NPASS Compound

Natural Product: NPC115906

Natural Product ID	NPC115906
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Hydrocodone
IUPAC Name	(4R,4aR,7aR,12bS)-9-methoxy-3-methyl-1,2,4,4a,5,6,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-7-one
Synonyms	Hydrocodone
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1457
PubChem CID	5284569
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000279] Alkaloids and derivatives [CHEMONTID:0000058] Morphinans

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 43 47 0 0 0 0 0 0 0 0999 V2000 -3.9854 -0.8720 0.1900 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6620 -1.4016 0.1213 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.0032 -1.5168 1.3912 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2439 -0.3183 1.8221 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5766 0.4579 0.7221 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5166 0.6080 -0.4366 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.9822 1.4245 -1.5571 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2666 2.6618 -1.1531 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0589 2.8153 0.2955 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1236 3.9693 0.7100 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.0472 1.7412 1.2890 C 0 0 2 0 0 0 0 0 0 0 0 0 1.2939 1.3483 1.6519 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7242 0.3804 0.7695 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9559 -0.1422 0.3466 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0026 -1.1508 -0.5959 C 0 0 0 0 0 0 0 0 0 0 0 0 1.8364 -1.6657 -1.1414 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6148 -1.1574 -0.7312 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6757 -1.6403 -1.2562 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8385 -0.7958 -0.8977 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6349 -0.1744 0.1911 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1094 0.3803 0.8985 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3489 -0.1312 0.4864 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7195 -1.7119 0.2894 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.1378 -0.0846 0.9345 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2172 -0.4098 -0.8081 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8123 -1.7023 2.1545 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3768 -2.4372 1.4115 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4233 -0.6637 2.5173 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8343 0.4108 2.4243 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4630 1.0364 -0.0447 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3526 0.7596 -2.2186 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8448 1.7159 -2.2084 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7436 2.6595 -1.6480 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7656 3.5881 -1.5608 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5856 1.9848 2.2272 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9713 -1.5207 -0.8900 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8383 -2.4538 -1.8798 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8563 -2.6582 -0.8228 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6154 -1.8100 -2.3577 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4950 -0.6810 -1.8029 H 0 0 0 0 0 0 0 0 0 0 0 0 6.1814 0.4795 0.8993 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4800 -0.1584 -0.6006 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4973 -1.1634 0.8685 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 5 4 1 1 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 9 10 2 0 9 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 1 0 18 19 1 0 17 20 2 0 14 21 1 0 21 22 1 0 19 2 1 0 20 5 1 0 11 5 1 0 20 13 1 0 19 6 1 0 1 23 1 0 1 24 1 0 1 25 1 0 3 26 1 0 3 27 1 0 4 28 1 0 4 29 1 0 6 30 1 1 7 31 1 0 7 32 1 0 8 33 1 0 8 34 1 0 11 35 1 1 15 36 1 0 16 37 1 0 18 38 1 0 18 39 1 0 19 40 1 6 22 41 1 0 22 42 1 0 22 43 1 0 M END

Standard InCHIKey	LLPOLZWFYMWNKH-CMKMFDCUSA-N
Standard InCHI	InChI=1S/C18H21NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3,6,11-12,17H,4-5,7-9H2,1-2H3/t11-,12+,17-,18-/m0/s1
SMILES	CN1CC[C@]23[C@H]4CCC(=O)[C@@H]3Oc3c(ccc(C[C@@H]14)c23)OC

Calculated Properties

Physi-Chem Properties

Molecular Weight:	299.15	Volume:	303.924 ? Van der Waals volume.
Dense:	0.984	LogP:	0.669 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.524 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.674 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	23.0
TPSA:	38.77 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	0.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.794	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.888	Fsp³:	0.611
MCE-18:	124.759 ? 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:	0.213	Fluc inhibitor:	0.005 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.15 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.235 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.015	Promiscuous compounds:	0.189

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.375	MDCK Permeability:	-4.657
Pgp-inhibitor:	0.163	Pgp-substrate:	0.713
PAMPA:	0.002 ? 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%):	0.001	30% Bioavailability (F30%):	0.002
50% Bioavailability (F50%):	0.095

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.993	MRP1:	0.692
Plasma Protein Binding (PPB):	31.227%	Volume Distribution (VD):	0.455
Fu:	63.188% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.994
OATP1B3 inhibitor:	0.99	BCRP inhibitor:	0.137
BSEP inhibitor:	0.835

ADMET: Metabolism

CYP1A2-inhibitor:	0.999	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	1.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.928	CYP2C9-substrate:	0.037
CYP2D6-inhibitor:	0.993	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	0.997	CYP3A4-substrate:	0.572
CYP2B6-substrate:	0.997	CYP2C8-inhibitor:	0.0
HLM stability:	0.168 ? 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):

10.999

Half-life (T1/2):

