NPASS Compound

Structure

CID270849 OpenBabel06191716072D 23 24 0 0 1 0 0 0 0 0999 V2000 -6.0622 -3.5000 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 -5.1962 -3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -2.0000 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 -4.3301 -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 -4.3301 -1.5000 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 -3.4641 -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 2 0 0 0 0 0 0 0 0 0 0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 0.0000 -2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -0.8660 -1.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -0.8660 -0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -2.0000 0.0000 O 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 -1.7321 -2.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -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 1 3 2 0 0 0 0 2 21 1 0 0 0 0 3 4 1 0 0 0 0 4 9 1 0 0 0 0 5 6 2 0 0 0 0 5 9 1 0 0 0 0 6 10 1 0 0 0 0 7 9 2 0 0 0 0 7 11 1 0 0 0 0 8 17 1 0 0 0 0 10 11 2 0 0 0 0 10 22 1 0 0 0 0 11 21 1 0 0 0 0 12 8 1 6 0 0 0 12 13 1 0 0 0 0 12 23 1 0 0 0 0 13 14 1 0 0 0 0 13 18 1 1 0 0 0 14 15 1 0 0 0 0 14 19 1 6 0 0 0 15 16 1 0 0 0 0 15 20 1 1 0 0 0 16 22 1 6 0 0 0 16 23 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	326.14
Volume:	319.165
LogP:	0.57
LogD:	0.511
LogS:	-1.731
# Rotatable Bonds:	6
TPSA:	108.61
# H-Bond Aceptor:	7
# H-Bond Donor:	4
# Rings:	2
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.527
Synthetic Accessibility Score:	3.552
Fsp3:	0.5
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.294
MDCK Permeability:	4.7760888264747337e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.003
Human Intestinal Absorption (HIA):	0.507
20% Bioavailability (F20%):	0.011
30% Bioavailability (F30%):	0.928

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.321
Plasma Protein Binding (PPB):	75.16621398925781%
Volume Distribution (VD):	0.615
Pgp-substrate:	13.706703186035156%

ADMET: Metabolism

CYP1A2-inhibitor:	0.078
CYP1A2-substrate:	0.19
CYP2C19-inhibitor:	0.021
CYP2C19-substrate:	0.782
CYP2C9-inhibitor:	0.004
CYP2C9-substrate:	0.512
CYP2D6-inhibitor:	0.046
CYP2D6-substrate:	0.752
CYP3A4-inhibitor:	0.017
CYP3A4-substrate:	0.11

ADMET: Excretion

Clearance (CL):	4.269
Half-life (T1/2):	0.835

ADMET: Toxicity

hERG Blockers:	0.059
Human Hepatotoxicity (H-HT):	0.056
Drug-inuced Liver Injury (DILI):	0.037
AMES Toxicity:	0.259
Rat Oral Acute Toxicity:	0.047
Maximum Recommended Daily Dose:	0.013
Skin Sensitization:	0.319
Carcinogencity:	0.403
Eye Corrosion:	0.004
Eye Irritation:	0.053
Respiratory Toxicity:	0.053

Download Data

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

Natural Product: NPC270849

Natural Product ID:	NPC270849
*Common Name:**	Citrusin C
IUPAC Name:	(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-(2-methoxy-4-prop-2-enylphenoxy)oxane-3,4,5-triol
Synonyms:	Citrusin C; Eugenyl Beta-D-Glucopyranoside
Standard InCHIKey:	VADSVXSGIFBZLI-IBEHDNSVSA-N
Standard InCHI:	InChI=1S/C16H22O7/c1-3-4-9-5-6-10(11(7-9)21-2)22-16-15(20)14(19)13(18)12(8-17)23-16/h3,5-7,12-20H,1,4,8H2,2H3/t12-,13-,14+,15-,16-/m1/s1
SMILES:	C=CCc1ccc(c(c1)OC)O[C@@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL463487
PubChem CID:	3084296
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

