NPASS Compound

Natural Product: NPC191489

Natural Product ID	NPC191489
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Deserpidine
IUPAC Name	methyl (1R,15S,17R,18R,19S,20S)-18-methoxy-17-(3,4,5-trimethoxybenzoyl)oxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
Synonyms	Deserpidine; Harmonyl; Recanescin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1200515
PubChem CID	8550
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 80 85 0 0 0 0 0 0 0 0999 V2000 -3.2931 -3.9094 2.6429 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4922 -3.2977 1.6751 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.5512 -2.2878 1.8897 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4205 -1.8899 3.0637 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8037 -1.7982 0.7045 C 0 0 2 0 0 0 0 0 0 0 0 0 0.3341 -0.8649 1.0478 C 0 0 1 0 0 0 0 0 0 0 0 0 1.3693 -1.6194 1.6600 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8252 -1.0162 2.8263 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8846 -0.4706 -0.3596 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.0652 0.4520 -1.0025 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5015 0.0862 -0.8580 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6692 -1.3722 -0.4188 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1355 -1.6204 -0.3301 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8883 -0.6993 0.5556 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0433 0.3651 1.0698 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.2319 1.0051 0.0554 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7239 1.4046 1.7733 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1792 1.5261 1.5986 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6437 1.0003 0.2578 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.0136 -0.1083 -0.2094 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.5983 -0.4069 -1.3921 N 0 0 0 0 0 0 0 0 0 0 0 0 -6.5737 0.5163 -1.6417 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.6163 1.4180 -0.5949 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.5248 2.4886 -0.6209 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3543 2.6574 -1.6452 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.3529 1.7759 -2.7359 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4558 0.7069 -2.7233 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1785 0.0377 -0.2531 O 0 0 0 0 0 0 0 0 0 0 0 0 3.2873 -0.7721 -0.3810 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1652 -2.0442 -0.5349 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6238 -0.2294 -0.3566 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9190 1.0702 -0.4292 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0403 1.8308 -0.4800 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6502 2.9387 -0.5470 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9964 4.2234 -0.6690 C 0 0 0 0 0 0 0 0 0 0 0 0 7.1784 0.7541 -0.4266 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9489 -0.5355 -0.3472 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7246 -1.1362 -0.3074 C 0 0 0 0 0 0 0 0 0 0 0 0 8.1263 -1.3520 -0.2924 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0509 -2.7264 -0.1931 C 0 0 0 0 0 0 0 0 0 0 0 0 8.4227 1.3250 -0.4756 O 0 0 0 0 0 0 0 0 0 0 0 0 9.0956 1.2259 -1.7221 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.1554 -5.0067 2.5227 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1121 -3.5248 3.6634 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3622 -3.7383 2.3048 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2309 -2.7454 0.3737 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1416 -0.0269 1.6685 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6461 -1.5953 3.3229 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0942 0.0538 2.6458 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0385 -0.9581 3.6239 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9613 -1.4445 -0.8426 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0644 1.4644 -0.4976 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2324 0.6366 -2.0601 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9769 0.1574 -1.8539 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3295 -1.9460 -1.3384 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4981 -1.3123 -1.3944 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4250 -2.6797 -0.3176 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3050 -1.2463 1.4124 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4468 1.6043 0.6056 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8940 1.7510 -0.4263 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5136 1.2563 2.8898 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2323 2.4129 1.5899 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7499 0.9526 2.4000 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5050 2.5696 1.6634 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3883 -1.1956 -2.0261 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4735 3.1800 0.2410 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0414 3.4595 -1.6954 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0435 1.9696 -3.5155 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.4341 0.0203 -3.5329 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9829 1.7683 -0.4380 H 0 0 0 0 0 0 0 0 0 0 0 0 6.7719 4.9356 -1.0794 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6323 4.5958 0.2759 H 0 0 0 0 0 0 0 0 0 0 0 0 5.2273 4.1460 -1.4899 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5121 -2.1545 -0.2563 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0708 -3.2134 -0.2478 H 0 0 0 0 0 0 0 0 0 0 0 0 8.5020 -3.0786 0.8033 H 0 0 0 0 0 0 0 0 0 0 0 0 8.7663 -3.1348 -0.9721 H 0 0 0 0 0 0 0 0 0 0 0 0 9.5340 0.1876 -1.7097 H 0 0 0 0 0 0 0 0 0 0 0 0 9.9085 1.9689 -1.8386 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3420 1.2594 -2.5243 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 6 9 1 0 9 10 1 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 15 17 1 0 17 18 1 0 18 19 1 0 19 20 2 0 20 21 1 0 21 22 1 0 22 23 2 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 9 28 1 0 28 29 1 0 29 30 2 0 29 31 1 0 31 32 2 0 32 33 1 0 33 34 1 0 34 35 1 0 33 36 2 0 36 37 1 0 37 38 2 0 37 39 1 0 39 40 1 0 36 41 1 0 41 42 1 0 12 5 1 0 20 14 1 0 27 22 1 0 38 31 1 0 16 11 1 0 23 19 1 0 1 43 1 0 1 44 1 0 1 45 1 0 5 46 1 6 6 47 1 1 8 48 1 0 8 49 1 0 8 50 1 0 9 51 1 6 10 52 1 0 10 53 1 0 11 54 1 6 12 55 1 6 13 56 1 0 13 57 1 0 14 58 1 1 16 59 1 0 16 60 1 0 17 61 1 0 17 62 1 0 18 63 1 0 18 64 1 0 21 65 1 0 24 66 1 0 25 67 1 0 26 68 1 0 27 69 1 0 32 70 1 0 35 71 1 0 35 72 1 0 35 73 1 0 38 74 1 0 40 75 1 0 40 76 1 0 40 77 1 0 42 78 1 0 42 79 1 0 42 80 1 0 M END

