NPASS Compound

Natural Product: NPC303409

Natural Product ID	NPC303409
Common Name ? The InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.	GUBGYTABKSRVRQ-TYAPZPMWSA-N
IUPAC Name	n.a.
Synonyms
Synthetic Gene Cluster	n.a.
ChEMBL Identifier	n.a.
PubChem CID	5288769
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:0002207] O-glycosyl compounds

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 45 46 0 0 0 0 0 0 0 0999 V2000 -3.1902 -1.4035 -2.2460 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6502 -0.6775 -1.0308 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.6237 0.4286 -0.6492 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.0456 1.1817 0.5022 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.5941 1.5337 0.3420 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8052 0.3600 -0.1992 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.4562 -0.0786 -1.3531 O 0 0 0 0 0 0 0 0 0 0 0 0 0.4781 0.7016 -0.5290 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4596 -0.0261 0.1859 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2360 0.9249 1.0053 C 0 0 1 0 0 0 0 0 0 0 0 0 1.7784 0.8754 2.4645 C 0 0 0 0 0 0 0 0 0 0 0 0 2.1380 -0.3432 2.9978 O 0 0 0 0 0 0 0 0 0 0 0 0 3.6006 0.7670 1.0502 O 0 0 0 0 0 0 0 0 0 0 0 0 4.0853 -0.4386 0.6290 C 0 0 1 0 0 0 0 0 0 0 0 0 3.6803 -0.5439 -0.8485 C 0 0 2 0 0 0 0 0 0 0 0 0 2.2041 -0.8154 -0.8334 C 0 0 1 0 0 0 0 0 0 0 0 0 2.0638 -2.1936 -0.5426 O 0 0 0 0 0 0 0 0 0 0 0 0 4.4140 -1.4873 -1.5120 O 0 0 0 0 0 0 0 0 0 0 0 0 5.4468 -0.4731 0.7946 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.4464 2.6618 -0.4622 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.7441 2.4044 0.6179 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.7935 -0.2103 -0.2286 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.4002 -2.0076 -1.9110 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.4575 -2.1380 -2.5878 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.3887 -0.6907 -3.0727 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.5922 -1.3763 -0.1934 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8373 1.0448 -1.5298 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.2195 0.5977 1.4410 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.2035 1.7687 1.3531 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.8731 -0.4377 0.5897 H 0 0 0 0 0 0 0 0 0 0 0 0 0.8774 -0.7053 0.8523 H 0 0 0 0 0 0 0 0 0 0 0 0 2.0547 1.9653 0.6326 H 0 0 0 0 0 0 0 0 0 0 0 0 0.7378 1.1444 2.6047 H 0 0 0 0 0 0 0 0 0 0 0 0 2.4172 1.6481 2.9845 H 0 0 0 0 0 0 0 0 0 0 0 0 1.4007 -0.8141 3.4563 H 0 0 0 0 0 0 0 0 0 0 0 0 3.5509 -1.2422 1.2112 H 0 0 0 0 0 0 0 0 0 0 0 0 3.8217 0.4677 -1.3263 H 0 0 0 0 0 0 0 0 0 0 0 0 1.7973 -0.7183 -1.8715 H 0 0 0 0 0 0 0 0 0 0 0 0 1.0873 -2.3778 -0.5034 H 0 0 0 0 0 0 0 0 0 0 0 0 4.8238 -1.1688 -2.3322 H 0 0 0 0 0 0 0 0 0 0 0 0 5.8238 -1.4056 0.7479 H 0 0 0 0 0 0 0 0 0 0 0 0 -0.7008 3.2279 -0.1425 H 0 0 0 0 0 0 0 0 0 0 0 0 -3.8064 2.7893 -0.2977 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.7933 -0.2744 0.7577 H 0 0 0 0 0 0 0 0 0 0 0 0 -4.3559 -2.4451 -1.0178 H 0 0 0 0 0 0 0 0 0 0 0 0 1 2 1 0 2 3 1 0 3 4 1 0 4 5 1 0 5 6 1 0 6 7 1 0 6 8 1 0 8 9 1 0 9 10 1 0 10 11 1 0 11 12 1 0 10 13 1 0 13 14 1 0 14 15 1 0 15 16 1 0 16 17 1 0 15 18 1 0 14 19 1 0 5 20 1 0 4 21 1 0 3 22 1 0 1 23 1 0 7 2 1 0 16 9 1 0 1 24 1 0 1 25 1 0 2 26 1 1 3 27 1 6 4 28 1 1 5 29 1 1 6 30 1 1 9 31 1 1 10 32 1 6 11 33 1 0 11 34 1 0 12 35 1 0 14 36 1 1 15 37 1 6 16 38 1 6 17 39 1 0 18 40 1 0 19 41 1 0 20 42 1 0 21 43 1 0 22 44 1 0 23 45 1 0 M END

