NPASS Compound

Natural Product: NPC42526

Natural Product ID	NPC42526
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	[(2R,12Z,15Z)-2-Hydroxy-4-Oxohenicosa-12,15-Dienyl] Acetate
IUPAC Name	[(2R,12Z,15Z)-2-hydroxy-4-oxohenicosa-12,15-dienyl] acetate
Synonyms	(+)-(R)-persin
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL465370
PubChem CID	6443027
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001334] Fatty alcohols [CHEMONTID:0002951] Long-chain fatty alcohols

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 67 66 0 0 0 0 0 0 0 0999 V2000 7.1277 -1.8476 1.0141 C 0 0 0 0 0 0 0 0 0 0 0 0 7.4201 -0.5608 0.2441 C 0 0 0 0 0 0 0 0 0 0 0 0 7.9702 -0.9356 -1.0900 C 0 0 0 0 0 0 0 0 0 0 0 0 8.2931 0.2511 -1.9312 C 0 0 0 0 0 0 0 0 0 0 0 0 7.0594 1.0529 -2.2578 C 0 0 0 0 0 0 0 0 0 0 0 0 6.0984 0.2413 -3.0203 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8829 0.0485 -2.6317 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2140 0.5676 -1.4146 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8005 -0.5912 -0.6175 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5858 -0.8894 -0.2730 C 0 0 0 0 0 0 0 0 0 0 0 0 1.4494 -0.0714 -0.6568 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7852 0.4118 0.6482 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.4079 1.2689 0.2995 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1309 1.7946 1.4850 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6839 0.7646 2.4032 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6776 -0.1581 1.7515 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8313 0.6711 1.2331 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8559 -0.2192 0.5701 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.6890 -1.4272 0.5158 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0422 0.4660 0.0084 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.0810 0.6125 1.1063 C 0 0 2 0 0 0 0 0 0 0 0 0 -7.4636 -0.7432 1.6041 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.0863 -1.5463 0.6723 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.2761 -1.3285 0.0658 C 0 0 0 0 0 0 0 0 0 0 0 0 -9.9536 -0.3167 0.3240 O 0 0 0 0 0 0 0 0 0 0 0 0 -9.8040 -2.3067 -0.9338 C 0 0 0 0 0 0 0 0 0 0 0 0 -8.1350 1.4071 0.6919 O 0 0 0 0 0 0 0 0 0 0 0 0 8.0924 -2.3596 1.2628 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5670 -2.5060 0.3214 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5013 -1.6622 1.9095 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5449 0.0734 0.1889 H 0 0 0 0 0 0 0 0 0 0 0 0 8.1979 0.0051 0.8170 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8785 -1.5770 -0.9033 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2187 -1.6069 -1.6130 H 0 0 0 0 0 0 0 0 0 0 0 0 8.8375 -0.0202 -2.8688 H 0 0 0 0 0 0 0 0 0 0 0 0 8.9490 0.9288 -1.3283 H 0 0 0 0 0 0 0 0 0 0 0 0 7.3468 1.9303 -2.9224 H 0 0 0 0 0 0 0 0 0 0 0 0 6.6770 1.4573 -1.3263 H 0 0 0 0 0 0 0 0 0 0 0 0 6.4460 -0.2208 -3.9709 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2417 -0.5817 -3.2743 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8469 1.2541 -0.8447 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3673 1.1914 -1.7990 H 0 0 0 0 0 0 0 0 0 0 0 0 4.6155 -1.2575 -0.2933 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4043 -1.7774 0.3211 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5733 0.7340 -1.3563 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7161 -0.7800 -1.1706 H 0 0 0 0 0 0 0 0 0 0 0 0 0.5532 -0.4478 1.2734 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5678 1.0079 1.1638 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0309 0.6910 -0.3994 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0194 2.1463 -0.2748 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9285 2.4760 1.1297 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4272 2.4279 2.0672 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2462 1.3109 3.2102 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.9037 0.1906 2.9138 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2386 -0.8094 0.9816 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0977 -0.8246 2.5401 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3412 1.1405 2.0770 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.5372 1.4056 0.4714 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7714 1.5207 -0.2834 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4488 -0.0274 -0.8817 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.6317 1.1557 1.9896 H 0 0 0 0 0 0 0 0 0 0 0 0 -8.0561 -0.6611 2.5652 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5019 -1.2595 1.8940 H 0 0 0 0 0 0 0 0 0 0 0 0 -10.7908 -2.6720 -0.6378 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.9006 -1.7321 -1.8982 H 0 0 0 0 0 0 0 0 0 0 0 0 -9.0615 -3.1119 -1.0924 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.7781 2.1853 0.2305 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 2 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 2 0 18 20 1 0 20 21 1 0 21 22 1 0 22 23 1 0 23 24 1 0 24 25 2 0 24 26 1 0 21 27 1 0 1 28 1 0 1 29 1 0 1 30 1 0 2 31 1 0 2 32 1 0 3 33 1 0 3 34 1 0 4 35 1 0 4 36 1 0 5 37 1 0 5 38 1 0 6 39 1 0 7 40 1 0 8 41 1 0 8 42 1 0 9 43 1 0 10 44 1 0 11 45 1 0 11 46 1 0 12 47 1 0 12 48 1 0 13 49 1 0 13 50 1 0 14 51 1 0 14 52 1 0 15 53 1 0 15 54 1 0 16 55 1 0 16 56 1 0 17 57 1 0 17 58 1 0 20 59 1 0 20 60 1 0 21 61 1 1 22 62 1 0 22 63 1 0 26 64 1 0 26 65 1 0 26 66 1 0 27 67 1 0 M END

