NPASS Compound

Natural Product: NPC258476

Natural Product ID	NPC258476
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	VXXKDWBEVHGANN-PQZGBVCXSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	102021738
Chemical Classification	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0004603] Organic oxygen compounds [CHEMONTID:0000323] Organooxygen compounds [CHEMONTID:0000011] Carbohydrates and carbohydrate conjugates [CHEMONTID:0002105] Glycosyl compounds [CHEMONTID:0004165] Phenolic glycosides

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 49 50 0 0 0 0 0 0 0 0999 V2000 2.2853 -0.3661 -3.4017 C 0 0 0 0 0 0 0 0 0 0 0 0 2.8424 -0.2283 -2.1270 O 0 0 0 0 0 0 0 0 0 0 0 0 2.0911 -0.1489 -0.9636 C 0 0 0 0 0 0 0 0 0 0 0 0 0.6934 -0.2035 -0.9987 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.1037 -0.1321 0.0967 C 0 0 0 0 0 0 0 0 0 0 0 0 0.5609 0.0054 1.3268 C 0 0 0 0 0 0 0 0 0 0 0 0 1.9319 0.0621 1.3952 C 0 0 0 0 0 0 0 0 0 0 0 0 2.6991 -0.0144 0.2557 C 0 0 0 0 0 0 0 0 0 0 0 0 4.1663 0.0426 0.3010 C 0 0 0 0 0 0 0 0 0 0 0 0 4.6983 0.2194 1.7085 C 0 0 1 0 0 0 0 0 0 0 0 0 6.2289 0.2694 1.6892 C 0 0 0 0 0 0 0 0 0 0 0 0 6.7674 -0.9412 1.2529 O 0 0 0 0 0 0 0 0 0 0 0 0 4.2986 1.4823 2.1594 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4730 -0.1775 0.1497 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.3055 -0.3083 -0.9587 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.0986 -1.6023 -0.9374 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.3474 -1.4786 -0.1341 C 0 0 2 0 0 0 0 0 0 0 0 0 -4.3988 -0.2034 0.6633 C 0 0 1 0 0 0 0 0 0 0 0 0 -4.0340 1.0063 -0.1373 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.6056 2.0920 0.8468 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4476 3.3098 0.1610 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.1372 0.7959 -1.1391 O 0 0 0 0 0 0 0 0 0 0 0 0 -5.7235 -0.0410 1.0971 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4918 -2.5492 0.7411 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4564 -1.8878 -2.2539 O 0 0 0 0 0 0 0 0 0 0 0 0 3.1150 -0.1592 -4.1379 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8482 -1.3596 -3.5937 H 0 0 0 0 0 0 0 0 0 0 0 0 1.5028 0.3913 -3.6199 H 0 0 0 0 0 0 0 0 0 0 0 0 0.2474 -0.3098 -1.9735 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.0104 0.0681 2.2358 H 0 0 0 0 0 0 0 0 0 0 0 0 2.3897 0.1682 2.3784 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5588 0.9019 -0.2954 H 0 0 0 0 0 0 0 0 0 0 0 0 4.5553 -0.8746 -0.1789 H 0 0 0 0 0 0 0 0 0 0 0 0 4.3831 -0.5957 2.3608 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5683 1.1169 1.0715 H 0 0 0 0 0 0 0 0 0 0 0 0 6.5308 0.3636 2.7639 H 0 0 0 0 0 0 0 0 0 0 0 0 7.2471 -0.8167 0.3768 H 0 0 0 0 0 0 0 0 0 0 0 0 4.2770 1.4798 3.1624 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.6948 -0.3597 -1.8753 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.4130 -2.3957 -0.5764 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.2760 -1.4819 -0.7745 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.7227 -0.2732 1.5466 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.9763 1.4115 -0.6111 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3860 2.1843 1.6182 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.6642 1.8576 1.3415 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8057 3.2060 -0.7714 H 0 0 0 0 0 0 0 0 0 0 0 0 -5.9872 0.9107 1.1427 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3118 -3.4227 0.3140 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.6160 -1.0136 -2.6977 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 9 10 1 0 10 11 1 0 11 12 1 0 10 13 1 0 5 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 17 18 1 0 18 19 1 0 19 20 1 0 20 21 1 0 19 22 1 0 18 23 1 0 17 24 1 0 16 25 1 0 8 3 1 0 22 15 1 0 1 26 1 0 1 27 1 0 1 28 1 0 4 29 1 0 6 30 1 0 7 31 1 0 9 32 1 0 9 33 1 0 10 34 1 1 11 35 1 0 11 36 1 0 12 37 1 0 13 38 1 0 15 39 1 6 16 40 1 1 17 41 1 6 18 42 1 1 19 43 1 6 20 44 1 0 20 45 1 0 21 46 1 0 23 47 1 0 24 48 1 0 25 49 1 0 M END

Standard InCHIKey	VXXKDWBEVHGANN-PQZGBVCXSA-N
Standard InCHI	InChI=1S/C16H24O9/c1-23-11-5-10(3-2-8(11)4-9(19)6-17)24-16-15(22)14(21)13(20)12(7-18)25-16/h2-3,5,9,12-22H,4,6-7H2,1H3/t9-,12+,13+,14-,15+,16+/m0/s1
SMILES	COc1cc(ccc1C[C@@H](CO)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	360.14	Volume:	339.382 ? Van der Waals volume.
Dense:	1.061	LogP:	-0.398 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	0.172 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	-1.366 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	7.0	Rigid Bonds:	12.0
TPSA:	149.07 ? Topological Polar Surface Area.	H-Bond Acceptor:	9.0
H-Bond Donor:	6.0	Rings:	2.0
Heavy Atoms:	9.0

