NPASS Compound

Natural Product: NPC474806

Natural Product ID	NPC474806
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(4As,6As,6As,6Br,10S,11S,12Ar,14Bs)-10,11-Dihydroxy-2,2,6A,6B,9,9,12A-Heptamethyl-1,3,4,5,6,6A,7,10,11,12,13,14B-Dodecahydropicene-4A-Carboxylic Acid
IUPAC Name	(4aS,6aS,6aS,6bR,10S,11S,12aR,14bS)-10,11-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,10,11,12,13,14b-dodecahydropicene-4a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL483444
PubChem CID	44576060
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001553] Triterpenoids

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 84 0 0 0 0 0 0 0 0999 V2000 -5.8440 -1.9263 -0.5966 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6042 -1.1651 -0.0854 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1358 -0.2757 1.0240 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0476 0.6013 1.4899 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5050 1.4371 0.3566 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4021 2.2663 0.9974 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2308 2.5282 0.1327 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.6267 1.3532 -0.5445 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6732 0.3623 -0.8943 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2022 -0.8172 -1.2989 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2442 -1.1309 -1.4006 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0016 -0.5645 -0.2146 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5468 0.7631 0.2178 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5829 1.8595 0.2657 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9476 1.3781 0.4834 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3809 0.1569 0.2449 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4758 -0.8472 -0.2798 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7649 -2.1213 0.4888 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1722 -2.5765 0.4839 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1901 -1.5261 0.7704 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8004 -0.1253 0.5074 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5676 0.4680 -0.6877 C 0 0 0 0 0 0 0 0 0 0 0 0 5.3049 0.7082 1.7058 C 0 0 0 0 0 0 0 0 0 0 0 0 6.3340 -1.8138 0.0164 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4447 -3.3120 -0.6845 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7670 -1.1822 -1.7411 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0711 0.6492 1.6832 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0864 0.6880 -0.8549 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0529 -0.3927 -1.2256 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1138 1.8939 -1.9092 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6055 2.3704 -0.0507 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6502 2.4293 0.5888 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4068 3.1571 -1.1620 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7303 -2.1850 0.5447 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.4999 -2.4486 -1.5166 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2328 -2.6228 0.1473 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6037 -1.1814 -0.9554 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3629 -1.0015 1.8663 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.0316 0.2469 0.7082 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2142 0.0415 1.9715 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3929 1.3424 2.2611 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1876 1.9589 2.0424 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8771 3.2923 1.1633 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5800 3.2821 -0.6444 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.5282 3.1406 0.7482 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9605 -1.5472 -1.5615 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6664 -0.8822 -2.3812 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2964 -2.2663 -1.3699 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6445 -1.3020 0.5939 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3664 2.5858 1.1091 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5885 2.5087 -0.6329 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6704 2.1170 0.8820 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4988 -1.8801 1.5617 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1193 -2.9336 0.0992 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2185 -3.3822 1.2847 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5436 -1.6776 1.8371 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3904 -0.2007 -1.0133 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0459 1.4378 -0.4443 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8769 0.6980 -1.5388 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6070 1.7268 1.3761 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5887 0.6897 2.5268 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2361 0.2161 2.0506 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0153 -2.2187 -0.8285 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0879 -4.0344 -0.5276 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5785 -0.3441 -2.4280 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2169 -2.1073 -1.9726 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8379 -1.4323 -1.8918 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8124 -0.0220 2.2284 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1142 1.5873 2.2099 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8455 0.0741 1.6689 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1964 1.4633 -1.7013 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9713 0.1551 -1.6365 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7687 -1.0366 -2.0396 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8467 1.4681 -2.1867 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0327 2.9987 -1.8591 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9004 1.7510 -2.6963 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8517 4.0869 -1.2050 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4634 -2.9357 -0.2349 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3282 -2.7169 1.3125 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7821 -1.8034 0.9508 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 4 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 2 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 21 23 1 0 20 24 1 0 19 25 1 0 17 26 1 0 13 27 1 0 9 28 1 0 28 29 1 0 8 30 1 0 5 31 1 0 31 32 2 0 31 33 1 0 2 34 1 0 29 2 1 0 28 5 1 0 13 8 1 0 17 12 1 0 21 16 1 0 1 35 1 0 1 36 1 0 1 37 1 0 3 38 1 0 3 39 1 0 4 40 1 0 4 41 1 0 6 42 1 0 6 43 1 0 7 44 1 0 7 45 1 0 10 46 1 0 11 47 1 0 11 48 1 0 12 49 1 0 14 50 1 0 14 51 1 0 15 52 1 0 18 53 1 0 18 54 1 0 19 55 1 0 20 56 1 0 22 57 1 0 22 58 1 0 22 59 1 0 23 60 1 0 23 61 1 0 23 62 1 0 24 63 1 0 25 64 1 0 26 65 1 0 26 66 1 0 26 67 1 0 27 68 1 0 27 69 1 0 27 70 1 0 28 71 1 0 29 72 1 0 29 73 1 0 30 74 1 0 30 75 1 0 30 76 1 0 33 77 1 0 34 78 1 0 34 79 1 0 34 80 1 0 M END

