NPASS Compound

Natural Product: NPC316618

Natural Product ID	NPC316618
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Adenosine-5'-Phosphosulfate
IUPAC Name	[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl sulfo hydrogen phosphate
Synonyms	Adenosine-5'-Phosphosulfate
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL572546
PubChem CID	10238
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000289] Nucleosides, nucleotides, and analogues [CHEMONTID:0001506] Purine nucleotides [CHEMONTID:0001544] Purine ribonucleotides [CHEMONTID:0001617] Purine ribonucleoside 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 41 43 0 0 0 0 0 0 0 0999 V2000 -4.1016 2.1833 -2.1410 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.8432 2.8457 -1.2523 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.7117 2.5809 0.0488 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8137 1.6279 0.4669 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0531 0.9492 -0.4486 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.2231 1.2525 -1.7456 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.2424 0.0652 0.1636 N 0 0 0 0 0 0 0 0 0 0 0 0 -2.4942 0.1875 1.4795 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4502 1.1373 1.6743 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.3066 -0.8165 -0.5028 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1904 -2.1516 0.1970 C 0 0 0 0 0 0 0 0 0 0 0 0 0.2735 -2.4839 -0.0262 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7142 -1.4099 -0.9624 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0139 -0.3009 -0.5303 O 0 0 0 0 0 0 0 0 0 0 0 0 2.2015 -1.1589 -0.9214 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6663 -0.8623 0.3361 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3354 -0.6063 0.2334 P 0 0 0 0 0 0 0 0 0 0 0 0 4.8576 -1.5869 -0.8103 O 0 0 0 0 0 0 0 0 0 0 0 0 5.1146 -0.8837 1.6847 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6831 0.9469 -0.3589 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7060 1.7683 0.7095 S 0 0 0 0 0 0 0 0 0 0 0 0 5.5645 1.2013 2.1098 O 0 0 0 0 0 0 0 0 0 0 0 0 7.1497 1.6074 0.3094 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2304 3.3778 0.6905 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4314 -3.7237 -0.6452 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.9923 -3.0740 -0.4778 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.4946 3.2753 1.0329 N 0 0 0 0 0 0 0 0 0 0 0 0 -4.1801 2.3704 -3.2035 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0046 -0.3863 2.2455 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6162 -1.0006 -1.5519 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4449 -2.0905 1.2737 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7672 -2.4476 0.9712 H 0 0 0 0 0 0 0 0 0 0 0 0 0.3785 -1.6563 -1.9697 H 0 0 0 0 0 0 0 0 0 0 0 0 2.6883 -2.0827 -1.3130 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4582 -0.3448 -1.6245 H 0 0 0 0 0 0 0 0 0 0 0 0 5.5493 -1.7739 1.6612 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3144 3.4938 0.3425 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0021 -4.4558 -0.1380 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4005 -2.6896 -1.2953 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4174 2.9703 1.3544 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0871 4.1458 1.4398 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 2 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 2 0 5 7 1 0 7 8 1 0 8 9 2 0 7 10 1 0 10 11 1 0 11 12 1 0 12 13 1 0 13 14 1 0 13 15 1 0 15 16 1 0 16 17 1 0 17 18 2 0 17 19 1 0 17 20 1 0 20 21 1 0 21 22 2 0 21 23 2 0 21 24 1 0 12 25 1 0 11 26 1 0 3 27 1 0 6 1 1 0 9 4 1 0 14 10 1 0 1 28 1 0 8 29 1 0 10 30 1 0 11 31 1 0 12 32 1 0 13 33 1 0 15 34 1 0 15 35 1 0 19 36 1 0 24 37 1 0 25 38 1 0 26 39 1 0 27 40 1 0 27 41 1 0 M END

Standard InCHIKey	IRLPACMLTUPBCL-KQYNXXCUSA-N
Standard InCHI	InChI=1S/C10H14N5O10PS/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(24-10)1-23-26(18,19)25-27(20,21)22/h2-4,6-7,10,16-17H,1H2,(H,18,19)(H2,11,12,13)(H,20,21,22)/t4-,6-,7-,10-/m1/s1
SMILES	C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)COP(=O)(O)OS(=O)(=O)O)O)O)N

Calculated Properties

Physi-Chem Properties

Molecular Weight:	427.02	Volume:	326.523 ? Van der Waals volume.
Dense:	1.308	LogP:	-2.175 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-0.04 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.555 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	18.0
TPSA:	229.44 ? Topological Polar Surface Area.	H-Bond Acceptor:	15.0
H-Bond Donor:	6.0	Rings:	3.0
Heavy Atoms:	17.0

MedChem Properties

QED Drug-Likeness Score:	0.247	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.21	Fsp³:	0.5
MCE-18:	81.267 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Accepted
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	1	PAINS Alert:	0
Colloidal aggregators:	0.003	Fluc inhibitor:	0.001 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.037 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.072 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.152	Promiscuous compounds:	0.03

