NPASS Compound

Structure

CID77660 OpenBabel06191715412D 32 35 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 -1.7321 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 -5.1962 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 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 -1.7321 2.0000 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 -2.5981 3.5000 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 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 -0.8660 -1.5000 0.0000 C 0 0 2 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 1 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 -2.5981 4.5000 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 -0.8660 -2.5000 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 -0.8660 1.5000 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 -0.0000 -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 8 1 0 0 0 0 2 10 1 0 0 0 0 3 8 2 0 0 0 0 3 11 1 0 0 0 0 4 9 2 0 0 0 0 4 12 1 0 0 0 0 5 9 1 0 0 0 0 5 15 2 0 0 0 0 6 13 1 0 0 0 0 6 14 2 0 0 0 0 7 22 1 0 0 0 0 8 14 1 0 0 0 0 9 30 1 0 0 0 0 10 11 2 0 0 0 0 10 23 1 0 0 0 0 11 24 1 0 0 0 0 12 17 2 0 0 0 0 12 25 1 0 0 0 0 13 17 1 0 0 0 0 13 26 2 0 0 0 0 14 31 1 0 0 0 0 15 17 1 0 0 0 0 15 31 1 0 0 0 0 16 7 1 6 0 0 0 16 18 1 0 0 0 0 16 32 1 0 0 0 0 18 19 1 0 0 0 0 18 27 1 1 0 0 0 19 20 1 0 0 0 0 19 28 1 6 0 0 0 20 21 1 0 0 0 0 20 29 1 1 0 0 0 21 30 1 1 0 0 0 21 32 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	448.1
Volume:	413.147
LogP:	1.09
LogD:	0.16
LogS:	-3.417
# Rotatable Bonds:	4
TPSA:	190.28
# H-Bond Aceptor:	11
# H-Bond Donor:	7
# Rings:	4
# Heavy Atoms:	11

MedChem Properties

QED Drug-Likeness Score:	0.261
Synthetic Accessibility Score:	3.924
Fsp3:	0.286
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.213
MDCK Permeability:	9.43069244385697e-06
Pgp-inhibitor:	0.003
Pgp-substrate:	0.965
Human Intestinal Absorption (HIA):	0.792
20% Bioavailability (F20%):	0.986
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.016
Plasma Protein Binding (PPB):	90.27525329589844%
Volume Distribution (VD):	0.74
Pgp-substrate:	9.99134349822998%

ADMET: Metabolism

CYP1A2-inhibitor:	0.439
CYP1A2-substrate:	0.05
CYP2C19-inhibitor:	0.03
CYP2C19-substrate:	0.052
CYP2C9-inhibitor:	0.051
CYP2C9-substrate:	0.177
CYP2D6-inhibitor:	0.193
CYP2D6-substrate:	0.205
CYP3A4-inhibitor:	0.1
CYP3A4-substrate:	0.021

ADMET: Excretion

Clearance (CL):	5.694
Half-life (T1/2):	0.829

ADMET: Toxicity

hERG Blockers:	0.162
Human Hepatotoxicity (H-HT):	0.082
Drug-inuced Liver Injury (DILI):	0.913
AMES Toxicity:	0.782
Rat Oral Acute Toxicity:	0.02
Maximum Recommended Daily Dose:	0.015
Skin Sensitization:	0.918
Carcinogencity:	0.358
Eye Corrosion:	0.003
Eye Irritation:	0.544
Respiratory Toxicity:	0.046

