NPASS Compound

Natural Product: NPC322801

Natural Product ID	NPC322801
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	2-Amino-2-Deoxy-D-Glucose
IUPAC Name	(3R,4R,5S,6R)-3-amino-6-(hydroxymethyl)oxane-2,4,5-triol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL493287
PubChem CID	439213
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0001540] Monosaccharides [CHEMONTID:0001498] Hexoses

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 25 25 0 0 0 0 0 0 0 0999 V2000 2.5419 0.1856 0.3978 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1702 -0.2589 -0.0415 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5055 0.7949 -0.8734 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.9419 0.9955 -0.5708 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6504 -0.2641 -0.1339 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.7414 -1.2994 0.4333 C 0 0 0 0 0 0 0 0 0 0 0 0 0.3795 -0.6876 1.0119 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.3895 -2.1526 1.3127 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.6090 0.1450 0.9054 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.6365 1.4884 -1.6720 O 0 0 0 0 0 0 0 0 0 0 0 0 0.6387 0.5337 -2.2405 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5226 1.2281 1.2873 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1199 -0.6654 0.8194 H 0 0 0 0 0 0 0 0 0 0 0 0 3.0824 0.5205 -0.5158 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3132 -1.1528 -0.7067 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0433 1.7513 -0.6917 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.0201 1.7953 0.2220 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.2249 -0.7315 -0.9635 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.3614 -1.9264 -0.4052 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8454 -2.1517 2.1555 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7456 -0.6934 1.5065 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0883 0.8432 1.4886 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2777 1.1464 -2.5278 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8730 -0.4082 -2.4201 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3420 0.9640 2.2227 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 1 0 6 8 1 0 5 9 1 0 4 10 1 0 3 11 1 0 1 12 1 0 7 2 1 0 1 13 1 0 1 14 1 0 2 15 1 0 3 16 1 0 4 17 1 0 5 18 1 0 6 19 1 0 8 20 1 0 9 21 1 0 9 22 1 0 10 23 1 0 11 24 1 0 12 25 1 0 M END

Standard InCHIKey	MSWZFWKMSRAUBD-IVMDWMLBSA-N
Standard InCHI	InChI=1S/C6H13NO5/c7-3-5(10)4(9)2(1-8)12-6(3)11/h2-6,8-11H,1,7H2/t2-,3-,4-,5-,6?/m1/s1
SMILES	C(C1C(C(C(C(O1)O)N)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	179.08	Volume:	158.724 ? Van der Waals volume.
Dense:	1.128	LogP:	-2.178 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-1.495 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	0.232 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	6.0
TPSA:	116.17 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	6.0	Rings:	1.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.288	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.844	Fsp³:	1.0
MCE-18:	22.667 ? 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:	Accepted	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.006	Fluc inhibitor:	0.004 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.056 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.292	Promiscuous compounds:	0.075

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.139	MDCK Permeability:	-5.114
Pgp-inhibitor:	0.0	Pgp-substrate:	0.976
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):	0.962
20% Bioavailability (F20%):	0.624	30% Bioavailability (F30%):	0.87
50% Bioavailability (F50%):	0.971

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.024	MRP1:	0.546
Plasma Protein Binding (PPB):	18.993%	Volume Distribution (VD):	-0.563
Fu:	84.797% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.093
OATP1B3 inhibitor:	0.919	BCRP inhibitor:	0.021
BSEP inhibitor:	0.0

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.998	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.053	CYP2C9-substrate:	0.002
CYP2D6-inhibitor:	0.063	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.033	CYP3A4-substrate:	0.002
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.078
HLM stability:	0.006 ? 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):

3.772

Half-life (T1/2):

2.144

ADMET: Toxicity

hERG Blockers:	0.064	hERG Blockers (10um):	0.36
Human Hepatotoxicity (H-HT):	0.528	Drug-induced Liver Injury (DILI):	0.168
AMES Toxicity:	0.643	Rat Oral Acute Toxicity:	0.309
Maximum Recommended Daily Dose:	0.146	Skin Sensitization:	0.43
Carcinogencity:	0.367	Eye Corrosion:	0.038
Eye Irritation:	0.775	Respiratory Toxicity:	0.238
Drug-induced Neurotoxicity:	0.422	Ototoxicity:	0.814
Hematotoxicity:	0.177	Drug-induced Nephrotoxicity:	0.16
Genotoxicity:	0.104	RPMI-8226 Immunitoxicity:	0.052
A549 Cytotoxicity:	0.034	Hek293 Cytotoxicity:	0.096
BCF:	0.09 ? 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:	1.104 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	1.804 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	0.851 ? 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
Inhibition	9
AC50	31
FC	1
GI	4
Hit score	1
Activity	55

Activity Type	# Activity
Individual protein	31
Tissue	4
Organism	63
Nucleic acid	1
Non-molecular	2
Protein complex	1

