NPASS Compound

Structure

CID323091 OpenBabel06191716172D 36 39 0 0 1 0 0 0 0 0999 V2000 0.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8660 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.8690 4.3126 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0873 5.7989 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 2.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 3.7321 1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -1.5308 5.7989 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6750 3.0878 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.6456 1.4067 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 1.3660 4.0388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.3147 0.6636 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -2.5089 6.0068 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.2218 4.8479 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3660 4.0388 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.8147 -0.2024 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -2.8179 6.9579 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.1781 5.2637 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.8909 4.1047 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.7218 6.3867 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 -0.2218 4.8479 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 2.6261 2.7788 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8535 2.3849 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.9538 4.8479 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3092 0.7681 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2215 -1.1160 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 -1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0000 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0570 3.0878 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8366 0.0055 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.0000 0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 P 0 0 3 0 0 0 0 0 0 0 0 0 2.0000 0.0000 0.0000 P 0 0 3 0 0 0 0 0 0 0 0 0 1 30 1 0 0 0 0 2 31 1 0 0 0 0 3 17 2 0 0 0 0 3 18 1 0 0 0 0 4 19 2 0 0 0 0 4 20 1 0 0 0 0 5 1 1 1 0 0 0 5 8 1 0 0 0 0 5 32 1 0 0 0 0 6 2 1 6 0 0 0 6 9 1 0 0 0 0 6 33 1 0 0 0 0 7 12 2 0 0 0 0 7 13 1 0 0 0 0 7 19 1 0 0 0 0 8 10 1 0 0 0 0 8 21 1 6 0 0 0 9 11 1 0 0 0 0 9 22 1 1 0 0 0 10 14 1 0 0 0 0 10 23 1 6 0 0 0 11 15 1 0 0 0 0 11 24 1 1 0 0 0 12 16 1 0 0 0 0 12 17 1 0 0 0 0 13 18 2 0 0 0 0 13 20 1 0 0 0 0 14 20 1 1 0 0 0 14 32 1 0 0 0 0 15 25 1 0 0 0 0 15 33 1 0 0 0 0 26 35 1 0 0 0 0 27 35 2 0 0 0 0 28 36 1 0 0 0 0 29 36 2 0 0 0 0 30 35 1 0 0 0 0 31 36 1 0 0 0 0 34 35 1 0 0 0 0 34 36 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	559.07
Volume:	440.926
LogP:	-3.633
LogD:	-2.115
LogS:	0.003
# Rotatable Bonds:	9
TPSA:	285.93
# H-Bond Aceptor:	19
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	21

MedChem Properties

QED Drug-Likeness Score:	0.15
Synthetic Accessibility Score:	6.035
Fsp3:	0.667
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Rejected
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.526
MDCK Permeability:	1.90176215255633e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.966
Human Intestinal Absorption (HIA):	0.968
20% Bioavailability (F20%):	0.991
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.461
Plasma Protein Binding (PPB):	18.99372100830078%
Volume Distribution (VD):	0.612
Pgp-substrate:	68.5776596069336%

ADMET: Metabolism

CYP1A2-inhibitor:	0.001
CYP1A2-substrate:	0.124
CYP2C19-inhibitor:	0.058
CYP2C19-substrate:	0.032
CYP2C9-inhibitor:	0.002
CYP2C9-substrate:	0.043
CYP2D6-inhibitor:	0.015
CYP2D6-substrate:	0.038
CYP3A4-inhibitor:	0.004
CYP3A4-substrate:	0.002

ADMET: Excretion

Clearance (CL):	1.584
Half-life (T1/2):	0.936

ADMET: Toxicity

hERG Blockers:	0.029
Human Hepatotoxicity (H-HT):	0.236
Drug-inuced Liver Injury (DILI):	0.971
AMES Toxicity:	0.082
Rat Oral Acute Toxicity:	0.043
Maximum Recommended Daily Dose:	0.922
Skin Sensitization:	0.307
Carcinogencity:	0.458
Eye Corrosion:	0.003
Eye Irritation:	0.012
Respiratory Toxicity:	0.811

