NPASS Compound

Natural Product: NPC66429

Natural Product ID	NPC66429
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	16Alpha-Hydroxy-3-Oxolanosta-7,9(11),24-Trien-21-Oic Acid
IUPAC Name	(2R)-2-[(5R,10S,13R,14R,16R,17R)-16-hydroxy-4,4,10,13,14-pentamethyl-3-oxo-1,2,5,6,12,15,16,17-octahydrocyclopenta[a]phenanthren-17-yl]-6-methylhept-5-enoic acid
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL497895
PubChem CID	44583859
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 78 81 0 0 0 0 0 0 0 0999 V2000 7.9430 0.6719 0.6142 C 0 0 0 0 0 0 0 0 0 0 0 0 6.9336 1.0093 -0.4264 C 0 0 0 0 0 0 0 0 0 0 0 0 5.9031 0.2378 -0.6557 C 0 0 0 0 0 0 0 0 0 0 0 0 5.6576 -1.0257 0.0956 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3491 -1.0198 0.8368 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1657 -0.8391 -0.1253 C 0 0 2 0 0 0 0 0 0 0 0 0 1.9295 -0.8507 0.7293 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0402 0.2965 1.7131 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3763 -0.1164 2.9864 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6463 0.9201 1.8092 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2231 -0.1146 1.1945 C 0 0 2 0 0 0 0 0 0 0 0 0 0.6644 -0.5909 0.0310 C 0 0 1 0 0 0 0 0 0 0 0 0 0.6982 0.5337 -0.9661 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0220 -1.7558 -0.5794 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4678 -1.5464 -0.8027 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1804 -0.5734 -0.2912 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.4644 0.3868 0.5797 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.9389 1.6044 0.7688 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2060 1.9504 0.0725 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1274 0.7511 0.2417 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6404 -0.4147 -0.5539 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.8528 -0.2441 -2.0399 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3576 -1.6556 -0.0596 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7482 -1.3845 0.4193 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.3395 -0.1600 -0.1300 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.4312 -0.1803 -0.6541 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.5619 1.1068 -0.0257 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7612 2.0028 -1.2034 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0723 1.8597 1.2098 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5379 -1.2322 2.1436 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1744 -1.8771 -1.1694 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2568 -1.6098 -2.4159 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0924 -3.2377 -0.8657 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1149 2.2561 -1.2154 C 0 0 0 0 0 0 0 0 0 0 0 0 8.7797 1.3905 0.6064 H 0 0 0 0 0 0 0 0 0 0 0 0 8.3691 -0.3392 0.4656 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5098 0.6957 1.6354 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1804 0.4990 -1.4159 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4569 -1.1083 0.8604 H 0 0 0 0 0 0 0 0 0 0 0 0 5.7695 -1.9137 -0.5600 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2807 -1.9703 1.3907 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3860 -0.2003 1.5695 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3414 0.1402 -0.6154 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8878 -1.8024 1.2597 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7210 1.0811 1.3667 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5112 -1.0817 3.0713 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3372 1.0900 2.8481 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6121 1.8901 1.2827 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5815 1.1674 -0.9008 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6873 0.1070 -2.0123 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1954 1.1902 -0.9228 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4278 -1.9105 -1.6041 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1124 -2.7141 -0.0574 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9699 -2.2720 -1.4509 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3968 2.2793 1.4068 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6632 2.8711 0.4501 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9576 2.0096 -1.0130 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0590 0.4707 1.3192 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9164 -0.1384 -2.2672 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5157 -1.1946 -2.5160 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2022 0.5463 -2.4132 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7628 -2.0341 0.8077 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3379 -2.4707 -0.8114 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.3731 -2.2593 0.1459 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8044 -1.3174 1.5383 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8444 2.2064 -1.7609 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1781 3.0120 -0.9156 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5648 1.5692 -1.8686 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.5108 1.4803 2.0886 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1402 1.6901 1.3792 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8119 2.9441 1.1123 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6475 -1.4111 2.1715 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0704 -2.1868 1.9041 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2911 -0.8786 3.1828 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6709 -3.9215 -1.4667 H 0 0 0 0 0 0 0 0 0 0 0 0 8.0805 2.1605 -1.7705 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3127 2.3885 -1.9576 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1853 3.0872 -0.4812 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 3 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 9 1 0 8 10 1 0 10 11 1 0 11 12 1 0 12 13 1 6 12 14 1 0 14 15 1 0 15 16 2 0 16 17 1 0 17 18 2 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 6 21 23 1 0 23 24 1 0 24 25 1 0 25 26 2 0 25 27 1 0 27 28 1 0 27 29 1 0 11 30 1 1 6 31 1 0 31 32 2 0 31 33 1 0 2 34 1 0 12 7 1 0 21 16 1 0 17 11 1 0 27 20 1 0 1 35 1 0 1 36 1 0 1 37 1 0 3 38 1 0 4 39 1 0 4 40 1 0 5 41 1 0 5 42 1 0 6 43 1 6 7 44 1 1 8 45 1 6 9 46 1 0 10 47 1 0 10 48 1 0 13 49 1 0 13 50 1 0 13 51 1 0 14 52 1 0 14 53 1 0 15 54 1 0 18 55 1 0 19 56 1 0 19 57 1 0 20 58 1 1 22 59 1 0 22 60 1 0 22 61 1 0 23 62 1 0 23 63 1 0 24 64 1 0 24 65 1 0 28 66 1 0 28 67 1 0 28 68 1 0 29 69 1 0 29 70 1 0 29 71 1 0 30 72 1 0 30 73 1 0 30 74 1 0 33 75 1 0 34 76 1 0 34 77 1 0 34 78 1 0 M END