*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
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11908994]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	Leaves	n.a.	n.a.	PMID[12088434]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	flowers	n.a.	n.a.	PMID[12193020]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12880314]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	whole plant	n.a.	PMID[1294695]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15104516]
NPO13353	Sedum sarmentosum	Species	Crassulaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[15577228]
NPO13968	Garcinia scortechinii	Species	Clusiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[16038540]
NPO14358	Rhodobacter sphaeroides	Species	Rhodobacteraceae	Bacteria	n.a.	n.a.	n.a.	PMID[1612412]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	leaves and twigs	Taiwan	n.a.	PMID[1659612]
NPO7728	Vitex agnus-castus	Species	Lamiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[17262892]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	root	n.a.	PMID[1823989]
NPO8068	Blumea mollis	Species	Asteraceae	Eukaryota	n.a.	leaf	n.a.	PMID[18566831]
NPO14162	Chlorophytum borivilianum	Species	Asparagaceae	Eukaryota	roots	n.a.	n.a.	PMID[19128156]
NPO7016	Gardenia tubifera	Species	Rubiaceae	Eukaryota	exudate	n.a.	n.a.	PMID[20028108]
NPO12357	Lycopus europaeus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[20674349]
NPO7728	Vitex agnus-castus	Species	Lamiaceae	Eukaryota	n.a.	fruit	n.a.	PMID[21163339]
NPO11492	Kopsia grandifolia	Species	Apocynaceae	Eukaryota	n.a.	leaf	n.a.	PMID[21428274]
NPO11492	Kopsia grandifolia	Species	Apocynaceae	Eukaryota	n.a.	stem	n.a.	PMID[21428274]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[21707257]
NPO13353	Sedum sarmentosum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[22085682]
NPO23708	Aster koraiensis	Species	Asteraceae	Eukaryota	aerial parts	Euidang-myun, Gongju city, Chungchengnam-do, Republic of Korea	2007-Aug	PMID[22264115]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	leaves	n.a.	n.a.	PMID[22272932]
NPO32535	dracocephalum ruyschiana	Species	Lamiaceae	Eukaryota	aerial parts	Mongolian	n.a.	PMID[23356964]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	fruits	n.a.	n.a.	PMID[24485782]
NPO32782	ducrosia ismaelis	Species	Apiaceae	Eukaryota	aerial parts	n.a.	n.a.	PMID[24953601]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	aerial parts	Nanning, Guangxi Zhuang Autonomous Region, Peoples Republic of China	2012-OCT	PMID[24955889]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25320841]
NPO1795	Fragaria vesca	Species	Rosaceae	Eukaryota	n.a.	fruit	n.a.	PMID[26169681]
NPO2722	Humulus japonicus	Species	Cannabaceae	Eukaryota	Aerial Parts	n.a.	n.a.	PMID[29254897]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[31747281]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[8594148]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	Essential Oil	n.a.	n.a.	Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	Leaf	n.a.	n.a.	Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	Plant	n.a.	n.a.	Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	Shoot	n.a.	n.a.	Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota		n.a.	n.a.	Database[FooDB]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[FooDB]
NPO22242.1	Phellodendron chinense var. glabriusculum	Varieties	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1795	Fragaria vesca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12357	Lycopus europaeus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13353	Sedum sarmentosum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO2722	Humulus japonicus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13014	Ipomoea cairica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.		Database[Phenol-Explorer]
NPO12357	Lycopus europaeus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13353	Sedum sarmentosum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13968	Garcinia scortechinii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3465	Aconitum leucostomum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO22242.1	Phellodendron chinense var. glabriusculum	Varieties	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13014	Ipomoea cairica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1795	Fragaria vesca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16703	Isodon lophanthoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO2722	Humulus japonicus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4004	Aquilegia ecalcarata	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13353	Sedum sarmentosum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO3465	Aconitum leucostomum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO2722	Humulus japonicus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO13014	Ipomoea cairica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13353	Sedum sarmentosum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO12509	Dipterocarpus dyeri	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4004	Aquilegia ecalcarata	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9385	Glycosmis ovoidea	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1795	Fragaria vesca	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14730	Bonnetia dinizii	Species	Bonnetiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14057	Apollonias barbujana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13014	Ipomoea cairica	Species	Convolvulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7728	Vitex agnus-castus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16703	Isodon lophanthoides	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5191	Penicillium cinerascens	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8650	Perilla frutescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2090	Baccharis thesioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4671	Persea mexicana	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14084	Roccella fucoides	Species	Roccellaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13353	Sedum sarmentosum	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2509	Strombus gigas	Species	Strombidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO368	Dendroaspis angusticeps	Species	Elapidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11492	Kopsia grandifolia	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19472	Thymus vulgaris	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11998	Ledebouria socialis	Species	Hyacinthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7016	Gardenia tubifera	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2722	Humulus japonicus	Species	Cannabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO746	Panax innovans	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8892	Sordaria araneosa	Species	Sordariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28679	Prunus mume	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12357	Lycopus europaeus	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14358	Rhodobacter sphaeroides	Species	Rhodobacteraceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO205	Lasianthus fordii	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5406	Veronica chamaedrys	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18458	Raukaua simplex	Species	Araliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15289	Scoparia dulcis	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10550	Artemisia hanseniana	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13968	Garcinia scortechinii	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8068	Blumea mollis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO23708	Aster koraiensis	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3465	Aconitum leucostomum	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13766	Ceanothus velutinus	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13467	Anarsia lineatella	Species	Gelechiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26351	Agastache rugosa	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14162	Chlorophytum borivilianum	Species	Asparagaceae	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

