NPASS Compound

Natural Product: NPC300424

Natural Product ID	NPC300424
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	DFUOJBWSSSODTR-SJKOYZFVSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	12468617
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes

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 43 44 0 0 0 0 0 0 0 0999 V2000 4.4108 -1.9237 -2.0185 C 0 0 0 0 0 0 0 0 0 0 0 0 4.7756 -1.6148 -0.6834 O 0 0 0 0 0 0 0 0 0 0 0 0 3.8405 -1.1999 0.2583 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5186 -1.0677 -0.0576 C 0 0 0 0 0 0 0 0 0 0 0 0 1.5841 -0.6574 0.8688 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0050 -0.3765 2.1418 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3588 -0.5069 2.4832 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2693 -0.9188 1.5360 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5972 -1.0330 1.9210 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1665 -0.5296 0.4694 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.6133 -1.5888 1.2025 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.5086 -1.4428 2.5725 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.3851 0.8515 0.6503 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.8020 0.9460 0.2337 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.7875 0.5929 1.1068 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.1293 0.6810 0.7250 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.4392 1.1279 -0.5403 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4685 1.4932 -1.4485 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.1635 1.3933 -1.0383 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8253 1.9271 -2.6834 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.0152 2.3405 -3.7404 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.7774 1.2259 -0.9484 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2202 1.3676 1.9210 O 0 0 0 0 0 0 0 0 0 0 0 0 3.7097 -2.8028 -2.0483 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8689 -1.0404 -2.4127 H 0 0 0 0 0 0 0 0 0 0 0 0 5.3272 -2.1474 -2.5889 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1812 -1.2877 -1.0589 H 0 0 0 0 0 0 0 0 0 0 0 0 1.3197 -0.0517 2.9113 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6585 -0.2787 3.4923 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3719 -0.8254 1.3076 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0752 -0.7856 -0.6292 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6731 -1.6264 0.9053 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.1383 -2.5837 0.9644 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0183 -2.1553 3.0220 H 0 0 0 0 0 0 0 0 0 0 0 0 0.1809 1.5432 -0.0353 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6073 0.2419 2.0994 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9086 0.3926 1.4404 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.3290 1.6654 -1.7071 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.9977 1.5273 -4.5254 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9915 2.4952 -3.4097 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4504 3.2500 -4.2350 H 0 0 0 0 0 0 0 0 0 0 0 0 -6.4993 1.0619 -0.2677 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.4711 2.3206 1.9008 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 2 0 6 7 1 0 7 8 2 0 8 9 1 0 5 10 1 0 10 11 1 0 11 12 1 0 10 13 1 0 13 14 1 0 14 15 2 0 15 16 1 0 16 17 2 0 17 18 1 0 18 19 2 0 18 20 1 0 20 21 1 0 17 22 1 0 13 23 1 0 8 3 1 0 19 14 1 0 1 24 1 0 1 25 1 0 1 26 1 0 4 27 1 0 6 28 1 0 7 29 1 0 9 30 1 0 10 31 1 6 11 32 1 0 11 33 1 0 12 34 1 0 13 35 1 6 15 36 1 0 16 37 1 0 19 38 1 0 21 39 1 0 21 40 1 0 21 41 1 0 22 42 1 0 23 43 1 0 M END

Standard InCHIKey	DFUOJBWSSSODTR-SJKOYZFVSA-N
Standard InCHI	InChI=1S/C17H20O6/c1-22-15-7-10(3-5-13(15)19)12(9-18)17(21)11-4-6-14(20)16(8-11)23-2/h3-8,12,17-21H,9H2,1-2H3/t12-,17-/m1/s1
SMILES	COc1cc(ccc1O)[C@@H](CO)[C@@H](c1ccc(c(c1)OC)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	320.13	Volume:	322.398 ? Van der Waals volume.
Dense:	0.993	LogP:	0.52 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.886 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.723 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	6.0	Rigid Bonds:	12.0
TPSA:	99.38 ? Topological Polar Surface Area.	H-Bond Acceptor:	6.0
H-Bond Donor:	4.0	Rings:	2.0
Heavy Atoms:	6.0

