NPASS Compound

Natural Product: NPC20525

Natural Product ID	NPC20525
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	PMTMAFAPLCGXGK-WGTGFREXSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	14037060
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0000513] Eicosanoids [CHEMONTID:0000514] Prostaglandins and related 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 49 49 0 0 0 0 0 0 0 0999 V2000 -6.6068 -1.3223 0.0108 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1399 -1.6559 0.2460 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.2920 -0.9067 -0.7032 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3540 -0.0343 -0.3898 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0453 0.2956 0.9982 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6183 -0.0165 1.3981 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6562 0.7763 0.5260 C 0 0 2 0 0 0 0 0 0 0 0 0 0.7672 0.4455 0.8608 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7956 1.1728 0.0674 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6529 0.8884 -1.4029 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7924 -0.5642 -1.6634 C 0 0 0 0 0 0 0 0 0 0 0 0 3.1220 -1.0729 -1.1987 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2259 -0.3571 -1.9266 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5363 -0.9640 -1.3939 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5497 -0.7057 0.0679 C 0 0 0 0 0 0 0 0 0 0 0 0 5.8134 0.4696 0.4392 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2901 -1.6826 1.0169 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.9144 2.1549 0.9957 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3397 2.1201 2.2423 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.3989 0.7147 2.7000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2938 0.2792 3.8503 O 0 0 0 0 0 0 0 0 0 0 0 0 -7.2577 -2.2150 0.1117 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.9819 -0.5734 0.7441 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.7527 -0.8763 -0.9956 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0523 -2.7442 -0.0796 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.8370 -1.6474 1.2833 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.4656 -1.1005 -1.7723 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.8055 0.4447 -1.1965 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7483 -0.0943 1.7514 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.1450 1.4268 1.1153 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3863 -1.0723 1.4644 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8907 0.6412 -0.5485 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9307 0.7631 1.9394 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9521 -0.6439 0.8733 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7140 2.2824 0.1629 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8402 0.9613 0.4355 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4253 1.5282 -1.9282 H 0 0 0 0 0 0 0 0 0 0 0 0 0.6279 1.2791 -1.6784 H 0 0 0 0 0 0 0 0 0 0 0 0 0.9999 -1.0899 -1.0889 H 0 0 0 0 0 0 0 0 0 0 0 0 1.6577 -0.7225 -2.7647 H 0 0 0 0 0 0 0 0 0 0 0 0 3.2641 -0.9361 -0.0962 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1995 -2.1879 -1.3898 H 0 0 0 0 0 0 0 0 0 0 0 0 4.1081 -0.5633 -3.0007 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2184 0.7305 -1.7468 H 0 0 0 0 0 0 0 0 0 0 0 0 5.4622 -2.0412 -1.5718 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3867 -0.4947 -1.9106 H 0 0 0 0 0 0 0 0 0 0 0 0 5.0141 -1.3465 1.9414 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7585 3.0287 0.3611 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6056 2.9933 2.8439 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 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 1 0 15 16 2 0 15 17 1 0 7 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 20 6 1 0 1 22 1 0 1 23 1 0 1 24 1 0 2 25 1 0 2 26 1 0 3 27 1 0 4 28 1 0 5 29 1 0 5 30 1 0 6 31 1 1 7 32 1 6 8 33 1 0 8 34 1 0 9 35 1 0 9 36 1 0 10 37 1 0 10 38 1 0 11 39 1 0 11 40 1 0 12 41 1 0 12 42 1 0 13 43 1 0 13 44 1 0 14 45 1 0 14 46 1 0 17 47 1 0 18 48 1 0 19 49 1 0 M END

Standard InCHIKey	PMTMAFAPLCGXGK-WGTGFREXSA-N
Standard InCHI	InChI=1S/C18H28O3/c1-2-3-7-11-16-15(13-14-17(16)19)10-8-5-4-6-9-12-18(20)21/h3,7,13-16H,2,4-6,8-12H2,1H3,(H,20,21)/b7-3-/t15-,16+/m1/s1
SMILES	CC/C=CC[C@H]1[C@H](CCCCCCCC(=O)O)C=CC1=O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	292.2	Volume:	327.153 ? Van der Waals volume.
Dense:	0.893	LogP:	4.124 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	2.891 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.448 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	11.0	Rigid Bonds:	8.0
TPSA:	54.37 ? Topological Polar Surface Area.	H-Bond Acceptor:	3.0
H-Bond Donor:	1.0	Rings:	1.0
Heavy Atoms:	3.0

MedChem Properties

QED Drug-Likeness Score:	0.449	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.434	Fsp³:	0.667
MCE-18:	14.933 ? 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:	0.177	Fluc inhibitor:	0.126 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.011 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.046 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.974	Promiscuous compounds:	0.405

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.133	MDCK Permeability:	-4.966
Pgp-inhibitor:	0.004	Pgp-substrate:	0.003
PAMPA:	0.512 ? 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):	0.048
20% Bioavailability (F20%):	0.128	30% Bioavailability (F30%):	0.473
50% Bioavailability (F50%):	0.17