Download Data

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

Natural Product: NPC77660

Natural Product ID:	NPC77660
*Common Name:**	2-(3,4-Dihydroxyphenyl)-5-Hydroxy-7-[(2R,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Oxan-2-Yl]Oxychromen-4-One
IUPAC Name:	2-(3,4-dihydroxyphenyl)-5-hydroxy-7-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
Synonyms:
Standard InCHIKey:	PEFNSGRTCBGNAN-RQXATKFSSA-N
Standard InCHI:	InChI=1S/C21H20O11/c22-7-16-18(27)19(28)20(29)21(32-16)30-9-4-12(25)17-13(26)6-14(31-15(17)5-9)8-1-2-10(23)11(24)3-8/h1-6,16,18-25,27-29H,7H2/t16-,18-,19+,20-,21+/m1/s1
SMILES:	c1cc(c(cc1c1cc(=O)c2c(cc(cc2o1)O[C@@H]1[C@@H]([C@H]([C@@H]([C@@H](CO)O1)O)O)O)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1159535
PubChem CID:	13093776
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
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[10654410]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[10843587]
NPO20142	Embelia schimperi	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11054840]
NPO28315	Jania rubens	Species	Corallinaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[11086730]
NPO18668	Asimina parviflora	Species	Annonaceae	Eukaryota	twigs	n.a.	n.a.	PMID[1453182]
NPO19667	Hypericum styphelioides	Species	Hypericaceae	Eukaryota	n.a.	leaf	n.a.	PMID[15165152]
NPO19667	Hypericum styphelioides	Species	Hypericaceae	Eukaryota	leaves	n.a.	n.a.	PMID[15165152]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[15568770]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	PMID[15911254]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16392664]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[16933887]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	roots	Hualien Hsien, Taiwan	2003-JUL	PMID[16933887]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	PMID[17951038]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18175961]
NPO20879	Clerodendrum bungei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[18348535]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	root	n.a.	PMID[18975262]
NPO3152	Morella rubra	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19407970]
NPO3152	Morella rubra	Species	Myricaceae	Eukaryota	n.a.	bark	n.a.	PMID[21553897]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24295087]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24333010]
NPO20598	Lythrum salicaria	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[24459770]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27575476]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[30298740]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	Roots	n.a.	n.a.	PMID[9868163]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	Database[Article]
NPO20598	Lythrum salicaria	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12373	Vinca minor	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10011	Myrsine capitellata	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21375	Euphorbia nematocypha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17334	Onopordum acanthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28667	Waltheria americana	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO12056	Chondrodendron tomentosum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21170	Embelia parviflora	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO28667	Waltheria americana	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12056	Chondrodendron tomentosum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10011	Myrsine capitellata	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20598	Lythrum salicaria	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16108	Eupatorium mikanioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17334	Onopordum acanthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20142	Embelia schimperi	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20680	Erythrina melanacantha	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20879	Clerodendrum bungei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21520	Corydalis thalictrifolia	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18668	Asimina parviflora	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21375	Euphorbia nematocypha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21170	Embelia parviflora	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3152	Morella rubra	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12373	Vinca minor	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6413	Viguiera stenoloba	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20489	Epilobium hirsutum	Species	Onagraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO7135	Mollugo spergula	Species	Molluginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21520	Corydalis thalictrifolia	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20598	Lythrum salicaria	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21375	Euphorbia nematocypha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20680	Erythrina melanacantha	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO17334	Onopordum acanthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO28667	Waltheria americana	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO21170	Embelia parviflora	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	Database[Title]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO28348	Filicium decipiens	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19667	Hypericum styphelioides	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15456	Sideritis soluta	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20879	Clerodendrum bungei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20084	Atraphaxis spinosa	Species	Polygonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11625	Markhamia stipulata	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12056	Chondrodendron tomentosum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20993	