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC323091

Natural Product ID:	NPC323091
*Common Name:**	[[(2R,3S,4R,5R)-5-(6-Aminopurin-9-Yl)-3,4-Dihydroxyoxolan-2-Yl]Methoxy-Hydroxyphosphoryl] [(2R,3S,4R)-3,4,5-Trihydroxyoxolan-2-Yl]Methyl Hydrogen Phosphate
IUPAC Name:	[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S,4R)-3,4,5-trihydroxyoxolan-2-yl]methyl hydrogen phosphate
Synonyms:
Standard InCHIKey:	SRNWOUGRCWSEMX-TYASJMOZSA-N
Standard InCHI:	InChI=1S/C15H23N5O14P2/c16-12-7-13(18-3-17-12)20(4-19-7)14-10(23)8(21)5(32-14)1-30-35(26,27)34-36(28,29)31-2-6-9(22)11(24)15(25)33-6/h3-6,8-11,14-15,21-25H,1-2H2,(H,26,27)(H,28,29)(H2,16,17,18)/t5-,6-,8-,9-,10-,11-,14-,15?/m1/s1
SMILES:	O[C@@H]1[C@@H](COP(=O)(OP(=O)(OC[C@H]2OC([C@@H]([C@@H]2O)O)O)O)O)O[C@H]([C@@H]1O)n1cnc2c1ncnc2N
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL2360089
PubChem CID:	33576
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000289] Nucleosides, nucleotides, and analogues [CHEMONTID:0001506] Purine nucleotides [CHEMONTID:0001293] Purine nucleotide sugars

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	DOI[10.1016/0006-291X(79)91731-5]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	DOI[10.1093/emboj/18.8.2021]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1172/JCI16309]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1371/journal.pone.0115359]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[10557354]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[1091286]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[10977898]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[1100617]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11034610]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11419736]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[11530998]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11745165]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[11750815]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1175644]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12369847]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12391014]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12467448]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[12805358]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12812989]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12840027]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[12878451]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	ChEBI[131529]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[13610867]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[13831814]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[14973046]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15031653]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15084647]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1521032]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15230696]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15292242]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[15314235]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[15610037]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[16112079]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[1644759]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[16630633]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[16770722]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[1687010]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[170247]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17116739]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17190852]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[17765195]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[17875433]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[179975]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18311922]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18544912]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[18799520]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19026742]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[19425150]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19514719]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[19561621]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[19961175]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20506249]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20601097]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	faeces	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	urine	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	bile	n.a.	PMID[20708442]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[20876113]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21437340]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[21798258]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21988831]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22289691]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[2268561]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[22711758]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22855027]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23315938]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23537328]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[23676670]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23717534]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23752203]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23810710]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23811455]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23868375]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[23919613]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24101735]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[241475]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24206068]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24399466]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24494566]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24558969]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24783849]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[24816727]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24831709]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24939187]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24966042]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24967680]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25114169]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25181601]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25293588]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[2543976]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[25644343]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[25867074]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26195826]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[26236990]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26337258]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26670289]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[26826371]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[27471436]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[29897754]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[30302998]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[3179836]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[318639]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[3283102]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[347637]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[398096]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[4696527]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[4877125]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[4879561]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[4908789]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[5332408]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[5432584]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[6102982]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6121420]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[6284709]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[6338507]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[6780563]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[7042909]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[7601837]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[8600370]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[8852895]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[8987136]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9192820]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	PMID[9470222]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	PMID[9800648]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO20338	Mus musculus	Species	Muridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	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	NP ID	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
EC50	1
Potency	1

Activity Type	# Activity
Individual Protein	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT50	Individual Protein	Tyrosyl-DNA phosphodiesterase 1	Homo sapiens	Potency	n.a.	16360.1	nM	PMID[461148]
NPT4506	Individual Protein	Transient receptor potential cation channel subfamily M member 2	Homo sapiens	EC50	=	100000.0	nM	PMID[461149]

