NPASS Compound

Natural Product: NPC81306

Natural Product ID	NPC81306
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(24S)-Ergost-5-Ene-3Beta,7Alpha-Diol
IUPAC Name	(3S,7S,8S,9S,10R,13R,14S,17R)-17-[(2R,5S)-5,6-dimethylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-3,7-diol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1784245
PubChem CID	12069911
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000258] Steroids and steroid derivatives [CHEMONTID:0003567] Ergostane steroids [CHEMONTID:0001403] Ergosterols and derivatives

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 6.7586 0.6880 2.7426 O 0 0 0 0 0 0 0 0 0 0 0 0 6.4736 -0.1499 1.6582 C 0 0 1 0 0 0 0 0 0 0 0 0 5.3692 -1.1232 1.9835 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0218 -0.4849 2.1110 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6741 0.3765 0.9032 C 0 0 1 0 0 0 0 0 0 0 0 0 4.7989 0.2424 -0.0513 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6505 -0.1976 -1.2847 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3587 -0.6145 -1.8826 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2586 0.0759 -1.1584 C 0 0 2 0 0 0 0 0 0 0 0 0 2.3651 -0.0717 0.3469 C 0 0 2 0 0 0 0 0 0 0 0 0 1.1872 0.6187 0.9889 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1335 0.2276 0.4430 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.2578 0.2747 -1.0551 C 0 0 1 0 0 0 0 0 0 0 0 0 0.9623 -0.5533 -1.5234 C 0 0 1 0 0 0 0 0 0 0 0 0 0.7136 -0.7955 -2.9542 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7554 -1.1675 -2.9237 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3163 -0.5576 -1.6296 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.6554 -0.0486 -1.9159 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4343 0.4830 -0.7466 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6546 -0.5951 0.3154 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4220 -0.0844 1.4851 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.7866 0.4339 1.1764 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.7015 -0.5831 0.5661 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.4169 0.8906 2.4853 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.5925 -1.2633 2.4474 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8254 0.8588 -3.0930 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1477 1.6870 -1.5004 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2909 -1.9923 -1.8549 O 0 0 0 0 0 0 0 0 0 0 0 0 6.1635 0.6180 0.3991 C 0 0 0 0 0 0 0 0 0 0 0 0 3.6640 1.8083 1.3842 C 0 0 0 0 0 0 0 0 0 0 0 0 7.2539 0.1555 3.4260 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4020 -0.7834 1.5373 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3784 -1.9734 1.2936 H 0 0 0 0 0 0 0 0 0 0 0 0 5.6194 -1.5401 3.0018 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2784 -1.3026 2.2201 H 0 0 0 0 0 0 0 0 0 0 0 0 3.9691 0.0944 3.0620 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5401 -0.2680 -1.9354 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3086 -0.3098 -2.9527 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3069 1.1642 -1.4400 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2456 -1.1562 0.5560 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2821 1.7092 1.0378 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1991 0.2785 2.0686 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3243 -0.8369 0.7404 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9057 0.8206 0.9640 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8628 -1.5078 -0.9683 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9189 0.0550 -3.6215 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3018 -1.6875 -3.3069 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8455 -2.2659 -2.9457 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3021 -0.7914 -3.8065 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4467 -1.4529 -0.9450 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2462 -0.9824 -2.2138 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4596 0.7790 -1.0768 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0092 1.3363 -0.2323 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7146 -1.0434 0.6754 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.2096 -1.4209 -0.1891 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8431 0.6935 2.0140 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7806 1.3215 0.5118 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2405 -1.2559 -0.1545 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.5124 -0.0330 0.0117 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1982 -1.1748 1.3766 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9431 1.8767 2.3610 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6703 1.0424 3.2808 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1988 0.1783 2.8222 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2596 -1.9785 1.9298 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5862 -1.7350 2.5719 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9283 -0.9531 3.4381 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2281 0.3649 -4.0016 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9202 1.4363 -3.3728 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5927 1.6576 -2.8542 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6309 2.1696 -0.8337 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0698 2.2152 -1.2823 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2710 1.8258 -2.5165 H 0 0 0 0 0 0 0 0 0 0 0 0 2.7820 -2.3667 -1.1107 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3009 1.7090 0.5175 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9390 0.3210 -0.3673 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3395 2.5023 0.5817 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6821 2.1347 1.6759 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0119 1.9769 2.2528 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 2 0 7 8 1 0 8 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 1 0 18 19 1 0 19 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 22 24 1 0 21 25 1 0 18 26 1 0 13 27 1 6 8 28 1 0 6 29 1 0 5 30 1 1 29 2 1 0 10 5 1 0 17 13 1 0 14 9 1 0 1 31 1 0 2 32 1 6 3 33 1 0 3 34 1 0 4 35 1 0 4 36 1 0 7 37 1 0 8 38 1 6 9 39 1 1 10 40 1 6 11 41 1 0 11 42 1 0 12 43 1 0 12 44 1 0 14 45 1 1 15 46 1 0 15 47 1 0 16 48 1 0 16 49 1 0 17 50 1 1 18 51 1 6 19 52 1 0 19 53 1 0 20 54 1 0 20 55 1 0 21 56 1 1 22 57 1 0 23 58 1 0 23 59 1 0 23 60 1 0 24 61 1 0 24 62 1 0 24 63 1 0 25 64 1 0 25 65 1 0 25 66 1 0 26 67 1 0 26 68 1 0 26 69 1 0 27 70 1 0 27 71 1 0 27 72 1 0 28 73 1 0 29 74 1 0 29 75 1 0 30 76 1 0 30 77 1 0 30 78 1 0 M END

