NPASS Compound

Natural Product: NPC562319

Natural Product ID	NPC562319
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(3~{S},10~{R},13~{S},16~{S},17~{R})-10,13-dimethyl-17-[(1~{R},4~{R})-1,4,5-trimethylhexyl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1~{H}-cyclopenta[a]phenanthrene-3,16-diol
IUPAC Name	(3~{S},10~{R},13~{S},16~{S},17~{R})-10,13-dimethyl-17-[(1~{R},4~{R})-1,4,5-trimethylhexyl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1~{H}-cyclopenta[a]phenanthrene-3,16-diol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 -8.3263 -0.9566 0.1477 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1227 -0.1225 0.5206 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.1581 1.1447 -0.3099 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8240 -0.8326 0.1709 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.7283 -2.1348 0.9023 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.7057 0.1128 0.4614 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3436 -0.4712 0.1561 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.2554 0.5692 0.4847 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.4194 0.8550 1.9503 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9671 -0.0529 0.0977 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.0006 -0.3746 -1.3844 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.6124 0.5987 -2.1322 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4831 -0.4147 -1.7763 C 0 0 0 0 0 0 0 0 0 0 0 0 0.9979 0.7348 -0.9471 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4761 0.7284 -0.8938 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0900 2.0040 -0.4085 C 0 0 0 0 0 0 0 0 0 0 0 0 4.5577 1.8586 -0.4442 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1638 0.7199 -0.2634 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6461 0.6754 -0.3179 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0068 -0.2789 -1.4452 C 0 0 1 0 0 0 0 0 0 0 0 0 8.3853 -0.4691 -1.4670 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3526 -1.6031 -1.2270 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8723 -1.5326 -1.0633 C 0 0 0 0 0 0 0 0 0 0 0 0 4.4410 -0.5294 -0.0068 C 0 0 1 0 0 0 0 0 0 0 0 0 4.8541 -1.1569 1.3279 C 0 0 0 0 0 0 0 0 0 0 0 0 2.9571 -0.4006 -0.0140 C 0 0 0 0 0 0 0 0 0 0 0 0 2.4592 -0.1277 1.3621 C 0 0 0 0 0 0 0 0 0 0 0 0 1.0034 0.0995 1.4973 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2805 0.7381 0.3584 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0187 2.1822 0.7182 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.2956 -1.1052 -0.9429 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.2217 -0.3524 0.4020 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.3927 -1.8892 0.7212 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1076 0.1669 1.5868 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6066 0.9760 -1.2562 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.1983 1.4409 -0.5485 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7016 1.9893 0.2411 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.8871 -1.0617 -0.9127 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7750 -2.6280 0.7115 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5228 -2.8067 0.4707 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9847 -2.0476 1.9811 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8313 1.0049 -0.1880 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6988 0.4821 1.4993 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3365 -0.7516 -0.8952 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1514 -1.3893 0.7500 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5416 1.4478 -0.1613 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9744 0.0450 2.4895 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0821 1.7635 2.0569 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5038 1.0169 2.5113 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9310 -1.0572 0.6097 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3642 -1.4037 -1.5844 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7097 0.2779 -3.0461 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9081 -1.3855 -1.5412 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5681 -0.2347 -2.8593 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6993 1.6596 -1.5303 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8605 0.5413 -1.9176 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8082 2.3066 0.6010 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7620 2.8116 -1.1112 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1229 2.7936 -0.6376 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9902 0.2700 0.6745 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0731 1.6832 -0.5028 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6371 0.1995 -2.3798 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8125 0.2958 -1.0078 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5400 -2.2115 -2.1605 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8766 -2.1602 -0.4229 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4153 -1.3341 -2.0449 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5120 -2.5299 -0.7278 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6947 -0.4752 2.1780 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3419 -2.1237 1.4173 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9517 -1.3910 1.2232 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5432 -1.3792 -0.3328 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7433 -1.0176 2.0001 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0358 0.7146 1.8478 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5218 -0.8816 1.7930 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8652 0.7205 2.4345 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0184 2.4884 0.6897 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5610 2.8981 0.0301 H 0 0 0 0 0 0 0 0 0 0 0 0 0.4102 2.4371 1.7368 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 2 4 1 0 4 5 1 0 4 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 11 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 0 20 21 1 0 20 22 1 0 22 23 1 0 23 24 1 0 24 25 1 1 24 26 1 0 26 27 1 0 27 28 1 0 28 29 1 0 29 30 1 1 29 10 1 0 29 14 1 0 26 15 1 0 24 18 1 0 1 31 1 0 1 32 1 0 1 33 1 0 2 34 1 0 3 35 1 0 3 36 1 0 3 37 1 0 4 38 1 6 5 39 1 0 5 40 1 0 5 41 1 0 6 42 1 0 6 43 1 0 7 44 1 0 7 45 1 0 8 46 1 6 9 47 1 0 9 48 1 0 9 49 1 0 10 50 1 1 11 51 1 1 12 52 1 0 13 53 1 0 13 54 1 0 14 55 1 0 15 56 1 0 16 57 1 0 16 58 1 0 17 59 1 0 19 60 1 0 19 61 1 0 20 62 1 6 21 63 1 0 22 64 1 0 22 65 1 0 23 66 1 0 23 67 1 0 25 68 1 0 25 69 1 0 25 70 1 0 26 71 1 0 27 72 1 0 27 73 1 0 28 74 1 0 28 75 1 0 30 76 1 0 30 77 1 0 30 78 1 0 M END