Standard InCHIKey	CVBMAZKKCSYWQR-WCGOZPBSSA-N
Standard InCHI	InChI=1S/C32H38N2O8/c1-37-24-12-17(13-25(38-2)29(24)39-3)31(35)42-26-14-18-16-34-11-10-20-19-8-6-7-9-22(19)33-28(20)23(34)15-21(18)27(30(26)40-4)32(36)41-5/h6-9,12-13,18,21,23,26-27,30,33H,10-11,14-16H2,1-5H3/t18-,21+,23-,26-,27+,30+/m1/s1
SMILES	COC(=O)[C@@H]1[C@@H](OC)[C@@H](C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c1[nH]c1c2cccc1)OC(=O)c1cc(OC)c(c(c1)OC)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	578.26	Volume:	579.276 ? Van der Waals volume.
Dense:	0.998	LogP:	2.675 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.6 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.212 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	9.0	Rigid Bonds:	33.0
TPSA:	108.55 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	1.0	Rings:	6.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.414	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.263	Fsp³:	0.5
MCE-18:	121.042 ? 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:	Accepted
Golden Triangle Rule:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.25	Fluc inhibitor:	0.17 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.287 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.361 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.001	Promiscuous compounds:	0.958

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.442	MDCK Permeability:	-5.165
Pgp-inhibitor:	0.958	Pgp-substrate:	0.92
PAMPA:	0.001 ? 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%):	0.045	30% Bioavailability (F30%):	0.009
50% Bioavailability (F50%):	0.25

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.984	MRP1:	0.997
Plasma Protein Binding (PPB):	96.284%	Volume Distribution (VD):	0.087
Fu:	2.907% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.002
OATP1B3 inhibitor:	0.013	BCRP inhibitor:	0.65
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.386	CYP1A2-substrate:	0.005
CYP2C19-inhibitor:	0.813	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.389
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.845
HLM stability:	0.001 ? 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):

5.937

Half-life (T1/2):

0.929

ADMET: Toxicity

hERG Blockers:	0.621	hERG Blockers (10um):	0.656
Human Hepatotoxicity (H-HT):	0.413	Drug-induced Liver Injury (DILI):	0.701
AMES Toxicity:	0.334	Rat Oral Acute Toxicity:	0.321
Maximum Recommended Daily Dose:	0.897	Skin Sensitization:	0.671
Carcinogencity:	0.658	Eye Corrosion:	0.0
Eye Irritation:	0.098	Respiratory Toxicity:	0.866
Drug-induced Neurotoxicity:	0.648	Ototoxicity:	0.469
Hematotoxicity:	0.153	Drug-induced Nephrotoxicity:	0.829
Genotoxicity:	0.653	RPMI-8226 Immunitoxicity:	0.064
A549 Cytotoxicity:	0.286	Hek293 Cytotoxicity:	0.484
BCF:	1.101 ? 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:	4.237 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.711 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.248 ? 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
NPO31253	Rauvolfia serpentina	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31253	Rauvolfia serpentina	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO31159	Rauvolfia vomitoria	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]

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
Potency	63
IC50	1
AC50	67
Hit score	1

Activity Type	# Activity
Individual protein	80
Single protein	3
Organism	2
Protein-protein interaction	1
Others	46

