NPASS Compound

Natural Product: NPC115919

Natural Product ID	NPC115919
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	RKCVEZHHZBFDSD-WVTGURRWSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	10564679
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000012] Lipids and lipid-like molecules [CHEMONTID:0003909] Fatty Acyls [CHEMONTID:0001766] Fatty acyl glycosides [CHEMONTID:0003861] Fatty acyl glycosides of mono- and disaccharides

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 39 39 0 0 0 0 0 0 0 0999 V2000 6.3007 1.8838 0.8764 C 0 0 0 0 0 0 0 0 0 0 0 0 5.2927 0.8609 0.9295 O 0 0 0 0 0 0 0 0 0 0 0 0 4.6515 0.4179 -0.2039 C 0 0 0 0 0 0 0 0 0 0 0 0 4.9313 0.8975 -1.3254 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6113 -0.6397 -0.1374 C 0 0 0 0 0 0 0 0 0 0 0 0 2.2787 0.0678 -0.1976 C 0 0 0 0 0 0 0 0 0 0 0 0 1.1131 -0.8932 -0.1467 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0915 -0.2047 -0.2016 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.1230 -1.1133 -0.1663 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.0120 -0.9504 1.0478 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4260 -1.2241 0.5807 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.7769 -0.0549 -0.3476 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.7404 -0.0513 -1.4528 C 0 0 1 0 0 0 0 0 0 0 0 0 -2.1162 1.3324 -1.5298 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.0950 2.3182 -1.6323 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.8319 -1.0602 -1.3536 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.0692 -0.1489 -0.8238 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3197 -1.2906 1.6431 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.6354 -1.8586 2.0438 O 0 0 0 0 0 0 0 0 0 0 0 0 5.7791 2.8184 1.2282 H 0 0 0 0 0 0 0 0 0 0 0 0 7.1536 1.6205 1.5056 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5331 2.0442 -0.1883 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6493 -1.2112 0.8222 H 0 0 0 0 0 0 0 0 0 0 0 0 3.6972 -1.3633 -0.9805 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2304 0.7524 0.6837 H 0 0 0 0 0 0 0 0 0 0 0 0 2.2364 0.6747 -1.1211 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1643 -1.5030 -1.0858 H 0 0 0 0 0 0 0 0 0 0 0 0 1.1336 -1.4918 0.7636 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.6938 -2.1330 -0.1056 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.9099 0.0690 1.4593 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.4015 -2.1554 -0.0114 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6766 0.8578 0.2714 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3032 -0.1924 -2.4003 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.4448 1.4365 -2.4040 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5244 1.5770 -0.6307 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.0730 2.9606 -0.8928 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.0253 -0.1178 -1.8107 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.0340 -0.7042 2.4002 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4328 -2.2275 2.5222 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 3 5 1 0 5 6 1 0 6 7 1 0 7 8 1 0 8 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 1 0 13 16 1 0 12 17 1 0 11 18 1 0 10 19 1 0 16 9 1 0 1 20 1 0 1 21 1 0 1 22 1 0 5 23 1 0 5 24 1 0 6 25 1 0 6 26 1 0 7 27 1 0 7 28 1 0 9 29 1 1 10 30 1 1 11 31 1 6 12 32 1 1 13 33 1 6 14 34 1 0 14 35 1 0 15 36 1 0 17 37 1 0 18 38 1 0 19 39 1 0 M END

Standard InCHIKey	RKCVEZHHZBFDSD-WVTGURRWSA-N
Standard InCHI	InChI=1S/C11H20O8/c1-17-7(13)3-2-4-18-11-10(16)9(15)8(14)6(5-12)19-11/h6,8-12,14-16H,2-5H2,1H3/t6-,8-,9+,10-,11-/m1/s1
SMILES	COC(=O)CCCO[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	280.12	Volume:	257.941 ? Van der Waals volume.
Dense:	1.086	LogP:	-1.346 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-1.006 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-0.445 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	7.0
TPSA:	125.68 ? Topological Polar Surface Area.	H-Bond Acceptor:	8.0
H-Bond Donor:	4.0	Rings:	1.0
Heavy Atoms:	8.0

MedChem Properties

QED Drug-Likeness Score:	0.318	GASA:	0.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	3.494	Fsp³:	0.909
MCE-18:	22.286 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Rejected	GSK Rule:	Rejected
Golden Triangle Rule:	Rejected	BMS Rule:	0
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.294	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.032 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.003 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.257	Promiscuous compounds:	0.018

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.532	MDCK Permeability:	-4.954
Pgp-inhibitor:	0.008	Pgp-substrate:	0.8
PAMPA:	0.876 ? 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):	0.774
20% Bioavailability (F20%):	0.121	30% Bioavailability (F30%):	0.924
50% Bioavailability (F50%):	0.823

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.055	MRP1:	0.392
Plasma Protein Binding (PPB):	27.689%	Volume Distribution (VD):	-0.592
Fu:	75.573% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.971
OATP1B3 inhibitor:	0.992	BCRP inhibitor:	0.075
BSEP inhibitor:	0.087

ADMET: Metabolism

CYP1A2-inhibitor:	0.006	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.049	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.001	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.002
CYP3A4-inhibitor:	0.001	CYP3A4-substrate:	0.085
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.61
HLM stability:	0.451 ? Human liver microsomal (HLM) stability. Category 0: stable+ (HLM > 30 min); Category 1: unstable- (HLM ≤ 30 min). The output value is the probability of human liver microsomal instability, where a value closer to 1 indicates a higher likelihood of instability.

