NPASS Compound

Natural Product: NPC578146

Natural Product ID	NPC578146
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	(2~{S},3~{S},4~{R},5~{R})-2-(hydroxymethyl)-5-[6-[[(~{Z})-4-hydroxy-3-methyl-but-2-enyl]amino]purin-9-yl]tetrahydrofuran-3,4-diol
IUPAC Name	(2~{S},3~{S},4~{R},5~{R})-2-(hydroxymethyl)-5-[6-[[(~{Z})-4-hydroxy-3-methyl-but-2-enyl]amino]purin-9-yl]tetrahydrofuran-3,4-diol
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	n.a.
Chemical Classification	CHEMONTID:0000000 [Organic compounds]

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 46 48 0 0 0 0 0 0 0 0999 V2000 4.7131 -1.9750 -1.5007 C 0 0 0 0 0 0 0 0 0 0 0 0 4.8487 -0.7923 -0.5095 C 0 0 0 0 0 0 0 0 0 0 0 0 3.9233 0.0991 -0.5730 C 0 0 0 0 0 0 0 0 0 0 0 0 3.8115 1.3150 0.2475 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5441 1.2127 0.9723 N 0 0 0 0 0 0 0 0 0 0 0 0 1.3454 1.2003 0.2278 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2436 1.2843 -1.1019 N 0 0 0 0 0 0 0 0 0 0 0 0 0.0818 1.2760 -1.7800 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0616 1.1770 -1.0855 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.0585 1.0894 0.2286 C 0 0 0 0 0 0 0 0 0 0 0 0 0.1388 1.0992 0.9097 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1726 0.9990 2.1954 N 0 0 0 0 0 0 0 0 0 0 0 0 -1.5060 0.9296 2.3146 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0791 0.9844 1.0968 N 0 0 0 0 0 0 0 0 0 0 0 0 -3.4967 0.9314 0.9192 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.9126 -0.3726 1.2035 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.5838 -1.0359 0.0228 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.1340 -2.4422 -0.0061 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.5972 -3.1447 1.0676 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2425 -0.1564 -1.0161 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.6094 -0.3707 -1.0374 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.9951 1.2259 -0.4291 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.2110 1.9443 -0.3593 O 0 0 0 0 0 0 0 0 0 0 0 0 5.9986 -0.8130 0.3860 C 0 0 0 0 0 0 0 0 0 0 0 0 6.1453 0.2061 1.2682 O 0 0 0 0 0 0 0 0 0 0 0 0 5.2588 -1.6542 -2.4018 H 0 0 0 0 0 0 0 0 0 0 0 0 5.1211 -2.8452 -0.9857 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6602 -2.1436 -1.7226 H 0 0 0 0 0 0 0 0 0 0 0 0 3.1243 -0.0920 -1.3494 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5968 1.5155 0.9649 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6557 2.2277 -0.4097 H 0 0 0 0 0 0 0 0 0 0 0 0 2.5801 1.1528 2.0057 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0732 1.3492 -2.8827 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0141 0.8418 3.2792 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0464 1.5783 1.6640 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4784 -1.0299 -0.1170 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2235 -2.3855 0.1080 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7903 -2.9181 -0.9345 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0253 -3.9064 0.7601 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7663 -0.2653 -2.0099 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.1075 0.2048 -0.3982 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3565 1.7708 -1.1092 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2114 2.5414 0.4461 H 0 0 0 0 0 0 0 0 0 0 0 0 6.0044 -1.8296 0.9183 H 0 0 0 0 0 0 0 0 0 0 0 0 6.9248 -0.7903 -0.2803 H 0 0 0 0 0 0 0 0 0 0 0 0 6.8863 0.8069 1.0576 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 2 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 2 0 7 8 1 0 8 9 2 0 9 10 1 0 10 11 2 0 11 12 1 0 12 13 2 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 17 20 1 0 20 21 1 0 20 22 1 0 22 23 1 0 2 24 1 0 24 25 1 0 11 6 1 0 22 15 1 0 14 10 1 0 1 26 1 0 1 27 1 0 1 28 1 0 3 29 1 0 4 30 1 0 4 31 1 0 5 32 1 0 8 33 1 0 13 34 1 0 15 35 1 1 17 36 1 6 18 37 1 0 18 38 1 0 19 39 1 0 20 40 1 6 21 41 1 0 22 42 1 6 23 43 1 0 24 44 1 0 24 45 1 0 25 46 1 0 M END

