NPASS Compound

Structure

CID326694 OpenBabel06191716192D 24 25 0 0 1 0 0 0 0 0999 V2000 1.5000 -0.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7989 -1.6448 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1434 -4.5361 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5000 -0.8660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.7989 -3.2628 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0878 -0.0570 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.0388 -0.3660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 6.1079 -4.2139 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8479 -2.9538 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.0388 -1.3660 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 5.4388 -4.9570 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 6.3867 -2.4538 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.0388 -3.5416 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 4.8479 -1.9538 0.0000 N 0 0 0 0 0 0 0 0 0 0 0 0 3.3344 -5.1239 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7788 0.8940 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.8479 0.2218 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 7.0861 -4.4218 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 -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 1.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 3.0878 -1.6750 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 0.0000 0.0000 P 0 0 0 0 0 0 0 0 0 0 0 0 1 22 1 0 0 0 0 2 12 2 0 0 0 0 2 14 1 0 0 0 0 3 13 2 3 0 0 0 3 15 1 0 0 0 0 4 1 1 6 0 0 0 4 6 1 0 0 0 0 4 23 1 0 0 0 0 5 8 1 0 0 0 0 5 9 2 0 0 0 0 5 12 1 0 0 0 0 6 7 1 0 0 0 0 6 16 1 1 0 0 0 7 10 1 0 0 0 0 7 17 1 1 0 0 0 8 11 1 0 0 0 0 8 18 2 0 0 0 0 9 13 1 0 0 0 0 9 14 1 0 0 0 0 10 14 1 6 0 0 0 10 23 1 0 0 0 0 19 24 1 0 0 0 0 20 24 1 0 0 0 0 21 24 2 0 0 0 0 22 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	366.06
Volume:	296.784
LogP:	-2.634
LogD:	-1.48
LogS:	-0.691
# Rotatable Bonds:	7
TPSA:	203.3
# H-Bond Aceptor:	13
# H-Bond Donor:	6
# Rings:	2
# Heavy Atoms:	14

MedChem Properties

QED Drug-Likeness Score:	0.252
Synthetic Accessibility Score:	5.07
Fsp3:	0.5
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.202
MDCK Permeability:	3.740382453543134e-05
Pgp-inhibitor:	0.0
Pgp-substrate:	0.679
Human Intestinal Absorption (HIA):	0.213
20% Bioavailability (F20%):	0.975
30% Bioavailability (F30%):	0.996

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.422
Plasma Protein Binding (PPB):	21.852630615234375%
Volume Distribution (VD):	0.359
Pgp-substrate:	83.13273620605469%

ADMET: Metabolism

CYP1A2-inhibitor:	0.003
CYP1A2-substrate:	0.035
CYP2C19-inhibitor:	0.039
CYP2C19-substrate:	0.038
CYP2C9-inhibitor:	0.013
CYP2C9-substrate:	0.115
CYP2D6-inhibitor:	0.041
CYP2D6-substrate:	0.093
CYP3A4-inhibitor:	0.006
CYP3A4-substrate:	0.009

ADMET: Excretion

Clearance (CL):	1.705
Half-life (T1/2):	0.824

ADMET: Toxicity

hERG Blockers:	0.036
Human Hepatotoxicity (H-HT):	0.107
Drug-inuced Liver Injury (DILI):	0.894
AMES Toxicity:	0.046
Rat Oral Acute Toxicity:	0.003
Maximum Recommended Daily Dose:	0.343
Skin Sensitization:	0.111
Carcinogencity:	0.075
Eye Corrosion:	0.003
Eye Irritation:	0.022
Respiratory Toxicity:	0.524

Download Data

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

Natural Product: NPC326694

Natural Product ID:	NPC326694
*Common Name:**	Faicar
IUPAC Name:	[(2R,3S,4R,5R)-5-(4-carbamoyl-5-formamidoimidazol-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate
Synonyms:
Standard InCHIKey:	ABCOOORLYAOBOZ-KQYNXXCUSA-N
Standard InCHI:	InChI=1S/C10H15N4O9P/c11-8(18)5-9(13-3-15)14(2-12-5)10-7(17)6(16)4(23-10)1-22-24(19,20)21/h2-4,6-7,10,16-17H,1H2,(H2,11,18)(H,13,15)(H2,19,20,21)/t4-,6-,7-,10-/m1/s1
SMILES:	OC=Nc1c(ncn1[C@@H]1O[C@@H]([C@H]([C@H]1O)O)COP(=O)(O)O)C(=O)N
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL521310
PubChem CID:	166760
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000289] Nucleosides, nucleotides, and analogues [CHEMONTID:0001997] Imidazole ribonucleosides and ribonucleotides [CHEMONTID:0001420] 1-ribosyl-imidazolecarboxamides