Standard InCHIKey	QZTNWQQTEVRSMC-JECVZSANSA-N
Standard InCHI	InChI=1S/C28H48O2/c1-17(2)18(3)7-8-19(4)22-9-10-23-26-24(12-14-28(22,23)6)27(5)13-11-21(29)15-20(27)16-25(26)30/h16-19,21-26,29-30H,7-15H2,1-6H3/t18-,19+,21-,22+,23-,24-,25+,26-,27-,28+/m0/s1
SMILES	O[C@H]1CC[C@]2(C(=C[C@H]([C@@H]3[C@@H]2CC[C@]2([C@H]3CC[C@@H]2[C@@H](CC[C@@H](C(C)C)C)C)C)O)C1)C

Calculated Properties

Physi-Chem Properties

Molecular Weight:	416.37	Volume:	473.562 ? Van der Waals volume.
Dense:	0.879	LogP:	5.768 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	4.588 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-5.547 ? 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:	4.585	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:	0.939	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:	0.367	Promiscuous compounds:	0.095

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.441	MDCK Permeability:	-5.059
Pgp-inhibitor:	0.008	Pgp-substrate:	0.272
PAMPA:	0.05 ? 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%):	0.017	30% Bioavailability (F30%):	0.498
50% Bioavailability (F50%):	0.989

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.043	MRP1:	0.041
Plasma Protein Binding (PPB):	84.176%	Volume Distribution (VD):	-0.129
Fu:	14.885% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.577
BSEP inhibitor:	0.017

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.003	CYP2C19-substrate:	0.137
CYP2C9-inhibitor:	0.0	CYP2C9-substrate:	0.026
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.319
CYP3A4-inhibitor:	0.995	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.993
HLM stability:	0.832 ? 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):

14.642

Half-life (T1/2):

