NPASS Compound

Structure

CID58716 OpenBabel06191715392D 33 36 0 0 1 0 0 0 0 0999 V2000 -6.0622 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -6.9282 2.0000 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 -2.5981 1.5000 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 -6.0622 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -7.7942 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 3.5000 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 -1.7321 2.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -1.0000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 -3.4641 3.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 0 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 -2.5981 3.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.7321 -1.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 -0.0000 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 0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 -0.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -8.6603 2.0000 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 -0.8660 3.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 -1.5000 0.0000 O 0 0 0 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 -4.3301 1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.8660 1.5000 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 2 2 0 0 0 0 1 7 1 0 0 0 0 2 8 1 0 0 0 0 3 7 2 0 0 0 0 3 9 1 0 0 0 0 4 10 1 0 0 0 0 4 11 2 0 0 0 0 5 12 2 0 0 0 0 5 13 1 0 0 0 0 6 22 1 0 0 0 0 7 11 1 0 0 0 0 8 9 2 0 0 0 0 8 23 1 0 0 0 0 9 24 1 0 0 0 0 10 15 1 0 0 0 0 10 25 2 0 0 0 0 11 31 1 0 0 0 0 12 15 1 0 0 0 0 12 31 1 0 0 0 0 13 16 2 0 0 0 0 13 32 1 0 0 0 0 14 6 1 6 0 0 0 14 17 1 0 0 0 0 14 33 1 0 0 0 0 15 18 2 0 0 0 0 16 18 1 0 0 0 0 16 26 1 0 0 0 0 17 19 1 0 0 0 0 17 27 1 1 0 0 0 18 28 1 0 0 0 0 19 20 1 0 0 0 0 19 29 1 6 0 0 0 20 21 1 0 0 0 0 20 30 1 1 0 0 0 21 32 1 6 0 0 0 21 33 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	464.1
Volume:	421.937
LogP:	0.083
LogD:	-0.226
LogS:	-3.299
# Rotatable Bonds:	4
TPSA:	210.51
# H-Bond Aceptor:	12
# H-Bond Donor:	8
# Rings:	4
# Heavy Atoms:	12

MedChem Properties

QED Drug-Likeness Score:	0.229
Synthetic Accessibility Score:	4.046
Fsp3:	0.286
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	2
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.323
MDCK Permeability:	8.684437489137053e-06
Pgp-inhibitor:	0.019
Pgp-substrate:	0.886
Human Intestinal Absorption (HIA):	0.801
20% Bioavailability (F20%):	0.21
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.011
Plasma Protein Binding (PPB):	90.32125091552734%
Volume Distribution (VD):	0.736
Pgp-substrate:	14.991844177246094%

ADMET: Metabolism

CYP1A2-inhibitor:	0.121
CYP1A2-substrate:	0.049
CYP2C19-inhibitor:	0.016
CYP2C19-substrate:	0.05
CYP2C9-inhibitor:	0.024
CYP2C9-substrate:	0.092
CYP2D6-inhibitor:	0.029
CYP2D6-substrate:	0.155
CYP3A4-inhibitor:	0.025
CYP3A4-substrate:	0.01

ADMET: Excretion

Clearance (CL):	3.619
Half-life (T1/2):	0.887

ADMET: Toxicity

hERG Blockers:	0.298
Human Hepatotoxicity (H-HT):	0.079
Drug-inuced Liver Injury (DILI):	0.962
AMES Toxicity:	0.771
Rat Oral Acute Toxicity:	0.014
Maximum Recommended Daily Dose:	0.006
Skin Sensitization:	0.938
Carcinogencity:	0.067
Eye Corrosion:	0.003
Eye Irritation:	0.688
Respiratory Toxicity:	0.032

