NPASS Compound

Natural Product: NPC282395

Natural Product ID	NPC282395
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	2Alpha,3Alpha,24-Trihydroxyolean-12-En-28-Oic Acid
IUPAC Name	(4aS,6aR,6aS,6bR,8aR,9S,10S,11R,12aR,14bS)-10,11-dihydroxy-9-(hydroxymethyl)-2,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL3342058
PubChem CID	69570248
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 83 87 0 0 0 0 0 0 0 0999 V2000 6.9434 0.5212 0.0713 O 0 0 0 0 0 0 0 0 0 0 0 0 5.5995 0.9118 0.3160 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7551 -0.1181 -0.3563 C 0 0 1 0 0 0 0 0 0 0 0 0 5.1567 -0.0493 -1.8465 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1164 -1.4870 0.1043 C 0 0 2 0 0 0 0 0 0 0 0 0 4.9546 -2.4297 -0.9153 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3913 -1.8915 1.3650 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6667 -3.2177 1.6198 O 0 0 0 0 0 0 0 0 0 0 0 0 2.9026 -1.7620 1.1520 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5286 -0.2910 0.8696 C 0 0 1 0 0 0 0 0 0 0 0 0 3.2887 0.0932 -0.3497 C 0 0 1 0 0 0 0 0 0 0 0 0 2.8493 1.4001 -0.9753 C 0 0 0 0 0 0 0 0 0 0 0 0 1.3950 1.2052 -1.3873 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5441 0.8530 -0.1872 C 0 0 2 0 0 0 0 0 0 0 0 0 1.0676 -0.3981 0.4116 C 0 0 2 0 0 0 0 0 0 0 0 0 0.1972 -1.0925 1.3881 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1988 -0.6068 1.3701 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7491 0.1695 0.4797 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8735 0.6197 -0.6513 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.0089 -0.3687 -1.7654 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4955 1.9242 -1.1383 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8056 1.5463 -1.7996 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7558 1.1276 -0.7017 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.1371 0.6387 0.5459 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1013 -0.1839 1.3262 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8904 -1.2050 0.5766 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7326 -0.4204 -0.4386 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7511 0.2098 -1.3698 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.9015 -1.7846 1.5499 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1502 -2.2765 -0.1120 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5545 2.3768 -0.3884 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5494 2.8952 0.7534 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.3127 2.9722 -1.3747 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5232 2.0645 0.6969 C 0 0 0 0 0 0 0 0 0 0 0 0 2.7309 0.4606 2.1102 C 0 0 0 0 0 0 0 0 0 0 0 0 7.3371 1.0546 -0.6587 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5163 1.9254 -0.0783 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5460 0.8635 1.4443 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3946 1.0116 -2.1134 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0814 -0.6238 -2.0181 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3188 -0.3713 -2.4908 H 0 0 0 0 0 0 0 0 0 0 0 0 6.2144 -1.4853 0.3566 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0671 -3.3235 -0.4597 H 0 0 0 0 0 0 0 0 0 0 0 0 4.7782 -1.2905 2.1852 H 0 0 0 0 0 0 0 0 0 0 0 0 4.9765 -3.3738 2.5617 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4061 -2.1232 2.0652 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6409 -2.3223 0.2400 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9170 -0.6632 -1.1258 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0340 2.2801 -0.3769 H 0 0 0 0 0 0 0 0 0 0 0 0 3.4215 1.5041 -1.9244 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1026 2.1345 -1.8904 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4001 0.3921 -2.1526 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2005 -1.1129 -0.4633 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5615 -1.0415 2.4372 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1597 -2.1817 1.1620 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8077 -0.9570 2.2105 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8195 0.1725 -2.7425 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9938 -0.8772 -1.7564 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2685 -1.1860 -1.7791 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8256 2.5620 -0.2650 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8995 2.4559 -1.8746 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7262 0.8187 -2.6029 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1457 2.4981 -2.3095 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0354 1.5847 1.2047 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7400 -0.5639 2.2983 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9159 0.5514 1.6666 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3881 -1.0736 -1.0107 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2966 0.3862 0.1058 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.3660 0.8740 -2.0542 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3027 -0.5265 -2.0331 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4895 -1.8607 2.5833 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.8012 -1.1289 1.6306 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2627 -2.7649 1.1798 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5004 -2.3569 -1.1639 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0625 -2.2224 -0.0972 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4406 -3.2695 0.3511 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4931 3.9858 -1.3959 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1389 2.9017 0.0341 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5233 2.4563 0.9742 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1300 1.9101 1.5704 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7676 0.7484 2.6340 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2450 -0.1581 2.9120 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3194 1.3803 2.0803 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 3 2 1 1 3 4 1 0 3 5 1 0 5 6 1 0 5 7 1 0 7 8 1 0 7 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 16 17 1 0 17 18 2 0 18 19 1 0 19 20 1 6 19 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 1 0 25 26 1 0 26 27 1 0 27 28 1 0 26 29 1 0 26 30 1 0 23 31 1 1 31 32 2 0 31 33 1 0 14 34 1 1 10 35 1 1 11 3 1 0 19 14 1 0 28 23 1 0 15 10 1 0 24 18 1 0 1 36 1 0 2 37 1 0 2 38 1 0 4 39 1 0 4 40 1 0 4 41 1 0 5 42 1 1 6 43 1 0 7 44 1 1 8 45 1 0 9 46 1 0 9 47 1 0 11 48 1 6 12 49 1 0 12 50 1 0 13 51 1 0 13 52 1 0 15 53 1 6 16 54 1 0 16 55 1 0 17 56 1 0 20 57 1 0 20 58 1 0 20 59 1 0 21 60 1 0 21 61 1 0 22 62 1 0 22 63 1 0 24 64 1 1 25 65 1 0 25 66 1 0 27 67 1 0 27 68 1 0 28 69 1 0 28 70 1 0 29 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 35 81 1 0 35 82 1 0 35 83 1 0 M END

