NPASS Compound

Natural Product: NPC148835

Natural Product ID	NPC148835
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	Fraxidin
IUPAC Name	8-hydroxy-6,7-dimethoxychromen-2-one
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL2334351
PubChem CID	3083616
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000145] Coumarins and derivatives [CHEMONTID:0002908] Hydroxycoumarins

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 26 27 0 0 0 0 0 0 0 0999 V2000 -2.5197 2.4361 0.2699 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.8599 1.7720 -0.7853 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8114 0.9032 -0.4762 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.1026 -0.4249 -0.2440 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4016 -0.8408 -0.3244 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.8535 -2.1502 -0.1163 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0525 -1.2739 0.0613 C 0 0 0 0 0 0 0 0 0 0 0 0 1.2452 -0.8352 0.1369 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5314 0.4939 -0.0962 C 0 0 0 0 0 0 0 0 0 0 0 0 0.4892 1.3544 -0.4028 C 0 0 0 0 0 0 0 0 0 0 0 0 0.7416 2.7149 -0.6465 O 0 0 0 0 0 0 0 0 0 0 0 0 2.7617 0.9547 -0.0335 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7823 0.1482 0.2593 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9364 0.6533 0.3033 O 0 0 0 0 0 0 0 0 0 0 0 0 3.5853 -1.1880 0.5052 C 0 0 0 0 0 0 0 0 0 0 0 0 2.3092 -1.6926 0.4457 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0602 1.7535 0.9473 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.7550 3.0581 0.7999 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2527 3.1711 -0.1615 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5883 -2.7432 -1.0226 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4577 -2.6076 0.8038 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.9625 -2.1248 -0.0806 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2939 -2.3068 0.2400 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0717 3.2994 0.0945 H 0 0 0 0 0 0 0 0 0 0 0 0 4.4294 -1.8084 0.7380 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0881 -2.7165 0.6252 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 2 0 4 5 1 0 5 6 1 0 4 7 1 0 7 8 2 0 8 9 1 0 9 10 2 0 10 11 1 0 9 12 1 0 12 13 1 0 13 14 2 0 13 15 1 0 15 16 2 0 10 3 1 0 16 8 1 0 1 17 1 0 1 18 1 0 1 19 1 0 6 20 1 0 6 21 1 0 6 22 1 0 7 23 1 0 11 24 1 0 15 25 1 0 16 26 1 0 M END

Standard InCHIKey	QNFBKOHHLAWWTC-UHFFFAOYSA-N
Standard InCHI	InChI=1S/C11H10O5/c1-14-7-5-6-3-4-8(12)16-10(6)9(13)11(7)15-2/h3-5,13H,1-2H3
SMILES	COc1c(OC)cc2c(c1O)oc(=O)cc2

Calculated Properties

Physi-Chem Properties

Molecular Weight:	222.05	Volume:	212.468 ? Van der Waals volume.
Dense:	1.045	LogP:	1.038 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	1.282 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-3.064 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	2.0	Rigid Bonds:	12.0
TPSA:	68.9 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	1.0	Rings:	2.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.78	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	2.341	Fsp³:	0.182
MCE-18:	12.0 ? 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:	0.418	Fluc inhibitor:	0.143 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.932 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.366 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.707	Promiscuous compounds:	0.77

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.033	MDCK Permeability:	-4.712
Pgp-inhibitor:	0.007	Pgp-substrate:	0.0
PAMPA:	0.309 ? 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):	0.021
20% Bioavailability (F20%):	0.707	30% Bioavailability (F30%):	0.546
50% Bioavailability (F50%):	0.443

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.001	MRP1:	0.996
Plasma Protein Binding (PPB):	85.354%	Volume Distribution (VD):	-0.474
Fu:	13.523% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.985
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.0
BSEP inhibitor:	0.895