Bystropogon mollis	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20142	Embelia schimperi	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28540	Aglaia ignea	Species	Meliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO944	Senecio sandersonii	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16569	Gymnocalycium schickendantzii	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20008	Odontocline hollickii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO18143	Dendronephthya griffini	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17258	Rhinella marina	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20421	Aplophyllum alberti-regelii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO18668	Asimina parviflora	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20489	Epilobium hirsutum	Species	Onagraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28389	Helianthopsis microphylla	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO19995	Baccharis neglecta	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21375	Euphorbia nematocypha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27367	Latrunculia magnifica	Species	Latrunculiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17849	Centaurea maculosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11523	Erysimum leptophyllum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22961	Cordia leucocephala	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22225	Calliandra eriophylla	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20680	Erythrina melanacantha	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6864	Lactarius spinosulus	Species	Russulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28072	Theonella conica	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28506	Onobrychis kachetica	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21243	Siphonaria capensis	Species	Siphonariidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22937	Vernonia fagifolia	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11342	Sideritis trojana	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4051	Tricholoma columbetta	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10011	Myrsine capitellata	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21108	Eria anomala	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20598	Lythrum salicaria	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9162	Nicotiana affinis	Species	Solanaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12313	Haplophyllum obtusifolium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21075	Phytolacca thyrsiflora	Species	Phytolaccaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20624	Simarouba glauca	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16108	Eupatorium mikanioides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16141	Piper regnellii	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12598	Osteospermum fruticosum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21562	Diospyros assimilis	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13327	Phomopsis leptostromiformis	Species	Valsaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17560	Pancratium sickenbergeri	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO15042	Lepraria membranacea	Species	Stereocaulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12373	Vinca minor	Species	Apocynaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13449	Syzygium polycephaloides	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO2471	Axinyssa variabilis	Species	Halichondriidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19810	Myxococcus stipitatus	Species	Myxococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO19968	Millettia ovalifolia	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9968	Shigella dysenteriae	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO14241	Planchonia grandis	Species	Asterolecaniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5805	Chlorociboria aeruginascens	Species	n.a.	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12241	Hypericum reflexum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21495	Abelia chinensis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21397	Venus mercenaria	Species	Veneridae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18866	Pteridium esculentum	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19912	Vellozia nanuzae	Species	Velloziaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20843	Monsonia senegalensis	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17334	Onopordum acanthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6413	Viguiera stenoloba	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18473	Plathymenia reticulata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21520	Corydalis thalictrifolia	Species	Papaveraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19036	Esenbeckia leiocarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7135	Mollugo spergula	Species	Molluginaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28667	Waltheria americana	Species	Malvaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19511	Dolabella californica	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28315	Jania rubens	Species	Corallinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21631	Faramea salicifolia	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21038	Lemaireocereus longispinus	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20575	Penicillium puberulum	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5903	Conus mus	Species	Conidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21170	Embelia parviflora	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28202	Helichrysum tenuifolium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3152	Morella rubra	Species	Myricaceae	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
GI50	58
Potency	11