*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.	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.	faeces	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]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO20338	Mus musculus	Species	Muridae	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	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
Ki	1

Activity Type	# Activity
Individual Protein	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT476	Individual Protein	AICAR transformylase	Homo sapiens	Ki	=	400.0	nM	PMID[478533]

☑ 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 NPC326694 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	732
0.1-0.2	29829
0.2-0.3	8124
0.3-0.4	3274
0.4-0.5	483
0.5-0.6	138
0.6-0.7	55
0.7-0.8	52
0.8-0.85	9
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
0.8904	High Similarity	NPC321052
0.8521	High Similarity	NPC30326
0.8231	Intermediate Similarity	NPC251233
0.8231	Intermediate Similarity	NPC211820
0.8176	Intermediate Similarity	NPC177169
0.8125	Intermediate Similarity	NPC320818
0.8121	Intermediate Similarity	NPC232408
0.8121	Intermediate Similarity	NPC64705
0.8108	Intermediate Similarity	NPC318590
0.8105	Intermediate Similarity	NPC130586
0.8105	Intermediate Similarity	NPC164952
0.8095	Intermediate Similarity	NPC186619
0.8092	Intermediate Similarity	NPC85689
0.8092	Intermediate Similarity	NPC185991
0.8092	Intermediate Similarity	NPC211025
0.8054	Intermediate Similarity	NPC274384
0.8054	Intermediate Similarity	NPC317746
0.8054	Intermediate Similarity	NPC89147
0.8052	Intermediate Similarity	NPC174802
0.8039	Intermediate Similarity	NPC321814
0.7987	Intermediate Similarity	NPC212551
0.7987	Intermediate Similarity	NPC302778
0.7949	Intermediate Similarity	NPC316618
0.7949	Intermediate Similarity	NPC226245
0.7895	Intermediate Similarity	NPC121222
0.7885	Intermediate Similarity	NPC224076
0.7857	Intermediate Similarity	NPC161224
0.7755	Intermediate Similarity	NPC61198
0.7702	Intermediate Similarity	NPC323091
0.7697	Intermediate Similarity	NPC156461
0.7697	Intermediate Similarity	NPC107374
0.7697	Intermediate Similarity	NPC21448
0.7687	Intermediate Similarity	NPC262926
0.7647	Intermediate Similarity	NPC189068
0.7647	Intermediate Similarity	NPC164665
0.7597	Intermediate Similarity	NPC309832
0.7597	Intermediate Similarity	NPC219313
0.7597	Intermediate Similarity	NPC269827
0.7566	Intermediate Similarity	NPC229974
0.75	Intermediate Similarity	NPC319221
0.7451	Intermediate Similarity	NPC315642
0.7451	Intermediate Similarity	NPC74306
0.7434	Intermediate Similarity	NPC161659
0.7434	Intermediate Similarity	NPC209525