Standard InCHIKey	IGLXIHMNQDKKLE-AGNULFBCSA-N
Standard InCHI	InChI=1S/C28H48O2/c1-17(2)18(3)7-8-19(4)26-25(30)16-24-22-10-9-20-15-21(29)11-13-27(20,5)23(22)12-14-28(24,26)6/h9,17-19,21-26,29-30H,7-8,10-16H2,1-6H3/t18-,19-,21+,22?,23?,24?,25+,26+,27+,28+/m1/s1
SMILES	CC(C)[C@H](C)CC[C@@H](C)[C@H]1[C@@H](O)CC2C3CC=C4C[C@@H](O)CC[C@]4(C)C3CC[C@@]21C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	416.37	Volume:	473.562 ? Van der Waals volume.
Dense:	0.879	LogP:	5.411 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.359 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.246 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	5.0	Rigid Bonds:	20.0
TPSA:	40.46 ? Topological Polar Surface Area.	H-Bond Acceptor:	2.0
H-Bond Donor:	2.0	Rings:	4.0
Heavy Atoms:	2.0

MedChem Properties

QED Drug-Likeness Score:	0.495	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.647	Fsp³:	0.929
MCE-18:	71.556 ? 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:	0.91	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.013 ? 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:	0.397	Promiscuous compounds:	0.004

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.194	MDCK Permeability:	-5.08
Pgp-inhibitor:	0.041	Pgp-substrate:	0.809
PAMPA:	0.42 ? 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%):	0.155	30% Bioavailability (F30%):	0.543
50% Bioavailability (F50%):	0.995

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.008	MRP1:	0.806
Plasma Protein Binding (PPB):	62.75%	Volume Distribution (VD):	0.026
Fu:	39.737% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.991
OATP1B3 inhibitor:	0.911	BCRP inhibitor:	0.179
BSEP inhibitor:	0.277

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.003
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.014
CYP2D6-inhibitor:	0.035	CYP2D6-substrate:	0.01
CYP3A4-inhibitor:	0.003	CYP3A4-substrate:	0.015
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.354
HLM stability:	0.767 ? 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):

17.38

Half-life (T1/2):

1.379

ADMET: Toxicity

hERG Blockers:	0.17	hERG Blockers (10um):	0.421
Human Hepatotoxicity (H-HT):	0.502	Drug-induced Liver Injury (DILI):	0.11
AMES Toxicity:	0.163	Rat Oral Acute Toxicity:	0.146
Maximum Recommended Daily Dose:	0.792	Skin Sensitization:	0.722
Carcinogencity:	0.741	Eye Corrosion:	0.013
Eye Irritation:	0.478	Respiratory Toxicity:	0.527
Drug-induced Neurotoxicity:	0.07	Ototoxicity:	0.726
Hematotoxicity:	0.076	Drug-induced Nephrotoxicity:	0.188
Genotoxicity:	0.003	RPMI-8226 Immunitoxicity:	0.06
A549 Cytotoxicity:	0.242	Hek293 Cytotoxicity:	0.482
BCF:	2.023 ? 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:	4.179 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.345 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.868 ? 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
NPO20146	Cladiella krempfi	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21861494]
NPO20146	Cladiella krempfi	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20146	Cladiella krempfi	Species	Alcyoniidae	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