Standard InCHIKey	RWNHLTKFBKYDOJ-ZDNZHVAWSA-N
Standard InCHI	InChI=1S/C30H48O5/c1-25(2)11-13-30(24(34)35)14-12-28(5)18(19(30)15-25)7-8-22-26(3)16-20(32)23(33)27(4,17-31)21(26)9-10-29(22,28)6/h7,19-23,31-33H,8-17H2,1-6H3,(H,34,35)/t19-,20+,21+,22+,23+,26-,27+,28+,29+,30-/m0/s1
SMILES	OC[C@@]1(C)[C@H](O)[C@H](O)C[C@]2([C@H]1CC[C@@]1([C@@H]2CC=C2[C@@]1(C)CC[C@@]1([C@H]2CC(CC1)(C)C)C(=O)O)C)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	488.35	Volume:	523.332 ? Van der Waals volume.
Dense:	0.933	LogP:	3.053 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.847 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.314 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	27.0
TPSA:	97.99 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	4.0	Rings:	5.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.402	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.924	Fsp³:	0.9
MCE-18:	108.07 ? 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:	0.704	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.019 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.343	Promiscuous compounds:	0.085

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.574	MDCK Permeability:	-5.099
Pgp-inhibitor:	0.0	Pgp-substrate:	0.021
PAMPA:	1.0 ? 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):	0.001
20% Bioavailability (F20%):	0.654	30% Bioavailability (F30%):	0.039
50% Bioavailability (F50%):	0.986

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.513	MRP1:	0.962
Plasma Protein Binding (PPB):	82.432%	Volume Distribution (VD):	-0.339
Fu:	16.238% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	0.727	BCRP inhibitor:	0.014
BSEP inhibitor:	0.834

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.001
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.023	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.018
HLM stability:	0.102 ? 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):

2.863

Half-life (T1/2):

1.496

ADMET: Toxicity

hERG Blockers:	0.02	hERG Blockers (10um):	0.059
Human Hepatotoxicity (H-HT):	0.64	Drug-induced Liver Injury (DILI):	0.453
AMES Toxicity:	0.126	Rat Oral Acute Toxicity:	0.276
Maximum Recommended Daily Dose:	0.465	Skin Sensitization:	0.909
Carcinogencity:	0.838	Eye Corrosion:	0.006
Eye Irritation:	0.47	Respiratory Toxicity:	0.848
Drug-induced Neurotoxicity:	0.026	Ototoxicity:	0.834
Hematotoxicity:	0.35	Drug-induced Nephrotoxicity:	0.883
Genotoxicity:	0.393	RPMI-8226 Immunitoxicity:	0.033
A549 Cytotoxicity:	0.031	Hek293 Cytotoxicity:	0.075
BCF:	0.922 ? 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:	3.586 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.268 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.418 ? 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
NPO14026.1	Vitex negundo var. cannabifolia	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25245917]
NPO14026.1	Vitex negundo var. cannabifolia	Varieties	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14026.1	Vitex negundo var. cannabifolia	Varieties	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
IC50	1

