adrenergic receptor alpha-1	Rattus norvegicus	Ki	=	398.11	nM	PMID[2153820]
NPT968	Protein family	Adrenergic receptor alpha-1	Rattus norvegicus	Kd	=	7.244	nM	PMID[6133953]
NPT968	Protein family	Adrenergic receptor alpha-1	Rattus norvegicus	Kd	=	323.59	nM	PMID[6133953]
NPT968	Protein family	Adrenergic receptor alpha-1	Rattus norvegicus	Kd	=	89.13	nM	PMID[2886664]
NPT968	Protein family	Adrenergic receptor alpha-1	Rattus norvegicus	Kd	=	263.03	nM	PMID[2838634]
NPT968	Protein family	Adrenergic receptor alpha-1	Rattus norvegicus	Ki	=	360.0	nM	PMID[3016265]
NPT968	Protein family	Adrenergic receptor alpha-1	Rattus norvegicus	Kd	=	302.0	nM	PMID[6139479]
NPT968	Protein family	Adrenergic receptor alpha-1	Rattus norvegicus	Kd	=	616.6	nM	PMID[6124635]
NPT968	Protein family	Adrenergic receptor alpha-1	Rattus norvegicus	IC50	=	1000.0	nM	PMID[2542561]
NPT968	Protein family	Adrenergic receptor alpha-1	Rattus norvegicus	Kd	=	346.74	nM	PMID[2542561]
NPT797	Individual protein	Cytoplasmic zinc-finger protein	Caenorhabditis elegans	EC50	>	300000.0	nM	PubChem BioAssay data set
NPT713	Individual protein	Bile salt export pump	Homo sapiens	IC50	=	254000.0	nM	PMID[22961681]
NPT23088	Single protein	C-C chemokine receptor type 8	Homo sapiens	Inhibition	=	5.0	%	PMID[31913038]
NPT23089	Single protein	C-X-C chemokine receptor type 4	Homo sapiens	Inhibition	=	21.0	%	PMID[31913038]
NPT987	Individual protein	Histamine H3 receptor	Homo sapiens	AC50	>	300.0	nM	PMID[37468498]
NPT5318	Individual protein	Corticotropin releasing factor receptor 1	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT30134	Single protein	Gastric inhibitory polypeptide receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT5301	Individual protein	Motilin receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT987	Individual protein	Histamine H3 receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT972	Protein family	Adrenergic receptor alpha	Rattus norvegicus	Selectivity index	=	-1.11	n.a.	PMID[6142954]
NPT972	Protein family	Adrenergic receptor alpha	Rattus norvegicus	Selectivity index	=	-0.89	n.a.	PMID[6142954]
NPT972	Protein family	Adrenergic receptor alpha	Rattus norvegicus	Selectivity ratio	=	32.0	n.a.	PMID[1671705]
NPT972	Protein family	Adrenergic receptor alpha	Rattus norvegicus	Selectivity	=	4.7	n.a.	PMID[2886664]
NPT972	Protein family	Adrenergic receptor alpha	Rattus norvegicus	Ratio	=	10.0	n.a.	PMID[2838634]
NPT972	Protein family	Adrenergic receptor alpha	Rattus norvegicus	Selectivity ratio	=	14.0	n.a.	PMID[6139479]
NPT795	Individual protein	Zinc finger protein mex-5	Caenorhabditis elegans	EC50	=	103486.0	nM	PubChem BioAssay data set
NPT940	Individual protein	Serine/threonine-protein kinase mTOR	Homo sapiens	Potency	=	14689.2	nM	PubChem BioAssay data set
NPT698	Individual protein	Regulator of G-protein signaling 4	Homo sapiens	Potency	n.a.	2117.2	nM	PubChem BioAssay data set
NPT21843	Single protein	Orexin receptor 2	Homo sapiens	Inhibition	=	9.0	%	PMID[31913038]
NPT5622	Individual protein	Prolactin-releasing peptide receptor	Homo sapiens	Inhibition	=	1.0	%	PMID[31913038]
NPT22722	Single protein	C-C chemokine receptor type 3	Homo sapiens	Inhibition	=	-13.0	%	PMID[32616180]
NPT23094	Single protein	C-X3-C chemokine receptor 1	Homo sapiens	Inhibition	=	22.0	%	PMID[32616180]
NPT973	Individual protein	Serotonin 1b (5-HT1b) receptor	Homo sapiens	Inhibition	=	86.0	%	PMID[32616180]
NPT30115	Protein complex group	20S proteasome	Homo sapiens	FC	=	0.82	n.a.	PMID[37938154]