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

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 NPC562319 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	27641
0.1-0.2	19874
0.2-0.3	2064
0.3-0.4	168
0.4-0.5	52
0.5-0.6	29
0.6-0.7	24
0.7-0.8	0
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8113	Intermediate Similarity	NPC477522
0.7451	Intermediate Similarity	NPC162742
0.7451	Intermediate Similarity	NPC304309
0.7451	Intermediate Similarity	NPC470228
0.7273	Intermediate Similarity	NPC1272
0.7273	Intermediate Similarity	NPC470614
0.717	Intermediate Similarity	NPC328313
0.6727	Remote Similarity	NPC230301
0.6667	Remote Similarity	NPC34019
0.6557	Remote Similarity	NPC176012
0.6429	Remote Similarity	NPC198968
0.6429	Remote Similarity	NPC285893
0.6364	Remote Similarity	NPC22105
0.6364	Remote Similarity	NPC107059
0.6271	Remote Similarity	NPC19607
0.625	Remote Similarity	NPC136188
0.625	Remote Similarity	NPC28657
0.625	Remote Similarity	NPC474216
0.625	Remote Similarity	NPC154330
0.614	Remote Similarity	NPC113733
0.614	Remote Similarity	NPC134847
0.6071	Remote Similarity	NPC221758
0.6071	Remote Similarity	NPC600590
0.6038	Remote Similarity	NPC96319
0.6034	Remote Similarity	NPC241290
0.6034	Remote Similarity	NPC164840
0.6034	Remote Similarity	NPC51014
0.6034	Remote Similarity	NPC484739
0.6034	Remote Similarity	NPC209944
0.6034	Remote Similarity	NPC264245
0.6034	Remote Similarity	NPC155986
0.5968	Remote Similarity	NPC475032
0.5932	Remote Similarity	NPC321381
0.5833	Remote Similarity	NPC472265
0.5833	Remote Similarity	NPC59453
0.5806	Remote Similarity	NPC47761
0.5781	Remote Similarity	NPC475033
0.5738	Remote Similarity	NPC124172
0.5738	Remote Similarity	NPC603646
0.569	Remote Similarity	NPC20688
0.5667	Remote Similarity	NPC328714
0.5645	Remote Similarity	NPC473943
0.5645	Remote Similarity	NPC155011
0.5593	Remote Similarity	NPC76879
0.5574	Remote Similarity	NPC318495
0.5574	Remote Similarity	NPC33913
0.5556	Remote Similarity	NPC488870
0.5517	Remote Similarity	NPC151519
0.5484	Remote Similarity	NPC26117
0.5397	Remote Similarity	NPC243985
0.5397	Remote Similarity	NPC280710
0.5397	Remote Similarity	NPC240650
0.5312	Remote Similarity	NPC474164
0.5303	Remote Similarity	NPC601043
0.5303	Remote Similarity	NPC605412
0.5152	Remote Similarity	NPC474970
0.5147	Remote Similarity	NPC91604
0.5085	Remote Similarity	NPC81306
0.5079	Remote Similarity	NPC474778
0.5079	Remote Similarity	NPC474733

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC562319 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8181
0.1-0.2	837
0.2-0.3	120
0.3-0.4	5
0.4-0.5	2
0.5-0.6	1
0.6-0.7	4
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
0.6727	Remote Similarity	NPD7339	Approved
0.625	Remote Similarity	NPD6942	Phase 4
0.6071	Remote Similarity	NPD4786	Phase 1
0.6038	Remote Similarity	NPD3701	Pre-clinical
0.5517	Remote Similarity	NPD3667	Phase 4

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