NPASS Compound

Natural Product: NPC58137

Natural Product ID	NPC58137
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	YLZYAUCOYZKLMA-SJKOYZFVSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	CHEMBL1983713
PubChem CID	373519
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002617] Furanoisoflavonoids [CHEMONTID:0001608] Pterocarpans

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 36 40 0 0 0 0 0 0 0 0999 V2000 -6.0862 1.2540 0.1227 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.6496 -0.0548 -0.1894 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.2963 -0.3090 -0.1614 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.8478 -1.5777 -0.4623 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.4967 -1.8671 -0.4436 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.5631 -0.8777 -0.1193 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.0105 0.4038 0.1850 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.3499 0.6484 0.1554 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.0267 1.3263 0.4954 O 0 0 0 0 0 0 0 0 0 0 0 0 0.1026 0.9796 1.2826 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6420 -0.3915 0.9621 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.1220 -1.1258 -0.0847 C 0 0 2 0 0 0 0 0 0 0 0 0 0.5437 -0.7089 -1.2701 O 0 0 0 0 0 0 0 0 0 0 0 0 1.8754 -0.4566 -0.9788 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9898 -0.2591 0.3704 C 0 0 0 0 0 0 0 0 0 0 0 0 3.2564 0.0084 0.8609 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3808 0.0827 0.0662 C 0 0 0 0 0 0 0 0 0 0 0 0 4.2613 -0.1168 -1.2930 C 0 0 0 0 0 0 0 0 0 0 0 0 3.0080 -0.3843 -1.7992 C 0 0 0 0 0 0 0 0 0 0 0 0 5.5317 0.0090 -1.8768 O 0 0 0 0 0 0 0 0 0 0 0 0 6.3833 0.6603 -0.9261 C 0 0 0 0 0 0 0 0 0 0 0 0 5.7307 0.3286 0.2941 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.6492 1.9263 -0.6502 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.6330 1.5239 1.1081 H 0 0 0 0 0 0 0 0 0 0 0 0 -7.1669 1.3400 0.2297 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.5187 -2.3902 -0.7219 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.0973 -2.8511 -0.6734 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6881 1.6617 0.3968 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.2363 1.0520 2.3533 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8815 1.7314 1.1298 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7780 -0.9915 1.8995 H 0 0 0 0 0 0 0 0 0 0 0 0 0.0469 -2.2120 0.0364 H 0 0 0 0 0 0 0 0 0 0 0 0 3.3378 0.1638 1.9345 H 0 0 0 0 0 0 0 0 0 0 0 0 2.9129 -0.5401 -2.8585 H 0 0 0 0 0 0 0 0 0 0 0 0 7.4137 0.2524 -0.9655 H 0 0 0 0 0 0 0 0 0 0 0 0 6.3615 1.7617 -1.0502 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 7 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 12 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 21 22 1 0 8 3 1 0 15 11 1 0 22 17 1 0 12 6 1 0 19 14 1 0 1 23 1 0 1 24 1 0 1 25 1 0 4 26 1 0 5 27 1 0 8 28 1 0 10 29 1 0 10 30 1 0 11 31 1 1 12 32 1 1 16 33 1 0 19 34 1 0 21 35 1 0 21 36 1 0 M END

Standard InCHIKey	YLZYAUCOYZKLMA-SJKOYZFVSA-N
Standard InCHI	InChI=1S/C17H14O5/c1-18-9-2-3-10-13(4-9)19-7-12-11-5-15-16(21-8-20-15)6-14(11)22-17(10)12/h2-6,12,17H,7-8H2,1H3/t12-,17-/m1/s1
SMILES	COc1ccc2c(c1)OC[C@H]1[C@@H]2Oc2c1cc1c(c2)OCO1

Calculated Properties

Physi-Chem Properties

Molecular Weight:	298.08	Volume:	287.938 ? Van der Waals volume.
Dense:	1.035	LogP:	3.211 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	3.19 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-4.781 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	1.0	Rigid Bonds:	24.0
TPSA:	46.15 ? Topological Polar Surface Area.	H-Bond Acceptor:	5.0
H-Bond Donor:	0.0	Rings:	5.0
Heavy Atoms:	5.0