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC323091 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	997
0.1-0.2	27139
0.2-0.3	10389
0.3-0.4	3430
0.4-0.5	460
0.5-0.6	130
0.6-0.7	57
0.7-0.8	39
0.8-0.85	23
0.85-0.9	22
0.9-0.95	10
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.9527	High Similarity	NPC174802
0.9459	High Similarity	NPC164952
0.9459	High Similarity	NPC130586
0.94	High Similarity	NPC226245
0.9324	High Similarity	NPC185991
0.9324	High Similarity	NPC161224
0.9324	High Similarity	NPC211025
0.9324	High Similarity	NPC85689
0.9262	High Similarity	NPC321814
0.92	High Similarity	NPC302778
0.92	High Similarity	NPC212551
0.9145	High Similarity	NPC316618
0.9122	High Similarity	NPC121222
0.9079	High Similarity	NPC224076
0.8919	High Similarity	NPC107374
0.8919	High Similarity	NPC21448
0.8919	High Similarity	NPC156461
0.8882	High Similarity	NPC326529
0.8859	High Similarity	NPC164665
0.8859	High Similarity	NPC189068
0.8827	High Similarity	NPC324198
0.8827	High Similarity	NPC319100
0.88	High Similarity	NPC219313
0.88	High Similarity	NPC269827
0.88	High Similarity	NPC309832
0.8784	High Similarity	NPC229974
0.875	High Similarity	NPC326082
0.8649	High Similarity	NPC209525
0.8649	High Similarity	NPC161659
0.8598	High Similarity	NPC189261
0.8571	High Similarity	NPC321458
0.8571	High Similarity	NPC324033
0.8533	High Similarity	NPC314152
0.8523	High Similarity	NPC317821
0.8516	High Similarity	NPC472816
0.8509	High Similarity	NPC261595
0.8418	Intermediate Similarity	NPC239737
0.828	Intermediate Similarity	NPC207633
0.8212	Intermediate Similarity	NPC129756
0.8153	Intermediate Similarity	NPC150853
0.8089	Intermediate Similarity	NPC136349
0.8075	Intermediate Similarity	NPC313754
0.8075	Intermediate Similarity	NPC311197
0.8075	Intermediate Similarity	NPC54320
0.805	Intermediate Similarity	NPC328479
0.8026	Intermediate Similarity	NPC30326
0.8013	Intermediate Similarity	NPC232408
0.8013	Intermediate Similarity	NPC64705
0.8012	Intermediate Similarity	NPC52238
0.7949	Intermediate Similarity	NPC177169
0.7949	Intermediate Similarity	NPC317746
0.7914	Intermediate Similarity	NPC195140
0.7908	Intermediate Similarity	NPC33996
0.7895	Intermediate Similarity	NPC320818
0.7885	Intermediate Similarity	NPC318590
0.7885	Intermediate Similarity	NPC211820