ADMET: Metabolism

CYP1A2-inhibitor:	0.604	CYP1A2-substrate:	0.038
CYP2C19-inhibitor:	0.502	CYP2C19-substrate:	0.028
CYP2C9-inhibitor:	0.857	CYP2C9-substrate:	0.012
CYP2D6-inhibitor:	0.747	CYP2D6-substrate:	0.032
CYP3A4-inhibitor:	0.383	CYP3A4-substrate:	0.124
CYP2B6-substrate:	0.697	CYP2C8-inhibitor:	0.777
HLM stability:	0.778 ? 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):

7.468

Half-life (T1/2):

1.184

ADMET: Toxicity

hERG Blockers:	0.083	hERG Blockers (10um):	0.369
Human Hepatotoxicity (H-HT):	0.451	Drug-induced Liver Injury (DILI):	0.733
AMES Toxicity:	0.457	Rat Oral Acute Toxicity:	0.455
Maximum Recommended Daily Dose:	0.53	Skin Sensitization:	0.358
Carcinogencity:	0.699	Eye Corrosion:	0.794
Eye Irritation:	0.983	Respiratory Toxicity:	0.698
Drug-induced Neurotoxicity:	0.312	Ototoxicity:	0.161
Hematotoxicity:	0.318	Drug-induced Nephrotoxicity:	0.209
Genotoxicity:	0.718	RPMI-8226 Immunitoxicity:	0.09
A549 Cytotoxicity:	0.083	Hek293 Cytotoxicity:	0.234
BCF:	0.315 ? 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:	2.851 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	3.927 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.427 ? 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
NPO28941	Pogonopus speciosus	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10514334]
NPO28697	Talaromyces convolutus	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10869198]
NPO1033	Plectranthus nummularius	Species	Lamiaceae	Eukaryota	n.a.	leaf	n.a.	PMID[11558608]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	fruits	n.a.	n.a.	PMID[12467621]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[12828478]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	Roots	n.a.	n.a.	PMID[14575431]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[15520511]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[15620254]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	root	n.a.	PMID[16212233]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[1624939]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	Whole plant	n.a.	n.a.	PMID[16643038]
NPO11507	Entada africana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16989528]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17027268]
NPO10872	Aglaia ponapensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17055270]
NPO16755	Saposhnikovia divaricata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17703773]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	root	n.a.	PMID[1800638]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19299148]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	roots	n.a.	n.a.	PMID[19299148]
NPO11530	Heterosigma akashiwo	Species	Chattonellaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19659728]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19715321]
NPO28941	Pogonopus speciosus	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1982768]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19919052]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[19931461]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20038159]
NPO29000	Nephila clavata	Species	Nephilidae	Eukaryota	n.a.	n.a.	n.a.	PMID[21188966]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	root bark	n.a.	n.a.	PMID[23282106]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23403897]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24467387]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	roots	n.a.	n.a.	PMID[25066952]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	aerial part	n.a.	n.a.	PMID[25442304]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25905468]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	Root Bark	n.a.	n.a.	PMID[26982999]
NPO5401	Monanchora unguiculata	Species	Crambeidae	Eukaryota	n.a.	n.a.	n.a.	PMID[28368118]
NPO9644	Euphorbia resinifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29667820]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31397570]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37446592]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38163555]
NPO16755	Saposhnikovia divaricata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38830452]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38961030]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	fruits	n.a.	n.a.	PMID[9090870]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21758	Thiocystis gelatinosa	Species	Chromatiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28875	Mycobacterium aurum	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29268	Phyllanthus simplex	Species	Leiothrichidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10872	Aglaia ponapensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12988	Blainvillea latifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11140	Coprinopsis cinerea	Species	Psathyrellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3924	Penicillium alutaceum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO893	Helichrysum sutherlandii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29000	Nephila clavata	Species	Nephilidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3564	Fraxinus stylosa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23778	Reseda luteola	Species	Resedaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5401	Monanchora unguiculata	Species	Crambeidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13494	Prosopis kuntzei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9644	Euphorbia resinifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14297	Dioscorea gracillima	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15212	Fraxinus chinensis	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28941	Pogonopus speciosus	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11684	Iberis sempervirens	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28697	Talaromyces convolutus	Species	Trichocomaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14049	Fumaria indica	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9024	Aralidium pinnatifidum	Species	Torricelliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15167	Eichhornia crassipes	Species	Pontederiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16755	Saposhnikovia divaricata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20383	Stenocereus thurberi	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20997	Eurycoma sp.	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9661	Fraxinus szaboana	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8220	Russula sardonia	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20318	Acinetobacter baumannii	Species	Moraxellaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12994	Choriaster granulatus	Species	Oreasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11530	Heterosigma akashiwo	Species	Chattonellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13604	Dermocybe cardinalis	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14297	Dioscorea gracillima	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9661	Fraxinus szaboana	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16755	Saposhnikovia divaricata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3564	Fraxinus stylosa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO31211	Eurycoma sp	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15212	Fraxinus chinensis	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15167	Eichhornia crassipes	Species	Pontederiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO29245	Nepeta leucophylla	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9644	Euphorbia resinifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10872	Aglaia ponapensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16755	Saposhnikovia divaricata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9644	Euphorbia resinifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16564	Euonymus phellomanus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1033	Plectranthus nummularius	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15167	Eichhornia crassipes	Species	Pontederiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20997	Eurycoma sp.	