NPASS Compound

Natural Product: NPC121222

Natural Product ID	NPC121222
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	[(2R,3S,5R)-5-(6-Aminopurin-9-Yl)-3-Hydroxyoxolan-2-Yl]Methyl Dihydrogen Phosphate
IUPAC Name	[(2R,3S,5R)-5-(6-aminopurin-9-yl)-3-hydroxyoxolan-2-yl]methyl dihydrogen phosphate
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1206239
PubChem CID	12599
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000289] Nucleosides, nucleotides, and analogues [CHEMONTID:0001506] Purine nucleotides [CHEMONTID:0002134] Purine deoxyribonucleotides [CHEMONTID:0002135] Purine deoxyribonucleoside monophosphates [CHEMONTID:0002141] Purine 2'-deoxyribonucleoside monophosphates

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 36 38 0 0 0 0 0 0 0 0999 V2000 0.0729 2.3556 -0.7818 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5796 2.1038 -0.8096 C 0 0 1 0 0 0 0 0 0 0 0 0 1.6324 0.6016 -0.7948 C 0 0 1 0 0 0 0 0 0 0 0 0 2.9133 0.0674 -0.2100 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8072 -1.3203 -0.1339 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2027 -2.0189 0.5134 P 0 0 0 0 0 0 0 0 0 0 0 0 5.1749 -2.4253 -0.5827 O 0 0 0 0 0 0 0 0 0 0 0 0 5.0117 -0.9456 1.5398 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7839 -3.3835 1.4212 O 0 0 0 0 0 0 0 0 0 0 0 0 0.5151 0.2815 -0.0232 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.4759 0.9750 -0.7392 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7676 0.8571 -0.1508 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.5655 1.8036 0.3463 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.7159 1.2329 0.8092 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.6153 -0.0752 0.5907 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4607 -1.1314 0.8474 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7032 -0.8756 1.4617 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.0976 -2.3973 0.5116 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.9146 -2.6264 -0.0714 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0934 -1.5911 -0.3195 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.4177 -0.3114 -0.0001 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0783 2.6229 -1.9987 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2092 2.9570 0.1050 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2672 2.8867 -1.6867 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0391 2.5694 0.0876 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4374 0.2408 -1.8160 H 0 0 0 0 0 0 0 0 0 0 0 0 3.7442 0.4163 -0.8235 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9689 0.4516 0.8378 H 0 0 0 0 0 0 0 0 0 0 0 0 5.9140 -0.7144 1.1942 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3120 -4.0510 0.8667 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4925 0.5341 -1.7679 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.3738 2.8673 0.3962 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.7703 -0.8320 2.4845 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.5406 -0.7334 0.8751 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5743 -3.6031 -0.3586 H 0 0 0 0 0 0 0 0 0 0 0 0 2.8677 3.2112 -1.8199 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 6 8 1 0 6 9 1 0 3 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 2 0 14 15 1 0 15 16 2 0 16 17 1 0 16 18 1 0 18 19 2 0 19 20 1 0 20 21 2 0 2 22 1 0 11 1 1 0 21 12 1 0 21 15 1 0 1 23 1 0 1 24 1 0 2 25 1 1 3 26 1 6 4 27 1 0 4 28 1 0 8 29 1 0 9 30 1 0 11 31 1 6 13 32 1 0 17 33 1 0 17 34 1 0 19 35 1 0 22 36 1 0 M END

Standard InCHIKey	KHWCHTKSEGGWEX-RRKCRQDMSA-N
Standard InCHI	InChI=1S/C10H14N5O6P/c11-9-8-10(13-3-12-9)15(4-14-8)7-1-5(16)6(21-7)2-20-22(17,18)19/h3-7,16H,1-2H2,(H2,11,12,13)(H2,17,18,19)/t5-,6+,7+/m0/s1
SMILES	C1[C@@H]([C@@H](COP(=O)(O)O)O[C@H]1n1cnc2c(N)ncnc12)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	331.07	Volume:	272.854 ? Van der Waals volume.
Dense:	1.213	LogP:	-1.586 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.11 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.986 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	16.0
TPSA:	165.84 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	5.0	Rings:	3.0
Heavy Atoms:	12.0

MedChem Properties

QED Drug-Likeness Score:	0.519	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.733	Fsp³:	0.5
MCE-18:	67.133 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.096	Fluc inhibitor:	0.002 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.019 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.014 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.052	Promiscuous compounds:	0.299

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.597	MDCK Permeability:	-5.244
Pgp-inhibitor:	0.005	Pgp-substrate:	0.0
PAMPA:	0.843 ? 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%):	0.0	30% Bioavailability (F30%):	0.004
50% Bioavailability (F50%):	0.014

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.076
Plasma Protein Binding (PPB):	18.996%	Volume Distribution (VD):	0.497
Fu:	70.782% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.019
BSEP inhibitor:	0.847

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.028	CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.011
HLM stability:	0.968 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

2.896

Half-life (T1/2):