Activity Type	# Activity
IC50	4
Others	1

Activity Type	# Activity
Cell Line	2
Individual Protein	1
Others	2

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT113	Cell Line	RAW264.7	Mus musculus	Activity	=	100.93	%	PMID[559439]
NPT113	Cell Line	RAW264.7	Mus musculus	IC50	=	1700.0	nM	PMID[559441]
NPT35	Others	n.a.		IC50	>	50000.0	nM	PMID[559437]
NPT68	Individual Protein	Aldose reductase	Rattus norvegicus	IC50	>	30000.0	nM	PMID[559437]
NPT1	Others	Radical scavenging activity		IC50	=	328000.0	nM	PMID[559438]

☑ 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 NPC270849 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	338
0.1-0.2	1463
0.2-0.3	4033
0.3-0.4	10534
0.4-0.5	8056
0.5-0.6	5363
0.6-0.7	8385
0.7-0.8	3486
0.8-0.85	758
0.85-0.9	212
0.9-0.95	55
0.95-1	14

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC26653
0.9919	High Similarity	NPC80600
0.9919	High Similarity	NPC472024
0.9756	High Similarity	NPC302378
0.968	High Similarity	NPC9912
0.9677	High Similarity	NPC248355
0.9677	High Similarity	NPC166040
0.9606	High Similarity	NPC187194
0.9528	High Similarity	NPC25821
0.9528	High Similarity	NPC215833
0.9528	High Similarity	NPC69513
0.9524	High Similarity	NPC65942
0.9524	High Similarity	NPC248307
0.9453	High Similarity	NPC251981
0.9453	High Similarity	NPC48863
0.9453	High Similarity	NPC476411
0.9453	High Similarity	NPC13745
0.9449	High Similarity	NPC162093
0.9385	High Similarity	NPC470413
0.9385	High Similarity	NPC138738
0.9375	High Similarity	NPC49074
0.9365	High Similarity	NPC307110
0.9302	High Similarity	NPC35731
0.9302	High Similarity	NPC470881
0.9297	High Similarity	NPC299144
0.9262	High Similarity	NPC469412
0.9262	High Similarity	NPC198734
0.9231	High Similarity	NPC55040
0.9231	High Similarity	NPC470236
0.9225	High Similarity	NPC6836
0.918	High Similarity	NPC469708
0.918	High Similarity	NPC60589
0.9173	High Similarity	NPC76871
0.916	High Similarity	NPC25695
0.916	High Similarity	NPC199459
0.916	High Similarity	NPC172818
0.916	High Similarity	NPC52277
0.916	High Similarity	NPC164857
0.916	High Similarity	NPC177035
0.916	High Similarity	NPC37468
0.9154	High Similarity	NPC107478
0.9147	High Similarity	NPC252833
0.912	High Similarity	NPC94276
0.912	High Similarity	NPC109822
0.9113	High Similarity	NPC476142
0.9113	High Similarity	NPC71090
0.9106	High Similarity	NPC269242
0.9104	High Similarity	NPC189115
0.9104	High Similarity	NPC60249
0.9104	High Similarity	NPC246947
0.9104	High Similarity	NPC469559
0.9098	High Similarity	NPC106944
0.9091	High Similarity	NPC304152
0.9077	High Similarity	NPC132895
0.907	High Similarity	NPC166168
0.9062	High Similarity	NPC86030
0.9062	High Similarity	NPC97326
0.9062	High Similarity	NPC5851
0.9055	High Similarity	NPC41706
0.9055	High Similarity	NPC163332
0.9055	High Similarity	NPC111247
0.9055	High Similarity	NPC319625
0.9055	High Similarity	NPC292056
0.9055	High Similarity	NPC118787
0.9055	High Similarity	NPC183181
0.9055	High Similarity	NPC147821
0.9037	High Similarity	NPC185307
0.9037	High Similarity	NPC46092
0.9037	High Similarity	NPC470950
0.903	High Similarity	NPC469661
0.9023	High Similarity	NPC98777
0.9023	High Similarity	NPC212770
0.9023	High Similarity	NPC100389
0.9015	High Similarity	NPC104167
0.9008	High Similarity	NPC87696
0.9	High Similarity	NPC470270
0.8984	High Similarity	NPC72529
0.8976	High Similarity	NPC178284
0.8976	High Similarity	NPC191037
0.8976	High Similarity	NPC58607
0.8971	High Similarity	NPC473045
0.8971	High Similarity	NPC79429
0.8971	High Similarity	NPC470235
0.8971	High Similarity	NPC217635
0.8971	High Similarity	NPC471063
0.8971	High Similarity	NPC283995
0.8971	High Similarity	NPC129417
0.8971	High Similarity	NPC471667