Download Data

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

Natural Product: NPC58716

Natural Product ID:	NPC58716
*Common Name:**	6-Hydroxyluteolin 7-O-Beta-D-Glucopyranoside
IUPAC Name:	2-(3,4-dihydroxyphenyl)-5,6-dihydroxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Synonyms:
Standard InCHIKey:	HYPKUHLLPBGDLF-IAAKTDFRSA-N
Standard InCHI:	InChI=1S/C21H20O12/c22-6-14-17(27)19(29)20(30)21(33-14)32-13-5-12-15(18(28)16(13)26)10(25)4-11(31-12)7-1-2-8(23)9(24)3-7/h1-5,14,17,19-24,26-30H,6H2/t14-,17-,19+,20-,21-/m1/s1
SMILES:	c1cc(c(cc1c1cc(=O)c2c(cc(c(c2O)O)O[C@H]2[C@@H]([C@H]([C@@H]([C@@H](CO)O2)O)O)O)o1)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL469621
PubChem CID:	185766
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000334] Flavonoids [CHEMONTID:0001111] Flavonoid glycosides [CHEMONTID:0001583] Flavonoid O-glycosides [CHEMONTID:0003533] Flavonoid-7-O-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
NPO17790	Trigonostemon reidioides	Species	Euphorbiaceae	Eukaryota	roots	Rat Buri Province, Thailand	1988-DEC	PMID[14987064]
NPO5912	Globularia alypum	Species	Plantaginaceae	Eukaryota	aerial parts	Morocco	n.a.	PMID[16124783]
NPO5912	Globularia alypum	Species	Plantaginaceae	Eukaryota	n.a.	aerial part	n.a.	PMID[16124783]
NPO17790	Trigonostemon reidioides	Species	Euphorbiaceae	Eukaryota	n.a.	root	n.a.	PMID[16204992]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	Fruits	n.a.	n.a.	PMID[16309325]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	Seoul, Korea	2000-Jun	PMID[16643034]
NPO8524	Pithecellobium clypearia	Species	Fabaceae	Eukaryota	n.a.	leaf	n.a.	PMID[16724853]
NPO8524	Pithecellobium clypearia	Species	Fabaceae	Eukaryota	leaves	n.a.	n.a.	PMID[16724853]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[18505286]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruit	n.a.	n.a.	PMID[19650637]
NPO16660	Phomopsis archeri	Species	Valsaceae	Eukaryota	n.a.	mycelium	n.a.	PMID[21341709]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	fruits	n.a.	n.a.	PMID[23305920]
NPO28626	Isodon rubescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[25590529]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[32141747]
NPO2733	Sarcomelicope argyrophylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[Article]
NPO13856	Bergenia purpurascens	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17637	Pimpinella saxifraga	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17706	Caragana tibetica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10436	Aristolochia maxima	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO13180	Jasminum officinale	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16620	Malus asiatica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17637	Pimpinella saxifraga	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO28626	Isodon rubescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13180	Jasminum officinale	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17790	Trigonostemon reidioides	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10436	Aristolochia maxima	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13856	Bergenia purpurascens	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17706	Caragana tibetica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17244	Montrouziera sphaeroidea	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO13180	Jasminum officinale	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28626	Isodon rubescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO8524	Pithecellobium clypearia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3585	Dicranum elongatum	Species	Dicranaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21802	Julocroton camporum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO16374	Crataegus sinaica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4184	Cyathea phalerata	Species	Cyatheaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17029	Tridacna gigas	Species	Tridacnidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17870	Euphorbia ferganensis	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15079	Polygala myrtifolia	Species	Polygalaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11559	Betula mandshurica	Species	Betulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1148	Phalium undulatum	Species	Cassidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9523	Nephroma antarcticum	Species	Nephromataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11831	Achillea collina	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2589	Solanum bahamense	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17244	Montrouziera sphaeroidea	Species	Clusiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15814	Rhodiola krylovii	Species	Crassulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15667	Ligularia platyglossa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9518	Gardenia jasminoides	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16620	Malus asiatica	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17175	Lasiocephalus ovatus	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2733	Sarcomelicope argyrophylla	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17790	Trigonostemon reidioides	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15964	Tropiometra afra	Species	Tropiometridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16660	Phomopsis archeri	Species	Valsaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12559	Mikania obtusata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16510	Ganoderma australe	Species	Ganodermataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6939	Vatica diospyroides	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17739	Macrotyloma axillare	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5912	Globularia alypum	Species	Plantaginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11420	Dolichospermum affine	Species	Aphanizomenonaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO17637	Pimpinella saxifraga	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18962	Actinobacillus pleuropneumoniae	Species	Pasteurellaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO11020	Streptomyces purpeofuscus	Species	Streptomycetaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO10436	Aristolochia maxima	Species	Aristolochiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17945	Arachniodes dimorphophylla	Species	Dryopteridaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17327	Cotoneaster orbicularis	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18709	Discaria crenata	Species	Rhamnaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17100	Artemisia vachanica	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12733	Pentapora fascialis	Species	Bitectiporidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3425	Acacia floribunda	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14698	Phyllospongia madagascarensis	Species	Thorectidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2152	Angophora hispida	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13856	Bergenia purpurascens	Species	Saxifragaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18027	Oreosolen wattii	Species	Scrophulariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17355	Bischofia trifoliata	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13422	Amoora yunnanensis	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO10534	Rosa foetida	Species	Rosaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17706	Caragana tibetica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5634	Wallago attu	Species	Siluridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11925	Mola mola	Species	Molidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26487	Tinospora smilacina	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16253	Rapanea myricoides	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28626	Isodon rubescens	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14408	Chrysolina fastuosa	Species	Chrysomelidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22469	Tropaeolum speciosum	Species	Tropaeolaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13180	Jasminum officinale	Species	Oleaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9428	Annona rensoniana	Species	Annonaceae	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	1