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.078	MRP1:	0.951
Plasma Protein Binding (PPB):	97.096%	Volume Distribution (VD):	-0.573
Fu:	2.587% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.016
OATP1B3 inhibitor:	0.79	BCRP inhibitor:	0.049
BSEP inhibitor:	0.955

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.03	CYP2C19-substrate:	0.074
CYP2C9-inhibitor:	0.999	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.007	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.612
CYP2B6-substrate:	0.729	CYP2C8-inhibitor:	0.616
HLM stability:	0.004 ? 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):

4.04

Half-life (T1/2):

0.646

ADMET: Toxicity

hERG Blockers:	0.052	hERG Blockers (10um):	0.176
Human Hepatotoxicity (H-HT):	0.594	Drug-induced Liver Injury (DILI):	0.151
AMES Toxicity:	0.266	Rat Oral Acute Toxicity:	0.134
Maximum Recommended Daily Dose:	0.151	Skin Sensitization:	0.969
Carcinogencity:	0.314	Eye Corrosion:	0.927
Eye Irritation:	0.988	Respiratory Toxicity:	0.872
Drug-induced Neurotoxicity:	0.155	Ototoxicity:	0.441
Hematotoxicity:	0.203	Drug-induced Nephrotoxicity:	0.464
Genotoxicity:	0.007	RPMI-8226 Immunitoxicity:	0.045
A549 Cytotoxicity:	0.013	Hek293 Cytotoxicity:	0.03
BCF:	1.234 ? 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:	3.958 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	5.284 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.604 ? 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
NPO20112	Syncephalastrum racemosum	Species	Syncephalastraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18558746]
NPO13906	Ficus mucuso	Species	Moraceae	Eukaryota	figs	Tongolo-Yaound, in the Central Region of Cameroon	2008-JUN	PMID[21619045]
NPO13906	Ficus mucuso	Species	Moraceae	Eukaryota	n.a.	fruit	n.a.	PMID[21619045]
NPO17503	Conospermum incurvum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	PMID[7853001]
NPO13906	Ficus mucuso	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20469	Acer caesium	Species	Aceraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19608	Aconitum likiangense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21612	Anthelia glauca	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21419	Biscogniauxia mediterranea	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19749	Carpolobia glabrescens	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3030	Chaenorhinum villosum	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17503	Conospermum incurvum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16895	Croton sarcopetalus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21000	Elysia halimedae	Species	Placobranchidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20662	Epinephelus drummondhayi	Species	Serranidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18782.1	Pulsatilla cernua var. koreana	Varieties	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21134	Thaumetopoea pityocampa	Species	Notodontidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1550	Talaromyces purpureogenus	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20112	Syncephalastrum racemosum	Species	Syncephalastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13003	Sogatella furcifera	Species	Delphacidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20044	Schistostephium crataegifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21224	Rubus pinfaensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7765	Quercus spicata	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20925	Fusarium culmorum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19874	Polygonatum glaberrimum	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18806	Neodilsea yendoana	Species	Dumontiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21540	Naucleopsis stipularis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21673	Lupinus caudatus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17763	Lobularia elongata	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12730	Heracleum maximum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12730	Heracleum maximum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18782.1	Pulsatilla cernua var. koreana	Varieties	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18782.1	Pulsatilla cernua var. koreana	Varieties	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18806	Neodilsea yendoana	Species	Dumontiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21224	Rubus pinfaensis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16895	Croton sarcopetalus	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20925	Fusarium culmorum	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21000	Elysia halimedae	Species	Placobranchidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13906	Ficus mucuso	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1550	Talaromyces purpureogenus	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7765	Quercus spicata	Species	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20112	Syncephalastrum racemosum	Species	Syncephalastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21540	Naucleopsis stipularis	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13003	Sogatella furcifera	Species	Delphacidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19749	Carpolobia glabrescens	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21134	Thaumetopoea pityocampa	Species	Notodontidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17503	Conospermum incurvum	Species	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO20469	Acer caesium	Species	Aceraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3030	Chaenorhinum villosum	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12730	Heracleum maximum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20044	Schistostephium crataegifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19608	Aconitum likiangense	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19874	Polygonatum glaberrimum	Species	Asparagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21419	Biscogniauxia mediterranea	Species	Xylariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21612	Anthelia glauca	Species	Xeniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17763	Lobularia elongata	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20662	Epinephelus drummondhayi	Species	Serranidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21673	Lupinus caudatus	Species	Fabaceae	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 NPC20525 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	24628
0.1-0.2	23981
0.2-0.3	1056
0.3-0.4	118
0.4-0.5	70
0.5-0.6	1
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	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC476614
0.5263	Remote Similarity	NPC192006

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC20525 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5492
0.1-0.2	3440
0.2-0.3	185
0.3-0.4	22
0.4-0.5	11
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