0.8971	High Similarity	NPC25292
0.8968	High Similarity	NPC287429
0.8968	High Similarity	NPC114901
0.8968	High Similarity	NPC293701
0.8968	High Similarity	NPC48990
0.8963	High Similarity	NPC475084
0.8963	High Similarity	NPC476356
0.8955	High Similarity	NPC210478
0.8947	High Similarity	NPC59324
0.8947	High Similarity	NPC65530
0.8943	High Similarity	NPC135961
0.8939	High Similarity	NPC184938
0.8939	High Similarity	NPC101624
0.8915	High Similarity	NPC190629
0.8915	High Similarity	NPC273295
0.8915	High Similarity	NPC285339
0.8915	High Similarity	NPC3439
0.8915	High Similarity	NPC226788
0.8915	High Similarity	NPC218856
0.8915	High Similarity	NPC202582
0.8915	High Similarity	NPC470258
0.8915	High Similarity	NPC222004
0.8915	High Similarity	NPC210623
0.8906	High Similarity	NPC474119
0.8905	High Similarity	NPC279298
0.8905	High Similarity	NPC18979
0.8905	High Similarity	NPC476301
0.8905	High Similarity	NPC22150
0.8905	High Similarity	NPC475096
0.8905	High Similarity	NPC38041
0.8905	High Similarity	NPC43508
0.8898	High Similarity	NPC194519
0.8897	High Similarity	NPC478239
0.8897	High Similarity	NPC473044
0.8889	High Similarity	NPC472711
0.8881	High Similarity	NPC156376
0.888	High Similarity	NPC470804
0.8872	High Similarity	NPC242028
0.8872	High Similarity	NPC157554
0.8872	High Similarity	NPC186418
0.8872	High Similarity	NPC203230
0.8846	High Similarity	NPC262606
0.8841	High Similarity	NPC276753
0.8841	High Similarity	NPC112861
0.8841	High Similarity	NPC190714
0.8841	High Similarity	NPC125755
0.8841	High Similarity	NPC205796
0.8841	High Similarity	NPC99515
0.8837	High Similarity	NPC474178
0.8837	High Similarity	NPC252307
0.8837	High Similarity	NPC245826
0.8824	High Similarity	NPC48309
0.8824	High Similarity	NPC253878
0.8824	High Similarity	NPC140502
0.8824	High Similarity	NPC157816
0.8815	High Similarity	NPC202700
0.8806	High Similarity	NPC195196
0.8806	High Similarity	NPC477797
0.8806	High Similarity	NPC477798
0.8797	High Similarity	NPC174191
0.8788	High Similarity	NPC263064
0.8788	High Similarity	NPC115022
0.8788	High Similarity	NPC294166
0.8779	High Similarity	NPC469625
0.8779	High Similarity	NPC121376
0.8779	High Similarity	NPC30043
0.8779	High Similarity	NPC469698
0.8779	High Similarity	NPC469613
0.8779	High Similarity	NPC472597
0.8779	High Similarity	NPC473412
0.8777	High Similarity	NPC193473
0.8777	High Similarity	NPC213074
0.8777	High Similarity	NPC15956
0.8777	High Similarity	NPC39657
0.8777	High Similarity	NPC224674
0.8777	High Similarity	NPC31325
0.8777	High Similarity	NPC114505
0.8777	High Similarity	NPC227902
0.8777	High Similarity	NPC275284
0.8768	High Similarity	NPC277867
0.8768	High Similarity	NPC469586
0.8768	High Similarity	NPC161700
0.876	High Similarity	NPC198798
0.8759	High Similarity	NPC113680
0.8759	High Similarity	NPC278961
0.8759	High Similarity	NPC252169
0.8759	High Similarity	NPC477898
0.875	High Similarity	NPC186406
0.875	High Similarity	NPC12308
0.875	High Similarity	NPC471414
0.875	High Similarity	NPC471908
0.8741	High Similarity	NPC226005
0.873	High Similarity	NPC266045
0.873	High Similarity	NPC226712
0.8722	High Similarity	NPC170694
0.8722	High Similarity	NPC47181
0.872	High Similarity	NPC148615
0.872	High Similarity	NPC177475
0.872	High Similarity	NPC35071
0.8714	High Similarity	NPC93924
0.8714	High Similarity	NPC270751
0.8714	High Similarity	NPC175976
0.8712	High Similarity	NPC259742
0.8712	High Similarity	NPC16208
0.8712	High Similarity	NPC104077
0.8712	High Similarity	NPC184447
0.8712	High Similarity	NPC26080
0.8712	High Similarity	NPC165686
0.8712	High Similarity	NPC303422
0.8712	High Similarity	NPC160991
0.8712	High Similarity	NPC471505
0.8712	High Similarity	NPC147616