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT291	Individual protein	Serotonin 2b (5-HT2b) receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT263	Individual protein	Muscarinic acetylcholine receptor M2	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT145	Individual protein	Mu opioid receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT30	Individual protein	Cyclooxygenase-1	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT222	Individual protein	Alpha-2a adrenergic receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT2769	Individual protein	Thromboxane A2 receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT228	Individual protein	Norepinephrine transporter	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT108	Individual protein	Estrogen receptor alpha	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT242	Individual protein	Dopamine D1 receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT1788	Individual protein	Alpha-1a adrenergic receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT2761	Individual protein	Phosphodiesterase 4A	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT262	Individual protein	Muscarinic acetylcholine receptor M1	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT1478	Individual protein	Vascular endothelial growth factor receptor 2	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT153	Individual protein	Androgen Receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT244	Individual protein	Dopamine D3 receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT295	Individual protein	Serotonin transporter	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT246	Individual protein	Dopamine transporter	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT204	Individual protein	Acetylcholinesterase	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT218	Individual protein	Adenosine A3 receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT261	Individual protein	Monoamine oxidase A	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT613	Individual protein	Solute carrier family 22 member 1	Homo sapiens	Inhibition	=	13.9	%	PMID[18788725]
NPT987	Individual protein	Histamine H3 receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT4383	Nucleic acid	Ribosomal RNA A-site	n.a.	Kd	~	1000000.0	nM	PMID[14741271]
NPT542	Individual protein	Progesterone receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT98	Individual protein	HERG	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT92	Individual protein	Serotonin 1a (5-HT1a) receptor	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT5104	Individual protein	Phosphodiesterase 3A	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT670	Individual protein	Thrombin	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20555	Organism	SARS-CoV-2	Severe acute respiratory syndrome coronavirus 2	Hit score	=	0.1709	n.a.	DOI[10.1101/2020.04.21.054387]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Inhibition	=	10.3	%	PMID[22501024]
NPT20529	Non-molecular	NON-PROTEIN TARGET	n.a.	Inhibition	=	14.1	%	PMID[22501024]
NPT834	Organism	Trametes versicolor	Trametes versicolor	GI	=	11.0	%	PMID[21308954]
NPT834	Organism	Trametes versicolor	Trametes versicolor	GI	=	0.0	%	PMID[21308954]
NPT29392	Protein complex	Gamma-aminobutyric acid receptor subunit alpha-1/alpha-2/beta-2/gamma-2	Homo sapiens	AC50	>	30000.0	nM	PMID[37468498]
NPT5271	Tissue	Cartilage	Bos taurus	Inhibition	=	19.0	%	PMID[22501024]
NPT5271	Tissue	Cartilage	Bos taurus	Inhibition	=	3.4	%	PMID[22501024]
NPT5271	Tissue	Cartilage	Bos taurus	Inhibition	=	0.8	%	PMID[22501024]
NPT5271	Tissue	Cartilage	Bos taurus	FC	=	2.0	n.a.	PMID[22501024]
NPT5329	Organism	Poria	Poria	GI	=	25.9	%	PMID[21308954]
NPT5329	Organism	Poria	Poria	GI	=	10.2	%	PMID[21308954]

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	1208.0	Karmen	PMID[15225726]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	5.45	nmol/g tissue	PMID[15225726]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	2.57	nmol/g tissue	PMID[15225726]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	2.33	nmol/g tissue	PMID[15225726]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	6.31	nmol/g tissue	PMID[15225726]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	26.31	nmol/g tissue	PMID[15225726]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	5.78	nmol/g tissue	PMID[15225726]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	13.83	nmol/g tissue	PMID[15225726]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	0.98	nmol/g tissue	PMID[15225726]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	7280.0	Karmen	PMID[15225726]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	1.94	nmol/g tissue	PMID[15225726]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	43.9	nmol/g tissue	PMID[15225726]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	36.2	nmol/g tissue	PMID[15225726]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	11.1	nmol/g tissue	PMID[15225726]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	11.5	nmol/g tissue	PMID[15225726]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	3.9	nmol/g tissue	PMID[15225726]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	2516.0	Karmen	PMID[15225726]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	5.6	nmol/g tissue	PMID[15225726]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	37.8	nmol/g tissue	PMID[15225726]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	35.6	nmol/g tissue	PMID[15225726]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	4.6	nmol/g tissue	PMID[15225726]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	7.1	nmol/g tissue	PMID[15225726]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	4.8	nmol/g tissue	PMID[15225726]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	7.0	nmol/g tissue	PMID[15225726]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	173.7	nmol/g tissue	PMID[15225726]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	166.3	nmol/g tissue	PMID[15225726]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	59.6	nmol/g tissue	PMID[15225726]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	18480.0	Karmen	PMID[15225726]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	67.2	nmol/g tissue	PMID[15225726]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	12.4	nmol/g tissue	PMID[15225726]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	1.06	nmol/g tissue	PMID[15225726]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	3.13	nmol/g tissue	PMID[15225726]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	0.18	nmol/g tissue	PMID[15225726]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	0.9	nmol/g tissue	PMID[15225726]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	0.42	nmol/g tissue	PMID[15225726]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	0.65	nmol/g tissue	PMID[15225726]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	1.16	nmol/g tissue	PMID[15225726]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	52.3	nmol/g	PMID[16530410]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	124.0	nmol/g	PMID[16530410]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	517.0	nmol/g	PMID[16530410]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	793.0	nmol/g	PMID[16530410]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	2560.0	nmol/g	PMID[16530410]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	25.8	nmol/g	PMID[16530410]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	49.7	nmol/g	PMID[16530410]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	295.0	nmol/g	PMID[16530410]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	426.0	nmol/g	PMID[16530410]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	1519.0	nmol/g	PMID[16530410]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	1571.0	nmol/g	PMID[16530410]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	1137.0	nmol/g	PMID[16530410]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	1118.0	nmol/g	PMID[16530410]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	1104.0	nmol/g	PMID[16530410]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Activity	=	978.0	nmol/g	PMID[16530410]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	15.17	%	PMID[17481895]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	16.12	%	PMID[17481895]
NPT29	Organism	Rattus norvegicus	Rattus norvegicus	Inhibition	=	21.61	%	PMID[17481895]

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 NPC322801 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.5 or Top200).

Similarity Score	Similarity Level	Natural Product ID

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC322801 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

Similarity Score	Similarity Level	Drug ID	Developmental Stage

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