4.544

ADMET: Toxicity

hERG Blockers:	0.194	hERG Blockers (10um):	0.402
Human Hepatotoxicity (H-HT):	0.728	Drug-induced Liver Injury (DILI):	0.105
AMES Toxicity:	0.711	Rat Oral Acute Toxicity:	0.673
Maximum Recommended Daily Dose:	0.698	Skin Sensitization:	0.822
Carcinogencity:	0.736	Eye Corrosion:	0.008
Eye Irritation:	0.739	Respiratory Toxicity:	0.821
Drug-induced Neurotoxicity:	0.597	Ototoxicity:	0.583
Hematotoxicity:	0.489	Drug-induced Nephrotoxicity:	0.528
Genotoxicity:	0.812	RPMI-8226 Immunitoxicity:	0.074
A549 Cytotoxicity:	0.046	Hek293 Cytotoxicity:	0.274
BCF:	0.757 ? 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:	3.533 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.143 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.519 ? 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
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1042/BA20020118]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1556/abot.45.2003.3-4.15]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15019787]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22029392]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23517479]
NPO41833	A new engineered strain of Aspergillus spp. [n.a.]	Strain	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23621425]
NPO41833	A new engineered strain of Aspergillus spp. [n.a.]	Strain	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34947068]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37685099]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	Latex Exudate	n.a.	n.a.	Database[FooDB]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9498	Papaver somniferum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9498	Papaver somniferum	Species	Papaveraceae	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
Potency	3
Inhibition	1
Ki	2
FC	3
IC50	3
AC50	94
Retention_time	1
ED50	14

Activity Type	# Activity
Individual protein	97
Single protein	7
Organism	16
Tissue	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT271	Individual protein	Delta opioid receptor	Homo sapiens	Inhibition	=	37.0	%	PMID[22439881]
NPT272	Individual protein	Kappa opioid receptor	Homo sapiens	Ki	=	260.0	nM	PMID[22439881]
NPT145	Individual protein	Mu opioid receptor	Homo sapiens	Ki	=	9.5	nM	PMID[22439881]
NPT222	Individual protein	Alpha-2a adrenergic receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT290	Individual protein	Serotonin 2a (5-HT2a) receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT243	Individual protein	Dopamine D2 receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT248	Individual protein	Estrogen receptor beta	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT108	Individual protein	Estrogen receptor alpha	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT246	Individual protein	Dopamine transporter	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT297	Individual protein	Neurokinin 1 receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT216	Individual protein	Adenosine A1 receptor	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]
NPT263	Individual protein	Muscarinic acetylcholine receptor M2	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT239	Individual protein	Cholecystokinin A receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT303	Individual protein	Vasopressin V1a receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT1410	Individual protein	GABA receptor alpha-1 subunit	Rattus norvegicus	AC50	>	10000.0	nM	PMID[37468498]
NPT1788	Individual protein	Alpha-1a adrenergic receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT242	Individual protein	Dopamine D1 receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT31	Individual protein	Cyclooxygenase-2	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT271	Individual protein	Delta opioid receptor	Homo sapiens	AC50	=	16000.0	nM	PMID[37468498]
NPT2769	Individual protein	Thromboxane A2 receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT272	Individual protein	Kappa opioid receptor	Homo sapiens	AC50	=	765.8	nM	PMID[37468498]
NPT218	Individual protein	Adenosine A3 receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT230	Individual protein	Bradykinin B2 receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT295	Individual protein	Serotonin transporter	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT226	Individual protein	Beta-2 adrenergic receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT227	Individual protein	Beta-3 adrenergic receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT290	Individual protein	Serotonin 2a (5-HT2a) receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT245	Individual protein	Dopamine D4 receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT225	Individual protein	Beta-1 adrenergic receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT1464	Individual protein	Phosphodiesterase 4D	Homo sapiens	AC50	=	9499.9	nM	PMID[37468498]
NPT249	Individual protein	Glucocorticoid receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT2856	Individual protein	Sodium channel protein type V alpha subunit	Homo sapiens	AC50	>	50000.0	nM	PMID[37468498]
NPT252	Individual protein	Histamine H2 receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT232	Individual protein	Cannabinoid CB1 receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT259	Individual protein	Melanocortin receptor 4	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT224	Individual protein	Alpha-2c adrenergic 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]
NPT291	Individual protein	Serotonin 2b (5-HT2b) receptor	Homo sapiens	AC50	>	10000.0	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]
NPT2879	Individual protein	Equilibrative nucleoside transporter 1	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT251	Individual protein	Histamine H1 receptor	Homo sapiens	AC50	>	10000.0	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	>	10000.0	nM	PMID[37468498]
NPT261	Individual protein	Monoamine oxidase A	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT292	Individual protein	Serotonin 2c (5-HT2c) receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT1814	Individual protein	Glucagon receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT262	Individual protein	Muscarinic acetylcholine receptor M1	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT267	Individual protein	Neuropeptide Y receptor type 1	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT244	Individual protein	Dopamine D3 receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT232	Individual protein	Cannabinoid CB1 receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT1647	Individual protein	Vasopressin V2 receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT223	Individual protein	Alpha-2b adrenergic receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT145	Individual protein	Mu opioid receptor	Homo sapiens	AC50	=	180.0	nM	PMID[37468498]
NPT247	Individual protein	Endothelin receptor ET-A	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT228	Individual protein	Norepinephrine transporter	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT264	Individual protein	Muscarinic acetylcholine receptor M3	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT145	Individual protein	Mu opioid receptor	Homo sapiens	AC50	=	340.0	nM	PMID[37468498]
NPT483	Individual protein	Prelamin-A/C	Homo sapiens	Potency	=	8912.5	nM	PubChem BioAssay data set
NPT613	Individual protein	Solute carrier family 22 member 1	Homo sapiens	FC	=	0.9	n.a.	PMID[31597043]
NPT613	Individual protein	Solute carrier family 22 member 1	Homo sapiens	FC	=	1.6	n.a.	PMID[31597043]
NPT613	Individual protein	Solute carrier family 22 member 1	Homo sapiens	FC	=	1.2	n.a.	PMID[31597043]
NPT613	Individual protein	Solute carrier family 22 member 1	Homo sapiens	IC50	=	536960.0	nM	PMID[31597043]
NPT987	Individual protein	Histamine H3 receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT5318	Individual protein	Corticotropin releasing factor receptor 1	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT5301	Individual protein	Motilin receptor	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT30134	Single protein	Gastric inhibitory polypeptide receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT3952	Individual protein	Endothelin receptor ET-B	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT29430	Single protein	Neuronal acetylcholine receptor protein alpha-4 subunit	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
NPT542	Individual protein	Progesterone 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]
NPT3735	Individual protein	Neurotensin receptor 1	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT98	Individual protein	HERG	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT4729	Individual protein	Cholecystokinin B receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT445	Individual protein	Peripheral myelin protein 22	Rattus norvegicus	Potency	n.a.	12817.8	nM	PubChem BioAssay data set
NPT28787	Single protein	Voltage-gated N-type calcium channel alpha-1B subunit	Rattus norvegicus	AC50	>	10000.0	nM	PMID[37468498]
NPT28448	Single protein	Corticotropin releasing factor receptor 2	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	>	30000.0	nM	PMID[37468498]
NPT28814	Single protein	Ghrelin 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]
NPT6127	Individual protein	Bradykinin B1 receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT5104	Individual protein	Phosphodiesterase 3A	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT53	Individual protein	4'-phosphopantetheinyl transferase ffp	Bacillus subtilis	Potency	=	112201.8	nM	PubChem BioAssay data set
NPT525	Individual protein	Hydroxycarboxylic acid receptor 2	Homo sapiens	AC50	>	10000.0	nM	PMID[37468498]
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]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
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]
NPT20913	Tissue	Whole blood	Homo sapiens	Retention_time	=	2.96	min	DOI[10.1007/s00044-012-9977-1]