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 NPC270849 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	288
0.1-0.2	850
0.2-0.3	1839
0.3-0.4	2755
0.4-0.5	1681
0.5-0.6	978
0.6-0.7	628
0.7-0.8	123
0.8-0.85	6
0.85-0.9	2
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.873	High Similarity	NPD1091	Approved
0.8583	High Similarity	NPD3705	Approved
0.8485	Intermediate Similarity	NPD3027	Phase 3
0.8478	Intermediate Similarity	NPD6674	Discontinued
0.8346	Intermediate Similarity	NPD1357	Approved
0.8296	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8296	Intermediate Similarity	NPD1613	Approved
0.8264	Intermediate Similarity	NPD1653	Approved
0.8201	Intermediate Similarity	NPD7266	Discontinued
0.8049	Intermediate Similarity	NPD2684	Approved
0.8	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD228	Approved
0.7937	Intermediate Similarity	NPD7843	Approved
0.7926	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7917	Intermediate Similarity	NPD5058	Phase 3
0.7891	Intermediate Similarity	NPD7157	Approved
0.7874	Intermediate Similarity	NPD5283	Phase 1
0.7823	Intermediate Similarity	NPD290	Approved
0.7817	Intermediate Similarity	NPD1375	Discontinued
0.773	Intermediate Similarity	NPD4536	Approved
0.773	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.773	Intermediate Similarity	NPD4538	Approved
0.7722	Intermediate Similarity	NPD7054	Approved
0.7708	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7705	Intermediate Similarity	NPD291	Approved
0.7673	Intermediate Similarity	NPD7074	Phase 3
0.7673	Intermediate Similarity	NPD7472	Approved
0.7664	Intermediate Similarity	NPD2861	Phase 2
0.763	Intermediate Similarity	NPD2982	Phase 2
0.763	Intermediate Similarity	NPD2983	Phase 2
0.7619	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD4237	Approved
0.7586	Intermediate Similarity	NPD4236	Phase 3
0.7574	Intermediate Similarity	NPD8651	Approved
0.7571	Intermediate Similarity	NPD1726	Clinical (unspecified phase)
0.7566	Intermediate Similarity	NPD37	Approved
0.7564	Intermediate Similarity	NPD7199	Phase 2
0.7559	Intermediate Similarity	NPD556	Approved
0.7556	Intermediate Similarity	NPD2981	Phase 2
0.7552	Intermediate Similarity	NPD5588	Approved
0.7552	Intermediate Similarity	NPD5960	Phase 3
0.7547	Intermediate Similarity	NPD3818	Discontinued
0.7536	Intermediate Similarity	NPD3018	Phase 2
0.7533	Intermediate Similarity	NPD3687	Approved
0.7533	Intermediate Similarity	NPD3686	Approved
0.7532	Intermediate Similarity	NPD4965	Approved
0.7532	Intermediate Similarity	NPD4966	Approved
0.7532	Intermediate Similarity	NPD4967	Phase 2
0.7531	Intermediate Similarity	NPD7808	Phase 3
0.7518	Intermediate Similarity	NPD1558	Phase 1
0.7516	Intermediate Similarity	NPD6797	Phase 2
0.7516	Intermediate Similarity	NPD2978	Approved
0.7516	Intermediate Similarity	NPD8455	Phase 2
0.7516	Intermediate Similarity	NPD2977	Approved
0.75	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD3685	Discontinued
0.75	Intermediate Similarity	NPD1774	Approved
0.7483	Intermediate Similarity	NPD2677	Approved
0.7482	Intermediate Similarity	NPD4908	Phase 1
0.7481	Intermediate Similarity	NPD6671	Approved
0.7469	Intermediate Similarity	NPD7251	Discontinued
0.7466	Intermediate Similarity	NPD4162	Approved
0.7466	Intermediate Similarity	NPD1652	Phase 2
0.7451	Intermediate Similarity	NPD1934	Approved