Activity Type	# Activity
Others	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT1	Others	Radical scavenging activity		IC50	=	11000.0	nM	PMID[543686]

☑ 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 NPC58716 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	460
0.1-0.2	1904
0.2-0.3	4385
0.3-0.4	10111
0.4-0.5	7957
0.5-0.6	4060
0.6-0.7	5153
0.7-0.8	5257
0.8-0.85	1562
0.85-0.9	1274
0.9-0.95	421
0.95-1	153

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC146792
1.0	High Similarity	NPC45618
0.9937	High Similarity	NPC58053
0.9937	High Similarity	NPC201292
0.9937	High Similarity	NPC226294
0.9937	High Similarity	NPC186807
0.9937	High Similarity	NPC93337
0.9937	High Similarity	NPC105025
0.9937	High Similarity	NPC475942
0.9937	High Similarity	NPC469931
0.9937	High Similarity	NPC45638
0.9874	High Similarity	NPC282987
0.9874	High Similarity	NPC245014
0.9874	High Similarity	NPC84265
0.9812	High Similarity	NPC48773
0.9812	High Similarity	NPC211594
0.9812	High Similarity	NPC205076
0.9812	High Similarity	NPC172807
0.9812	High Similarity	NPC259152
0.9812	High Similarity	NPC476405
0.9812	High Similarity	NPC3583
0.9812	High Similarity	NPC254540
0.9812	High Similarity	NPC117260
0.9812	High Similarity	NPC307518
0.9811	High Similarity	NPC471457
0.9811	High Similarity	NPC112755
0.9811	High Similarity	NPC170675
0.9809	High Similarity	NPC191306
0.9809	High Similarity	NPC270335
0.9752	High Similarity	NPC169977
0.9752	High Similarity	NPC204693
0.9752	High Similarity	NPC21666
0.9752	High Similarity	NPC42773
0.9752	High Similarity	NPC24043
0.9752	High Similarity	NPC45522
0.9752	High Similarity	NPC101026
0.975	High Similarity	NPC471416
0.975	High Similarity	NPC183357
0.975	High Similarity	NPC34287
0.975	High Similarity	NPC105511
0.975	High Similarity	NPC22195
0.975	High Similarity	NPC21190
0.975	High Similarity	NPC224462
0.9747	High Similarity	NPC22832
0.9747	High Similarity	NPC311830
0.9745	High Similarity	NPC189142
0.9745	High Similarity	NPC77660
0.9691	High Similarity	NPC210094
0.9691	High Similarity	NPC477848
0.9691	High Similarity	NPC135277
0.9691	High Similarity	NPC49344
0.9691	High Similarity	NPC101191
0.9691	High Similarity	NPC237435
0.9691	High Similarity	NPC472607
0.9691	High Similarity	NPC115760
0.9691	High Similarity	NPC43211
0.9688	High Similarity	NPC472383
0.9688	High Similarity	NPC95855
0.9688	High Similarity	NPC210042
0.9688	High Similarity	NPC472381
0.9686	High Similarity	NPC21100
0.9686	High Similarity	NPC99957
0.9686	High Similarity	NPC181616
0.9686	High Similarity	NPC197285
0.9684	High Similarity	NPC284960
0.9684	High Similarity	NPC88043
0.9684	High Similarity	NPC19709
0.9684	High Similarity	NPC309025
0.9684	High Similarity	NPC222936
0.9684	High Similarity	NPC243930
0.9684	High Similarity	NPC94777
0.9684	High Similarity	NPC168822
0.9684	High Similarity	NPC88023
0.9632	High Similarity	NPC233994
0.9632	High Similarity	NPC472991
0.9632	High Similarity	NPC472385
0.9632	High Similarity	NPC211532
0.9632	High Similarity	NPC169733
0.9632	High Similarity	NPC198324
0.9632	High Similarity	NPC8573
0.9632	High Similarity	NPC472992
0.963	High Similarity	NPC239549
0.963	High Similarity	NPC51774
0.963	High Similarity	NPC236191
0.9627	High Similarity	NPC44558
0.9627	High Similarity	NPC474434
0.9625	High Similarity	NPC229729
0.9625	High Similarity	NPC45400
0.9625	High Similarity	NPC93099
0.9625	High Similarity	NPC135345
0.9623	High Similarity	NPC165720
0.9623	High Similarity	NPC277205
0.962	High Similarity	NPC473043