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14297	Dioscorea gracillima	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28835	Gentianella nitida	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9661	Fraxinus szaboana	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15212.1	Fraxinus chinensis subsp. rhynchophylla	Subspecies	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3564	Fraxinus stylosa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15212	Fraxinus chinensis	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO29245	Nepeta leucophylla	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7043	Fuligo candida	Species	Physaraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10872	Aglaia ponapensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO893	Helichrysum sutherlandii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9661	Fraxinus szaboana	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14297	Dioscorea gracillima	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15212	Fraxinus chinensis	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3564	Fraxinus stylosa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16755	Saposhnikovia divaricata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15212.1	Fraxinus chinensis subsp. rhynchophylla	Subspecies	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO3564	Fraxinus stylosa	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO15212	Fraxinus chinensis	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9661	Fraxinus szaboana	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9024	Aralidium pinnatifidum	Species	Torricelliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13604	Dermocybe cardinalis	Species	Cortinariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29165	Toona febrifuga	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1418	Boletinus paluster	Species	Gyrodontaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12994	Choriaster granulatus	Species	Oreasteridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2084	Acinetobacter calcoaceticus	Species	Moraxellaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO6626	Pteris spinulosa	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20318	Acinetobacter baumannii	Species	Moraxellaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO5401	Monanchora unguiculata	Species	Crambeidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11072	Geigeria schinzii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6014	Goniothalamus undulatus	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14280	Helichrysum angustifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3576	Bersama swinnyi	Species	Melianthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14297	Dioscorea gracillima	Species	Dioscoreaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3924	Penicillium alutaceum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11530	Heterosigma akashiwo	Species	Chattonellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28941	Pogonopus speciosus	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11507	Entada africana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9644	Euphorbia resinifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8820	Lophocereus marginatus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8220	Russula sardonia	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14049	Fumaria indica	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13692	Leontice kiangnanensis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12026	Papaver radicatum	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6370	Roemeria carica	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2505	Pachycereus pringlei	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20383	Stenocereus thurberi	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9375	Medium grandiflorum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO893	Helichrysum sutherlandii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29367	Ormosia excelsa	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13494	Prosopis kuntzei	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13798	Cheilanthes marantae	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22888	Lophiostoma vaginatispora	Species	Lophiostomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15167	Eichhornia crassipes	Species	Pontederiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28875	Mycobacterium aurum	Species	Mycobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO12890	Ophryosporus charua	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8640	Nemuaron humboldtii	Species	Atherospermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9358	Pseuduvaria indochinensis	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12577	Pinus glauca	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29000	Nephila clavata	Species	Nephilidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11684	Iberis sempervirens	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4360	Hendersonula toruloidea	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO12988	Blainvillea latifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29221	Sarcandra glabra	Species	Chloranthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21758	Thiocystis gelatinosa	Species	Chromatiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO29268	Phyllanthus simplex	Species	Leiothrichidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9786	Monomeria barbata	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7043	Fuligo candida	Species	Physaraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11140	Coprinopsis cinerea	Species	Psathyrellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13383	Schumanniophyton magnificum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29245	Nepeta leucophylla	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8401	Pteris setuloso-costulata	Species	Pteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11153	Entada polystachya	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15449	Echium rubrum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14865	Vitex limonifolia	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1033	Plectranthus nummularius	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10872	Aglaia ponapensis	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10425	Dichotomophthora lutea	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17823	Lycium chinense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28915	Tephrosia barbigera	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23429	Lycium barbarum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17585	Senecio dolichodoryius	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28890	Geranium sanguineum	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28835	Gentianella nitida	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16251	Aconitum gigas	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15212	Fraxinus chinensis	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23778	Reseda luteola	Species	Resedaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16564	Euonymus phellomanus	Species	Celastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29232	Polysiphonia fastigiata	Species	Rhodomelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17704	Ceanothus sanguineus	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3976	Artemisia mesatlantica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15212.1	Fraxinus chinensis subsp. rhynchophylla	Subspecies	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10510	Aconitum naviculare	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28697	Talaromyces convolutus	Species	Trichocomaceae	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
NPO16755	Saposhnikovia divaricata	n.a.	Roots	190.02608, 162.03116, 179.03395, 134.03632	n.a.	n.a.	%	PMID[38830452]
NPO16755	Saposhnikovia divaricata	n.a.	Roots	0.10	n.a.	n.a.	%	PMID[38830452]
NPO16755	Saposhnikovia divaricata	n.a.	Roots	0.01	n.a.	n.a.	%	PMID[38830452]