0.7447	Intermediate Similarity	NPD6233	Phase 2
0.7438	Intermediate Similarity	NPD7228	Approved
0.7436	Intermediate Similarity	NPD6234	Discontinued
0.7423	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7415	Intermediate Similarity	NPD4110	Phase 3
0.7413	Intermediate Similarity	NPD6653	Approved
0.7403	Intermediate Similarity	NPD5773	Approved
0.7403	Intermediate Similarity	NPD5772	Approved
0.7394	Intermediate Similarity	NPD4060	Phase 1
0.7394	Intermediate Similarity	NPD3619	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD3620	Phase 2
0.7376	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7372	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD5536	Phase 2
0.7361	Intermediate Similarity	NPD7097	Phase 1
0.7358	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7357	Intermediate Similarity	NPD5752	Clinical (unspecified phase)
0.7353	Intermediate Similarity	NPD1610	Phase 2
0.7347	Intermediate Similarity	NPD3060	Approved
0.7343	Intermediate Similarity	NPD5735	Approved
0.7333	Intermediate Similarity	NPD5126	Approved
0.7333	Intermediate Similarity	NPD5125	Phase 3
0.7333	Intermediate Similarity	NPD4123	Phase 3
0.7333	Intermediate Similarity	NPD6516	Phase 2
0.7333	Intermediate Similarity	NPD5846	Approved
0.7329	Intermediate Similarity	NPD5763	Approved
0.7329	Intermediate Similarity	NPD5762	Approved
0.7313	Intermediate Similarity	NPD1548	Phase 1
0.731	Intermediate Similarity	NPD4108	Discontinued
0.7305	Intermediate Similarity	NPD3179	Approved
0.7305	Intermediate Similarity	NPD7095	Approved
0.7305	Intermediate Similarity	NPD3180	Approved
0.7299	Intermediate Similarity	NPD2235	Phase 2
0.7299	Intermediate Similarity	NPD2231	Phase 2
0.7297	Intermediate Similarity	NPD4628	Phase 3
0.729	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD7526	Approved
0.7285	Intermediate Similarity	NPD7527	Clinical (unspecified phase)
0.7285	Intermediate Similarity	NPD52	Approved
0.7279	Intermediate Similarity	NPD2424	Discontinued
0.7279	Intermediate Similarity	NPD3496	Discontinued
0.7261	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.726	Intermediate Similarity	NPD2161	Phase 2
0.7256	Intermediate Similarity	NPD7240	Approved
0.7256	Intermediate Similarity	NPD7685	Pre-registration
0.7254	Intermediate Similarity	NPD6798	Discontinued
0.7254	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7254	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7252	Intermediate Similarity	NPD821	Approved
0.7246	Intermediate Similarity	NPD4749	Approved
0.7244	Intermediate Similarity	NPD3817	Phase 2
0.7222	Intermediate Similarity	NPD6355	Discontinued
0.7208	Intermediate Similarity	NPD4675	Approved
0.7208	Intermediate Similarity	NPD4678	Approved
0.7206	Intermediate Similarity	NPD1778	Approved
0.7205	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD6166	Phase 2
0.7205	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7203	Intermediate Similarity	NPD4062	Phase 3
0.7202	Intermediate Similarity	NPD6842	Approved
0.7202	Intermediate Similarity	NPD6843	Phase 3
0.7202	Intermediate Similarity	NPD6841	Approved
0.7197	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD968	Approved
0.7188	Intermediate Similarity	NPD3787	Discontinued
0.7181	Intermediate Similarity	NPD4535	Phase 3
0.7181	Intermediate Similarity	NPD6331	Phase 2
0.7179	Intermediate Similarity	NPD2801	Approved