Activity Type	# Activity
Cell line	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
NPT113	Cell line	RAW264.7	Mus musculus	IC50	=	40500.0	nM	PMID[15270567]

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 NPC282395 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	23125
0.1-0.2	23298
0.2-0.3	2694
0.3-0.4	389
0.4-0.5	184
0.5-0.6	91
0.6-0.7	40
0.7-0.8	0
0.8-0.85	2
0.85-0.9	5
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC231063
0.8689	High Similarity	NPC110308
0.8689	High Similarity	NPC609452
0.8525	High Similarity	NPC84319
0.8525	High Similarity	NPC52021
0.8525	High Similarity	NPC599947
0.8387	Intermediate Similarity	NPC88116
0.8125	Intermediate Similarity	NPC201657
0.7969	Intermediate Similarity	NPC145667
0.7937	Intermediate Similarity	NPC307282
0.7656	Intermediate Similarity	NPC270768
0.7656	Intermediate Similarity	NPC59263
0.7656	Intermediate Similarity	NPC210106
0.7538	Intermediate Similarity	NPC173744
0.7538	Intermediate Similarity	NPC204961
0.7538	Intermediate Similarity	NPC472149
0.7538	Intermediate Similarity	NPC73004
0.7538	Intermediate Similarity	NPC481314
0.7463	Intermediate Similarity	NPC481316
0.7424	Intermediate Similarity	NPC32407
0.7424	Intermediate Similarity	NPC263548
0.7424	Intermediate Similarity	NPC606320
0.7313	Intermediate Similarity	NPC247139
0.7273	Intermediate Similarity	NPC106112
0.7273	Intermediate Similarity	NPC261935
0.7273	Intermediate Similarity	NPC481360
0.7101	Intermediate Similarity	NPC20235
0.7101	Intermediate Similarity	NPC299996
0.7	Intermediate Similarity	NPC481315
0.697	Remote Similarity	NPC480946
0.697	Remote Similarity	NPC130577
0.697	Remote Similarity	NPC142415
0.697	Remote Similarity	NPC102683
0.6866	Remote Similarity	NPC282616
0.6765	Remote Similarity	NPC158141
0.6761	Remote Similarity	NPC479743
0.6667	Remote Similarity	NPC298554
0.6618	Remote Similarity	NPC275809
0.6618	Remote Similarity	NPC121798
0.6618	Remote Similarity	NPC306541
0.6618	Remote Similarity	NPC32118
0.6618	Remote Similarity	NPC234346
0.6615	Remote Similarity	NPC604575
0.6522	Remote Similarity	NPC130278
0.6522	Remote Similarity	NPC37221
0.6486	Remote Similarity	NPC188833
0.6471	Remote Similarity	NPC474806
0.6471	Remote Similarity	NPC133579
0.6377	Remote Similarity	NPC37038
0.6338	Remote Similarity	NPC88847
0.6286	Remote Similarity	NPC271614
0.6286	Remote Similarity	NPC71074
0.6286	Remote Similarity	NPC605937
0.6212	Remote Similarity	NPC478657
0.6197	Remote Similarity	NPC259733
0.6197	Remote Similarity	NPC158371
0.6197	Remote Similarity	NPC207922
0.6176	Remote Similarity	NPC280654
0.6143	Remote Similarity	NPC182797
0.6143	Remote Similarity	NPC64872
0.6143	Remote Similarity	NPC25906
0.6143	Remote Similarity	NPC52169
0.6143	Remote Similarity	NPC488562
0.6111	Remote Similarity	NPC9613
0.6027	Remote Similarity	NPC25299
0.6027	Remote Similarity	NPC481322
0.6027	Remote Similarity	NPC130520
0.6	Remote Similarity	NPC474727
0.6	Remote Similarity	NPC198664
0.5972	Remote Similarity	NPC305464
0.5972	Remote Similarity	NPC291028
0.5972	Remote Similarity	NPC200752
0.5972	Remote Similarity	NPC19376
0.5972	Remote Similarity	NPC120840
0.5972	Remote Similarity	NPC25848