Standard InCHIKey	GUBGYTABKSRVRQ-TYAPZPMWSA-N
Standard InCHI	InChI=1S/C12H22O11/c13-1-3-5(15)6(16)9(19)12(22-3)23-10-4(2-14)21-11(20)8(18)7(10)17/h3-20H,1-2H2/t3-,4-,5-,6+,7-,8+,9+,10-,11+,12+/m1/s1
SMILES	C([C@@H]1[C@H]([C@@H]([C@@H]([C@@H](O1)O[C@@H]1[C@@H](CO)O[C@@H]([C@H]([C@H]1O)O)O)O)O)O)O

Calculated Properties

Physi-Chem Properties

Molecular Weight:	342.12	Volume:	295.688 ? Van der Waals volume.
Dense:	1.157	LogP:	-2.833 ? The logarithm of the n-octanol/water distribution coefficients.
logD7.4:	-2.279 ? The logarithm of the n-octanol/water distribution coefficient at pH=7.4.	LogS:	0.224 ? The logarithm of aqueous solubility value.
Rotatable Bonds:	4.0	Rigid Bonds:	12.0
TPSA:	189.53 ? Topological Polar Surface Area.	H-Bond Acceptor:	11.0
H-Bond Donor:	8.0	Rings:	2.0
Heavy Atoms:	11.0

MedChem Properties

QED Drug-Likeness Score:	0.243	GASA:	1.0 ? GASA represents the probability of being difficult to synthesize, ranging from 0 to 1.
Synthetic Accessibility Score:	4.282	Fsp³:	1.0
MCE-18:	45.333 ? MCE-18 stands for medicinal chemistry evolution.MCE-18≥45 is considered a suitable value.	Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected	GSK Rule:	Rejected
Golden Triangle Rule:	Accepted	BMS Rule:	1
Chelating Alert:	0	PAINS Alert:	0
Colloidal aggregators:	0.18	Fluc inhibitor:	0.0 ? The fluc inhibitor value is the probability of being fLuc inhibitors, within the range of 0 to 1.
Blue fluorescence:	0.042 ? The blue fluorescence value is the probability of being blue fluorescence, within the range of 0 to 1	Green fluorescence:	0.0 ? The green fluorescence value is the probability of being green fluorescence, within the range of 0 to 1
Reactive compounds:	0.506	Promiscuous compounds:	0.017

ADMET Properties (ADMETlab3.0)

ADMET: Absorption

Caco-2 Permeability:	-6.777	MDCK Permeability:	-4.956
Pgp-inhibitor:	0.0	Pgp-substrate:	0.815
PAMPA:	1.0 ? 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):	0.994
20% Bioavailability (F20%):	0.431	30% Bioavailability (F30%):	0.967
50% Bioavailability (F50%):	0.949

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.066	MRP1:	0.03
Plasma Protein Binding (PPB):	28.259%	Volume Distribution (VD):	-0.496
Fu:	75.363% ? The fraction unbound in plasms.	OATP1B1 inhibitor:	0.947
OATP1B3 inhibitor:	0.981	BCRP inhibitor:	0.024
BSEP inhibitor:	0.001

ADMET: Metabolism

CYP1A2-inhibitor:	0.0	CYP1A2-substrate:	0.0
CYP2C19-inhibitor:	0.0	CYP2C19-substrate:	0.0
CYP2C9-inhibitor:	0.014	CYP2C9-substrate:	0.0
CYP2D6-inhibitor:	0.0	CYP2D6-substrate:	0.0
CYP3A4-inhibitor:	0.0	CYP3A4-substrate:	0.0
CYP2B6-substrate:	0.0	CYP2C8-inhibitor:	0.972
HLM stability:	0.008 ? 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):

0.846

Half-life (T1/2):

