NPASS Compound

Structure

NPC140310 OpenBabel06302215322D 31 34 0 0 1 0 0 0 0 0999 V2000 1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.4641 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -3.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -4.3301 -3.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -5.1962 -3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 3 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 6 2 0 0 0 0 1 2 1 0 0 0 0 2 3 2 0 0 0 0 3 4 1 0 0 0 0 3 31 1 0 0 0 0 4 5 2 0 0 0 0 5 6 1 0 0 0 0 6 7 1 0 0 0 0 7 30 1 0 0 0 0 7 8 2 0 0 0 0 8 9 1 0 0 0 0 9 10 2 0 0 0 0 9 11 1 0 0 0 0 11 16 2 0 0 0 0 11 12 1 0 0 0 0 12 13 2 0 0 0 0 12 30 1 0 0 0 0 13 14 1 0 0 0 0 14 15 2 0 0 0 0 14 29 1 0 0 0 0 15 16 1 0 0 0 0 16 17 1 0 0 0 0 18 15 1 1 0 0 0 18 19 1 0 0 0 0 18 25 1 0 0 0 0 19 20 1 0 0 0 0 19 28 1 0 0 0 0 20 21 1 0 0 0 0 20 27 1 1 0 0 0 21 22 1 0 0 0 0 21 26 1 6 0 0 0 22 23 1 0 0 0 0 22 25 1 0 0 0 0 23 24 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	432.11
Volume:	404.357
LogP:	0.942
LogD:	0.179
LogS:	-3.795
# Rotatable Bonds:	3
TPSA:	181.05
# H-Bond Aceptor:	10
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	10

MedChem Properties

QED Drug-Likeness Score:	0.3
Synthetic Accessibility Score:	3.943
Fsp3:	0.286
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.999
MDCK Permeability:	5.425524705060525e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.952
Human Intestinal Absorption (HIA):	0.849
20% Bioavailability (F20%):	0.956
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.025
Plasma Protein Binding (PPB):	90.15953826904297%
Volume Distribution (VD):	0.956
Pgp-substrate:	14.005563735961914%

ADMET: Metabolism

CYP1A2-inhibitor:	0.084
CYP1A2-substrate:	0.04
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.057
CYP2C9-inhibitor:	0.021
CYP2C9-substrate:	0.61
CYP2D6-inhibitor:	0.031
CYP2D6-substrate:	0.174
CYP3A4-inhibitor:	0.028
CYP3A4-substrate:	0.018

ADMET: Excretion

Clearance (CL):	3.021
Half-life (T1/2):	0.763

ADMET: Toxicity

hERG Blockers:	0.14
Human Hepatotoxicity (H-HT):	0.151
Drug-inuced Liver Injury (DILI):	0.96
AMES Toxicity:	0.709
Rat Oral Acute Toxicity:	0.058
Maximum Recommended Daily Dose:	0.016
Skin Sensitization:	0.626
Carcinogencity:	0.074
Eye Corrosion:	0.003
Eye Irritation:	0.073
Respiratory Toxicity:	0.069

Download Data

Data Type	Select
General Info & Identifiers & Properties
Structure MOL file
Source Organisms
Biological Activities
Similar NPs/Drugs

Natural Product: NPC140310

Natural Product ID:	NPC140310
*Common Name:**	MYXNWGACZJSMBT-AKCZXNEISA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	MYXNWGACZJSMBT-AKCZXNEISA-N
Standard InCHI:	InChI=1S/C21H20O10/c22-7-14-17(26)19(28)20(29)21(31-14)16-11(25)6-13-15(18(16)27)10(24)5-12(30-13)8-1-3-9(23)4-2-8/h1-6,14,17,19-23,25-29H,7H2/t14?,17-,19+,20?,21+/m1/s1
SMILES:	c1cc(ccc1c1cc(=O)c2c(cc(c(c2O)[C@H]2C([C@H]([C@@H](C(CO)O2)O)O)O)O)o1)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	n.a.
PubChem CID:	44257794
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001737] Flavonoid C-glycosides

*Note: the InCHIKey will be temporarily assigned as the "Common Name" if no IUPAC name or alternative short name is available.
**Note: the Chemical Classification was calculated by NPClassifier Version 1.5. Reference: PMID:34662515.