0.9573	High Similarity	NPC168584
0.9571	High Similarity	NPC264735
0.9568	High Similarity	NPC301683
0.9568	High Similarity	NPC472386
0.9568	High Similarity	NPC267254
0.9565	High Similarity	NPC86008
0.9565	High Similarity	NPC219904
0.9565	High Similarity	NPC225434
0.9565	High Similarity	NPC209296
0.9565	High Similarity	NPC203050
0.9565	High Similarity	NPC229687
0.9565	High Similarity	NPC223747
0.9565	High Similarity	NPC120099
0.9565	High Similarity	NPC183036
0.9565	High Similarity	NPC195257
0.9563	High Similarity	NPC88789
0.9563	High Similarity	NPC179950
0.9563	High Similarity	NPC8856
0.9563	High Similarity	NPC5778
0.9563	High Similarity	NPC118284
0.9563	High Similarity	NPC281131
0.9563	High Similarity	NPC56077
0.9563	High Similarity	NPC115674
0.9563	High Similarity	NPC276222
0.9563	High Similarity	NPC236934
0.9563	High Similarity	NPC308404
0.9563	High Similarity	NPC253662
0.9563	High Similarity	NPC210073
0.9563	High Similarity	NPC274618
0.9563	High Similarity	NPC145038
0.956	High Similarity	NPC29830
0.9557	High Similarity	NPC182045
0.9515	High Similarity	NPC126784
0.9515	High Similarity	NPC470443
0.9515	High Similarity	NPC473571
0.9515	High Similarity	NPC470444
0.9515	High Similarity	NPC110941
0.9515	High Similarity	NPC241423
0.9515	High Similarity	NPC473682
0.9512	High Similarity	NPC65563
0.9512	High Similarity	NPC268533
0.9512	High Similarity	NPC470949
0.9509	High Similarity	NPC4390
0.9506	High Similarity	NPC149011
0.9506	High Similarity	NPC235260
0.9506	High Similarity	NPC20505
0.9506	High Similarity	NPC204937
0.9506	High Similarity	NPC285197
0.9506	High Similarity	NPC206123
0.9506	High Similarity	NPC51326
0.9506	High Similarity	NPC231194
0.9506	High Similarity	NPC155763
0.9503	High Similarity	NPC223424
0.9503	High Similarity	NPC52550
0.9503	High Similarity	NPC226304
0.9503	High Similarity	NPC317489
0.9503	High Similarity	NPC127546
0.9503	High Similarity	NPC116745
0.9503	High Similarity	NPC173637
0.9503	High Similarity	NPC265530
0.9503	High Similarity	NPC325555
0.9503	High Similarity	NPC84362
0.95	High Similarity	NPC55786
0.95	High Similarity	NPC19388
0.95	High Similarity	NPC240431
0.9497	High Similarity	NPC127782
0.9497	High Similarity	NPC300537
0.9494	High Similarity	NPC110349
0.9458	High Similarity	NPC473073
0.9458	High Similarity	NPC222674
0.9458	High Similarity	NPC473071
0.9455	High Similarity	NPC476618
0.9455	High Similarity	NPC476620
0.9455	High Similarity	NPC476622
0.9455	High Similarity	NPC476619
0.9455	High Similarity	NPC476621
0.9455	High Similarity	NPC476623
0.9451	High Similarity	NPC102028
0.9451	High Similarity	NPC142996
0.9448	High Similarity	NPC60735
0.9448	High Similarity	NPC153755
0.9448	High Similarity	NPC156977
0.9448	High Similarity	NPC175107
0.9448	High Similarity	NPC475155
0.9448	High Similarity	NPC190003
0.9448	High Similarity	NPC256760
0.9448	High Similarity	NPC235575
0.9448	High Similarity	NPC26230
0.9448	High Similarity	NPC180918
0.9444	High Similarity	NPC471287
0.9444	High Similarity	NPC138927
0.9441	High Similarity	NPC254306
0.9441	High Similarity	NPC328940
0.9441	High Similarity	NPC73855
0.9441	High Similarity	NPC113968
0.9441	High Similarity	NPC277174
0.9441	High Similarity	NPC135599
0.9437	High Similarity	NPC127415
0.9437	High Similarity	NPC470178
0.9427	High Similarity	NPC261866
0.9401	High Similarity	NPC470446
0.9401	High Similarity	NPC473072
0.9401	High Similarity	NPC470449
0.9401	High Similarity	NPC470447
0.9401	High Similarity	NPC36138
0.9401	High Similarity	NPC470445
0.9401	High Similarity	NPC107987