Activity Type	# Activity
Cell Line	58
Individual Protein	9
Others	1
Protein-Protein Interaction	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT47	Individual Protein	ATP-dependent DNA helicase Q1	Homo sapiens	Potency	=	19952.6	nM	PMID[543308]
NPT48	Individual Protein	Lysine-specific demethylase 4D-like	Homo sapiens	Potency	=	11220.2	nM	PMID[543308]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	15848.9	nM	PMID[543308]
NPT51	Individual Protein	Microtubule-associated protein tau	Homo sapiens	Potency	=	11220.2	nM	PMID[543308]
NPT55	Individual Protein	Putative fructose-1,6-bisphosphate aldolase	Giardia intestinalis	Potency	=	44562.5	nM	PMID[543308]
NPT199	Individual Protein	DNA polymerase kappa	Homo sapiens	Potency	n.a.	891.3	nM	PMID[543309]
NPT368	Cell Line	SN12C	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[543310]
NPT367	Cell Line	MDA-N	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[543310]
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[543310]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	65463.62	nM	PMID[543310]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	11194.38	nM	PMID[543310]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[543310]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	37670.38	nM	PMID[543310]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[543310]
NPT90	Cell Line	DU-145	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[543310]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[543310]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	70145.53	nM	PMID[543310]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	78162.78	nM	PMID[543310]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	81658.24	nM	PMID[543310]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[543310]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	21379.62	nM	PMID[543310]
NPT378	Cell Line	NCI/ADR-RES	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[543310]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[543310]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[543310]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[543310]
NPT82	Cell Line	MDA-MB-231	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[543310]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	75857.76	nM	PMID[543310]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[543310]
NPT385	Cell Line	SR	Homo sapiens	GI50	n.a.	5688.53	nM	PMID[543310]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[543310]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	38018.94	nM	PMID[543310]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	41304.75	nM	PMID[543310]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[543310]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	73451.39	nM	PMID[543310]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	68233.87	nM	PMID[543310]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[543310]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	35645.11	nM	PMID[543310]
NPT457	Cell Line	BT-549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[543310]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	99770.01	nM	PMID[543310]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	79799.47	nM	PMID[543310]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	20183.66	nM	PMID[543310]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[543310]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	28773.98	nM	PMID[543310]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	41495.4	nM	PMID[543310]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	62086.9	nM	PMID[543310]
NPT83	Cell Line	MCF7	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[543310]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	56623.93	nM	PMID[543310]
NPT306	Cell Line	PC-3	Homo sapiens	GI50	n.a.	70631.76	nM	PMID[543310]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[543310]
NPT396	Cell Line	T47D	Homo sapiens	GI50	n.a.	89125.09	nM	PMID[543310]
NPT398	Cell Line	UACC-62	Homo sapiens	GI50	n.a.	93110.79	nM	PMID[543310]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	34833.73	nM	PMID[543310]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	89949.76	nM	PMID[543310]
NPT400	Cell Line	MDA-MB-435	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[543310]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[543310]
NPT458	Cell Line	IGROV-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[543310]
NPT402	Cell Line	Hs-578T	Homo sapiens	GI50	n.a.	29308.93	nM	PMID[543310]
NPT403	Cell Line	UACC-257	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[543310]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[543310]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[543310]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	67764.15	nM	PMID[543310]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	59292.53	nM	PMID[543310]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[543310]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[543310]
NPT49	Individual Protein	DNA-(apurinic or apyrimidinic site) lyase	Homo sapiens	Potency	n.a.	2818.4	nM	PMID[543308]
NPT197	Protein-Protein Interaction	Menin/Histone-lysine N-methyltransferase MLL	Homo sapiens	Potency	=	39810.7	nM	PMID[543308]
NPT94	Individual Protein	Aldehyde dehydrogenase 1A1	Homo sapiens	Potency	=	39810.7	nM	PMID[543308]
NPT888	Individual Protein	78 kDa glucose-regulated protein	Homo sapiens	Potency	n.a.	28183.8	nM	PMID[543309]
NPT2	Others	Unspecified		Potency	n.a.	6309.6	nM	PMID[543309]