2.764

ADMET: Toxicity

hERG Blockers:	0.003	hERG Blockers (10um):	0.081
Human Hepatotoxicity (H-HT):	0.39	Drug-induced Liver Injury (DILI):	0.549
AMES Toxicity:	0.823	Rat Oral Acute Toxicity:	0.011
Maximum Recommended Daily Dose:	0.004	Skin Sensitization:	0.997
Carcinogencity:	0.025	Eye Corrosion:	0.0
Eye Irritation:	0.404	Respiratory Toxicity:	0.01
Drug-induced Neurotoxicity:	0.004	Ototoxicity:	0.987
Hematotoxicity:	0.327	Drug-induced Nephrotoxicity:	0.891
Genotoxicity:	0.047	RPMI-8226 Immunitoxicity:	0.136
A549 Cytotoxicity:	0.037	Hek293 Cytotoxicity:	0.023
BCF:	0.087 ? 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:	1.318 ? 48 hour Tetrahymena pyriformis IGC50. The unit of IGC50 is -log10[(mg/L)/(1000*MW)].
LC50DM:	2.567 ? 48 hour Daphnia magna LC50. The unit of LC50DM is -log10[(mg/L)/(1000*MW)].	LC50FM:	1.788 ? 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
NPO7019	Hypericum sampsonii	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.phytochem.2004.08.014]
NPO17509	Gentiana bellidifolia	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/S0040-4020(01)98434-0]
NPO12113	Aconitum forrestii	Species	Ranunculaceae	Eukaryota	n.a.	root	n.a.	DOI[10.1021/np50033a013]
NPO17406	Calophyllum lanigerum	Species	Calophyllaceae	Eukaryota	n.a.	Sarawak, Malaysia	n.a.	PMID[11430019]
NPO17406	Calophyllum lanigerum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[1379639]
NPO12900	Sarcococca hookeriana	Species	Buxaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[17827771]
NPO7019	Hypericum sampsonii	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18038963]
NPO14832	Calocedrus macrolepis	Species	Cupressaceae	Eukaryota	n.a.	leaf	n.a.	PMID[18206367]
NPO2421	Picea glauca	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18636777]
NPO12900	Sarcococca hookeriana	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18681480]
NPO12900	Sarcococca hookeriana	Species	Buxaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[18681480]
NPO19447	Daphniphyllum subverticillatum	Species	Daphniphyllaceae	Eukaryota	leaves	n.a.	n.a.	PMID[19739650]
NPO18442	Capsicum baccatum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21535519]
NPO19581	Marchantia polymorpha	Species	Marchantiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21625478]
NPO3807	Morinda lucida	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26048790]
NPO691	Tarchonanthus camphoratus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[29244495]
NPO284	Albizia procera	Species	Fabaceae	Eukaryota	Bark	n.a.	n.a.	PMID[30520635]
NPO1539	Artemisia giraldii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[36364129]
NPO11662	Solanum virginianum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[39081888]
NPO18682	Piper puberulum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[7623032]
NPO17406	Calophyllum lanigerum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8792623]
NPO9099	Carissa spinarum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19849	Melilotus officinalis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19377	Podocarpus blumei	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19432	Millettia pinnata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3963	Hortonia floribunda	Species	Monimiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO691	Tarchonanthus camphoratus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17406	Calophyllum lanigerum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19581	Marchantia polymorpha	Species	Marchantiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO4421	Penicillium cyclopium	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3255	Lampranthus sociorum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3807	Morinda lucida	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18608	Fagopyrum cymosum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5981	Achlys triphylla	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7770	Lactuca laciniata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO17648	Subergorgia hicksoni	Species	Subergorgiidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15880	Microlepia marginata	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18064	Lycopodium paniculatum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO5588	Bursera tonkinensis	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO15183	Salvia horminum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO14266	Borassus flabellifer	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19447	Daphniphyllum subverticillatum	Species	Daphniphyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7019	Hypericum sampsonii	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO3415	Perymenium mendezii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12900	Sarcococca hookeriana	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18361	Mollugo cerviana	Species	Molluginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8920	Balanocarpus heimii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2421	Picea glauca	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO19525	Tephrosia bracteolata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO284	Albizia procera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO18778	Paullinia pinnata	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO8770	Euphorbia wallichii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO2708	Agaricus nebularis	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12113	Aconitum forrestii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO1539	Artemisia giraldii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO11331	Phellinus tremulae	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO13433	Adenium obesum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO565	Poria obliqua	Species	Coccinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO12283	Macrothelypteris torresiana	Species	Thelypteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO16571	Canarium muelleri	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[COCONUT]
NPO7019	Hypericum sampsonii	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5588	Bursera tonkinensis	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18608	Fagopyrum cymosum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19581	Marchantia polymorpha	Species	Marchantiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15880	Microlepia marginata	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3807	Morinda lucida	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18682	Piper puberulum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7155	Cypripedium calceolus	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12113	Aconitum forrestii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8770	Euphorbia wallichii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7770	Lactuca laciniata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO99	Artemisia porrecta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO3807	Morinda lucida	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8770	Euphorbia wallichii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO99	Artemisia porrecta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19432	Millettia pinnata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5588	Bursera tonkinensis	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15880	Microlepia