Standard InCHIKey	GOSWTRUMMSCNCW-MLFWJJQPSA-N
Standard InCHI	InChI=1S/C15H21N5O5/c1-8(4-21)2-3-16-13-10-14(18-6-17-13)20(7-19-10)15-12(24)11(23)9(5-22)25-15/h2,6-7,9,11-12,15,21-24H,3-5H2,1H3,(H,16,17,18)/b8-2-/t9-,11+,12+,15+/m0/s1
SMILES	C/C(=C/CNC1=NC=NC2=C1N=CN2[C@@H]1O[C@@H](CO)[C@@H](O)[C@H]1O)CO

Calculated Properties

Physi-Chem Properties

Molecular Weight:	351.15	Volume:	328.08 ? Van der Waals volume.
Dense:	1.07	LogP:	-0.015 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.563 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.917 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	16.0
TPSA:	145.78 ? Topological Polar Surface Area.	H-Bond Acceptor:	10.0
H-Bond Donor:	5.0	Rings:	3.0
Heavy Atoms:	10.0

MedChem Properties

QED Drug-Likeness Score:	0.404	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.956	Fsp³:	0.533
MCE-18:	60.261 ? 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:	0	PAINS Alert:	0
Colloidal aggregators:	0.11	Fluc inhibitor:	0.03 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.062 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.078 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.018	Promiscuous compounds:	0.002

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.665	MDCK Permeability:	-5.229
Pgp-inhibitor:	0.0	Pgp-substrate:	0.597
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):	0.37
20% Bioavailability (F20%):	0.262	30% Bioavailability (F30%):	0.898
50% Bioavailability (F50%):	0.98

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.002	MRP1:	0.358
Plasma Protein Binding (PPB):	60.382%	Volume Distribution (VD):	-0.177
Fu:	38.939% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.808
OATP1B3 inhibitor:	0.68	BCRP inhibitor:	0.099
BSEP inhibitor:	0.022

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.035	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.008	CYP2D6-substrate:	0.044
CYP3A4-inhibitor:	0.011	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.976
HLM stability:	0.003 ? 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):

8.587

Half-life (T1/2):