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	=	2.4	umol.kg-1	PMID[6153723]
NPT32	Organism	Mus musculus	Mus musculus	ED50	=	1.06	mg.kg-1	PMID[6181259]
NPT32	Organism	Mus musculus	Mus musculus	ED50	=	2.36	umol.kg-1	PMID[7192744]
NPT32	Organism	Mus musculus	Mus musculus	ED50	=	2.4	uM	PMID[6153723]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	ED50	=	5.2	umol.kg-1	PMID[7192744]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	ED50	=	5.2	uM	PMID[7192744]

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 NPC115906 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	25702
0.1-0.2	23647
0.2-0.3	470
0.3-0.4	27
0.4-0.5	5
0.5-0.6	3
0.6-0.7	3
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	Natural Product ID
0.6866	Remote Similarity	NPC67346
0.6618	Remote Similarity	NPC214629
0.6143	Remote Similarity	NPC174783
0.5753	Remote Similarity	NPC43069
0.5616	Remote Similarity	NPC66909
0.5325	Remote Similarity	NPC311781

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC115906 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4029
0.1-0.2	4885
0.2-0.3	195
0.3-0.4	21
0.4-0.5	5
0.5-0.6	7
0.6-0.7	5
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	NPD2971	Phase 4
0.8358	Intermediate Similarity	NPD2968	Approved
0.6866	Remote Similarity	NPD2490	Phase 4
0.6866	Remote Similarity	NPD3057	Phase 4
0.6765	Remote Similarity	NPD2488	Approved
0.6667	Remote Similarity	NPD4107	Pre-clinical
0.6053	Remote Similarity	NPD3051	Approved
0.5753	Remote Similarity	NPD2972	Phase 4
0.5616	Remote Similarity	NPD2975	Phase 4
0.5541	Remote Similarity	NPD2974	Approved
0.5526	Remote Similarity	NPD2970	Approved
0.5385	Remote Similarity	NPD2969	Approved
0.5325	Remote Similarity	NPD4482	Phase 4
0.5256	Remote Similarity	NPD4481	Phase 3

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