Standard InCHIKey	KNEXUHUBWRLDNK-ABDCSFLRSA-N
Standard InCHI	InChI=1S/C30H46O4/c1-25(2)12-14-30(24(33)34)15-13-28(6)18(19(30)16-25)8-9-22-27(5)17-20(31)23(32)26(3,4)21(27)10-11-29(22,28)7/h8,10,19-20,22-23,31-32H,9,11-17H2,1-7H3,(H,33,34)/t19-,20-,22+,23+,27-,28+,29+,30-/m0/s1
SMILES	CC1(CCC2(CCC3(C(=CCC4C3(CC=C5C4(CC(C(C5(C)C)O)O)C)C)C2C1)C)C(=O)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	470.34	Volume:	511.905 ? Van der Waals volume.
Dense:	0.919	LogP:	4.017 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.492 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.023 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	27.0
TPSA:	77.76 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	3.0	Rings:	5.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.403	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.049	Fsp³:	0.833
MCE-18:	106.182 ? 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:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.438	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.002 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.094 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.303	Promiscuous compounds:	0.002

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.384	MDCK Permeability:	-4.954
Pgp-inhibitor:	0.0	Pgp-substrate:	0.04
PAMPA:	0.99 ? 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):	0.021
20% Bioavailability (F20%):	0.038	30% Bioavailability (F30%):	0.025
50% Bioavailability (F50%):	0.954

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.107	MRP1:	1.0
Plasma Protein Binding (PPB):	88.28%	Volume Distribution (VD):	-0.082
Fu:	9.224% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.315
OATP1B3 inhibitor:	0.723	BCRP inhibitor:	0.0
BSEP inhibitor:	0.652

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.009	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.936	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.007	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.003	CYP2C8-inhibitor:	0.07
HLM stability:	0.002 ? 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):

2.792

Half-life (T1/2):

1.261

ADMET: Toxicity

hERG Blockers:	0.036	hERG Blockers (10um):	0.117
Human Hepatotoxicity (H-HT):	0.551	Drug-induced Liver Injury (DILI):	0.301
AMES Toxicity:	0.081	Rat Oral Acute Toxicity:	0.471
Maximum Recommended Daily Dose:	0.694	Skin Sensitization:	0.019
Carcinogencity:	0.134	Eye Corrosion:	0.0
Eye Irritation:	0.005	Respiratory Toxicity:	0.283
Drug-induced Neurotoxicity:	0.151	Ototoxicity:	0.959
Hematotoxicity:	0.24	Drug-induced Nephrotoxicity:	0.228
Genotoxicity:	0.18	RPMI-8226 Immunitoxicity:	0.033
A549 Cytotoxicity:	0.036	Hek293 Cytotoxicity:	0.177
BCF:	1.235 ? 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:	3.993 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.772 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.78 ? 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
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[12828478]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[15520511]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[15620254]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[1624939]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17027268]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19715321]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19931461]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23403897]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38163555]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14602	Vitex negundo	Species	Lamiaceae	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
Inhibition	1

Activity Type	# Activity
Organism	1

Molecular-level activity

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

In vitro activity

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

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	34.3	%	DOI[10.1039/C5MD00247H]

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 NPC474806 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	25193
0.1-0.2	22236
0.2-0.3	2021
0.3-0.4	235
0.4-0.5	128
0.5-0.6	30
0.6-0.7	10
0.7-0.8	0
0.8-0.85	0
0.85-0.9	1
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC133579
0.85	High Similarity	NPC32118
0.6567	Remote Similarity	NPC307282
0.6567	Remote Similarity	NPC84319
0.6567	Remote Similarity	NPC52021
0.6567	Remote Similarity	NPC599947
0.6471	Remote Similarity	NPC231063
0.6471	Remote Similarity	NPC282395
0.6471	Remote Similarity	NPC110308
0.6	Remote Similarity	NPC106112
0.6	Remote Similarity	NPC261935
0.6	Remote Similarity	NPC481360
0.5857	Remote Similarity	NPC64872
0.5857	Remote Similarity	NPC25906
0.5775	Remote Similarity	NPC130278
0.5714	Remote Similarity	NPC480946
0.5714	Remote Similarity	NPC130577
0.5714	Remote Similarity	NPC142415
0.5714	Remote Similarity	NPC102683
0.5694	Remote Similarity	NPC291028
0.5634	Remote Similarity	NPC270768
0.5634	Remote Similarity	NPC59263
0.5634	Remote Similarity	NPC210106
0.5634	Remote Similarity	NPC282616
0.5634	Remote Similarity	NPC275809
0.5556	Remote Similarity	NPC88116
0.5556	Remote Similarity	NPC472149
0.5556	Remote Similarity	NPC609452
0.5479	Remote Similarity	NPC298554
0.5417	Remote Similarity	NPC37038
0.5362	Remote Similarity	NPC604575
0.5342	Remote Similarity	NPC158141
0.5342	Remote Similarity	NPC481314
0.5333	Remote Similarity	NPC481316
0.5325	Remote Similarity	NPC474727
0.527	Remote Similarity	NPC145667
0.5211	Remote Similarity	NPC280654
0.5205	Remote Similarity	NPC306541
0.52	Remote Similarity	NPC201657
0.52	Remote Similarity	NPC474963
0.5172	Remote Similarity	NPC266365
0.5135	Remote Similarity	NPC271614

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC474806 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6760
0.1-0.2	2356
0.2-0.3	33
0.3-0.4	1
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