Standard InCHIKey	IBDVBNUJEGRVQN-RHNLGMIQSA-N
Standard InCHI	InChI=1S/C23H40O4/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-22(25)19-23(26)20-27-21(2)24/h7-8,10-11,23,26H,3-6,9,12-20H2,1-2H3/b8-7-,11-10-/t23-/m1/s1
SMILES	CCCCC/C=CC/C=CCCCCCCCC(=O)C[C@H](COC(=O)C)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	380.29	Volume:	430.979 ? Van der Waals volume.
Dense:	0.882	LogP:	5.523 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.871 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.054 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	19.0	Rigid Bonds:	4.0
TPSA:	63.6 ? Topological Polar Surface Area.	H-Bond Acceptor:	4.0
H-Bond Donor:	1.0	Rings:	0.0
Heavy Atoms:	4.0

MedChem Properties

QED Drug-Likeness Score:	0.189	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.12	Fsp³:	0.739
MCE-18:	3.0 ? 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:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.447	Fluc inhibitor:	0.028 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.004 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.001 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.954	Promiscuous compounds:	0.607

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.087	MDCK Permeability:	-4.92
Pgp-inhibitor:	0.765	Pgp-substrate:	0.009
PAMPA:	0.002 ? 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%):	0.146	30% Bioavailability (F30%):	0.733
50% Bioavailability (F50%):	0.976

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.999
Plasma Protein Binding (PPB):	97.844%	Volume Distribution (VD):	0.272
Fu:	1.952% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.74
OATP1B3 inhibitor:	0.979	BCRP inhibitor:	0.855
BSEP inhibitor:	1.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.988
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.01
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	0.215
CYP2D6-inhibitor:	0.906	CYP2D6-substrate:	0.988
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	1.0
HLM stability:	0.918 ? 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):

5.758

Half-life (T1/2):