marginata	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18608	Fagopyrum cymosum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16148	Neoboutonia glabrescens	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19581	Marchantia polymorpha	Species	Marchantiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7019	Hypericum sampsonii	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12113	Aconitum forrestii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7155	Cypripedium calceolus	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7770	Lactuca laciniata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO11662	Solanum virginianum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13433	Adenium obesum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18682	Piper puberulum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18608	Fagopyrum cymosum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3807	Morinda lucida	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7155	Cypripedium calceolus	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9099	Carissa spinarum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1539	Artemisia giraldii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4421	Penicillium cyclopium	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18682	Piper puberulum	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5981	Achlys triphylla	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13433	Adenium obesum	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15183	Salvia horminum	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11331	Phellinus tremulae	Species	Hymenochaetaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17648	Subergorgia hicksoni	Species	Subergorgiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3963	Hortonia floribunda	Species	Monimiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO284	Albizia procera	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19377	Podocarpus blumei	Species	Podocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15880	Microlepia marginata	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18361	Mollugo cerviana	Species	Molluginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17406	Calophyllum lanigerum	Species	Calophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4952	Pertusaria amara	Species	Pertusariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20860	Lygodium pinnatifidum	Species	Lygodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18940	Selinum papyraceum	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8770	Euphorbia wallichii	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO565	Poria obliqua	Species	Coccinellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3415	Perymenium mendezii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18608	Fagopyrum cymosum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19432	Millettia pinnata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7616	Melanargia galathea	Species	Nymphalidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3263	Thea sasanqua	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO99	Artemisia porrecta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO691	Tarchonanthus camphoratus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7464	Uruparia lanosa	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO12113	Aconitum forrestii	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12900	Sarcococca hookeriana	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19314	Albizia schimperana	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16148	Neoboutonia glabrescens	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19581	Marchantia polymorpha	Species	Marchantiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7155	Cypripedium calceolus	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2421	Picea glauca	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18272	Mikania oblongifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11662	Solanum virginianum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14266	Borassus flabellifer	Species	Arecaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18860	Pelea madagascarica	Species	Bovidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6844	Bulbophyllum protractum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3255	Lampranthus sociorum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18064	Lycopodium paniculatum	Species	Lycopodiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19525	Tephrosia bracteolata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2963	Diospyros glaucifolia	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13869	Ranunculus bulbosus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18540	Berkheya radula	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4117	Nauclea rhynchophylla	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19722	Tephrosia odorata	Species	Geometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15597	Calystegia pubescens	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19447	Daphniphyllum subverticillatum	Species	Daphniphyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19098	Hypotrachyna quaesita	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO29287	Alectoria ochroleuca	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3807	Morinda lucida	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16274	Calonectria lauri	Species	Nectriaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19249	Garcinia latissima	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO855	Elymnias thryallis	Species	Nymphalidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7770	Lactuca laciniata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19842	Sideritis condensata	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5588	Bursera tonkinensis	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10175	Anaptychia obscura	Species	Physciaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16571	Canarium muelleri	Species	Burseraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17509	Gentiana bellidifolia	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19849	Melilotus officinalis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18442	Capsicum baccatum	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2708	Agaricus nebularis	Species	Agaricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8920	Balanocarpus heimii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO14832	Calocedrus macrolepis	Species	Cupressaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18778	Paullinia pinnata	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17793	Parkia javanica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27385	Calamus insignis	Species	Sparidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22826	Buxus rolfei	Species	Buxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8451	Chilo sacchariphagus	Species	Crambidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7019	Hypericum sampsonii	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12283	Macrothelypteris torresiana	Species	Thelypteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3523	Botryllus tyreus	Species	Styelidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16249	Dendrobium bicameratum	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