0.7432	Intermediate Similarity	NPC324009
0.7423	Intermediate Similarity	NPC14590
0.7394	Intermediate Similarity	NPC261595
0.7358	Intermediate Similarity	NPC472816
0.7349	Intermediate Similarity	NPC321458
0.7349	Intermediate Similarity	NPC324033
0.7338	Intermediate Similarity	NPC314152
0.7337	Intermediate Similarity	NPC326529
0.732	Intermediate Similarity	NPC317821
0.7294	Intermediate Similarity	NPC319100
0.7294	Intermediate Similarity	NPC189261
0.7294	Intermediate Similarity	NPC324198
0.7202	Intermediate Similarity	NPC326082
0.7178	Intermediate Similarity	NPC239737
0.7143	Intermediate Similarity	NPC207633
0.7123	Intermediate Similarity	NPC109322
0.7032	Intermediate Similarity	NPC129756
0.7019	Intermediate Similarity	NPC150853
0.697	Remote Similarity	NPC313754
0.697	Remote Similarity	NPC54320
0.697	Remote Similarity	NPC311197
0.6957	Remote Similarity	NPC136349
0.6923	Remote Similarity	NPC324484
0.6909	Remote Similarity	NPC52238
0.6901	Remote Similarity	NPC290959
0.6882	Remote Similarity	NPC325906
0.6846	Remote Similarity	NPC180493
0.6829	Remote Similarity	NPC328479
0.6752	Remote Similarity	NPC33996
0.6735	Remote Similarity	NPC327579
0.6643	Remote Similarity	NPC47936
0.6627	Remote Similarity	NPC195140
0.6568	Remote Similarity	NPC93365
0.6484	Remote Similarity	NPC24589
0.6467	Remote Similarity	NPC78941
0.6467	Remote Similarity	NPC282458
0.6438	Remote Similarity	NPC256849
0.6389	Remote Similarity	NPC75131
0.6376	Remote Similarity	NPC278549
0.6327	Remote Similarity	NPC303899
0.6278	Remote Similarity	NPC313897
0.6184	Remote Similarity	NPC252603
0.6154	Remote Similarity	NPC276373
0.6133	Remote Similarity	NPC148385
0.6122	Remote Similarity	NPC5802
0.6091	Remote Similarity	NPC157821
0.6067	Remote Similarity	NPC199790
0.6034	Remote Similarity	NPC33382
0.6013	Remote Similarity	NPC158847
0.6	Remote Similarity	NPC168702
0.6	Remote Similarity	NPC125659
0.5977	Remote Similarity	NPC60537
0.5964	Remote Similarity	NPC76544
0.5964	Remote Similarity	NPC167285
0.5964	Remote Similarity	NPC226184
0.5947	Remote Similarity	NPC313514
0.5934	Remote Similarity	NPC222174
0.5904	Remote Similarity	NPC210947
0.5855	Remote Similarity	NPC313547
0.5818	Remote Similarity	NPC470140
0.581	Remote Similarity	NPC321393
0.5808	Remote Similarity	NPC470139
0.5794	Remote Similarity	NPC107160
0.578	Remote Similarity	NPC158055
0.5758	Remote Similarity	NPC126634
0.5731	Remote Similarity	NPC174020
0.5714	Remote Similarity	NPC21461
0.5705	Remote Similarity	NPC119133
0.5689	Remote Similarity	NPC470141
0.568	Remote Similarity	NPC185903
0.5617	Remote Similarity	NPC180462
0.561	Remote Similarity	NPC246193
0.5607	Remote Similarity	NPC327477