1.563

ADMET: Toxicity

hERG Blockers:	0.054	hERG Blockers (10um):	0.267
Human Hepatotoxicity (H-HT):	0.795	Drug-induced Liver Injury (DILI):	0.344
AMES Toxicity:	0.756	Rat Oral Acute Toxicity:	0.032
Maximum Recommended Daily Dose:	0.03	Skin Sensitization:	0.981
Carcinogencity:	0.481	Eye Corrosion:	0.0
Eye Irritation:	0.422	Respiratory Toxicity:	0.224
Drug-induced Neurotoxicity:	0.167	Ototoxicity:	0.888
Hematotoxicity:	0.24	Drug-induced Nephrotoxicity:	0.626
Genotoxicity:	0.713	RPMI-8226 Immunitoxicity:	0.055
A549 Cytotoxicity:	0.022	Hek293 Cytotoxicity:	0.036
BCF:	0.157 ? 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:	2.649 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	4.322 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.295 ? 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
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11356-018-3422-z]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jarmap.2018.11.004]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2005.08.001]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0014-5793(03)00033-4]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)89267-5]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)98060-9]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1021/ac991142i]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1034/j.1399-3054.2003.00030.x]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1042/bst0160071]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1046/j.1365-3040.2001.00686.x]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.274.1.397]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.M302362200]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.M314195200]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1074/jbc.M411109200]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1104/pp.103.022368]
NPO18321	Medicago sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1104/pp.84.1.73]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1246/bcsj.30.618]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	cone	n.a.	PMID[10336650]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	leaf	n.a.	PMID[10952545]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10952545]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11005203]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11559179]
NPO18321	Medicago sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12232319]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12637544]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12805618]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12882150]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14745019]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15280363]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15286289]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15516765]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15666542]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15679315]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15820655]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15834012]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[15844959]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16252923]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1684022]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17611796]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	cone	n.a.	PMID[17624889]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18001808]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18057039]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18235971]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18318836]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18611049]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18768384]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19476340]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	leaf	n.a.	PMID[19521717]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	PMID[20947202]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20954721]
NPO2848	Ipomoea batatas	Species	Convolvulaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[20961090]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20973550]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21193570]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21194489]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21395888]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21800258]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21912858]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	cone	n.a.	PMID[22111577]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	flower	n.a.	PMID[22166201]
NPO18321	Medicago sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22208890]
NPO13726	Agrobacterium tumefaciens	Species	Rhizobiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[22466953]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23370715]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23479199]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23700450]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23790907]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	leaf	n.a.	PMID[23849114]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23950498]
NPO2848	Ipomoea batatas	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24074359]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	PMID[24163311]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24253552]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24285094]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24310066]
NPO13726	Agrobacterium tumefaciens	Species	Rhizobiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[24450804]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24948953]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[25433632]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	PMID[25457500]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25564559]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	PMID[26860358]
NPO2848	Ipomoea batatas	Species	Convolvulaceae	Eukaryota	n.a.	leaf	n.a.	PMID[27132824]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	PMID[27363486]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27432888]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27466882]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29154541]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30384263]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		PMID[31861466]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36500609]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37631012]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38354824]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38792127]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39199155]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	trunk bark	n.a.	PMID[556731]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8278506]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8987503]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO64426	Euglena gracilis	Species	Euglenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2848	Ipomoea batatas	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18321	Medicago sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13726	Agrobacterium tumefaciens	Species	Rhizobiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO46579	Corynebacterium fascians	Species	Nocardiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO31286	Dolichos lablab	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO53294	Mercurialis ambigua	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO55652	Ecklonia maxima	Species	Lessoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO18321	Medicago sativa	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO2848	Ipomoea batatas	Species	Convolvulaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO2848	Ipomoea batatas	Species	Convolvulaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Petiole	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Protoplast	n.a.	n.a.	Database[FooDB]
NPO2848	Ipomoea batatas	Species	Convolvulaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Sprout Seedling	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Tissue Culture	n.a.	n.a.	Database[FooDB]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	Tuber	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Wax	n.a.	n.a.	Database[FooDB]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO2848	Ipomoea batatas	Species	Convolvulaceae	Eukaryota	Tubers	n.a.		Database[FooDB]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	Tubers	n.a.		Database[FooDB]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18321	Medicago sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2848	Ipomoea batatas	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	root	n.a.	Database[MetaboLights]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[MetaboLights]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	seed	n.a.	Database[MetaboLights]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	Seeds	n.a.		Database[Phenol-Explorer]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO2848	Ipomoea batatas	Species	Convolvulaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	Fruits	n.a.		Database[Phenol-Explorer]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18321	Medicago sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2848	Ipomoea batatas	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO31286	Dolichos lablab	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18321	Medicago sativa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29314	Mangifera indica	Species	Anacardiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17694	Nicotiana tabacum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13879	Humulus lupulus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13726	Agrobacterium tumefaciens	Species	Rhizobiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO8541	Oryza sativa	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4359	Solanum tuberosum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11043	Pisum sativum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19866	Arabidopsis thaliana	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2848	Ipomoea batatas	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18321	Medicago sativa	Species	Fabaceae	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

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

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 NPC578146 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	26502
0.1-0.2	23161
0.2-0.3	96
0.3-0.4	50
0.4-0.5	35
0.5-0.6	5
0.6-0.7	5
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	1
0.95-1	0

Similarity Score	Similarity Level	Natural Product ID
0.9	High Similarity	NPC239737
0.7903	Intermediate Similarity	NPC605318
0.6508	Remote Similarity	NPC156461
0.6508	Remote Similarity	NPC107374
0.6508	Remote Similarity	NPC600382
0.6508	Remote Similarity	NPC612067
0.6	Remote Similarity	NPC250178
0.5692	Remote Similarity	NPC317821
0.5373	Remote Similarity	NPC54320
0.5352	Remote Similarity	NPC136349
0.5352	Remote Similarity	NPC219313
0.5325	Remote Similarity	NPC195140

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC578146 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6623
0.1-0.2	2380
0.2-0.3	81
0.3-0.4	35
0.4-0.5	21
0.5-0.6	4
0.6-0.7	5
0.7-0.8	0
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
0.6571	Remote Similarity	NPD1750	Clinical (unspecified phase)
0.6508	Remote Similarity	NPD249	Phase 4
0.6508	Remote Similarity	NPD250	Phase 4
0.6338	Remote Similarity	NPD1369	Phase 2
0.6081	Remote Similarity	NPD2965	Phase 2
0.5373	Remote Similarity	NPD219	Phase 4
0.5373	Remote Similarity	NPD220	Clinical (unspecified phase)
0.5352	Remote Similarity	NPD548	Clinical (unspecified phase)
0.506	Remote Similarity	NPD2624	Phase 2

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