0.7885	Intermediate Similarity	NPC251233
0.7834	Intermediate Similarity	NPC274384
0.7834	Intermediate Similarity	NPC89147
0.7784	Intermediate Similarity	NPC324484
0.7771	Intermediate Similarity	NPC14590
0.7756	Intermediate Similarity	NPC186619
0.7751	Intermediate Similarity	NPC290959
0.7738	Intermediate Similarity	NPC325906
0.7702	Intermediate Similarity	NPC326694
0.7636	Intermediate Similarity	NPC93365
0.7571	Intermediate Similarity	NPC24589
0.7542	Intermediate Similarity	NPC78941
0.7542	Intermediate Similarity	NPC282458
0.7436	Intermediate Similarity	NPC61198
0.7372	Intermediate Similarity	NPC262926
0.7371	Intermediate Similarity	NPC313897
0.7289	Intermediate Similarity	NPC321052
0.7197	Intermediate Similarity	NPC319221
0.7134	Intermediate Similarity	NPC324009
0.7068	Intermediate Similarity	NPC276373
0.7055	Intermediate Similarity	NPC315642
0.7055	Intermediate Similarity	NPC74306
0.7031	Intermediate Similarity	NPC5802
0.6995	Remote Similarity	NPC157821
0.6973	Remote Similarity	NPC313514
0.6942	Remote Similarity	NPC107160
0.6842	Remote Similarity	NPC21461
0.6836	Remote Similarity	NPC33382
0.6798	Remote Similarity	NPC125659
0.6798	Remote Similarity	NPC168702
0.6722	Remote Similarity	NPC222174
0.661	Remote Similarity	NPC321393
0.6589	Remote Similarity	NPC158055
0.6474	Remote Similarity	NPC327579
0.638	Remote Similarity	NPC246193
0.6364	Remote Similarity	NPC250178
0.6303	Remote Similarity	NPC57279
0.628	Remote Similarity	NPC104011
0.6267	Remote Similarity	NPC476564
0.6174	Remote Similarity	NPC174114
0.6174	Remote Similarity	NPC87981
0.6173	Remote Similarity	NPC248007
0.6078	Remote Similarity	NPC103388
0.6073	Remote Similarity	NPC160666
0.6065	Remote Similarity	NPC4837
0.6065	Remote Similarity	NPC312187
0.5988	Remote Similarity	NPC287876
0.5988	Remote Similarity	NPC139776
0.5967	Remote Similarity	NPC472834
0.5928	Remote Similarity	NPC14330
0.5844	Remote Similarity	NPC18335
0.5803	Remote Similarity	NPC164845
0.5758	Remote Similarity	NPC265111
0.5733	Remote Similarity	NPC324815
0.5723	Remote Similarity	NPC109322
0.5714	Remote Similarity	NPC473585
0.5674	Remote Similarity	NPC217656
0.5665	Remote Similarity	NPC314774
0.5665	Remote Similarity	NPC315126
0.5644	Remote Similarity	NPC68938
0.5642	Remote Similarity	NPC89139
0.5625	Remote Similarity	NPC296437

Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC323091 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	200
0.1-0.2	2543
0.2-0.3	3219
0.3-0.4	2198
0.4-0.5	664
0.5-0.6	149
0.6-0.7	106
0.7-0.8	41
0.8-0.85	14
0.85-0.9	12
0.9-0.95	4
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9527	High Similarity	NPD339	Approved
0.9459	High Similarity	NPD338	Approved
0.9324	High Similarity	NPD283	Approved
0.92	High Similarity	NPD242	Approved
0.9079	High Similarity	NPD169	Phase 2
0.8919	High Similarity	NPD249	Approved
0.8919	High Similarity	NPD250	Approved
0.8827	High Similarity	NPD4171	Clinical (unspecified phase)
0.8824	High Similarity	NPD1369	Phase 2
0.88	High Similarity	NPD195	Approved
0.88	High Similarity	NPD186	Discovery
0.8701	High Similarity	NPD1750	Clinical (unspecified phase)
0.8667	High Similarity	NPD4716	Approved
0.8614	High Similarity	NPD4744	Clinical (unspecified phase)
0.8581	High Similarity	NPD3107	Discontinued
0.8545	High Similarity	NPD1412	Clinical (unspecified phase)
0.8535	High Similarity	NPD2624	Phase 2
0.8535	High Similarity	NPD1732	Phase 3
0.8533	High Similarity	NPD185	Approved
0.8509	High Similarity	NPD7988	Suspended
0.8509	High Similarity	NPD247	Clinical (unspecified phase)
0.8438	Intermediate Similarity	NPD3083	Approved
0.8421	Intermediate Similarity	NPD166	Approved
0.8418	Intermediate Similarity	NPD2646	Discontinued
0.84	Intermediate Similarity	NPD193	Suspended
0.8304	Intermediate Similarity	NPD6417	Clinical (unspecified phase)
0.8103	Intermediate Similarity	NPD2631	Clinical (unspecified phase)
0.8103	Intermediate Similarity	NPD2632	Approved
0.8103	Intermediate Similarity	NPD2630	Approved
0.8089	Intermediate Similarity	NPD548	Clinical (unspecified phase)
0.8075	Intermediate Similarity	NPD219	Phase 3
0.8075	Intermediate Similarity	NPD216	Approved
0.8075	Intermediate Similarity	NPD218	Approved
0.8075	Intermediate Similarity	NPD217	Approved
0.8075	Intermediate Similarity	NPD220	Clinical (unspecified phase)
0.8012	Intermediate Similarity	NPD2647	Phase 3
0.7888	Intermediate Similarity	NPD213	Clinical (unspecified phase)
0.7888	Intermediate Similarity	NPD214	Approved
0.7882	Intermediate Similarity	NPD5666	Phase 2
0.7812	Intermediate Similarity	NPD3085	Phase 1
0.7806	Intermediate Similarity	NPD3695	Approved
0.7806	Intermediate Similarity	NPD3696	Approved
0.7805	Intermediate Similarity	NPD4074	Clinical (unspecified phase)
0.7764	Intermediate Similarity	NPD3086	Phase 3
0.7738	Intermediate Similarity	NPD1776	Approved
0.7738	Intermediate Similarity	NPD1777	Approved
0.7722	Intermediate Similarity	NPD7158	Phase 1
0.7682	Intermediate Similarity	NPD248	Discontinued
0.767	Intermediate Similarity	NPD1692	Approved
0.7636	Intermediate Similarity	NPD546	Clinical (unspecified phase)
0.7616	Intermediate Similarity	NPD9633	Phase 3
0.7566	Intermediate Similarity	NPD9632	Phase 3
0.7556	Intermediate Similarity	NPD4054	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD870	Clinical (unspecified phase)
0.7533	Intermediate Similarity	NPD9408	Phase 3
0.7486	Intermediate Similarity	NPD5683	Clinical (unspecified phase)
0.7486	Intermediate Similarity	NPD5682	Phase 3
0.7486	Intermediate Similarity	NPD5684	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD4240	Approved
0.7436	Intermediate Similarity	NPD252	Clinical (unspecified phase)
0.7391	Intermediate Similarity	NPD171	Discontinued
0.7347	Intermediate Similarity	NPD5080	Phase 2
0.7296	Intermediate Similarity	NPD5079	Phase 2
0.7294	Intermediate Similarity	NPD516	Clinical (unspecified phase)
0.7273	Intermediate Similarity	NPD3708	Phase 2
0.725	Intermediate Similarity	NPD549	Approved
0.7152	Intermediate Similarity	NPD194	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD536	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD582	Approved
0.6973	Remote Similarity	NPD7138	Phase 2
0.6923	Remote Similarity	NPD353	Discontinued
