NPASS Compound

Natural Product: NPC476922

Natural Product ID	NPC476922
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	sodium;[(E)-[(1R,4aR,4bS,8aS,10aS)-4b,8,8,10a-tetramethyl-1-[2-[5-oxo-1-(2-sulfoethyl)-2H-pyrrol-3-yl]ethyl]-1,3,4,4a,5,6,7,8a,9,10-decahydrophenanthren-2-ylidene]methyl] sulfate
IUPAC Name	sodium;[(E)-[(1R,4aR,4bS,8aS,10aS)-4b,8,8,10a-tetramethyl-1-[2-[5-oxo-1-(2-sulfoethyl)-2H-pyrrol-3-yl]ethyl]-1,3,4,4a,5,6,7,8a,9,10-decahydrophenanthren-2-ylidene]methyl] sulfate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	90683097
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0000259] Prenol lipids [CHEMONTID:0001552] Sesterterpenoids [CHEMONTID:0002881] Cheilanthane sesterterpenoids

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 81 83 0 0 0 0 0 0 0 0999 V2000 -4.3707 -1.4190 0.0107 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6120 -0.2174 0.5644 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.4405 0.2598 1.7676 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.8549 0.3897 1.3334 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0836 1.3033 0.1759 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.9700 1.4254 -0.8003 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.6395 0.9485 -0.3789 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.7447 0.5416 -1.5225 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3337 0.6452 -1.0109 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0908 0.0609 0.3413 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.2578 -0.6657 0.9426 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.0262 -2.1548 0.8517 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8829 -2.4785 1.8298 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2842 -1.7554 1.3379 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4510 -1.9573 1.8755 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6266 -2.8741 2.9439 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9969 -4.4863 2.4890 S 0 0 0 0 0 0 0 0 0 0 0 0 1.2306 -5.4740 3.3139 O 0 0 0 0 0 0 0 0 0 0 0 0 1.6216 -4.7348 1.0446 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6402 -4.7342 2.6269 O 0 0 0 0 0 1 0 0 0 0 0 0 0.1350 -0.8076 0.2306 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3599 -0.2238 -0.3200 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0178 0.9412 0.3094 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2944 1.2942 -0.4709 C 0 0 0 0 0 0 0 0 0 0 0 0 3.5725 2.4280 -1.0763 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8828 2.3619 -1.7006 C 0 0 0 0 0 0 0 0 0 0 0 0 5.4545 3.2627 -2.3560 O 0 0 0 0 0 0 0 0 0 0 0 0 5.3957 1.0765 -1.4262 N 0 0 0 0 0 0 0 0 0 0 0 0 4.4258 0.3645 -0.6508 C 0 0 0 0 0 0 0 0 0 0 0 0 6.6974 0.5406 -1.8524 C 0 0 0 0 0 0 0 0 0 0 0 0 7.7570 0.8385 -0.8139 C 0 0 0 0 0 0 0 0 0 0 0 0 9.3156 0.1765 -1.3601 S 0 0 0 0 0 0 0 0 0 0 0 0 9.7274 0.7798 -2.6780 O 0 0 0 0 0 0 0 0 0 0 0 0 10.3857 0.4693 -0.3568 O 0 0 0 0 0 0 0 0 0 0 0 0 9.2239 -1.4857 -1.5763 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7849 1.2160 1.2806 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.3762 0.8280 -2.1574 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8214 2.9382 -1.0835 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 Na 0 0 0 0 0 15 0 0 0 0 0 0 -3.7573 -2.0300 -0.6638 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2734 -1.1152 -0.5581 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7728 -2.0251 0.8755 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3838 -0.4567 2.5937 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0872 1.2790 2.0809 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4361 0.7436 2.2361 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.2561 -0.6504 1.1672 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4159 2.2955 0.6060 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9866 0.9333 -0.3652 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1171 1.7844 0.1608 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8401 1.1874 -2.3976 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8845 -0.5539 -1.7673 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0670 1.7424 -1.0630 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7067 0.1876 -1.8273 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.1939 -0.4755 2.0692 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8899 -2.7179 1.3366 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.8409 -2.5243 -0.1551 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7836 -3.5810 1.7941 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2122 -2.1965 2.8360 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3841 -1.4766 1.5893 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2070 -1.5354 -0.6394 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1700 -1.0367 -0.3571 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2166 -0.0507 -1.4438 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4343 1.8820 0.2351 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3648 0.8511 1.3310 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8895 3.2973 -1.0949 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1398 -0.5301 -1.2554 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8553 0.0524 0.3311 H 0 0 0 0 0 0 0 0 0 0 0 0 7.0115 0.9592 -2.8282 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6054 -0.5391 -1.9510 H 0 0 0 0 0 0 0 0 0 0 0 0 7.5207 0.3346 0.1456 H 0 0 0 0 0 0 0 0 0 0 0 0 7.8543 1.9089 -0.5952 H 0 0 0 0 0 0 0 0 0 0 0 0 9.6825 -1.9972 -0.8773 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6033 1.3190 2.0547 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7604 2.1875 0.7927 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0846 0.9262 1.8895 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4061 0.3694 -2.0640 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.6450 0.0953 -2.5310 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.4869 1.5903 -2.9479 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0503 3.3827 -0.4250 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7966 3.4548 -0.8925 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5589 3.1064 -2.1447 H 0 0 0 0 0 0 0 0 0 0 0 0 2 1 1 6 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 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 1 0 17 18 2 0 17 19 2 0 17 20 1 0 14 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 25 26 1 0 26 27 2 0 26 28 1 0 28 29 1 0 28 30 1 0 30 31 1 0 31 32 1 0 32 33 2 0 32 34 2 0 32 35 1 0 10 36 1 1 6 37 1 0 6 38 1 0 7 2 1 0 11 2 1 0 21 10 1 0 29 24 1 0 1 40 1 0 1 41 1 0 1 42 1 0 3 43 1 0 3 44 1 0 4 45 1 0 4 46 1 0 5 47 1 0 5 48 1 0 7 49 1 1 8 50 1 0 8 51 1 0 9 52 1 0 9 53 1 0 11 54 1 1 12 55 1 0 12 56 1 0 13 57 1 0 13 58 1 0 15 59 1 0 21 60 1 6 22 61 1 0 22 62 1 0 23 63 1 0 23 64 1 0 25 65 1 0 29 66 1 0 29 67 1 0 30 68 1 0 30 69 1 0 31 70 1 0 31 71 1 0 35 72 1 0 36 73 1 0 36 74 1 0 36 75 1 0 37 76 1 0 37 77 1 0 37 78 1 0 38 79 1 0 38 80 1 0 38 81 1 0 M CHG 2 20 -1 39 1 M END