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT153	Individual protein	Androgen Receptor	Homo sapiens	Potency	n.a.	21313.8	nM	PubChem BioAssay data set
NPT153	Individual protein	Androgen Receptor	Homo sapiens	Potency	n.a.	3757.8	nM	PubChem BioAssay data set
NPT153	Individual protein	Androgen Receptor	Homo sapiens	Potency	n.a.	2131.4	nM	PubChem BioAssay data set
NPT153	Individual protein	Androgen Receptor	Homo sapiens	Potency	n.a.	8412.7	nM	PubChem BioAssay data set
NPT153	Individual protein	Androgen Receptor	Homo sapiens	Potency	n.a.	18995.9	nM	PubChem BioAssay data set
NPT198	Individual protein	Vitamin D receptor	Homo sapiens	Potency	n.a.	35481.3	nM	PubChem BioAssay data set
NPT199	Individual protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	3981.1	nM	PubChem BioAssay data set
NPT10	Individual protein	Geminin	Homo sapiens	Potency	n.a.	3349.8	nM	PubChem BioAssay data set
NPT108	Individual protein	Estrogen receptor alpha	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT226	Individual protein	Beta-2 adrenergic receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT2769	Individual protein	Thromboxane A2 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]
NPT1464	Individual protein	Phosphodiesterase 4D	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT1410	Individual protein	GABA receptor alpha-1 subunit	Rattus norvegicus	AC50	>	10000.0	nM	PMID[37468498]
NPT242	Individual protein	Dopamine D1 receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT232	Individual protein	Cannabinoid CB1 receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT1647	Individual protein	Vasopressin V2 receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT264	Individual protein	Muscarinic acetylcholine receptor M3	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT292	Individual protein	Serotonin 2c (5-HT2c) receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT261	Individual protein	Monoamine oxidase A	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]
NPT259	Individual protein	Melanocortin receptor 4	Homo sapiens	AC50	=	8600.0	nM	PMID[37468498]
NPT290	Individual protein	Serotonin 2a (5-HT2a) receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT145	Individual protein	Mu opioid receptor	Homo sapiens	AC50	=	8300.0	nM	PMID[37468498]
NPT244	Individual protein	Dopamine D3 receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT1788	Individual protein	Alpha-1a adrenergic receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT224	Individual protein	Alpha-2c adrenergic receptor	Homo sapiens	AC50	=	12000.0	nM	PMID[37468498]
NPT218	Individual protein	Adenosine A3 receptor	Homo sapiens	AC50	=	15800.1	nM	PMID[37468498]
NPT246	Individual protein	Dopamine transporter	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT223	Individual protein	Alpha-2b adrenergic receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT271	Individual protein	Delta opioid receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT225	Individual protein	Beta-1 adrenergic receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT239	Individual protein	Cholecystokinin A receptor	Homo sapiens	AC50	=	34400.1	nM	PMID[37468498]
NPT222	Individual protein	Alpha-2a adrenergic receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT228	Individual protein	Norepinephrine transporter	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT303	Individual protein	Vasopressin V1a receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT243	Individual protein	Dopamine D2 receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT263	Individual protein	Muscarinic acetylcholine receptor M2	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT272	Individual protein	Kappa opioid receptor	Homo sapiens	AC50	=	13694.9	nM	PMID[37468498]
NPT267	Individual protein	Neuropeptide Y receptor type 1	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT299	Individual protein	Androgen Receptor	Rattus norvegicus	AC50	>	30000.0	nM	PMID[37468498]
NPT217	Individual protein	Adenosine A2a receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT230	Individual protein	Bradykinin B2 receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT249	Individual protein	Glucocorticoid receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT295	Individual protein	Serotonin transporter	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT252	Individual protein	Histamine H2 receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT2879	Individual protein	Equilibrative nucleoside transporter 1	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT31	Individual protein	Cyclooxygenase-2	Homo sapiens	AC50	=	20199.9	nM	PMID[37468498]
NPT251	Individual protein	Histamine H1 receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT1163	Individual protein	Glutamate (NMDA) receptor subunit zeta 1	Rattus norvegicus	AC50	>	10000.0	nM	PMID[37468498]
NPT216	Individual protein	Adenosine A1 receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT262	Individual protein	Muscarinic acetylcholine receptor M1	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT531	Individual protein	Nuclear receptor ROR-gamma	Mus musculus	Potency	=	7079.5	nM	PubChem BioAssay data set
NPT5301	Individual protein	Motilin receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT444	Individual protein	Ubiquitin carboxyl-terminal hydrolase 1	Homo sapiens	Potency	n.a.	56234.1	nM	PubChem BioAssay data set
NPT98	Individual protein	HERG	Homo sapiens	AC50	=	2449.0	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	>	10000.0	nM	PMID[37468498]
NPT542	Individual protein	Progesterone receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT29430	Single protein	Neuronal acetylcholine receptor protein alpha-4 subunit	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT459	Individual protein	Human immunodeficiency virus type 1 reverse transcriptase	Human immunodeficiency virus 1	IC50	>	200.0	ug.mL-1	PMID[1710653]
NPT445	Individual protein	Peripheral myelin protein 22	Rattus norvegicus	Potency	n.a.	3978.1	nM	PubChem BioAssay data set
NPT445	Individual protein	Peripheral myelin protein 22	Rattus norvegicus	Potency	n.a.	907.4	nM	PubChem BioAssay data set
NPT5104	Individual protein	Phosphodiesterase 3A	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT92	Individual protein	Serotonin 1a (5-HT1a) receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT5975	Individual protein	Cyclooxygenase-1	Rattus norvegicus	AC50	=	34299.7	nM	PMID[37468498]
NPT28814	Single protein	Ghrelin receptor	Homo sapiens	AC50	=	24600.3	nM	PMID[37468498]
NPT197	Protein-protein interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	7943.3	nM	PubChem BioAssay data set
NPT443	Individual protein	Histone acetyltransferase GCN5	Homo sapiens	Potency	n.a.	7079.5	nM	PubChem BioAssay data set
NPT5	Individual protein	Histone-lysine N-methyltransferase, H3 lysine-9 specific 3	Homo sapiens	Potency	n.a.	1122.0	nM	PubChem BioAssay data set
NPT425	Individual protein	Serotonin 3a (5-HT3a) receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT30151	Single protein	Melanocortin receptor 3	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT543	Individual protein	Pregnane X 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
NPT6	Organism	Plasmodium falciparum	Plasmodium falciparum	Potency	n.a.	379.3	nM	PubChem BioAssay data set
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Hit score	=	0.0138	n.a.	DOI[10.1101/2020.04.21.054387]
NPT2	Others	Unspecified	n.a.	Potency	n.a.	3349.1	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.	4216.3	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.	Potency	n.a.	11985.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	29849.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	1188.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	14125.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	26603.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	15848.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	13333.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	26832.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	21131.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	6682.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	15089	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	2113.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	1198.6	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	7497.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	10590.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	600.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	12589.3	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	21313.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	1678.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	2391.4	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	1059.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	11883.2	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	5308	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	5955.7	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	5102.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	31622.8	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	3548.1	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	10000.0	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	2511.9	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	8912.5	nM	PubChem BioAssay data set
NPT2	Others	Unspecified	n.a.	Potency	n.a.	5011.9	nM	PubChem BioAssay data set