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
Ki	6

Activity Type	# Activity
Individual protein	6

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT233	Individual protein	Carbonic anhydrase II	Homo sapiens	Ki	>	100000.0	nM	PMID[22892213]
NPT3101	Individual protein	Carbonic anhydrase XIII	Homo sapiens	Ki	=	95700.0	nM	PMID[22892213]
NPT955	Individual protein	Carbonic anhydrase VII	Homo sapiens	Ki	=	5560.0	nM	PMID[22892213]
NPT949	Individual protein	Carbonic anhydrase XII	Homo sapiens	Ki	=	7840.0	nM	PMID[22892213]
NPT948	Individual protein	Carbonic anhydrase IX	Homo sapiens	Ki	=	850.0	nM	PMID[22892213]
NPT947	Individual protein	Carbonic anhydrase I	Homo sapiens	Ki	=	9890.0	nM	PMID[22892213]

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 NPC148835 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	30871
0.1-0.2	16533
0.2-0.3	2144
0.3-0.4	256
0.4-0.5	42
0.5-0.6	9
0.6-0.7	2
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	Natural Product ID
0.7347	Intermediate Similarity	NPC606257
0.6444	Remote Similarity	NPC95162
0.6087	Remote Similarity	NPC26673
0.5745	Remote Similarity	NPC82271
0.5556	Remote Similarity	NPC240722
0.5435	Remote Similarity	NPC244799
0.5417	Remote Similarity	NPC20511
0.5417	Remote Similarity	NPC52086
0.5417	Remote Similarity	NPC76336
0.537	Remote Similarity	NPC471763
0.5319	Remote Similarity	NPC92830
0.5102	Remote Similarity	NPC139548

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC148835 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5606
0.1-0.2	3456
0.2-0.3	80
0.3-0.4	7
0.4-0.5	1
0.5-0.6	0
0.6-0.7	0
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
		NPD

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