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.836	MDCK Permeability:	-5.129
Pgp-inhibitor:	0.0	Pgp-substrate:	0.0
PAMPA:	0.999 ? 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):	0.985
20% Bioavailability (F20%):	0.035	30% Bioavailability (F30%):	0.989
50% Bioavailability (F50%):	0.351

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.0	MRP1:	0.715
Plasma Protein Binding (PPB):	20.674%	Volume Distribution (VD):	-0.758
Fu:	74.076% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.986
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.002
BSEP inhibitor:	0.234

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.671	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.0 ? 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):

2.365

Half-life (T1/2):

1.745

ADMET: Toxicity

hERG Blockers:	0.016	hERG Blockers (10um):	0.033
Human Hepatotoxicity (H-HT):	0.507	Drug-induced Liver Injury (DILI):	0.988
AMES Toxicity:	0.475	Rat Oral Acute Toxicity:	0.267
Maximum Recommended Daily Dose:	0.965	Skin Sensitization:	0.921
Carcinogencity:	0.762	Eye Corrosion:	0.0
Eye Irritation:	0.407	Respiratory Toxicity:	0.883
Drug-induced Neurotoxicity:	0.783	Ototoxicity:	0.789
Hematotoxicity:	0.31	Drug-induced Nephrotoxicity:	0.894
Genotoxicity:	1.0	RPMI-8226 Immunitoxicity:	0.061
A549 Cytotoxicity:	0.012	Hek293 Cytotoxicity:	0.221
BCF:	0.098 ? 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:	2.347 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	3.553 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.463 ? 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
Kd	1
Ki	1

Activity Type	# Activity
Others	2

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT2	Others	Unspecified	n.a.	Kd	=	200.0	nM	PMID[19678707]
NPT2	Others	Unspecified	n.a.	Ki	=	200.0	nM	PMID[19678707]

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 NPC316618 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	31023
0.1-0.2	18641
0.2-0.3	69
0.3-0.4	52
0.4-0.5	32
0.5-0.6	22
0.6-0.7	8
0.7-0.8	3
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.7606	Intermediate Similarity	NPC324198
0.7606	Intermediate Similarity	NPC326529
0.7606	Intermediate Similarity	NPC319100
0.7536	Intermediate Similarity	NPC185991
0.7536	Intermediate Similarity	NPC321814
0.75	Intermediate Similarity	NPC130586
0.7297	Intermediate Similarity	NPC174802
0.72	Intermediate Similarity	NPC606410
0.7105	Intermediate Similarity	NPC323091
0.7059	Intermediate Similarity	NPC136349
0.7059	Intermediate Similarity	NPC219313
0.6494	Remote Similarity	NPC324484
0.6486	Remote Similarity	NPC328479
0.6098	Remote Similarity	NPC484199
0.6087	Remote Similarity	NPC156461
0.6087	Remote Similarity	NPC107374
0.6087	Remote Similarity	NPC600382
0.6087	Remote Similarity	NPC612067
0.6029	Remote Similarity	NPC317821
0.5914	Remote Similarity	NPC21461
0.5833	Remote Similarity	NPC484196
0.5696	Remote Similarity	NPC302778
0.5696	Remote Similarity	NPC329404
0.5696	Remote Similarity	NPC212551
0.567	Remote Similarity	NPC90902
0.557	Remote Similarity	NPC164952
0.5542	Remote Similarity	NPC606116
0.5443	Remote Similarity	NPC121222
0.5432	Remote Similarity	NPC195140
0.5375	Remote Similarity	NPC472816
0.5375	Remote Similarity	NPC600171
0.5357	Remote Similarity	NPC161224
0.5357	Remote Similarity	NPC481375
0.5347	Remote Similarity	NPC611055
0.5309	Remote Similarity	NPC324033
0.5301	Remote Similarity	NPC321458
0.5256	Remote Similarity	NPC261595
0.5256	Remote Similarity	NPC85689
0.5176	Remote Similarity	NPC325906
0.5135	Remote Similarity	NPC229974
0.5063	Remote Similarity	NPC211025

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC316618 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5257
0.1-0.2	3744
0.2-0.3	71
0.3-0.4	46
0.4-0.5	20
0.5-0.6	5
0.6-0.7	4
0.7-0.8	3
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
0.7536	Intermediate Similarity	NPD283	Phase 4
0.7297	Intermediate Similarity	NPD339	Phase 2
0.7059	Intermediate Similarity	NPD548	Clinical (unspecified phase)
0.6622	Remote Similarity	NPD4171	Clinical (unspecified phase)
0.6447	Remote Similarity	NPD338	Approved
0.6087	Remote Similarity	NPD249	Phase 4
0.6087	Remote Similarity	NPD250	Phase 4
0.567	Remote Similarity	NPD4716	Approved
0.557	Remote Similarity	NPD242	Phase 4
0.5412	Remote Similarity	NPD1776	Approved
0.5256	Remote Similarity	NPD247	Clinical (unspecified phase)
0.5176	Remote Similarity	NPD1777	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