NPT3952	Individual protein	Endothelin receptor ET-B	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT98	Individual protein	HERG	Homo sapiens	AC50	=	29148.8	nM	PMID[37468498]
NPT542	Individual protein	Progesterone receptor	Homo sapiens	AC50	>	300.0	nM	PMID[37468498]
NPT29430	Single protein	Neuronal acetylcholine receptor protein alpha-4 subunit	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT3735	Individual protein	Neurotensin receptor 1	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT30115	Protein complex group	20S proteasome	Homo sapiens	FC	<	3.0	n.a.	PMID[37938154]
NPT542	Individual protein	Progesterone receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT4729	Individual protein	Cholecystokinin B receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT4358	Individual protein	Type-1 angiotensin II receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT971	Protein family	Adrenergic receptor alpha-2	Homo sapiens	pC30	=	8.1	n.a.	PMID[6142954]
NPT971	Protein family	Adrenergic receptor alpha-2	Homo sapiens	IC50	=	8.0	nM	PMID[3037080]
NPT971	Protein family	Adrenergic receptor alpha-2	Homo sapiens	Selectivity	=	44.7	n.a.	PMID[6133953]
NPT971	Protein family	Adrenergic receptor alpha-2	Homo sapiens	Ki	=	0.9	nM	PMID[7658428]
NPT971	Protein family	Adrenergic receptor alpha-2	Homo sapiens	Ki	=	1.8	nM	PMID[7658428]
NPT971	Protein family	Adrenergic receptor alpha-2	Homo sapiens	Ki	=	3.0	nM	PMID[7658428]
NPT971	Protein family	Adrenergic receptor alpha-2	Homo sapiens	Ki	=	4.0	nM	PMID[7658428]
NPT971	Protein family	Adrenergic receptor alpha-2	Homo sapiens	Ki	=	3.8	nM	PMID[7658428]
NPT971	Protein family	Adrenergic receptor alpha-2	Homo sapiens	Ki	=	4.1	nM	PMID[7658428]
NPT971	Protein family	Adrenergic receptor alpha-2	Homo sapiens	Ki	=	0.4	nM	PMID[7658428]
NPT971	Protein family	Adrenergic receptor alpha-2	Homo sapiens	Ki	=	0.6	nM	PMID[7658428]
NPT971	Protein family	Adrenergic receptor alpha-2	Homo sapiens	Ki	=	33.0	nM	PMID[7658428]
NPT971	Protein family	Adrenergic receptor alpha-2	Homo sapiens	Ki	=	35.0	nM	PMID[7658428]
NPT971	Protein family	Adrenergic receptor alpha-2	Homo sapiens	Ki	=	70.0	nM	PMID[7658428]
NPT971	Protein family	Adrenergic receptor alpha-2	Homo sapiens	Kd	=	43.65	nM	PMID[2886664]
NPT970	Protein family	Adrenergic receptor alpha-1	Homo sapiens	Kd	=	147.91	nM	PMID[2886664]
NPT970	Protein family	Adrenergic receptor alpha-1	Homo sapiens	Relative potency	=	1.0	n.a.	PMID[2886664]
NPT1774	Protein family	Sodium channel alpha subunits; brain (Types I, II, III)	Homo sapiens	IC50	=	33000.0	nM	PMID[2579237]
NPT1774	Protein family	Sodium channel alpha subunits; brain (Types I, II, III)	Homo sapiens	Inhibition	=	25.6	%	PMID[2579237]
NPT970	Protein family	Adrenergic receptor alpha-1	Homo sapiens	Kd	=	794.33	nM	PMID[2570150]
NPT971	Protein family	Adrenergic receptor alpha-2	Homo sapiens	Kd	=	31.62	nM	PMID[2570150]
NPT3052	Protein family	Dopamine receptor	Rattus norvegicus	Ki	=	2000.0	nM	PMID[3016265]
NPT971	Protein family	Adrenergic receptor alpha-2	Homo sapiens	Kd	=	25.7	nM	PMID[2542561]
NPT971	Protein family	Adrenergic receptor alpha-2	Homo sapiens	IC50	=	195000.0	nM	DOI[10.1016/0960-894X(96)00406-4]
NPT971	Protein family	Adrenergic receptor alpha-2	Homo sapiens	IC50	=	170.0	nM	DOI[10.1016/0960-894X(96)00406-4]
NPT971	Protein family	Adrenergic receptor alpha-2	Homo sapiens	IC50	=	398000.0	nM	DOI[10.1016/0960-894X(96)00406-4]
NPT971	Protein family	Adrenergic receptor alpha-2	Homo sapiens	IC50	=	1800.0	nM	DOI[10.1016/0960-894X(96)00406-4]