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 NPC58716 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	421
0.1-0.2	958
0.2-0.3	1994
0.3-0.4	2707
0.4-0.5	1730
0.5-0.6	891
0.6-0.7	285
0.7-0.8	125
0.8-0.85	13
0.85-0.9	15
0.9-0.95	10
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9691	High Similarity	NPD4338	Clinical (unspecified phase)
0.9565	High Similarity	NPD7054	Approved
0.9506	High Similarity	NPD7472	Approved
0.9503	High Similarity	NPD3818	Discontinued
0.9387	High Similarity	NPD7074	Phase 3
0.9329	High Similarity	NPD6797	Phase 2
0.9273	High Similarity	NPD7251	Discontinued
0.9245	High Similarity	NPD4381	Clinical (unspecified phase)
0.9217	High Similarity	NPD7808	Phase 3
0.9177	High Similarity	NPD2801	Approved
0.8994	High Similarity	NPD1934	Approved
0.8909	High Similarity	NPD6168	Clinical (unspecified phase)
0.8909	High Similarity	NPD6167	Clinical (unspecified phase)
0.8909	High Similarity	NPD6166	Phase 2
0.882	High Similarity	NPD2393	Clinical (unspecified phase)
0.875	High Similarity	NPD7804	Clinical (unspecified phase)
0.8726	High Similarity	NPD1511	Approved
0.8712	High Similarity	NPD4868	Clinical (unspecified phase)
0.865	High Similarity	NPD3817	Phase 2
0.8634	High Similarity	NPD4380	Phase 2
0.8616	High Similarity	NPD1512	Approved
0.8598	High Similarity	NPD3882	Suspended
0.8537	High Similarity	NPD5402	Approved
0.8509	High Similarity	NPD1653	Approved
0.8443	Intermediate Similarity	NPD5494	Approved
0.8382	Intermediate Similarity	NPD6559	Discontinued
0.8324	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8228	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8214	Intermediate Similarity	NPD7075	Discontinued
0.8208	Intermediate Similarity	NPD5844	Phase 1
0.8176	Intermediate Similarity	NPD1549	Phase 2
0.8144	Intermediate Similarity	NPD1465	Phase 2
0.811	Intermediate Similarity	NPD5403	Approved
0.8098	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8084	Intermediate Similarity	NPD6801	Discontinued
0.8068	Intermediate Similarity	NPD7685	Pre-registration
0.8066	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8046	Intermediate Similarity	NPD3751	Discontinued
0.8036	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD6232	Discontinued
0.8023	Intermediate Similarity	NPD3787	Discontinued
0.7989	Intermediate Similarity	NPD7473	Discontinued
0.7988	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.7988	Intermediate Similarity	NPD5401	Approved
0.7987	Intermediate Similarity	NPD1510	Phase 2
0.7956	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7943	Intermediate Similarity	NPD7228	Approved
0.7937	Intermediate Similarity	NPD2796	Approved
0.7929	Intermediate Similarity	NPD7819	Suspended
0.7927	Intermediate Similarity	NPD6799	Approved
0.7917	Intermediate Similarity	NPD7411	Suspended
0.7892	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7879	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.7877	Intermediate Similarity	NPD8313	Approved
0.7877	Intermediate Similarity	NPD8312	Approved
0.7861	Intermediate Similarity	NPD6959	Discontinued
0.7861	Intermediate Similarity	NPD7199	Phase 2
0.7849	Intermediate Similarity	NPD6234	Discontinued
0.7848	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7848	Intermediate Similarity	NPD1613	Approved
0.779	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7766	Intermediate Similarity	NPD6781	Approved