MedChem Properties

QED Drug-Likeness Score:	0.81	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.245	Fsp³:	0.294
MCE-18:	80.727 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted	GSK Rule:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.705	Fluc inhibitor:	0.97 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.349 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.122 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.337	Promiscuous compounds:	0.562

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-4.867	MDCK Permeability:	-4.678
Pgp-inhibitor:	0.458	Pgp-substrate:	0.037
PAMPA:	0.009 ? 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):	0.001
20% Bioavailability (F20%):	0.045	30% Bioavailability (F30%):	0.01
50% Bioavailability (F50%):	0.431

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.899	MRP1:	0.654
Plasma Protein Binding (PPB):	92.424%	Volume Distribution (VD):	0.019
Fu:	8.427% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.988
OATP1B3 inhibitor:	0.987	BCRP inhibitor:	0.368
BSEP inhibitor:	0.997

ADMET: Metabolism

CYP1A2-inhibitor:	1.0	CYP1A2-substrate:	0.997
CYP2C19-inhibitor:	0.998	CYP2C19-substrate:	0.525
CYP2C9-inhibitor:	1.0	CYP2C9-substrate:	1.0
CYP2D6-inhibitor:	1.0	CYP2D6-substrate:	1.0
CYP3A4-inhibitor:	0.031	CYP3A4-substrate:	1.0
CYP2B6-substrate:	0.961	CYP2C8-inhibitor:	0.0
HLM stability:	0.689 ? 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):

5.749

Half-life (T1/2):