Standard InCHIKey	OKLAXQYKCQBVKC-MNMNNRCESA-M
Standard InCHI	InChI=1S/C27H43NO8S2.Na/c1-25(2)11-5-12-27(4)22(25)10-13-26(3)21(20(7-9-23(26)27)18-36-38(33,34)35)8-6-19-16-24(29)28(17-19)14-15-37(30,31)32;/h16,18,21-23H,5-15,17H2,1-4H3,(H,30,31,32)(H,33,34,35);/q;+1/p-1/b20-18+;/t21-,22-,23-,26+,27-;/m0./s1
SMILES	C[C@]12CCCC([C@@H]1CC[C@]3([C@@H]2CC/C(=C\OS(=O)(=O)[O-])/[C@@H]3CCC4=CC(=O)N(C4)CCS(=O)(=O)O)C)(C)C.[Na+]

Calculated Properties

Physi-Chem Properties

Molecular Weight:	572.24	Volume:	550.431 ? Van der Waals volume.
Dense:	1.04	LogP:	3.313 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.095 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.939 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	8.0	Rigid Bonds:	27.0
TPSA:	141.11 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	1.0	Rings:	4.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.256	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	5.093	Fsp³:	0.815
MCE-18:	87.429 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.278	Fluc inhibitor:	0.009 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.009 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.295 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.014	Promiscuous compounds:	0.068