0.7766	Intermediate Similarity	NPD6777	Approved
0.7766	Intermediate Similarity	NPD6780	Approved
0.7766	Intermediate Similarity	NPD6779	Approved
0.7766	Intermediate Similarity	NPD6782	Approved
0.7766	Intermediate Similarity	NPD6776	Approved
0.7766	Intermediate Similarity	NPD6778	Approved
0.7765	Intermediate Similarity	NPD37	Approved
0.7759	Intermediate Similarity	NPD1247	Approved
0.7744	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7736	Intermediate Similarity	NPD943	Approved
0.7733	Intermediate Similarity	NPD4965	Approved
0.7733	Intermediate Similarity	NPD4966	Approved
0.7733	Intermediate Similarity	NPD4967	Phase 2
0.7697	Intermediate Similarity	NPD6190	Approved
0.767	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD7266	Discontinued
0.7647	Intermediate Similarity	NPD6599	Discontinued
0.7644	Intermediate Similarity	NPD7435	Discontinued
0.7636	Intermediate Similarity	NPD3750	Approved
0.7627	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7625	Intermediate Similarity	NPD1240	Approved
0.7622	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7617	Intermediate Similarity	NPD7584	Approved
0.7605	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7586	Intermediate Similarity	NPD3749	Approved
0.7578	Intermediate Similarity	NPD230	Phase 1
0.7578	Intermediate Similarity	NPD1933	Approved
0.7571	Intermediate Similarity	NPD3926	Phase 2
0.7552	Intermediate Similarity	NPD7696	Phase 3
0.7552	Intermediate Similarity	NPD7697	Approved
0.7552	Intermediate Similarity	NPD7698	Approved
0.7551	Intermediate Similarity	NPD7783	Phase 2
0.7551	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7547	Intermediate Similarity	NPD3027	Phase 3
0.7543	Intermediate Similarity	NPD919	Approved
0.7538	Intermediate Similarity	NPD8151	Discontinued
0.7532	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7531	Intermediate Similarity	NPD1607	Approved
0.7514	Intermediate Similarity	NPD8455	Phase 2
0.7513	Intermediate Similarity	NPD7870	Phase 2
0.7513	Intermediate Similarity	NPD7871	Phase 2
0.75	Intermediate Similarity	NPD1551	Phase 2
0.75	Intermediate Similarity	NPD6823	Phase 2
0.75	Intermediate Similarity	NPD6535	Approved
0.75	Intermediate Similarity	NPD6534	Approved
0.75	Intermediate Similarity	NPD2935	Discontinued
0.7487	Intermediate Similarity	NPD7701	Phase 2
0.7473	Intermediate Similarity	NPD7240	Approved
0.7469	Intermediate Similarity	NPD447	Suspended
0.7429	Intermediate Similarity	NPD7768	Phase 2
0.7425	Intermediate Similarity	NPD4628	Phase 3
0.7411	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7411	Intermediate Similarity	NPD7874	Approved
0.7391	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD7699	Phase 2
0.7382	Intermediate Similarity	NPD7700	Phase 2
0.7374	Intermediate Similarity	NPD7801	Approved
0.7356	Intermediate Similarity	NPD6844	Discontinued
0.7353	Intermediate Similarity	NPD2533	Approved
0.7353	Intermediate Similarity	NPD2534	Approved
0.7353	Intermediate Similarity	NPD2532	Approved
0.7333	Intermediate Similarity	NPD3748	Approved
0.7333	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7306	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7267	Intermediate Similarity	NPD920	Approved
0.7263	Intermediate Similarity	NPD6213	Phase 3
0.7263	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD6212	Phase 3