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:	3.74	Fsp³:	0.625
MCE-18:	50.769 ? 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:	0.525	Fluc inhibitor:	0.011 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.054 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.035 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.208	Promiscuous compounds:	0.029

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-5.877	MDCK Permeability:	-4.979
Pgp-inhibitor:	0.0	Pgp-substrate:	0.483
PAMPA:	0.955 ? 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):	0.124
20% Bioavailability (F20%):	0.031	30% Bioavailability (F30%):	0.745
50% Bioavailability (F50%):	0.787

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.003	MRP1:	0.017
Plasma Protein Binding (PPB):	54.851%	Volume Distribution (VD):	-0.396
Fu:	45.847% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	1.0
OATP1B3 inhibitor:	1.0	BCRP inhibitor:	0.117
BSEP inhibitor:	0.002

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.04	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.002
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.0
HLM stability:	0.002 ? 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):

2.018

Half-life (T1/2):

3.402

ADMET: Toxicity

hERG Blockers:	0.023	hERG Blockers (10um):	0.051
Human Hepatotoxicity (H-HT):	0.612	Drug-induced Liver Injury (DILI):	0.502
AMES Toxicity:	0.971	Rat Oral Acute Toxicity:	0.017
Maximum Recommended Daily Dose:	0.007	Skin Sensitization:	0.999
Carcinogencity:	0.22	Eye Corrosion:	0.0
Eye Irritation:	0.181	Respiratory Toxicity:	0.007
Drug-induced Neurotoxicity:	0.027	Ototoxicity:	0.977
Hematotoxicity:	0.345	Drug-induced Nephrotoxicity:	0.836
Genotoxicity:	0.089	RPMI-8226 Immunitoxicity:	0.106
A549 Cytotoxicity:	0.398	Hek293 Cytotoxicity:	0.13
BCF:	0.195 ? 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:	2.27 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	3.869 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	2.983 ? 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 NPC258476 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	17762
0.1-0.2	27333
0.2-0.3	3702
0.3-0.4	727
0.4-0.5	258
0.5-0.6	62
0.6-0.7	9
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
0.6491	Remote Similarity	NPC218685
0.6379	Remote Similarity	NPC472024
0.6182	Remote Similarity	NPC60589
0.6182	Remote Similarity	NPC469708
0.6111	Remote Similarity	NPC153149
0.6038	Remote Similarity	NPC276195
0.6038	Remote Similarity	NPC212729
0.6038	Remote Similarity	NPC604498
0.6	Remote Similarity	NPC25817
0.5938	Remote Similarity	NPC479030
0.5926	Remote Similarity	NPC217854
0.5926	Remote Similarity	NPC269242
0.5893	Remote Similarity	NPC609376
0.5833	Remote Similarity	NPC479028
0.5833	Remote Similarity	NPC23084
0.5833	Remote Similarity	NPC479031
0.5818	Remote Similarity	NPC294470
0.569	Remote Similarity	NPC221090
0.569	Remote Similarity	NPC80098
0.5616	Remote Similarity	NPC93924
0.5593	Remote Similarity	NPC48863
0.5593	Remote Similarity	NPC251981
0.5593	Remote Similarity	NPC13745
0.5574	Remote Similarity	NPC270849
0.5536	Remote Similarity	NPC192810
0.5522	Remote Similarity	NPC210192
0.5517	Remote Similarity	NPC200092
0.5507	Remote Similarity	NPC108674
0.5469	Remote Similarity	NPC220560
0.5424	Remote Similarity	NPC69513
0.5345	Remote Similarity	NPC299144
0.5333	Remote Similarity	NPC166040
0.5323	Remote Similarity	NPC604356
0.5312	Remote Similarity	NPC290069
0.5312	Remote Similarity	NPC104167
0.5303	Remote Similarity	NPC294166
0.5303	Remote Similarity	NPC115022
0.5294	Remote Similarity	NPC475096
0.5283	Remote Similarity	NPC228907
0.5254	Remote Similarity	NPC226712
0.5254	Remote Similarity	NPC608788
0.5246	Remote Similarity	NPC310661
0.5246	Remote Similarity	NPC215833
0.5246	Remote Similarity	NPC9912
0.5238	Remote Similarity	NPC26653
0.5238	Remote Similarity	NPC26080
0.5238	Remote Similarity	NPC80600
0.5238	Remote Similarity	NPC165686
0.5231	Remote Similarity	NPC34456
0.5217	Remote Similarity	NPC99233
0.5211	Remote Similarity	NPC76128
0.5179	Remote Similarity	NPC142319
0.5172	Remote Similarity	NPC152722
0.5167	Remote Similarity	NPC145900
0.5161	Remote Similarity	NPC49074
0.5156	Remote Similarity	NPC248355
0.5156	Remote Similarity	NPC479029
0.5147	Remote Similarity	NPC604892
0.5139	Remote Similarity	NPC219163
0.5139	Remote Similarity	NPC486379
0.5135	Remote Similarity	NPC300537
0.5082	Remote Similarity	NPC610709
0.5079	Remote Similarity	NPC251102
0.5079	Remote Similarity	NPC210298
0.5079	Remote Similarity	NPC19470
0.5072	Remote Similarity	NPC175275
0.5072	Remote Similarity	NPC189115
0.507	Remote Similarity	NPC271479
0.507	Remote Similarity	NPC604833
0.5068	Remote Similarity	NPC48640
0.5068	Remote Similarity	NPC106625

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC258476 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	3988
0.1-0.2	4967
0.2-0.3	168
0.3-0.4	26
0.4-0.5	0
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
0.5254	Remote Similarity	NPD1091	Pre-clinical

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