NPT971	Protein family	Adrenergic receptor alpha-2	Homo sapiens	Kd	=	47000.0	nM	DOI[10.1016/0960-894X(96)00406-4]
NPT971	Protein family	Adrenergic receptor alpha-2	Homo sapiens	Kd	=	2300.0	nM	DOI[10.1016/0960-894X(96)00406-4]
NPT971	Protein family	Adrenergic receptor alpha-2	Homo sapiens	Kd	=	60.0	nM	DOI[10.1016/0960-894X(96)00406-4]
NPT971	Protein family	Adrenergic receptor alpha-2	Homo sapiens	Kd	=	120.0	nM	DOI[10.1016/0960-894X(96)00406-4]
NPT971	Protein family	Adrenergic receptor alpha-2	Homo sapiens	Kd	=	5400000.0	nM	DOI[10.1016/0960-894X(96)00406-4]
NPT971	Protein family	Adrenergic receptor alpha-2	Homo sapiens	Kd	=	150000.0	nM	DOI[10.1016/0960-894X(96)00406-4]
NPT971	Protein family	Adrenergic receptor alpha-2	Homo sapiens	Kd	=	4800.0	nM	DOI[10.1016/0960-894X(96)00406-4]
NPT971	Protein family	Adrenergic receptor alpha-2	Homo sapiens	Kd	=	62000.0	nM	DOI[10.1016/0960-894X(96)00406-4]
NPT971	Protein family	Adrenergic receptor alpha-2	Homo sapiens	IC50	=	95.0	nM	PMID[16250647]
NPT66	Individual protein	Acetylcholinesterase	Electrophorus electricus	IC50	=	431000.0	nM	DOI[10.1021/np960070c]
NPT478	Individual protein	Ataxin-2	Homo sapiens	Potency	n.a.	22387.2	nM	PubChem BioAssay data set
NPT755	Individual protein	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	Homo sapiens	Potency	n.a.	35481.3	nM	PubChem BioAssay data set
NPT971	Protein family	Adrenergic receptor alpha-2	Homo sapiens	IC50	=	36.0	nM	PMID[23582449]
NPT971	Protein family	Adrenergic receptor alpha-2	Homo sapiens	Ki	=	25.0	nM	PMID[23466604]
NPT971	Protein family	Adrenergic receptor alpha-2	Homo sapiens	IC50	=	58.0	nM	PMID[23466604]
NPT6197	Individual protein	Glucose-dependent insulinotropic receptor	Homo sapiens	Inhibition	=	8.0	%	PMID[31913038]
NPT28787	Single protein	Voltage-gated N-type calcium channel alpha-1B subunit	Rattus norvegicus	AC50	>	10000.0	nM	PMID[37468498]
NPT5104	Individual protein	Phosphodiesterase 3A	Homo sapiens	AC50	>	300.0	nM	PMID[37468498]
NPT5104	Individual protein	Phosphodiesterase 3A	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT28448	Single protein	Corticotropin releasing factor receptor 2	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT29454	Single protein	Deoxynucleoside triphosphate triphosphohydrolase SAMHD1	Homo sapiens	Inhibition	=	-6.79	%	PMID[38318365]
NPT5975	Individual protein	Cyclooxygenase-1	Rattus norvegicus	AC50	>	30000.0	nM	PMID[37468498]
NPT92	Individual protein	Serotonin 1a (5-HT1a) receptor	Homo sapiens	AC50	=	644.2	nM	PMID[37468498]
NPT92	Individual protein	Serotonin 1a (5-HT1a) receptor	Homo sapiens	AC50	=	75.2	nM	PMID[37468498]
NPT6127	Individual protein	Bradykinin B1 receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT20859	Single protein	Neuropeptide Y receptor type 2	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT28814	Single protein	Ghrelin receptor	Homo sapiens	AC50	=	4100.0	nM	PMID[37468498]
NPT92	Individual protein	Serotonin 1a (5-HT1a) receptor	Homo sapiens	AC50	=	66.1	nM	PMID[37468498]
NPT92	Individual protein	Serotonin 1a (5-HT1a) receptor	Homo sapiens	AC50	=	240.0	nM	PMID[37468498]
NPT969	Protein family	Adrenergic receptor alpha-2	Rattus norvegicus	Kd	=	19.95	nM	PMID[7310808]
NPT969	Protein family	Adrenergic receptor alpha-2	Rattus norvegicus	IC50	=	67.0	nM	PMID[11020279]
NPT969	Protein family	Adrenergic receptor alpha-2	Rattus norvegicus	Kd	=	147.91	nM	PMID[6142954]
NPT969	Protein family	Adrenergic receptor alpha-2	Rattus norvegicus	IC50	=	165.0	nM	PMID[6142954]