0.6919	Remote Similarity	NPD1063	Phase 2
0.6786	Remote Similarity	NPD2965	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD2877	Clinical (unspecified phase)
0.6751	Remote Similarity	NPD2876	Phase 3
0.6686	Remote Similarity	NPD231	Clinical (unspecified phase)
0.6683	Remote Similarity	NPD2824	Phase 2
0.6595	Remote Similarity	NPD1046	Clinical (unspecified phase)
0.659	Remote Similarity	NPD9605	Phase 3
0.6589	Remote Similarity	NPD6840	Approved
0.6552	Remote Similarity	NPD2902	Phase 2
0.6552	Remote Similarity	NPD2903	Clinical (unspecified phase)
0.6535	Remote Similarity	NPD4495	Phase 1
0.6516	Remote Similarity	NPD9606	Approved
0.6474	Remote Similarity	NPD9607	Approved
0.6429	Remote Similarity	NPD9584	Phase 2
0.6364	Remote Similarity	NPD209	Clinical (unspecified phase)
0.6337	Remote Similarity	NPD1730	Discontinued
0.6329	Remote Similarity	NPD9409	Discontinued
0.6312	Remote Similarity	NPD798	Discontinued
0.6303	Remote Similarity	NPD545	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD527	Clinical (unspecified phase)
0.6228	Remote Similarity	NPD1119	Phase 2
0.6218	Remote Similarity	NPD9374	Approved
0.6205	Remote Similarity	NPD547	Clinical (unspecified phase)
0.6199	Remote Similarity	NPD1430	Approved
0.6199	Remote Similarity	NPD1431	Approved
0.6194	Remote Similarity	NPD9373	Approved
0.619	Remote Similarity	NPD535	Approved
0.6173	Remote Similarity	NPD9084	Phase 2
0.6168	Remote Similarity	NPD1058	Discontinued
0.6164	Remote Similarity	NPD307	Approved
0.6154	Remote Similarity	NPD2152	Clinical (unspecified phase)
0.6145	Remote Similarity	NPD282	Approved
0.6105	Remote Similarity	NPD2253	Discontinued
0.608	Remote Similarity	NPD775	Approved
0.6059	Remote Similarity	NPD4458	Phase 2
0.6059	Remote Similarity	NPD4459	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD7531	Clinical (unspecified phase)
0.6023	Remote Similarity	NPD1808	Phase 1
0.599	Remote Similarity	NPD207	Discontinued
0.5988	Remote Similarity	NPD8829	Clinical (unspecified phase)
0.5976	Remote Similarity	NPD9083	Clinical (unspecified phase)
0.5964	Remote Similarity	NPD1127	Approved
0.5964	Remote Similarity	NPD1128	Approved
0.593	Remote Similarity	NPD799	Phase 1
0.5926	Remote Similarity	NPD6381	Phase 2
0.5919	Remote Similarity	NPD7502	Clinical (unspecified phase)
0.5906	Remote Similarity	NPD1121	Approved
0.5906	Remote Similarity	NPD1120	Approved
0.5872	Remote Similarity	NPD6112	Approved
0.5862	Remote Similarity	NPD1118	Discontinued
0.5845	Remote Similarity	NPD4715	Clinical (unspecified phase)
0.5845	Remote Similarity	NPD34	Approved
0.5845	Remote Similarity	NPD4714	Approved
0.5845	Remote Similarity	NPD4713	Clinical (unspecified phase)
0.5844	Remote Similarity	NPD8836	Approved
0.5843	Remote Similarity	NPD281	Approved
0.5797	Remote Similarity	NPD5486	Discontinued
0.5789	Remote Similarity	NPD5340	Clinical (unspecified phase)
0.5775	Remote Similarity	NPD2593	Clinical (unspecified phase)
0.5753	Remote Similarity	NPD6036	Suspended
0.5733	Remote Similarity	NPD8250	Phase 2
0.5732	Remote Similarity	NPD9416	Phase 3
0.5732	Remote Similarity	NPD9417	Phase 3
0.5723	Remote Similarity	NPD9375	Discontinued
0.5714	Remote Similarity	NPD7842	Phase 2
0.5714	Remote Similarity	NPD5458	Discontinued
0.5707	Remote Similarity	NPD9582	Phase 3
0.5706	Remote Similarity	NPD1117	Clinical (unspecified phase)
0.5687	Remote Similarity	NPD2450	Phase 2
0.5687	Remote Similarity	NPD2451	Phase 2
0.5687	Remote Similarity	NPD2453	Phase 2
0.5687	Remote Similarity	NPD2452	Phase 2
0.5669	Remote Similarity	NPD1816	Clinical (unspecified phase)
0.5665	Remote Similarity	NPD9484	Clinical (unspecified phase)
0.5641	Remote Similarity	NPD9626	Clinical (unspecified phase)
0.5631	Remote Similarity	NPD691	Discontinued
0.5621	Remote Similarity	NPD515	Phase 1
0.5613	Remote Similarity	NPD796	Phase 2

Bioactivity similarity: Similar Natural Products in NPASS

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