1.943

ADMET: Toxicity

hERG Blockers:	0.021	hERG Blockers (10um):	0.057
Human Hepatotoxicity (H-HT):	0.541	Drug-induced Liver Injury (DILI):	0.97
AMES Toxicity:	0.432	Rat Oral Acute Toxicity:	0.097
Maximum Recommended Daily Dose:	0.969	Skin Sensitization:	0.739
Carcinogencity:	0.898	Eye Corrosion:	0.001
Eye Irritation:	0.575	Respiratory Toxicity:	0.964
Drug-induced Neurotoxicity:	0.837	Ototoxicity:	0.42
Hematotoxicity:	0.203	Drug-induced Nephrotoxicity:	0.985
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.137
A549 Cytotoxicity:	0.018	Hek293 Cytotoxicity:	0.307
BCF:	0.064 ? 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:	2.395 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	3.849 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.338 ? 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
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[COCONUT]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO730	Escherichia coli	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	DOI[https://doi.org/10.1016/j.jbiosc.2016.12.008]
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	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
Potency	10
Kcat/Km	2
Kcat	2

Activity Type	# Activity
Individual protein	9
Protein-protein interaction	1
Single protein	4

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT152	Individual protein	Nuclear factor erythroid 2-related factor 2	Homo sapiens	Potency	n.a.	25929.0	nM	PubChem BioAssay data set
NPT135	Individual protein	Chromobox protein homolog 1	Homo sapiens	Potency	n.a.	44668.4	nM	PubChem BioAssay data set
NPT10	Individual protein	Geminin	Homo sapiens	Potency	n.a.	25929.0	nM	PubChem BioAssay data set
NPT156	Individual protein	Sphingomyelin phosphodiesterase	Homo sapiens	Potency	n.a.	31622.8	nM	PubChem BioAssay data set
NPT533	Protein-protein interaction	Runt-related transcription factor 1/Core-binding factor subunit beta	Homo sapiens	Potency	n.a.	31622.8	nM	PubChem BioAssay data set
NPT8	Individual protein	DNA polymerase iota	Homo sapiens	Potency	n.a.	14125.4	nM	PubChem BioAssay data set
NPT861	Individual protein	Isocitrate dehydrogenase [NADP] cytoplasmic	Homo sapiens	Potency	n.a.	10322.5	nM	PubChem BioAssay data set
NPT920	Individual protein	Alpha-synuclein	Homo sapiens	Potency	n.a.	14125.4	nM	PubChem BioAssay data set
NPT26086	Single protein	Adenylate kinase 1	Homo sapiens	Kcat/Km	=	0.16	10'6/M/s	PMID[25091927]
NPT26086	Single protein	Adenylate kinase 1	Homo sapiens	Kcat	=	240.0	/s	PMID[25091927]
NPT56	Individual protein	Beta-lactamase AmpC	Escherichia coli K-12	Potency	=	562.3	nM	PubChem BioAssay data set
NPT532	Individual protein	Lysine-specific demethylase 4A	Homo sapiens	Potency	n.a.	79432.8	nM	PubChem BioAssay data set
NPT24261	Single protein	Adenylate kinase 2	Homo sapiens	Kcat	=	110.0	/s	PMID[25091927]
NPT24261	Single protein	Adenylate kinase 2	Homo sapiens	Kcat/Km	=	0.5	10'6/M/s	PMID[25091927]

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 NPC121222 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	28506
0.1-0.2	21148
0.2-0.3	92
0.3-0.4	43
0.4-0.5	34
0.5-0.6	25
0.6-0.7	3
0.7-0.8	1
0.8-0.85	1
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.8333	Intermediate Similarity	NPC161224
0.7671	Intermediate Similarity	NPC326082
0.7121	Intermediate Similarity	NPC185991
0.7121	Intermediate Similarity	NPC321814
0.7049	Intermediate Similarity	NPC209525
0.7049	Intermediate Similarity	NPC161659
0.6429	Remote Similarity	NPC164952
0.6164	Remote Similarity	NPC130586
0.6	Remote Similarity	NPC174802
0.5921	Remote Similarity	NPC481375
0.5921	Remote Similarity	NPC606410
0.5857	Remote Similarity	NPC211025
0.5857	Remote Similarity	NPC85689
0.5811	Remote Similarity	NPC324198
0.5811	Remote Similarity	NPC326529
0.5811	Remote Similarity	NPC319100
0.5676	Remote Similarity	NPC302778
0.5676	Remote Similarity	NPC329404
0.5676	Remote Similarity	NPC212551
0.5652	Remote Similarity	NPC136349
0.5652	Remote Similarity	NPC219313
0.5616	Remote Similarity	NPC328479
0.5538	Remote Similarity	NPC317821
0.5522	Remote Similarity	NPC229974
0.5443	Remote Similarity	NPC316618
0.5443	Remote Similarity	NPC323091
0.5373	Remote Similarity	NPC156461
0.5373	Remote Similarity	NPC107374
0.5373	Remote Similarity	NPC600382
0.5373	Remote Similarity	NPC612067
0.5217	Remote Similarity	NPC609472
0.5147	Remote Similarity	NPC33996
0.5143	Remote Similarity	NPC309832
0.5063	Remote Similarity	NPC324484

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC121222 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5116
0.1-0.2	3870
0.2-0.3	92
0.3-0.4	49
0.4-0.5	14
0.5-0.6	7
0.6-0.7	1
0.7-0.8	1
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
0.7121	Intermediate Similarity	NPD283	Phase 4
0.6	Remote Similarity	NPD339	Phase 2
0.5652	Remote Similarity	NPD548	Clinical (unspecified phase)
0.5373	Remote Similarity	NPD249	Phase 4
0.5373	Remote Similarity	NPD250	Phase 4
0.5333	Remote Similarity	NPD4171	Clinical (unspecified phase)
0.5195	Remote Similarity	NPD338	Approved
0.5143	Remote Similarity	NPD193	Phase 2
0.5132	Remote Similarity	NPD242	Phase 4

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