0.7171	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.7154	Intermediate Similarity	NPD3022	Approved
0.7154	Intermediate Similarity	NPD3021	Approved
0.7153	Intermediate Similarity	NPD4140	Approved
0.7152	Intermediate Similarity	NPD6559	Discontinued
0.7134	Intermediate Similarity	NPD2560	Approved
0.7134	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD2563	Approved
0.7133	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7132	Intermediate Similarity	NPD1358	Approved
0.7124	Intermediate Similarity	NPD2122	Discontinued
0.7124	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7121	Intermediate Similarity	NPD5535	Approved
0.7114	Intermediate Similarity	NPD5177	Phase 3
0.7103	Intermediate Similarity	NPD4340	Discontinued
0.7103	Intermediate Similarity	NPD5124	Phase 1
0.7103	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7101	Intermediate Similarity	NPD422	Phase 1
0.7092	Intermediate Similarity	NPD6584	Phase 3
0.7092	Intermediate Similarity	NPD558	Phase 2
0.7089	Intermediate Similarity	NPD3882	Suspended
0.7086	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7083	Intermediate Similarity	NPD2674	Phase 3
0.7075	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7075	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD7804	Clinical (unspecified phase)
0.7073	Intermediate Similarity	NPD5844	Phase 1
0.7063	Intermediate Similarity	NPD4625	Phase 3
0.705	Intermediate Similarity	NPD1608	Approved
0.7047	Intermediate Similarity	NPD7153	Discontinued
0.7034	Intermediate Similarity	NPD2238	Phase 2
0.7034	Intermediate Similarity	NPD5837	Clinical (unspecified phase)
0.7032	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7027	Intermediate Similarity	NPD6032	Approved
0.7021	Intermediate Similarity	NPD1820	Approved
0.7021	Intermediate Similarity	NPD1818	Approved
0.7021	Intermediate Similarity	NPD1817	Approved
0.7021	Intermediate Similarity	NPD1819	Approved
0.702	Intermediate Similarity	NPD6190	Approved
0.7019	Intermediate Similarity	NPD8127	Discontinued
0.7007	Intermediate Similarity	NPD5585	Approved
0.7006	Intermediate Similarity	NPD7945	Clinical (unspecified phase)
0.7	Intermediate Similarity	NPD5327	Phase 3
0.6993	Remote Similarity	NPD3688	Clinical (unspecified phase)
0.6993	Remote Similarity	NPD4739	Approved
0.6993	Remote Similarity	NPD3146	Approved
0.6986	Remote Similarity	NPD447	Suspended
0.6986	Remote Similarity	NPD1933	Approved
0.698	Remote Similarity	NPD3540	Phase 1
0.698	Remote Similarity	NPD2029	Clinical (unspecified phase)
0.6978	Remote Similarity	NPD776	Approved
0.6975	Remote Similarity	NPD6071	Discontinued
0.6975	Remote Similarity	NPD3051	Approved
0.6972	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6972	Remote Similarity	NPD3690	Phase 2
0.6972	Remote Similarity	NPD3691	Phase 2
0.6968	Remote Similarity	NPD4210	Discontinued
0.6967	Remote Similarity	NPD9365	Approved
0.6966	Remote Similarity	NPD554	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD5563	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD6818	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD7033	Discontinued
0.6954	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD1940	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD7314	Clinical (unspecified phase)
0.6944	Remote Similarity	NPD3167	Approved
0.6944	Remote Similarity	NPD3166	Approved

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