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

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 NPC191489 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	26531
0.1-0.2	22459
0.2-0.3	691
0.3-0.4	126
0.4-0.5	27
0.5-0.6	20
0.6-0.7	1
0.7-0.8	0
0.8-0.85	3
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8444	Intermediate Similarity	NPC100734
0.8444	Intermediate Similarity	NPC88923
0.8444	Intermediate Similarity	NPC315634
0.6505	Remote Similarity	NPC284685
0.5851	Remote Similarity	NPC313985
0.5851	Remote Similarity	NPC249150
0.5851	Remote Similarity	NPC33619
0.5789	Remote Similarity	NPC81654
0.5745	Remote Similarity	NPC486452
0.5745	Remote Similarity	NPC74591
0.5521	Remote Similarity	NPC486443
0.5521	Remote Similarity	NPC486446
0.5361	Remote Similarity	NPC486449
0.5361	Remote Similarity	NPC63199
0.5361	Remote Similarity	NPC111602
0.5361	Remote Similarity	NPC102338
0.5361	Remote Similarity	NPC196251
0.52	Remote Similarity	NPC312870
0.52	Remote Similarity	NPC199851
0.52	Remote Similarity	NPC294909
0.52	Remote Similarity	NPC254240
0.52	Remote Similarity	NPC128265
0.52	Remote Similarity	NPC604675
0.5051	Remote Similarity	NPC273374

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC191489 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4435
0.1-0.2	4591
0.2-0.3	114
0.3-0.4	2
0.4-0.5	0
0.5-0.6	4
0.6-0.7	2
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD7708	Phase 4
0.8444	Intermediate Similarity	NPD7803	Phase 4
0.6505	Remote Similarity	NPD7955	Phase 4
0.6505	Remote Similarity	NPD7956	Approved
0.5851	Remote Similarity	NPD4601	Phase 4
0.5789	Remote Similarity	NPD4600	Approved
0.52	Remote Similarity	NPD4500	Approved
0.52	Remote Similarity	NPD4501	Approved

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