2.692

ADMET: Toxicity

hERG Blockers:	0.289	hERG Blockers (10um):	0.579
Human Hepatotoxicity (H-HT):	0.633	Drug-induced Liver Injury (DILI):	0.914
AMES Toxicity:	0.693	Rat Oral Acute Toxicity:	0.322
Maximum Recommended Daily Dose:	0.458	Skin Sensitization:	0.38
Carcinogencity:	0.819	Eye Corrosion:	0.025
Eye Irritation:	0.931	Respiratory Toxicity:	0.658
Drug-induced Neurotoxicity:	0.546	Ototoxicity:	0.47
Hematotoxicity:	0.482	Drug-induced Nephrotoxicity:	0.574
Genotoxicity:	0.243	RPMI-8226 Immunitoxicity:	0.108
A549 Cytotoxicity:	0.238	Hek293 Cytotoxicity:	0.48
BCF:	1.539 ? 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:	4.052 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	6.897 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	5.442 ? 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
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10654410]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[10843587]
NPO20142	Embelia schimperi	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11054840]
NPO18668	Asimina parviflora	Species	Annonaceae	Eukaryota	twigs	n.a.	n.a.	PMID[1453182]
NPO19667	Hypericum styphelioides	Species	Hypericaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15165152]
NPO19667	Hypericum styphelioides	Species	Hypericaceae	Eukaryota	leaves	n.a.	n.a.	PMID[15165152]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[15568770]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15911254]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16392664]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	roots	Hualien Hsien, Taiwan	2003-JUL	PMID[16933887]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16933887]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[17951038]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18175961]
NPO20879	Clerodendrum bungei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18348535]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	root	n.a.	PMID[18975262]
NPO3152	Morella rubra	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19407970]
NPO3152	Morella rubra	Species	Myricaceae	Eukaryota	n.a.	bark	n.a.	PMID[21553897]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24295087]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24333010]
NPO20598	Lythrum salicaria	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24459770]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27575476]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30298740]
NPO20879	Clerodendrum bungei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[34142352]
NPO20489	Epilobium hirsutum	Species	Onagraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36670952]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[9868163]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO21495	Abelia chinensis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20421	Aplophyllum alberti-regelii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18668	Asimina parviflora	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20084	Atraphaxis spinosa	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19995	Baccharis neglecta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17849	Centaurea maculosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12056	Chondrodendron tomentosum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20879	Clerodendrum bungei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5903	Conus mus	Species	Conidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22961	Cordia leucocephala	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18143	Dendronephthya griffini	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21562	Diospyros assimilis	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19511	Dolabella californica	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21170	Embelia parviflora	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20142	Embelia schimperi	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20489	Epilobium hirsutum	Species	Onagraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21108	Eria anomala	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11523	Erysimum leptophyllum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20680	Erythrina melanacantha	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19036	Esenbeckia leiocarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21375	Euphorbia nematocypha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21631	Faramea salicifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16569	Gymnocalycium schickendantzii	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12313	Haplophyllum obtusifolium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28202	Helichrysum tenuifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19667	Hypericum styphelioides	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO27367	Latrunculia magnifica	Species	Latrunculiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21038	Lemaireocereus longispinus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20598	Lythrum salicaria	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20843	Monsonia senegalensis	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3152	Morella rubra	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19810	Myxococcus stipitatus	Species	Myxococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17334	Onopordum acanthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17560	Pancratium sickenbergeri	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16141	Piper regnellii	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14241	Planchonia grandis	Species	Asterolecaniidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18473	Plathymenia reticulata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18866	Pteridium esculentum	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17258	Rhinella marina	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO9968	Shigella dysenteriae	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20624	Simarouba glauca	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21243	Siphonaria capensis	Species	Siphonariidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13449	Syzygium polycephaloides	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO28072	Theonella conica	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4051	Tricholoma columbetta	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19912	Vellozia nanuzae	Species	Velloziaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22937	Vernonia fagifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17334	Onopordum acanthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21170	Embelia parviflora	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21375	Euphorbia nematocypha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20598	Lythrum salicaria	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12056	Chondrodendron tomentosum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17334	Onopordum acanthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20598	Lythrum salicaria	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18668	Asimina parviflora	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3152	Morella rubra	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21375	Euphorbia nematocypha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20489	Epilobium hirsutum	Species	Onagraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20142	Embelia schimperi	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20680	Erythrina melanacantha	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20879	Clerodendrum bungei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21170	Embelia parviflora	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12056	Chondrodendron tomentosum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20680	Erythrina melanacantha	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20598	Lythrum salicaria	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21170	Embelia parviflora	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21375	Euphorbia nematocypha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17334	Onopordum acanthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18473	Plathymenia reticulata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21631	Faramea salicifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21170	Embelia parviflora	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20084	Atraphaxis spinosa	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16569	Gymnocalycium schickendantzii	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20489	Epilobium hirsutum	Species	Onagraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17849	Centaurea maculosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20680	Erythrina melanacantha	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4051	Tricholoma columbetta	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12313	Haplophyllum obtusifolium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21562	Diospyros assimilis	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9968	Shigella dysenteriae	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO21495	Abelia chinensis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17334	Onopordum acanthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19511	Dolabella californica	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5903	Conus mus	Species	Conidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3152	Morella rubra	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20879	Clerodendrum bungei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20142	Embelia schimperi	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20421	Aplophyllum alberti-regelii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO21375	Euphorbia nematocypha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21243	Siphonaria capensis	Species	Siphonariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21108	Eria anomala	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16141	Piper regnellii	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17560	Pancratium sickenbergeri	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19810	Myxococcus stipitatus	Species	Myxococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO20843	Monsonia senegalensis	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19036	Esenbeckia leiocarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21038	Lemaireocereus longispinus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28202	Helichrysum tenuifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19667	Hypericum styphelioides	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18143	Dendronephthya griffini	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19995	Baccharis neglecta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11523	Erysimum leptophyllum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28072	Theonella conica	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13449	Syzygium polycephaloides	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14241	Planchonia grandis	Species	Asterolecaniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18866	Pteridium esculentum	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18668	Asimina parviflora	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27367	Latrunculia magnifica	Species	Latrunculiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22961	Cordia leucocephala	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22937	Vernonia fagifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20598	Lythrum salicaria	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12056	Chondrodendron tomentosum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17258	Rhinella marina	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20624	Simarouba glauca	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19912	Vellozia nanuzae	Species	Velloziaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	Organism Name	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