ADMET: Excretion

Clearance (CL):

3.634

Half-life (T1/2):

1.626

ADMET: Toxicity

hERG Blockers:	0.016	hERG Blockers (10um):	0.088
Human Hepatotoxicity (H-HT):	0.428	Drug-induced Liver Injury (DILI):	0.389
AMES Toxicity:	0.79	Rat Oral Acute Toxicity:	0.023
Maximum Recommended Daily Dose:	0.013	Skin Sensitization:	0.989
Carcinogencity:	0.459	Eye Corrosion:	0.023
Eye Irritation:	0.648	Respiratory Toxicity:	0.023
Drug-induced Neurotoxicity:	0.026	Ototoxicity:	0.861
Hematotoxicity:	0.389	Drug-induced Nephrotoxicity:	0.717
Genotoxicity:	0.007	RPMI-8226 Immunitoxicity:	0.055
A549 Cytotoxicity:	0.024	Hek293 Cytotoxicity:	0.036
BCF:	0.192 ? Bioconcentration factors are used for considering secondary poisoning potential and assessing risks to human health via the food chain. The unit is -log10[(mg/L)/(1000*MW)].	IGC50:	1.788 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	3.138 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	2.457 ? 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
NPO22104	Trifolium pratense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0031-9422(00)94679-X]
NPO21079	Actinomadura hibisca	Species	Thermomonosporaceae	Bacteria	n.a.	n.a.	n.a.	DOI[10.1021/jo00272a013]
NPO21587	Hypericum papuanum	Species	Hypericaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[10650088]
NPO20889	Anastrepha suspensa	Species	Tephritidae	Eukaryota	n.a.	n.a.	n.a.	PMID[10706642]
NPO20635	Dalbergia frutescens	Species	Fabaceae	Eukaryota	bark	n.a.	n.a.	PMID[11076565]
NPO21587	Hypericum papuanum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11421727]
NPO18141	Solanum torvum	Species	Solanaceae	Eukaryota	n.a.	fruit	n.a.	PMID[11830167]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	underground organs	n.a.	n.a.	PMID[14738379]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	leaves	n.a.	n.a.	PMID[14738379]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	dried aerial organs	n.a.	n.a.	PMID[14738379]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	dried aerial organs	n.a.	n.a.	PMID[14738379]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	roots and stolons	n.a.	n.a.	PMID[14738379]
NPO21023	Astilbe koreana	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16580200]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	seed	n.a.	PMID[21049975]
NPO21079	Actinomadura hibisca	Species	Thermomonosporaceae	Bacteria	n.a.	n.a.	n.a.	PMID[21119678]
NPO21470	Conoideocrella tenuis	Species	Clavicipitaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21473608]
NPO21470	Conoideocrella tenuis	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21473608]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[25154406]
NPO13106	Rhodomyrtus tomentosa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25466012]
NPO13106	Rhodomyrtus tomentosa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[28245113]
NPO22104	Trifolium pratense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30199256]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[30551419]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31815461]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[35999251]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36432786]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36840093]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37420038]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[37653914]
NPO20045	Burkholderia cepacia	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[3839140]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38592874]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[38719900]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39065713]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39683666]
NPO20045	Burkholderia cepacia	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	PMID[7684040]
NPO24658	Dillenia papuana	Species	Dilleniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7798959]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21079	Actinomadura hibisca	Species	Thermomonosporaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20889	Anastrepha suspensa	Species	Tephritidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22880	Aspergillus caespitosus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21023	Astilbe koreana	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20827	Boronia muelleri	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20045	Burkholderia cepacia	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22689	Cassia carnaval	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20696	Colchicum macedonicum	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21470	Conoideocrella tenuis	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20953	Coprosma acerosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO29262	Cranfillia vulcanica	Species	Blechnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO10757	Cyanospira rippkae	Species	Aphanizomenonaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21839	Cymathere triplicata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20635	Dalbergia frutescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20134	Dicliptera riparia	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO24658	Dillenia papuana	Species	Dilleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19799	Erwinia rhapontici	Species	Erwiniaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20764	Euphorbia caducifolia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8570	Ficus elastica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21905	Helianthopsis bishopii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21587	Hypericum papuanum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20316	Hypselodoris cantabrica	Species	Chromodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20508	Ilex kaushue	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22298	Inula thapsoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22042	Kaunia arbuscularis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22490	Limeum pterocarpum	Species	Limeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21400	Macrocystidia cucumis	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21270	Nerita albicilla	Species	Neritidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20190	Oxandra xylopioides	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19880	Palicourea alpina	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15871	Parmelia enteromorpha	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4785	Persicaria thunbergii	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20077	Posoqueria latifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13106	Rhodomyrtus tomentosa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22746	Salix sieboldiana	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO6873	Salvia xalapensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22227	Sambucus ebulus	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21212	Scrophularia smithii	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18141	Solanum torvum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17581	Streptomyces fulvoviridis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4771	Tanacetum santolinoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22551	Trifolium alexandrium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22104	Trifolium pratense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO22362	Tylophora flava	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO20012	Wunderlichia mirabilis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21775	Zilla spinosa	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	Root	n.a.	n.a.	