0.7262	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7262	Intermediate Similarity	NPD2800	Approved
0.7261	Intermediate Similarity	NPD1091	Approved
0.7251	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7251	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.724	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7228	Intermediate Similarity	NPD5953	Discontinued
0.7222	Intermediate Similarity	NPD7585	Approved
0.7205	Intermediate Similarity	NPD9494	Approved
0.7184	Intermediate Similarity	NPD3226	Approved
0.7181	Intermediate Similarity	NPD8150	Discontinued
0.7181	Intermediate Similarity	NPD8434	Phase 2
0.7178	Intermediate Similarity	NPD2313	Discontinued
0.7172	Intermediate Similarity	NPD7583	Approved
0.7165	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.716	Intermediate Similarity	NPD6674	Discontinued
0.7151	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7135	Intermediate Similarity	NPD4360	Phase 2
0.7135	Intermediate Similarity	NPD4363	Phase 3
0.7135	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD7033	Discontinued
0.712	Intermediate Similarity	NPD7286	Phase 2
0.7107	Intermediate Similarity	NPD7680	Approved
0.7086	Intermediate Similarity	NPD7458	Discontinued
0.7083	Intermediate Similarity	NPD6100	Approved
0.7083	Intermediate Similarity	NPD6099	Approved
0.7081	Intermediate Similarity	NPD1203	Approved
0.7079	Intermediate Similarity	NPD5353	Approved
0.7071	Intermediate Similarity	NPD8320	Phase 1
0.7071	Intermediate Similarity	NPD8319	Approved
0.7063	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1652	Phase 2
0.7059	Intermediate Similarity	NPD1243	Approved
0.7055	Intermediate Similarity	NPD6832	Phase 2
0.7055	Intermediate Similarity	NPD4908	Phase 1
0.7053	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7044	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7041	Intermediate Similarity	NPD2344	Approved
0.7041	Intermediate Similarity	NPD2346	Discontinued
0.7037	Intermediate Similarity	NPD2798	Approved
0.703	Intermediate Similarity	NPD6233	Phase 2
0.7024	Intermediate Similarity	NPD2799	Discontinued
0.7006	Intermediate Similarity	NPD6651	Approved
0.7006	Intermediate Similarity	NPD1548	Phase 1
0.7	Intermediate Similarity	NPD9269	Phase 2
0.6995	Remote Similarity	NPD5242	Approved
0.6994	Remote Similarity	NPD7390	Discontinued
0.6994	Remote Similarity	NPD2861	Phase 2
0.6989	Remote Similarity	NPD5808	Clinical (unspecified phase)
0.697	Remote Similarity	NPD5006	Approved
0.697	Remote Similarity	NPD5005	Approved
0.697	Remote Similarity	NPD4907	Clinical (unspecified phase)
0.6968	Remote Similarity	NPD7549	Discontinued
0.6957	Remote Similarity	NPD7784	Clinical (unspecified phase)
0.6954	Remote Similarity	NPD7422	Clinical (unspecified phase)
0.695	Remote Similarity	NPD7211	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD5124	Phase 1
0.6946	Remote Similarity	NPD1899	Clinical (unspecified phase)
0.6946	Remote Similarity	NPD5123	Clinical (unspecified phase)
0.694	Remote Similarity	NPD5711	Approved
0.694	Remote Similarity	NPD5710	Approved
0.6937	Remote Similarity	NPD1610	Phase 2
0.6923	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6914	Remote Similarity	NPD3225	Approved
0.691	Remote Similarity	NPD6386	Approved
0.691	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.691	Remote Similarity	NPD6385	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