NPT969	Protein family	Adrenergic receptor alpha-2	Rattus norvegicus	Ki	=	12.59	nM	PMID[2153820]
NPT969	Protein family	Adrenergic receptor alpha-2	Rattus norvegicus	ID50	=	0.185	mg.kg-1	PMID[1671705]
NPT969	Protein family	Adrenergic receptor alpha-2	Rattus norvegicus	ID50	=	2.8	mg.kg-1	PMID[1671705]
NPT969	Protein family	Adrenergic receptor alpha-2	Rattus norvegicus	IC50	=	30.0	nM	PMID[8960552]
NPT969	Protein family	Adrenergic receptor alpha-2	Rattus norvegicus	Ki	=	1.0	nM	PMID[7658428]
NPT969	Protein family	Adrenergic receptor alpha-2	Rattus norvegicus	Ki	=	5.0	nM	PMID[7658428]
NPT3050	Protein family	Alpha-2 adrenergic receptor	Mus musculus	Ki	=	0.6	nM	PMID[7658428]
NPT969	Protein family	Adrenergic receptor alpha-2	Rattus norvegicus	Ki	=	8.7	nM	PMID[7658428]
NPT969	Protein family	Adrenergic receptor alpha-2	Rattus norvegicus	Ki	=	0.6	nM	PMID[7658428]
NPT3050	Protein family	Alpha-2 adrenergic receptor	Mus musculus	Ki	=	3.8	nM	PMID[7658428]
NPT969	Protein family	Adrenergic receptor alpha-2	Rattus norvegicus	Ki	=	2.4	nM	PMID[7658428]
NPT969	Protein family	Adrenergic receptor alpha-2	Rattus norvegicus	Ki	=	54.0	nM	PMID[7658428]
NPT969	Protein family	Adrenergic receptor alpha-2	Rattus norvegicus	Ki	=	104.0	nM	PMID[7658428]
NPT969	Protein family	Adrenergic receptor alpha-2	Rattus norvegicus	Ki	=	52.0	nM	PMID[7658428]
NPT3050	Protein family	Alpha-2 adrenergic receptor	Mus musculus	Ki	=	54.0	nM	PMID[7658428]
NPT969	Protein family	Adrenergic receptor alpha-2	Rattus norvegicus	Kd	=	19.05	nM	PMID[2886664]
NPT969	Protein family	Adrenergic receptor alpha-2	Rattus norvegicus	Kd	=	25.7	nM	PMID[2886664]
NPT969	Protein family	Adrenergic receptor alpha-2	Rattus norvegicus	Kd	=	26.3	nM	PMID[2838634]
NPT969	Protein family	Adrenergic receptor alpha-2	Rattus norvegicus	Ki	=	78.0	nM	PMID[3039138]
NPT969	Protein family	Adrenergic receptor alpha-2	Rattus norvegicus	Kd	=	12.3	nM	PMID[2887657]
NPT969	Protein family	Adrenergic receptor alpha-2	Rattus norvegicus	Ki	=	150.0	nM	PMID[6296387]
NPT969	Protein family	Adrenergic receptor alpha-2	Rattus norvegicus	Ki	=	45.0	nM	PMID[3016265]
NPT969	Protein family	Adrenergic receptor alpha-2	Rattus norvegicus	Ki	=	48.0	nM	PMID[3016265]
NPT969	Protein family	Adrenergic receptor alpha-2	Rattus norvegicus	Ki	=	56.23	nM	PMID[2153820]
NPT969	Protein family	Adrenergic receptor alpha-2	Rattus norvegicus	Ratio	=	0.2	n.a.	PMID[2153820]
NPT969	Protein family	Adrenergic receptor alpha-2	Rattus norvegicus	Kd	=	22.39	nM	PMID[6139479]
NPT969	Protein family	Adrenergic receptor alpha-2	Rattus norvegicus	Kd	=	19.5	nM	PMID[6124635]
NPT969	Protein family	Adrenergic receptor alpha-2	Rattus norvegicus	IC50	=	9.1	nM	PMID[2542561]
NPT969	Protein family	Adrenergic receptor alpha-2	Rattus norvegicus	Ki	=	84.0	nM	PMID[2887657]
NPT969	Protein family	Adrenergic receptor alpha-2	Rattus norvegicus	Ki	=	190.0	nM	PMID[2887657]
NPT969	Protein family	Adrenergic receptor alpha-2	Rattus norvegicus	Kd	=	123.03	nM	PMID[2887657]
NPT3050	Protein family	Alpha-2 adrenergic receptor	Mus musculus	Kd	=	10.47	nM	PMID[6143826]
NPT969	Protein family	Adrenergic receptor alpha-2	Rattus norvegicus	AD50	=	1.04	mg kg-1	PMID[6139479]
NPT969	Protein family	Adrenergic receptor alpha-2	Rattus norvegicus	Ki	=	10.0	nM	PMID[2999400]
NPT969	Protein family	Adrenergic receptor alpha-2	Rattus norvegicus	IC50	=	58.0	nM	PMID[20875743]
NPT443	Individual protein	Histone acetyltransferase GCN5	Homo sapiens	Potency	n.a.	31622.8	nM	PubChem BioAssay data set
NPT5	Individual protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	21192.3	nM	PubChem BioAssay data set