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

NP Quantity Composition/Concentration

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

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

Biological Activity

Molecular-level activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vitro activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

In vivo activity

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference

Experimental ADME

Experiment Model	Experiment Tissue	ADME Type	ADME Relation	ADME Value	ADME Unit	Reference

Experimental Toxicity

Quantitative toxicity

Experiment Model	Experiment Organism	Toxicity Type	Toxicity Relation	Toxicity Value	Toxicity Unit	Reference

Common Abbreviations:
LC: Lethal Concentration; LD: Lethal Dose; LT:Lethal Time; NOAEL: No-observed-adverse-effect Level; BMDL: Benchmark Dose Lower Confidence Limit; BMD: Benchmark Dose; BMC:Benchmark Concentration; LOAEL: Lowest Observed Adverse Effect Level; RfD:Reference Dose; RfC:Reference Concentration; MRL: Minimal Risk Level; MEG: Maximum Exposure Guideline; PAC: Protective Action Criteria

Categorical toxicity labels

Hepatotoxicity	Carcinogenicity	Mutagenicity	Cardiotoxicity	Respiratory Toxicity	Eye Irritation	Endocrine Disruption

Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP toxicity records from domain-specific databases. These databases include:
☉ ToxValDB: a curated database that compiles quantitative toxicity values for chemicals from diverse public sources to support toxicological research and risk assessment.
☉ TOXRIC: a comprehensive, free-to-access, online database providing toxicological/feature data. The toxicity labels are retrieved from this database. [PMID: 36400569]

Chemically structural similarity

Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes approximately 50,000 NPs with experimentally-derived bioactivity available in NPASS)

Similarity is measured using the Tanimoto coefficient (Tc) , which compares the binary fingerprints of two molecules. Tc is calculated as the intersection divided by the union of '1' bits in the fingerprints, ranging from 0 to 1, with 1 indicating highest similarity.

● The left chart: Distribution of similarity level between NPC303409 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	36646
0.1-0.2	10002
0.2-0.3	2786
0.3-0.4	346
0.4-0.5	50
0.5-0.6	19
0.6-0.7	1
0.7-0.8	0
0.8-0.85	0
0.85-0.9	2
0.9-0.95	0
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC246558
1.0	High Similarity	NPC67660
1.0	High Similarity	NPC165198
1.0	High Similarity	NPC209753
1.0	High Similarity	NPC58629
0.8947	High Similarity	NPC317023
0.8947	High Similarity	NPC489878
0.6111	Remote Similarity	NPC23134
0.5455	Remote Similarity	NPC323361
0.5435	Remote Similarity	NPC89145
0.5435	Remote Similarity	NPC157514
0.5435	Remote Similarity	NPC322314
0.5435	Remote Similarity	NPC269166
0.5405	Remote Similarity	NPC42503
0.5405	Remote Similarity	NPC282143
0.5405	Remote Similarity	NPC107914
0.5405	Remote Similarity	NPC242073
0.5405	Remote Similarity	NPC299781
0.5405	Remote Similarity	NPC157193
0.5405	Remote Similarity	NPC608193
0.5208	Remote Similarity	NPC604425
0.5102	Remote Similarity	NPC477750
0.5102	Remote Similarity	NPC477763
0.5102	Remote Similarity	NPC477757
0.5102	Remote Similarity	NPC477762
0.5102	Remote Similarity	NPC477755
0.5102	Remote Similarity	NPC477753

Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC303409 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.5 or Top200).

range	Tanimoto Coefficient
0-0.1	8322
0.1-0.2	714
0.2-0.3	76
0.3-0.4	17
0.4-0.5	13
0.5-0.6	3
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	5

Similarity Score	Similarity Level	Drug ID	Developmental Stage
1.0	High Similarity	NPD888	Phase 3
1.0	High Similarity	NPD890	Clinical (unspecified phase)
1.0	High Similarity	NPD891	Phase 3
1.0	High Similarity	NPD892	Phase 3
1.0	High Similarity	NPD893	Approved
0.5455	Remote Similarity	NPD889	Approved
0.5455	Remote Similarity	NPD894	Phase 4
0.5366	Remote Similarity	NPD905	Phase 4

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