MedChem Properties

QED Drug-Likeness Score:	0.649	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.022	Fsp³:	0.294
MCE-18:	28.0 ? 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:	0.425	Fluc inhibitor:	0.333 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.012 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.072 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.456	Promiscuous compounds:	0.58

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.142	MDCK Permeability:	-4.852
Pgp-inhibitor:	0.009	Pgp-substrate:	0.107
PAMPA:	0.423 ? 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):	0.014
20% Bioavailability (F20%):	0.426	30% Bioavailability (F30%):	0.645
50% Bioavailability (F50%):	0.992

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.004	MRP1:	0.771
Plasma Protein Binding (PPB):	64.334%	Volume Distribution (VD):	0.12
Fu:	33.892% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.997
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.467
BSEP inhibitor:	0.104

ADMET: Metabolism

CYP1A2-inhibitor:	0.743	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.926	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.999	CYP2C9-substrate:	0.001
CYP2D6-inhibitor:	0.942	CYP2D6-substrate:	0.207
CYP3A4-inhibitor:	0.118	CYP3A4-substrate:	0.932
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.529
HLM stability:	0.088 ? 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):

7.931

Half-life (T1/2):

2.277

ADMET: Toxicity

hERG Blockers:	0.087	hERG Blockers (10um):	0.333
Human Hepatotoxicity (H-HT):	0.752	Drug-induced Liver Injury (DILI):	0.127
AMES Toxicity:	0.267	Rat Oral Acute Toxicity:	0.075
Maximum Recommended Daily Dose:	0.352	Skin Sensitization:	0.608
Carcinogencity:	0.202	Eye Corrosion:	0.001
Eye Irritation:	0.812	Respiratory Toxicity:	0.197
Drug-induced Neurotoxicity:	0.265	Ototoxicity:	0.888
Hematotoxicity:	0.107	Drug-induced Nephrotoxicity:	0.521
Genotoxicity:	0.424	RPMI-8226 Immunitoxicity:	0.094
A549 Cytotoxicity:	0.227	Hek293 Cytotoxicity:	0.519
BCF:	0.666 ? 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:	2.913 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	3.708 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	3.213 ? 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
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[12828478]
NPO24490	Cussonia bancoensis	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[14510614]
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]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	seeds	n.a.	n.a.	PMID[1624939]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[17027268]
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]
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]
NPO24490	Cussonia bancoensis	Species	Araliaceae	Eukaryota	n.a.	stem	n.a.	PMID[21443171]
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]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25905468]
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]
NPO24110	Lippia alba	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37631258]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38163555]
NPO24110	Lippia alba	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38897034]
NPO16693	Byrsonima crassifolia	Species	Malpighiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO26304	Hymenocallis littoralis	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21741	Araucaria angustifolia	Species	Araucariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14602	Vitex negundo	Species	Lamiaceae	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]
NPO17757	Plectranthus saccatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3924	Penicillium alutaceum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5016	Glossogyne tenuifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23737	Allium turcomanicum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19677	Cephalaria transsylvanica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24490	Cussonia bancoensis	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO25027	Cynoglossum creticum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2617	Dracocephalum multicaule	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24684	Eremanthus crotonoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21168	Erylus lendenfeldi	Species	Geodiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24110	Lippia alba	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22352	Lysimachia heterogenea	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24869	Nicotiana rustica	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23423	Phellopterus littoralis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12731	Porodaedalea pini	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24716	Pulvinula constellatio	Species	Pyronemataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22021	Teucrium spinosum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO23283	Triptilion benaventei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14889	Vachellia farnesiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO893	Helichrysum sutherlandii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16210	Androcymbium palaestinum	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18071	Euryops pedunculatus	Species	Asteraceae	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]
NPO9024	Aralidium pinnatifidum	Species	Torricelliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12630	Senecio oxyodontus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20383	Stenocereus thurberi	Species	Cactaceae	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]
NPO15594	Aplidiopsis confluata	n.a.	n.a.	n.a.	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]