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 NPC326694 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	175
0.1-0.2	2553
0.2-0.3	3417
0.3-0.4	2254
0.4-0.5	457
0.5-0.6	184
0.6-0.7	80
0.7-0.8	26
0.8-0.85	4
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8523	High Similarity	NPD9605	Phase 3
0.8105	Intermediate Similarity	NPD338	Approved
0.8092	Intermediate Similarity	NPD283	Approved
0.8052	Intermediate Similarity	NPD339	Approved
0.8028	Intermediate Similarity	NPD9632	Phase 3
0.7987	Intermediate Similarity	NPD242	Approved
0.7885	Intermediate Similarity	NPD169	Phase 2
0.7792	Intermediate Similarity	NPD3085	Phase 1
0.7755	Intermediate Similarity	NPD252	Clinical (unspecified phase)
0.7742	Intermediate Similarity	NPD3086	Phase 3
0.7697	Intermediate Similarity	NPD250	Approved
0.7697	Intermediate Similarity	NPD249	Approved
0.7603	Intermediate Similarity	NPD282	Approved
0.7597	Intermediate Similarity	NPD195	Approved
0.7597	Intermediate Similarity	NPD186	Discovery
0.7568	Intermediate Similarity	NPD1119	Phase 2
0.7562	Intermediate Similarity	NPD4074	Clinical (unspecified phase)
0.755	Intermediate Similarity	NPD549	Approved
0.7451	Intermediate Similarity	NPD582	Approved
0.745	Intermediate Similarity	NPD194	Clinical (unspecified phase)
0.7423	Intermediate Similarity	NPD3083	Approved
0.7394	Intermediate Similarity	NPD247	Clinical (unspecified phase)
0.7386	Intermediate Similarity	NPD2253	Discontinued
0.7338	Intermediate Similarity	NPD185	Approved
0.7312	Intermediate Similarity	NPD1369	Phase 2
0.7312	Intermediate Similarity	NPD3107	Discontinued
0.7312	Intermediate Similarity	NPD1750	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD4171	Clinical (unspecified phase)
0.7289	Intermediate Similarity	NPD7988	Suspended
0.7279	Intermediate Similarity	NPD1127	Approved
0.7279	Intermediate Similarity	NPD1128	Approved
0.7261	Intermediate Similarity	NPD7531	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD281	Approved
0.7251	Intermediate Similarity	NPD1412	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD536	Clinical (unspecified phase)
0.7244	Intermediate Similarity	NPD166	Approved
0.7208	Intermediate Similarity	NPD193	Suspended
0.7188	Intermediate Similarity	NPD353	Discontinued
0.7178	Intermediate Similarity	NPD2646	Discontinued
0.7178	Intermediate Similarity	NPD1732	Phase 3
0.7178	Intermediate Similarity	NPD2624	Phase 2
0.7168	Intermediate Similarity	NPD4716	Approved
0.7159	Intermediate Similarity	NPD6417	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD4744	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD535	Approved
0.6987	Remote Similarity	NPD1118	Discontinued
0.697	Remote Similarity	NPD219	Phase 3
0.697	Remote Similarity	NPD217	Approved
0.697	Remote Similarity	NPD218	Approved
0.697	Remote Similarity	NPD216	Approved
0.697	Remote Similarity	NPD220	Clinical (unspecified phase)
0.6957	Remote Similarity	NPD548	Clinical (unspecified phase)
0.6899	Remote Similarity	NPD1117	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD2632	Approved
0.6889	Remote Similarity	NPD2631	Clinical (unspecified phase)
0.6889	Remote Similarity	NPD2630	Approved
0.6882	Remote Similarity	NPD1777	Approved
0.6882	Remote Similarity	NPD1776	Approved
0.6846	Remote Similarity	NPD78	Approved
0.6846	Remote Similarity	NPD9544	Approved
0.6842	Remote Similarity	NPD2647	Phase 3
0.6839	Remote Similarity	NPD5666	Phase 2
0.6788	Remote Similarity	NPD214	Approved
0.6788	Remote Similarity	NPD213	Clinical (unspecified phase)
0.6781	Remote Similarity	NPD9606	Approved
0.6781	Remote Similarity	NPD578	Discontinued
0.6735	Remote Similarity	NPD9607	Approved
0.6645	Remote Similarity	NPD1085	Approved
0.6645	Remote Similarity	NPD1775	Approved
0.6644	Remote Similarity	NPD2221	Clinical (unspecified phase)
0.6625	Remote Similarity	NPD1430	Approved
0.6625	Remote Similarity	NPD1431	Approved
0.6603	Remote Similarity	NPD209	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD5684	Clinical (unspecified phase)
0.6593	Remote Similarity	NPD5682	Phase 3