0.336

ADMET: Toxicity

hERG Blockers:	0.194	hERG Blockers (10um):	0.465
Human Hepatotoxicity (H-HT):	0.059	Drug-induced Liver Injury (DILI):	0.0
AMES Toxicity:	0.372	Rat Oral Acute Toxicity:	0.023
Maximum Recommended Daily Dose:	0.038	Skin Sensitization:	1.0
Carcinogencity:	0.021	Eye Corrosion:	0.99
Eye Irritation:	0.993	Respiratory Toxicity:	0.181
Drug-induced Neurotoxicity:	0.013	Ototoxicity:	0.17
Hematotoxicity:	0.004	Drug-induced Nephrotoxicity:	0.417
Genotoxicity:	0.0	RPMI-8226 Immunitoxicity:	0.035
A549 Cytotoxicity:	0.37	Hek293 Cytotoxicity:	0.113
BCF:	1.626 ? 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:	4.991 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.083 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.089 ? 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
NPO40791	Avocado idioblast	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[9748393]
NPO12601.1	Pueraria candollei var. mirifica	Varieties	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22333	Operophtera brumata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17353	Iris brevicaulis	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12786	Dysoxylum beddomei	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15647	Aloe ruspoliana	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24921	Acanthophyllum lilacinum	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23106	Piper solmsianum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15647	Aloe ruspoliana	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23106	Piper solmsianum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23106	Piper solmsianum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12601.1	Pueraria candollei var. mirifica	Varieties	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15647	Aloe ruspoliana	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12601.1	Pueraria candollei var. mirifica	Varieties	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12786	Dysoxylum beddomei	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15647	Aloe ruspoliana	Species	Xanthorrhoeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22333	Operophtera brumata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24921	Acanthophyllum lilacinum	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17353	Iris brevicaulis	Species	Iridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23106	Piper solmsianum	Species	Piperaceae	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
IC50	13

Activity Type	# Activity
Cell line	13
Organism	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
NPT83	Cell line	MCF7	Homo sapiens	IC50	=	15100.0	nM	PMID[22044656]
NPT396	Cell line	T47D	Homo sapiens	IC50	=	30300.0	nM	PMID[22044656]
NPT784	Cell line	MDA-MB-468	Homo sapiens	IC50	=	25000.0	nM	PMID[22044656]
NPT2463	Cell line	MDA-MB-157	Homo sapiens	IC50	=	12800.0	nM	PMID[22044656]
NPT134	Cell line	SK-BR-3	Homo sapiens	IC50	=	19700.0	nM	PMID[22044656]
NPT402	Cell line	Hs-578T	Homo sapiens	IC50	=	32100.0	nM	PMID[22044656]
NPT82	Cell line	MDA-MB-231	Homo sapiens	IC50	>	39000.0	nM	PMID[22044656]
NPT2257	Cell line	MCF-10A	Homo sapiens	IC50	>	39000.0	nM	PMID[22044656]
NPT377	Cell line	OVCAR-3	Homo sapiens	IC50	=	27900.0	nM	PMID[22044656]
NPT458	Cell line	IGROV-1	Homo sapiens	IC50	=	15600.0	nM	PMID[22044656]
NPT306	Cell line	PC-3	Homo sapiens	IC50	=	30000.0	nM	PMID[22044656]
NPT858	Cell line	LNCaP	Homo sapiens	IC50	=	22000.0	nM	PMID[22044656]
NPT2779	Organism	Spodoptera exigua	Spodoptera exigua	Activity	=	80.0	%	PMID[9748393]

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 NPC42526 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	17025
0.1-0.2	29914
0.2-0.3	2500
0.3-0.4	369
0.4-0.5	41
0.5-0.6	8
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	Natural Product ID
0.5957	Remote Similarity	NPC480503
0.561	Remote Similarity	NPC477458
0.5435	Remote Similarity	NPC475443
0.5435	Remote Similarity	NPC473829
0.5319	Remote Similarity	NPC330426
0.5319	Remote Similarity	NPC127091
0.5319	Remote Similarity	NPC22101
0.5106	Remote Similarity	NPC321919

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC42526 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5913
0.1-0.2	3104
0.2-0.3	116
0.3-0.4	16
0.4-0.5	1
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