NPO15954	Pyrenula japonica	Species	Pyrenulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16693	Byrsonima crassifolia	Species	Malpighiaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO16693	Byrsonima crassifolia	Species	Malpighiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO16693	Byrsonima crassifolia	Species	Malpighiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO21741	Araucaria angustifolia	Species	Araucariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9644	Euphorbia resinifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24869	Nicotiana rustica	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26304	Hymenocallis littoralis	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9644	Euphorbia resinifera	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21741	Araucaria angustifolia	Species	Araucariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24869	Nicotiana rustica	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15954	Pyrenula japonica	Species	Pyrenulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26304	Hymenocallis littoralis	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO893	Helichrysum sutherlandii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24490	Cussonia bancoensis	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21741	Araucaria angustifolia	Species	Araucariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO24869	Nicotiana rustica	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14602	Vitex negundo	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16326	Scopolia parviflora	Species	Solanaceae	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]
NPO1418	Boletinus paluster	Species	Gyrodontaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14001	Ceroplastes pseudoceriferus	Species	Coccidae	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]
NPO5016	Glossogyne tenuifolia	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]
NPO22021	Teucrium spinosum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23283	Triptilion benaventei	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3924	Penicillium alutaceum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22352	Lysimachia heterogenea	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26304	Hymenocallis littoralis	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11530	Heterosigma akashiwo	Species	Chattonellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24869	Nicotiana rustica	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23737	Allium turcomanicum	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9965	Eurycoma longifolia	Species	Simaroubaceae	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]
NPO15740	Garcinia purpurea	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13692	Leontice kiangnanensis	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14507.1	Quercus ithaburensis subsp. macrolepis	Subspecies	Fagaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16049	Cryptocarya pleurosperma	Species	Lauraceae	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]
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]
NPO24110	Lippia alba	Species	Verbenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16210	Androcymbium palaestinum	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO893	Helichrysum sutherlandii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12731	Porodaedalea pini	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16693	Byrsonima crassifolia	Species	Malpighiaceae	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]
NPO24684	Eremanthus crotonoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22888	Lophiostoma vaginatispora	Species	Lophiostomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21741	Araucaria angustifolia	Species	Araucariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2617	Dracocephalum multicaule	Species	Lamiaceae	Eukaryota	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]
NPO12577	Pinus glauca	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14889	Vachellia farnesiana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23423	Phellopterus littoralis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO24716	Pulvinula constellatio	Species	Pyronemataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18071	Euryops pedunculatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17917	Thamnophis sirtalis	Species	Colubridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12988	Blainvillea latifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24490	Cussonia bancoensis	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11755	Banisteriopsis caapi	Species	Malpighiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17600	Gnathotrichus sulcatus	Species	Curculionidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15594	Aplidiopsis confluata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO19677	Cephalaria transsylvanica	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25027	Cynoglossum creticum	Species	Boraginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16326	Scopolia parviflora	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17444	Gleichenia japonica	Species	Gleicheniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15954	Pyrenula japonica	Species	Pyrenulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12630	Senecio oxyodontus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21168	Erylus lendenfeldi	Species	Geodiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17757	Plectranthus saccatus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10751	Bothriocline laxa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11280	Aphanoascus terreus	Species	Onygenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO619	Ankistrodesmus braunii	Species	Selenastraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17141	Lonchocarpus longistylus	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 NPC300424 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	26442
0.1-0.2	19445
0.2-0.3	3384
0.3-0.4	450
0.4-0.5	117
0.5-0.6	9
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	2

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC165045
1.0	High Similarity	NPC118533
0.6829	Remote Similarity	NPC476343
0.65	Remote Similarity	NPC320987
0.6047	Remote Similarity	NPC35071
0.6047	Remote Similarity	NPC177475
0.6047	Remote Similarity	NPC148615
0.5952	Remote Similarity	NPC326599
0.5952	Remote Similarity	NPC181969
0.5952	Remote Similarity	NPC329595
0.587	Remote Similarity	NPC239608
0.587	Remote Similarity	NPC46161
0.5435	Remote Similarity	NPC195292
0.5349	Remote Similarity	NPC160380
0.5349	Remote Similarity	NPC38996
0.5283	Remote Similarity	NPC92164

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC300424 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	4894
0.1-0.2	4055
0.2-0.3	192
0.3-0.4	7
0.4-0.5	2
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