0.5915	Remote Similarity	NPC156981
0.589	Remote Similarity	NPC474963
0.5875	Remote Similarity	NPC204407
0.5802	Remote Similarity	NPC28198
0.5802	Remote Similarity	NPC476123
0.5802	Remote Similarity	NPC606107
0.5753	Remote Similarity	NPC40092
0.5753	Remote Similarity	NPC228784
0.5753	Remote Similarity	NPC324341
0.5753	Remote Similarity	NPC601810
0.5733	Remote Similarity	NPC296164
0.5733	Remote Similarity	NPC116457
0.5694	Remote Similarity	NPC229281
0.5676	Remote Similarity	NPC191412
0.5676	Remote Similarity	NPC114159
0.5676	Remote Similarity	NPC6818
0.5658	Remote Similarity	NPC96580
0.5647	Remote Similarity	NPC284807
0.5641	Remote Similarity	NPC96693
0.5616	Remote Similarity	NPC61543
0.5616	Remote Similarity	NPC293048
0.5616	Remote Similarity	NPC225585
0.561	Remote Similarity	NPC283849
0.56	Remote Similarity	NPC607666
0.56	Remote Similarity	NPC608261
0.56	Remote Similarity	NPC611078
0.5541	Remote Similarity	NPC87095
0.5526	Remote Similarity	NPC222047
0.5526	Remote Similarity	NPC117663
0.5526	Remote Similarity	NPC481318
0.5517	Remote Similarity	NPC171007
0.5517	Remote Similarity	NPC190849
0.5476	Remote Similarity	NPC286347
0.5455	Remote Similarity	NPC164194
0.5417	Remote Similarity	NPC43686
0.5412	Remote Similarity	NPC100383
0.5405	Remote Similarity	NPC111214
0.5402	Remote Similarity	NPC266365
0.5402	Remote Similarity	NPC191410
0.5395	Remote Similarity	NPC471588
0.5395	Remote Similarity	NPC127689
0.5341	Remote Similarity	NPC475472
0.5333	Remote Similarity	NPC136877
0.5333	Remote Similarity	NPC12288
0.5333	Remote Similarity	NPC136697
0.5333	Remote Similarity	NPC605663
0.5325	Remote Similarity	NPC324063
0.5316	Remote Similarity	NPC481320
0.5316	Remote Similarity	NPC601365
0.5287	Remote Similarity	NPC294112
0.5287	Remote Similarity	NPC473538
0.5281	Remote Similarity	NPC270667
0.5275	Remote Similarity	NPC25605
0.5263	Remote Similarity	NPC35239
0.525	Remote Similarity	NPC481319
0.525	Remote Similarity	NPC481362
0.5222	Remote Similarity	NPC198621
0.5222	Remote Similarity	NPC216940
0.5217	Remote Similarity	NPC109079
0.5195	Remote Similarity	NPC62516
0.5172	Remote Similarity	NPC43353
0.5165	Remote Similarity	NPC488214
0.5161	Remote Similarity	NPC488561
0.5135	Remote Similarity	NPC96916
0.5135	Remote Similarity	NPC187722
0.5132	Remote Similarity	NPC202728
0.5132	Remote Similarity	NPC158059
0.5128	Remote Similarity	NPC174663
0.5128	Remote Similarity	NPC600832
0.5111	Remote Similarity	NPC22676
0.5109	Remote Similarity	NPC174679
0.5109	Remote Similarity	NPC279554
0.5109	Remote Similarity	NPC59804
0.5106	Remote Similarity	NPC22956
0.5104	Remote Similarity	NPC601567
0.5104	Remote Similarity	NPC606631
0.5067	Remote Similarity	NPC51700
0.5067	Remote Similarity	NPC88716
0.5067	Remote Similarity	NPC68160
0.5067	Remote Similarity	NPC606443
0.5065	Remote Similarity	NPC263393
0.5065	Remote Similarity	NPC91010
0.5065	Remote Similarity	NPC132824
0.5063	Remote Similarity	NPC6255
0.5054	Remote Similarity	NPC127056

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC282395 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6447
0.1-0.2	2655
0.2-0.3	43
0.3-0.4	3
0.4-0.5	2
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