1.13

ADMET: Toxicity

hERG Blockers:	0.119	hERG Blockers (10um):	0.364
Human Hepatotoxicity (H-HT):	0.66	Drug-induced Liver Injury (DILI):	0.297
AMES Toxicity:	0.382	Rat Oral Acute Toxicity:	0.14
Maximum Recommended Daily Dose:	0.404	Skin Sensitization:	0.991
Carcinogencity:	0.885	Eye Corrosion:	0.435
Eye Irritation:	0.983	Respiratory Toxicity:	0.74
Drug-induced Neurotoxicity:	0.058	Ototoxicity:	0.551
Hematotoxicity:	0.588	Drug-induced Nephrotoxicity:	0.69
Genotoxicity:	0.01	RPMI-8226 Immunitoxicity:	0.1
A549 Cytotoxicity:	0.741	Hek293 Cytotoxicity:	0.442
BCF:	2.792 ? 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:	4.459 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.19 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.107 ? 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
NPO9888	Lobophytum laevigatum	Species	Alcyoniidae	Eukaryota	n.a.	Vietnamese	n.a.	PMID[21458279]
NPO9888	Lobophytum laevigatum	Species	Alcyoniidae	Eukaryota	n.a.	Vietnamese soft coral	n.a.	PMID[21507644]
NPO9888	Lobophytum laevigatum	Species	Alcyoniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9888	Lobophytum laevigatum	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

Activity Type	# Activity
FC	2

Activity Type	# Activity
Others	2

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
NPT2	Others	Unspecified	n.a.	FC	=	1.2	n.a.	PMID[22194678]
NPT2	Others	Unspecified	n.a.	FC	=	2.5	n.a.	PMID[22194678]

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 NPC81306 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	25899
0.1-0.2	21638
0.2-0.3	2066
0.3-0.4	154
0.4-0.5	50
0.5-0.6	31
0.6-0.7	6
0.7-0.8	0
0.8-0.85	6
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8936	High Similarity	NPC28862
0.8333	Intermediate Similarity	NPC109546
0.8333	Intermediate Similarity	NPC47982
0.8163	Intermediate Similarity	NPC84694
0.8163	Intermediate Similarity	NPC143182
0.8163	Intermediate Similarity	NPC609126
0.8	Intermediate Similarity	NPC317927
0.7959	Intermediate Similarity	NPC189972
0.7692	Intermediate Similarity	NPC474634
0.7407	Intermediate Similarity	NPC475789
0.7308	Intermediate Similarity	NPC234193
0.6607	Remote Similarity	NPC152808
0.6538	Remote Similarity	NPC162742
0.6538	Remote Similarity	NPC304309
0.6538	Remote Similarity	NPC470228
0.6364	Remote Similarity	NPC23852
0.625	Remote Similarity	NPC209620
0.5932	Remote Similarity	NPC293287
0.5893	Remote Similarity	NPC230301
0.5818	Remote Similarity	NPC34019
0.5763	Remote Similarity	NPC474752
0.5763	Remote Similarity	NPC474683
0.5714	Remote Similarity	NPC218186
0.569	Remote Similarity	NPC145879
0.5614	Remote Similarity	NPC198968
0.5614	Remote Similarity	NPC285893
0.5593	Remote Similarity	NPC50964
0.5536	Remote Similarity	NPC22105
0.5536	Remote Similarity	NPC107059
0.5439	Remote Similarity	NPC136188
0.5439	Remote Similarity	NPC28657
0.5439	Remote Similarity	NPC474216
0.5424	Remote Similarity	NPC31564
0.5424	Remote Similarity	NPC601967
0.5362	Remote Similarity	NPC470434
0.5345	Remote Similarity	NPC134847
0.5333	Remote Similarity	NPC474778
0.5333	Remote Similarity	NPC474733
0.5254	Remote Similarity	NPC241290
0.5254	Remote Similarity	NPC164840
0.5254	Remote Similarity	NPC484739
0.5254	Remote Similarity	NPC209944
0.5254	Remote Similarity	NPC155986
0.5246	Remote Similarity	NPC474759
0.5167	Remote Similarity	NPC321381
0.5167	Remote Similarity	NPC26959
0.5161	Remote Similarity	NPC601883
0.5082	Remote Similarity	NPC59453

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC81306 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	7870
0.1-0.2	1165
0.2-0.3	84
0.3-0.4	26
0.4-0.5	2
0.5-0.6	3
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
0.5893	Remote Similarity	NPD7339	Approved
0.5714	Remote Similarity	NPD4751	Phase 2
0.5439	Remote Similarity	NPD6942	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