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.316	MDCK Permeability:	-4.904
Pgp-inhibitor:	0.013	Pgp-substrate:	0.0
PAMPA:	0.958 ? 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):	0.574
20% Bioavailability (F20%):	0.066	30% Bioavailability (F30%):	0.455
50% Bioavailability (F50%):	0.109

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.231
Plasma Protein Binding (PPB):	97.71%	Volume Distribution (VD):	-0.319
Fu:	2.009% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.0
BSEP inhibitor:	0.999

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.813	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.039	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.004	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.604	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.039 ? 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):

2.725

Half-life (T1/2):

0.974

ADMET: Toxicity

hERG Blockers:	0.029	hERG Blockers (10um):	0.041
Human Hepatotoxicity (H-HT):	0.902	Drug-induced Liver Injury (DILI):	0.911
AMES Toxicity:	0.198	Rat Oral Acute Toxicity:	0.182
Maximum Recommended Daily Dose:	0.835	Skin Sensitization:	0.991
Carcinogencity:	0.601	Eye Corrosion:	0.003
Eye Irritation:	0.233	Respiratory Toxicity:	0.834
Drug-induced Neurotoxicity:	0.054	Ototoxicity:	0.677
Hematotoxicity:	0.924	Drug-induced Nephrotoxicity:	0.966
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.011
A549 Cytotoxicity:	0.003	Hek293 Cytotoxicity:	0.125
BCF:	0.633 ? 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:	4.05 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.033 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	4.931 ? 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
NPO33616	Coscinoderma sp.	Species	Spongiidae	Eukaryota	n.a.	at a depth of 15 m off the coast of Weno Island, Chuuk state, Micronesia	2010-FEB	PMID[24828374]
NPO33616	Coscinoderma sp.	Species	Spongiidae	Eukaryota	n.a.	at a depth of 15 m off the coast of Weno Island, Chuuk state, Federated States of Micronesia	2010-FEB	PMID[24828374]
NPO33616	Coscinoderma sp.	Species	Spongiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]

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
MIC	8
IC50	1

Activity Type	# Activity
Organism	5
Others	4

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
NPT1190	Organism	Salmonella enterica	Salmonella enterica	MIC	>	100	ug/ml	PMID[24828374]
NPT16	Organism	Staphylococcus aureus	Staphylococcus aureus	MIC	>	100	ug/ml	PMID[24828374]
NPT3145	Organism	Bacillus subtilis subsp. spizizenii ATCC 6633	Bacillus subtilis subsp. spizizenii ATCC 6633	MIC	>	100	ug/ml	PMID[24828374]
NPT19	Organism	Escherichia coli	Escherichia coli	MIC	>	100	ug/ml	PMID[24828374]
NPT2	Others	Unspecified	n.a.	MIC	=	50	ug/ml	PMID[24828374]
NPT2	Others	Unspecified	n.a.	MIC	=	60	ug/ml	PMID[24828374]
NPT2	Others	Unspecified	n.a.	IC50	>	100000	nM	PMID[24828374]
NPT3147	Organism	Kocuria rhizophila	Kocuria rhizophila	MIC	>	100	ug/ml	PMID[24828374]
NPT2	Others	Unspecified	n.a.	MIC	>	100	ug/ml	PMID[24828374]

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 NPC476922 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	24633
0.1-0.2	23588
0.2-0.3	1559
0.3-0.4	65
0.4-0.5	2
0.5-0.6	6
0.6-0.7	3
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	Natural Product ID
0.7397	Intermediate Similarity	NPC476920
0.7397	Intermediate Similarity	NPC476921
0.6154	Remote Similarity	NPC476926
0.6111	Remote Similarity	NPC318515
0.6026	Remote Similarity	NPC476918
0.5921	Remote Similarity	NPC319692
0.5921	Remote Similarity	NPC325960
0.5897	Remote Similarity	NPC476919
0.5867	Remote Similarity	NPC324243
0.5789	Remote Similarity	NPC324078
0.506	Remote Similarity	NPC319030

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC476922 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6688
0.1-0.2	2415
0.2-0.3	46
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