Species Source

Organism ID	Organism Name	Taxonomy Level	Family	SuperKingdom	Isolation Part	Collection Location	Collection Time	Reference
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	Seeds	n.a.		DOI[10.1002/ejlt.201100207]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1007/s11746-997-0093-1]
NPO7530	Cucumis sativus	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2004.07.004]
NPO7530	Cucumis sativus	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.jfca.2005.08.001]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	Seeds	n.a.		DOI[10.5219/332]
NPO26343	Fagopyrum esculentum	Species	Polygonaceae	Eukaryota	n.a.	seed	n.a.	PMID[10898633]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11599360]
NPO7530	Cucumis sativus	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12379786]
NPO30942	Drymaria diandra	Species	Caryophyllaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[15270576]
NPO7530	Cucumis sativus	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18460139]
NPO13450	Cucumis melo	Species	Cucurbitaceae	Eukaryota	Stems	n.a.	n.a.	PMID[19348465]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	seed	n.a.	PMID[21381697]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22537213]
NPO2350	Microcos paniculata	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23327794]
NPO7530	Cucumis sativus	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[23507362]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24417583]
NPO20608	Gleditsia sinensis	Species	Fabaceae	Eukaryota	anomalous fruits	n.a.	n.a.	PMID[25442304]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	Seeds	n.a.	n.a.	PMID[26923696]
NPO17171	Tripterospermum taiwanense	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO13450	Cucumis melo	Species	Cucurbitaceae	Eukaryota	Cotyledon	n.a.	n.a.	Database[FooDB]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO7530	Cucumis sativus	Species	Cucurbitaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO26343	Fagopyrum esculentum	Species	Polygonaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO26343	Fagopyrum esculentum	Species	Polygonaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO13450	Cucumis melo	Species	Cucurbitaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO24492	Tamarindus indica	Species	Fabaceae	Eukaryota	Flower	n.a.	n.a.	Database[FooDB]
NPO7530	Cucumis sativus	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	Seed Oil	n.a.	n.a.	Database[FooDB]
NPO24492	Tamarindus indica	Species	Fabaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO7530	Cucumis sativus	Species	Cucurbitaceae	Eukaryota	Seed Oil	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO26343	Fagopyrum esculentum	Species	Polygonaceae	Eukaryota	Stem	n.a.	n.a.	Database[FooDB]
NPO7530	Cucumis sativus	Species	Cucurbitaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO13450	Cucumis melo	Species	Cucurbitaceae	Eukaryota	Fruit	n.a.	n.a.	Database[FooDB]
NPO26343	Fagopyrum esculentum	Species	Polygonaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO24492	Tamarindus indica	Species	Fabaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO26343	Fagopyrum esculentum	Species	Polygonaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO26343	Fagopyrum esculentum	Species	Polygonaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO13450	Cucumis melo	Species	Cucurbitaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO26343	Fagopyrum esculentum	Species	Polygonaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO7530	Cucumis sativus	Species	Cucurbitaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO24492	Tamarindus indica	Species	Fabaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO24492	Tamarindus indica	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO7530	Cucumis sativus	Species	Cucurbitaceae	Eukaryota	Cotyledon	n.a.	n.a.	Database[FooDB]
NPO24492	Tamarindus indica	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	Seed	n.a.	n.a.	Database[FooDB]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13450	Cucumis melo	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2433	Vitex lucens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5665	Ulva pertusa	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18560	Tripterospermum japonicum	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO14381	Swertia pseudochinensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20608	Gleditsia sinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17171	Tripterospermum taiwanense	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26212	Fagopyrum tataricum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO26343	Fagopyrum esculentum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO30942	Drymaria diandra	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7530	Cucumis sativus	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO24492	Tamarindus indica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO7952	Commelina communis	Species	Commelinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO14381	Swertia pseudochinensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5665	Ulva pertusa	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24492	Tamarindus indica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9002	Herba patriniae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO7530	Cucumis sativus	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26212	Fagopyrum tataricum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2433	Vitex lucens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17171	Tripterospermum taiwanense	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2350	Microcos paniculata	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15542	Herba nerviliae	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[TCMID]
NPO13450	Cucumis melo	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18560	Tripterospermum japonicum	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26343	Fagopyrum esculentum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7952	Commelina communis	Species	Commelinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO27397	Drymaria cordata	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20608	Gleditsia sinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO24492	Tamarindus indica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO5665	Ulva pertusa	Species	Ulvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20608	Gleditsia sinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7530	Cucumis sativus	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO14381	Swertia pseudochinensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO26343	Fagopyrum esculentum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO7952	Commelina communis	Species	Commelinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2350	Microcos paniculata	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO14381	Swertia pseudochinensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO20608	Gleditsia sinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO2433	Vitex lucens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2350	Microcos paniculata	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7530	Cucumis sativus	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18560	Tripterospermum japonicum	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26343	Fagopyrum esculentum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO24492	Tamarindus indica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13450	Cucumis melo	Species	Cucurbitaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26212	Fagopyrum tataricum	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO25114	Linum usitatissimum	Species	Linaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14381	Swertia pseudochinensis	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27397	Drymaria cordata	Species	Caryophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17171	Tripterospermum taiwanense	Species	Gentianaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8210	Trigonella foenum-graecum	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20608	Gleditsia sinensis	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7952	Commelina communis	Species	Commelinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5665	Ulva pertusa	Species	Ulvaceae	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	NP ID	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

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

☑ Note for Activity Records:
☉ The quantitative biological activities were primarily integrated from ChEMBL (Version-30) database and were also directly collected from PubMed literature. PubMed PMID was provided as the reference link for each activity record.

Chemically structural similarity: I. Similar Active Natural Products in NPASS

Top-200 similar NPs were calculated against the active-NP-set (includes 4,3285 NPs with experimentally-derived bioactivity available in NPASS)

Similarity level is defined by Tanimoto coefficient (Tc) between two molecules. Tc lies between [0, 1] where '1' indicates the highest similarity. What is Tanimoto coefficient

● The left chart: Distribution of similarity level between NPC140310 and all remaining natural products in the NPASS database.
● The right table: Most similar natural products (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	425
0.1-0.2	1654
0.2-0.3	3640
0.3-0.4	9418
0.4-0.5	9240
0.5-0.6	3922
0.6-0.7	5557
0.7-0.8	4482
0.8-0.85	2247
0.85-0.9	1846
0.9-0.95	250
0.95-1	16

Similarity Score	Similarity Level	Natural Product ID

Chemically structural similarity: II. Similar Clinical/Approved Drugs

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

● The left chart: Distribution of similarity level between NPC140310 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	398
0.1-0.2	843
0.2-0.3	1680
0.3-0.4	2640
0.4-0.5	1957
0.5-0.6	1080
0.6-0.7	357
0.7-0.8	136
0.8-0.85	29
0.85-0.9	27
0.9-0.95	2
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage

Bioactivity similarity: Similar Natural Products in NPASS

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