0.6593	Remote Similarity	NPD5683	Clinical (unspecified phase)
0.6577	Remote Similarity	NPD9290	Approved
0.6577	Remote Similarity	NPD9409	Discontinued
0.6575	Remote Similarity	NPD9406	Approved
0.6568	Remote Similarity	NPD546	Clinical (unspecified phase)
0.6538	Remote Similarity	NPD545	Clinical (unspecified phase)
0.6516	Remote Similarity	NPD248	Discontinued
0.651	Remote Similarity	NPD580	Discontinued
0.6503	Remote Similarity	NPD7158	Phase 1
0.6486	Remote Similarity	NPD4054	Clinical (unspecified phase)
0.6463	Remote Similarity	NPD9374	Approved
0.6452	Remote Similarity	NPD9633	Phase 3
0.6438	Remote Similarity	NPD9373	Approved
0.6438	Remote Similarity	NPD9359	Approved
0.6438	Remote Similarity	NPD9358	Approved
0.6438	Remote Similarity	NPD1808	Phase 1
0.6433	Remote Similarity	NPD547	Clinical (unspecified phase)
0.6405	Remote Similarity	NPD579	Clinical (unspecified phase)
0.64	Remote Similarity	NPD307	Approved
0.6393	Remote Similarity	NPD1692	Approved
0.6364	Remote Similarity	NPD9408	Phase 3
0.6351	Remote Similarity	NPD9086	Approved
0.6312	Remote Similarity	NPD1121	Approved
0.6312	Remote Similarity	NPD1120	Approved
0.6301	Remote Similarity	NPD8955	Approved
0.6301	Remote Similarity	NPD8954	Approved
0.6287	Remote Similarity	NPD775	Approved
0.6282	Remote Similarity	NPD870	Clinical (unspecified phase)
0.6264	Remote Similarity	NPD516	Clinical (unspecified phase)
0.6258	Remote Similarity	NPD3695	Approved
0.6258	Remote Similarity	NPD3696	Approved
0.6213	Remote Similarity	NPD3708	Phase 2
0.6184	Remote Similarity	NPD9288	Approved
0.6184	Remote Similarity	NPD9292	Approved
0.6184	Remote Similarity	NPD9289	Approved
0.6184	Remote Similarity	NPD76	Approved
0.6169	Remote Similarity	NPD4262	Discontinued
0.6145	Remote Similarity	NPD4240	Approved
0.6136	Remote Similarity	NPD5768	Phase 2
0.6133	Remote Similarity	NPD9584	Phase 2
0.6092	Remote Similarity	NPD3697	Discontinued
0.6087	Remote Similarity	NPD6381	Phase 2
0.6082	Remote Similarity	NPD7842	Phase 2
0.6064	Remote Similarity	NPD1063	Phase 2
0.6054	Remote Similarity	NPD9417	Phase 3
0.6054	Remote Similarity	NPD9416	Phase 3
0.6012	Remote Similarity	NPD1731	Clinical (unspecified phase)
0.6	Remote Similarity	NPD2152	Clinical (unspecified phase)
0.5977	Remote Similarity	NPD2180	Approved
0.5959	Remote Similarity	NPD9626	Clinical (unspecified phase)
0.5956	Remote Similarity	NPD3081	Clinical (unspecified phase)
0.5947	Remote Similarity	NPD7138	Phase 2
0.5933	Remote Similarity	NPD9375	Discontinued
0.5924	Remote Similarity	NPD798	Discontinued
0.5909	Remote Similarity	NPD2604	Approved
0.5905	Remote Similarity	NPD6036	Suspended
0.5893	Remote Similarity	NPD2179	Discontinued
0.5862	Remote Similarity	NPD231	Clinical (unspecified phase)
0.5824	Remote Similarity	NPD171	Discontinued
0.5821	Remote Similarity	NPD2965	Clinical (unspecified phase)
0.5817	Remote Similarity	NPD5080	Phase 2
0.5813	Remote Similarity	NPD515	Phase 1
0.5806	Remote Similarity	NPD9360	Approved
0.5793	Remote Similarity	NPD5340	Clinical (unspecified phase)
0.5792	Remote Similarity	NPD2877	Clinical (unspecified phase)
0.5792	Remote Similarity	NPD2876	Phase 3
0.578	Remote Similarity	NPD6840	Approved
0.5778	Remote Similarity	NPD3130	Discontinued
0.5772	Remote Similarity	NPD1816	Clinical (unspecified phase)
0.5769	Remote Similarity	NPD5079	Phase 2
0.5754	Remote Similarity	NPD5321	Phase 3
0.575	Remote Similarity	NPD4812	Phase 1
0.5745	Remote Similarity	NPD1046	Clinical (unspecified phase)
0.5742	Remote Similarity	NPD1368	Approved
0.5735	Remote Similarity	NPD2824	Phase 2
0.5731	Remote Similarity	NPD9627	Approved
0.5705	Remote Similarity	NPD237	Clinical (unspecified phase)
0.5705	Remote Similarity	NPD9291	Approved
0.5698	Remote Similarity	NPD1730	Discontinued
0.565	Remote Similarity	NPD5665	Clinical (unspecified phase)
0.5632	Remote Similarity	NPD4183	Phase 3
0.5632	Remote Similarity	NPD4182	Phase 3
0.5625	Remote Similarity	NPD2903	Clinical (unspecified phase)
0.5625	Remote Similarity	NPD2902	Phase 2
0.5614	Remote Similarity	NPD1451	Approved

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