Standard InCHIKey	LVYOXPQJURJWPC-MVQHSHHOSA-N
Standard InCHI	InChI=1S/C30H44O4/c1-18(2)9-8-10-19(26(33)34)25-22(31)17-30(7)21-11-12-23-27(3,4)24(32)14-15-28(23,5)20(21)13-16-29(25,30)6/h9,11,13,19,22-23,25,31H,8,10,12,14-17H2,1-7H3,(H,33,34)/t19-,22-,23+,25+,28-,29-,30+/m1/s1
SMILES	CC(=CCC[C@H]([C@H]1[C@H](O)C[C@@]2([C@]1(C)CC=C1C2=CC[C@@H]2[C@]1(C)CCC(=O)C2(C)C)C)C(=O)O)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	468.32	Volume:	515.189 ? Van der Waals volume.
Dense:	0.909	LogP:	4.183 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.19 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.955 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	23.0
TPSA:	74.6 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.452	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.015	Fsp³:	0.733
MCE-18:	81.231 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.895	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.098 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.007 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.38	Promiscuous compounds:	0.174

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.468	MDCK Permeability:	-5.107
Pgp-inhibitor:	0.013	Pgp-substrate:	0.001
PAMPA:	0.992 ? 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%):	0.004	30% Bioavailability (F30%):	0.001
50% Bioavailability (F50%):	0.461

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.033	MRP1:	0.995
Plasma Protein Binding (PPB):	87.723%	Volume Distribution (VD):	-0.07
Fu:	14.434% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	0.998	BCRP inhibitor:	0.007
BSEP inhibitor:	0.996

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.052
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.21
CYP3A4-inhibitor:	1.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.965
HLM stability:	0.254 ? 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):

5.828

Half-life (T1/2):

0.734

ADMET: Toxicity

hERG Blockers:	0.04	hERG Blockers (10um):	0.118
Human Hepatotoxicity (H-HT):	0.512	Drug-induced Liver Injury (DILI):	0.24
AMES Toxicity:	0.16	Rat Oral Acute Toxicity:	0.358
Maximum Recommended Daily Dose:	0.157	Skin Sensitization:	0.966
Carcinogencity:	0.547	Eye Corrosion:	0.013
Eye Irritation:	0.289	Respiratory Toxicity:	0.544
Drug-induced Neurotoxicity:	0.266	Ototoxicity:	0.605
Hematotoxicity:	0.505	Drug-induced Nephrotoxicity:	0.834
Genotoxicity:	0.703	RPMI-8226 Immunitoxicity:	0.101
A549 Cytotoxicity:	0.084	Hek293 Cytotoxicity:	0.117
BCF:	0.677 ? 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:	3.637 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.327 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.4 ? 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
NPO7904	Ganoderma applanatum	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)91122-1]
NPO7904	Ganoderma applanatum	Species	Polyporaceae	Eukaryota	n.a.	Sri Lankan	n.a.	PMID[16933889]
NPO7904	Ganoderma applanatum	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27996259]
NPO7904	Ganoderma applanatum	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7904	Ganoderma applanatum	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7904	Ganoderma applanatum	Species	Polyporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7904	Ganoderma applanatum	Species	Polyporaceae	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
Activity	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
NPT168	Cell line	P388	Mus musculus	Activity	=	237.0	uM	PMID[12105963]

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 NPC66429 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	17804
0.1-0.2	28249
0.2-0.3	3445
0.3-0.4	281
0.4-0.5	35
0.5-0.6	30
0.6-0.7	5
0.7-0.8	0
0.8-0.85	2
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8125	Intermediate Similarity	NPC152897
0.8	Intermediate Similarity	NPC155676
0.7231	Intermediate Similarity	NPC222845
0.7231	Intermediate Similarity	NPC296577
0.7077	Intermediate Similarity	NPC83569
0.6857	Remote Similarity	NPC263347
0.6429	Remote Similarity	NPC484975
0.6429	Remote Similarity	NPC48647
0.6429	Remote Similarity	NPC321301
0.6232	Remote Similarity	NPC247406
0.5833	Remote Similarity	NPC45324
0.5833	Remote Similarity	NPC162001
0.5753	Remote Similarity	NPC186810
0.5694	Remote Similarity	NPC69279
0.5676	Remote Similarity	NPC484967
0.5658	Remote Similarity	NPC288464
0.5658	Remote Similarity	NPC484969
0.5658	Remote Similarity	NPC477813
0.5658	Remote Similarity	NPC607198
0.5479	Remote Similarity	NPC87552
0.5342	Remote Similarity	NPC84271
0.5342	Remote Similarity	NPC102414
0.5333	Remote Similarity	NPC484966
0.5325	Remote Similarity	NPC478312
0.5278	Remote Similarity	NPC89077
0.5278	Remote Similarity	NPC4166
0.5278	Remote Similarity	NPC311092
0.527	Remote Similarity	NPC54689
0.5263	Remote Similarity	NPC123854
0.52	Remote Similarity	NPC243866
0.5195	Remote Similarity	NPC7165
0.5128	Remote Similarity	NPC285702
0.5128	Remote Similarity	NPC166745
0.5128	Remote Similarity	NPC235464
0.5068	Remote Similarity	NPC201912
0.5068	Remote Similarity	NPC38350
0.5068	Remote Similarity	NPC601139
0.5067	Remote Similarity	NPC48866
0.5067	Remote Similarity	NPC44181
0.5067	Remote Similarity	NPC606857

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC66429 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5774
0.1-0.2	3261
0.2-0.3	115
0.3-0.4	0
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