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio_Papp	=	1.17	n.a.	PMID[11602674]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	Ratio_ATPase activity	=	1.05	n.a.	PMID[11602674]
NPT668	Individual protein	P-glycoprotein 1	Homo sapiens	% maximum response	=	4.23	%	PMID[11602674]
NPT969	Protein family	Adrenergic receptor alpha-2	Rattus norvegicus	IC50	=	96.0	nM	PMID[26988801]
NPT5390	Individual protein	Formyl peptide receptor 1	Homo sapiens	Inhibition	=	-6.0	%	PMID[31913038]
NPT5621	Individual protein	Follicle stimulating hormone receptor	Homo sapiens	Inhibition	=	4.0	%	PMID[32616180]
NPT5015	Individual protein	Oxytocin receptor	Homo sapiens	Inhibition	=	5.0	%	PMID[32616180]
NPT670	Individual protein	Thrombin	Homo sapiens	AC50	>	300.0	nM	PMID[37468498]
NPT30151	Single protein	Melanocortin receptor 3	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT425	Individual protein	Serotonin 3a (5-HT3a) receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT116	Cell line	HL-60	Homo sapiens	IC50	=	84000.0	nM	PMID[15974606]
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	20000.0	nM	DOI[10.6019/CHEMBL4651402]
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	IC50	>	19952.62	nM	DOI[10.6019/CHEMBL4651402]
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	EC50	>	50000.0	nM	PMID[34058709]
NPT3055	Others	Serotonin receptor (2b and 2c)	Homo sapiens	Ratio	=	83.0	n.a.	PMID[8709108]
NPT23085	Protein family	Cerebral cortex alpha adrenergic receptor	Bos taurus	Selectivity ratio	=	4.5	n.a.	PMID[6139479]
NPT312	Organism	Saccharomyces cerevisiae	Saccharomyces cerevisiae	Potency	=	23109.3	nM	PubChem BioAssay data set
NPT29392	Protein complex	Gamma-aminobutyric acid receptor subunit alpha-1/alpha-2/beta-2/gamma-2	Homo sapiens	AC50	>	300.0	nM	PMID[37468498]
NPT419	Organism	Oryctolagus cuniculus	Oryctolagus cuniculus	Kb	=	4000.0	nM	PMID[6136611]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	26603.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	23710.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	18833.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	33491.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	8412.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Ratio	=	15.0	n.a.	PMID[2570150]
NPT2	Others	Unspecified	n.a.	Ki	=	49.0	nM	PMID[6088770]
NPT2	Others	Unspecified	n.a.	Ratio	=	13.5	n.a.	PMID[8709108]
NPT2	Others	Unspecified	n.a.	Ratio	=	29.0	n.a.	PMID[6143826]
NPT2	Others	Unspecified	n.a.	Kb	<	100.0	nM	PMID[18378462]
NPT2	Others	Unspecified	n.a.	Kb	>	300.0	nM	PMID[18378462]
NPT2	Others	Unspecified	n.a.	IC50	=	100.0	nM	PMID[18983139]
NPT2	Others	Unspecified	n.a.	Ki	=	43.0	nM	PMID[18983139]
NPT2	Others	Unspecified	n.a.	IC50	=	125000.0	nM	PMID[15974606]
NPT2	Others	Unspecified	n.a.	IC50	=	38.0	nM	PMID[18588282]
NPT2	Others	Unspecified	n.a.	EC50	>	110000.0	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Ki	=	33.0	nM	PMID[21726069]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	10000.0	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	IC50	=	157.0	nM	DrugMatrix in vitro pharmacology data
NPT2	Others	Unspecified	n.a.	Ki	=	105.0	nM	DrugMatrix in vitro pharmacology data
NPT2	Others	Unspecified	n.a.	Potency	n.a.	316.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	AC50	n.a.	39810.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	AC50	n.a.	631.0	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	AC50	n.a.	707.9	nM	PubChem BioAssay data set