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

Biological Activity

Activity Type	# Activity
GI50	53

Activity Type	# Activity
Cell line	53

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
NPT370	Cell line	NCI-H23	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT369	Cell line	ACHN	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT371	Cell line	UO-31	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT116	Cell line	HL-60	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT372	Cell line	HOP-92	Homo sapiens	GI50	n.a.	69984.2	nM	PubChem BioAssay data set
NPT374	Cell line	SF-539	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT375	Cell line	Malme-3M	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT373	Cell line	SK-MEL-5	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT111	Cell line	K562	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT377	Cell line	OVCAR-3	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT376	Cell line	A498	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT379	Cell line	HOP-62	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT112	Cell line	MOLT-4	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT380	Cell line	U-251	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT381	Cell line	OVCAR-8	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT382	Cell line	OVCAR-5	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT572	Cell line	DMS-273	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT383	Cell line	SNB-19	Homo sapiens	GI50	n.a.	30408.85	nM	PubChem BioAssay data set
NPT384	Cell line	TK-10	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT323	Cell line	SW-620	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT455	Cell line	NCI-H522	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT387	Cell line	M14	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT574	Cell line	XF498	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT386	Cell line	KM12	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT388	Cell line	NCI-H322M	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT389	Cell line	RPMI-8226	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT456	Cell line	OVCAR-4	Homo sapiens	GI50	n.a.	35727.28	nM	PubChem BioAssay data set
NPT390	Cell line	LOX IMVI	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT147	Cell line	SK-MEL-2	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT575	Cell line	KM-20L2	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT81	Cell line	A549	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT391	Cell line	HCC 2998	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT392	Cell line	SNB-75	Homo sapiens	GI50	n.a.	11587.77	nM	PubChem BioAssay data set
NPT148	Cell line	HCT-15	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT395	Cell line	SF-268	Homo sapiens	GI50	n.a.	74989.42	nM	PubChem BioAssay data set
NPT393	Cell line	HCT-116	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT394	Cell line	EKVX	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT731	Cell line	LXFL 529	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT576	Cell line	DMS-114	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT146	Cell line	SK-OV-3	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT397	Cell line	NCI-H460	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT308	Cell line	CAKI-1	Homo sapiens	GI50	n.a.	58479.01	nM	PubChem BioAssay data set
NPT399	Cell line	SF-295	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT578	Cell line	SNB-78	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT401	Cell line	786-0	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT579	Cell line	DLD-1	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT404	Cell line	CCRF-CEM	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT405	Cell line	NCI-H226	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT139	Cell line	HT-29	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT170	Cell line	SK-MEL-28	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT406	Cell line	RXF 393	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT407	Cell line	COLO 205	Homo sapiens	GI50	n.a.	100000.0	nM	PubChem BioAssay data set
NPT732	Cell line	HOP-18	Homo sapiens	GI50	n.a.	37153.52	nM	PubChem BioAssay data set

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 NPC58137 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	34134
0.1-0.2	13821
0.2-0.3	1765
0.3-0.4	91
0.4-0.5	15
0.5-0.6	15
0.6-0.7	12
0.7-0.8	0
0.8-0.85	0
0.85-0.9	0
0.9-0.95	0
0.95-1	1

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC300798
0.7593	Intermediate Similarity	NPC80326
0.72	Intermediate Similarity	NPC294156
0.72	Intermediate Similarity	NPC256015
0.6981	Remote Similarity	NPC474478
0.6981	Remote Similarity	NPC606219
0.6833	Remote Similarity	NPC71288
0.6833	Remote Similarity	NPC301961
0.6724	Remote Similarity	NPC474749
0.661	Remote Similarity	NPC178014
0.661	Remote Similarity	NPC42716
0.661	Remote Similarity	NPC11422
0.6557	Remote Similarity	NPC166584
0.6522	Remote Similarity	NPC238140
0.6167	Remote Similarity	NPC226540
0.6066	Remote Similarity	NPC605383
0.5846	Remote Similarity	NPC205316
0.5833	Remote Similarity	NPC32633
0.5667	Remote Similarity	NPC27495
0.5574	Remote Similarity	NPC39064
0.5574	Remote Similarity	NPC47283
0.5507	Remote Similarity	NPC240521
0.5397	Remote Similarity	NPC162193
0.5397	Remote Similarity	NPC174522
0.5362	Remote Similarity	NPC71726
0.5323	Remote Similarity	NPC309124
0.5211	Remote Similarity	NPC609291
0.5079	Remote Similarity	NPC184797
0.5079	Remote Similarity	NPC232164
0.5079	Remote Similarity	NPC473739
0.507	Remote Similarity	NPC108674

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC58137 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	5765
0.1-0.2	3243
0.2-0.3	139
0.3-0.4	3
0.4-0.5	0
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