Database[FooDB]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO13106	Rhodomyrtus tomentosa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22104	Trifolium pratense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18141	Solanum torvum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19953	Lupinus formosus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21587	Hypericum papuanum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20508	Ilex kaushue	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22104	Trifolium pratense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18141	Solanum torvum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20134	Dicliptera riparia	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13106	Rhodomyrtus tomentosa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4785	Persicaria thunbergii	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19953	Lupinus formosus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22104	Trifolium pratense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18141	Solanum torvum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13106	Rhodomyrtus tomentosa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO22490	Limeum pterocarpum	Species	Limeaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21270	Nerita albicilla	Species	Neritidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22298	Inula thapsoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22689	Cassia carnaval	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21460	Anethum graveolens	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21334	Artemisia dracunculus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22227	Sambucus ebulus	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20012	Wunderlichia mirabilis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4785	Persicaria thunbergii	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21775	Zilla spinosa	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22622	Coptis deltoidea	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10757	Cyanospira rippkae	Species	Aphanizomenonaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO20316	Hypselodoris cantabrica	Species	Chromodorididae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4771	Tanacetum santolinoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22362	Tylophora flava	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20077	Posoqueria latifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22042	Kaunia arbuscularis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29262	Cranfillia vulcanica	Species	Blechnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19953	Lupinus formosus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21587	Hypericum papuanum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17581	Streptomyces fulvoviridis	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO21079	Actinomadura hibisca	Species	Thermomonosporaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO19880	Palicourea alpina	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20190	Oxandra xylopioides	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20889	Anastrepha suspensa	Species	Tephritidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21400	Macrocystidia cucumis	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24658	Dillenia papuana	Species	Dilleniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20764	Euphorbia caducifolia	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22104	Trifolium pratense	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22880	Aspergillus caespitosus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18141	Solanum torvum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21470	Conoideocrella tenuis	Species	Clavicipitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21212	Scrophularia smithii	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13106	Rhodomyrtus tomentosa	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8570	Ficus elastica	Species	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21839	Cymathere triplicata	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO20508	Ilex kaushue	Species	Aquifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21023	Astilbe koreana	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15871	Parmelia enteromorpha	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20635	Dalbergia frutescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20045	Burkholderia cepacia	Species	Burkholderiaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO20696	Colchicum macedonicum	Species	Colchicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20134	Dicliptera riparia	Species	Acanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6873	Salvia xalapensis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22746	Salix sieboldiana	Species	Salicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20953	Coprosma acerosa	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21905	Helianthopsis bishopii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO22551	Trifolium alexandrium	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20827	Boronia muelleri	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19799	Erwinia rhapontici	Species	Erwiniaceae	Bacteria	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 NPC115919 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	19980
0.1-0.2	24541
0.2-0.3	4404
0.3-0.4	774
0.4-0.5	133
0.5-0.6	19
0.6-0.7	4
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
0.7179	Intermediate Similarity	NPC233726
0.6829	Remote Similarity	NPC155457
0.6512	Remote Similarity	NPC606861
0.6512	Remote Similarity	NPC607126
0.6042	Remote Similarity	NPC277570
0.5897	Remote Similarity	NPC124963
0.5833	Remote Similarity	NPC147292
0.5778	Remote Similarity	NPC13143
0.5778	Remote Similarity	NPC294813
0.575	Remote Similarity	NPC326533
0.5682	Remote Similarity	NPC268243
0.5526	Remote Similarity	NPC42503
0.5526	Remote Similarity	NPC282143
0.5526	Remote Similarity	NPC299781
0.5526	Remote Similarity	NPC157193
0.5526	Remote Similarity	NPC608193
0.5294	Remote Similarity	NPC206601
0.5283	Remote Similarity	NPC280367
0.5185	Remote Similarity	NPC488690
0.5128	Remote Similarity	NPC107914
0.5128	Remote Similarity	NPC242073
0.5106	Remote Similarity	NPC603514
0.5094	Remote Similarity	NPC471879
0.5094	Remote Similarity	NPC12040

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC115919 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	6716
0.1-0.2	2271
0.2-0.3	135
0.3-0.4	14
0.4-0.5	13
0.5-0.6	1
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
0.5227	Remote Similarity	NPD904	Phase 3

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