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT32	Organism	Mus musculus	Mus musculus	ED50	=	0.56	mg.kg-1	PMID[11020279]
NPT32	Organism	Mus musculus	Mus musculus	ED50	=	1.23	mg.kg-1	PMID[11020279]
NPT32	Organism	Mus musculus	Mus musculus	ED50	>	8.0	mg.kg-1	PMID[8558529]
NPT32	Organism	Mus musculus	Mus musculus	ED50	=	0.6	mg.kg-1	PMID[2887657]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	35.9	n.a.	PMID[17181165]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	15.8	n.a.	PMID[17181165]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	28.5	n.a.	PMID[17181165]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	27.8	n.a.	PMID[17181165]
NPT32	Organism	Mus musculus	Mus musculus	Activity	=	31.7	n.a.	PMID[17629262]
NPT938	Organism	Cavia porcellus	Cavia porcellus	Kd	=	12.59	nM	PMID[1671705]
NPT605	Organism	Homo sapiens	Homo sapiens	IC50	=	1100.0	nM	PMID[2157007]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	ID50	=	0.185	mg.kg-1	PMID[2570150]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	ID50	=	2.8	mg.kg-1	PMID[2570150]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Ki	=	505.0	nM	PMID[8093734]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Kd	=	22.39	nM	PMID[2999400]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Kd	=	302.0	nM	PMID[2999400]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	ED50	=	1.04	mg.kg-1	PMID[2999400]

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference
Homo sapiens	Liver	CL	=	34.4	mL.min-1.g-1	PMID[22197392]
Homo sapiens	n.a.	T1/2	<	1.0	hr	PMID[38516587]
Mus musculus	n.a.	T1/2	=	0.06167	hr	PMID[38516587]

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC49196 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	17429
0.1-0.2	32043
0.2-0.3	377
0.3-0.4	8
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC195461

Similar Clinical/Approved Drugs

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules.

● The left chart: Distribution of similarity level between NPC49196 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3530
0.1-0.2	5440
0.2-0.3	178
0.3-0.4	2
0.4-0.5	0
0.5-0.6	0
0.6-0.7	0
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
		NPD

Bioactivity similarity

Similar Natural Products in NPASS

Similarity level is defined by Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.
Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity

B: biological targets similarity

C: networks similarity

D: cell-based bioactivity similarity

E: similarity based on clinical data