☑ 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 NPC77660 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	445
0.1-0.2	1835
0.2-0.3	4139
0.3-0.4	9743
0.4-0.5	8335
0.5-0.6	4113
0.6-0.7	5112
0.7-0.8	5204
0.8-0.85	1975
0.85-0.9	1251
0.9-0.95	404
0.95-1	141

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC189142
0.9935	High Similarity	NPC270335
0.9935	High Similarity	NPC168822
0.9935	High Similarity	NPC19709
0.9935	High Similarity	NPC191306
0.9871	High Similarity	NPC277205
0.9871	High Similarity	NPC311830
0.9871	High Similarity	NPC22832
0.987	High Similarity	NPC473043
0.9808	High Similarity	NPC8856
0.9808	High Similarity	NPC21100
0.9808	High Similarity	NPC276222
0.9808	High Similarity	NPC274618
0.9808	High Similarity	NPC308404
0.9808	High Similarity	NPC281131
0.9808	High Similarity	NPC179950
0.9808	High Similarity	NPC210073
0.9808	High Similarity	NPC88789
0.9808	High Similarity	NPC197285
0.9808	High Similarity	NPC115674
0.9808	High Similarity	NPC145038
0.9808	High Similarity	NPC253662
0.9808	High Similarity	NPC56077
0.9808	High Similarity	NPC118284
0.9806	High Similarity	NPC309025
0.9806	High Similarity	NPC29830
0.9806	High Similarity	NPC243930
0.9806	High Similarity	NPC222936
0.9806	High Similarity	NPC284960
0.9806	High Similarity	NPC88023
0.9745	High Similarity	NPC317489
0.9745	High Similarity	NPC229729
0.9745	High Similarity	NPC146792
0.9745	High Similarity	NPC52550
0.9745	High Similarity	NPC58716
0.9745	High Similarity	NPC223424
0.9745	High Similarity	NPC45618
0.9745	High Similarity	NPC84362
0.9745	High Similarity	NPC173637
0.9745	High Similarity	NPC127546
0.9744	High Similarity	NPC55786
0.9744	High Similarity	NPC19388
0.9744	High Similarity	NPC240431
0.9742	High Similarity	NPC300537
0.9742	High Similarity	NPC127782
0.9684	High Similarity	NPC225434
0.9684	High Similarity	NPC226294
0.9684	High Similarity	NPC86008
0.9684	High Similarity	NPC105025
0.9684	High Similarity	NPC219904
0.9684	High Similarity	NPC209296
0.9684	High Similarity	NPC201292
0.9684	High Similarity	NPC58053
0.9684	High Similarity	NPC475942
0.9684	High Similarity	NPC120099
0.9684	High Similarity	NPC469931
0.9684	High Similarity	NPC186807
0.9684	High Similarity	NPC45638
0.9684	High Similarity	NPC203050
0.9684	High Similarity	NPC195257
0.9684	High Similarity	NPC223747
0.9684	High Similarity	NPC93337
0.9682	High Similarity	NPC5778
0.9682	High Similarity	NPC236934
0.9682	High Similarity	NPC135599
0.9682	High Similarity	NPC277174
0.9682	High Similarity	NPC73855
0.9682	High Similarity	NPC328940
0.9682	High Similarity	NPC113968
0.9679	High Similarity	NPC88043
0.9677	High Similarity	NPC182045
0.9673	High Similarity	NPC261866
0.9623	High Similarity	NPC78734
0.9623	High Similarity	NPC84265
0.9623	High Similarity	NPC67326
0.9623	High Similarity	NPC244776
0.9623	High Similarity	NPC150767
0.9623	High Similarity	NPC235260
0.9623	High Similarity	NPC20505
0.9623	High Similarity	NPC245014
0.9623	High Similarity	NPC156869
0.9623	High Similarity	NPC155763
0.9623	High Similarity	NPC259896
0.9623	High Similarity	NPC254855
0.9623	High Similarity	NPC285197
0.9623	High Similarity	NPC206123
0.9623	High Similarity	NPC95866
0.9623	High Similarity	NPC218488
0.9623	High Similarity	NPC255157
0.9623	High Similarity	NPC231194
0.9623	High Similarity	NPC29958
0.9623	High Similarity	NPC282987
0.9623	High Similarity	NPC51326
0.9623	High Similarity	NPC136042
0.9623	High Similarity	NPC67105
0.9623	High Similarity	NPC116864
0.962	High Similarity	NPC226304
0.962	High Similarity	NPC45400
0.962	High Similarity	NPC325555
0.962	High Similarity	NPC265530
0.962	High Similarity	NPC275454
0.962	High Similarity	NPC92565
0.962	High Similarity	NPC160156
0.9618	High Similarity	NPC165720
0.9613	High Similarity	NPC110349
0.9563	High Similarity	NPC134532
0.9563	High Similarity	NPC117260
0.9563	High Similarity	NPC245452
0.9563	High Similarity	NPC203259
0.9563	High Similarity	NPC175107
0.9563	High Similarity	NPC33054
0.9563	High Similarity	NPC259152
0.9563	High Similarity	NPC471748
0.9563	High Similarity	NPC254540
0.9563	High Similarity	NPC26230
0.9563	High Similarity	NPC476405
0.9563	High Similarity	NPC153755
0.9563	High Similarity	NPC256760
0.9563	High Similarity	NPC235575
0.9563	High Similarity	NPC176740
0.9563	High Similarity	NPC205076
0.9563	High Similarity	NPC180918
0.9563	High Similarity	NPC155877
0.9563	High Similarity	NPC3583
0.9563	High Similarity	NPC211594
0.9563	High Similarity	NPC60735
0.9563	High Similarity	NPC190003
0.9563	High Similarity	NPC307518
0.9563	High Similarity	NPC471725
0.9563	High Similarity	NPC172807
0.9563	High Similarity	NPC48773
0.956	High Similarity	NPC227508
0.956	High Similarity	NPC170675
0.956	High Similarity	NPC270578
0.956	High Similarity	NPC229687
0.956	High Similarity	NPC52382
0.956	High Similarity	NPC471457
0.956	High Similarity	NPC138927
0.956	High Similarity	NPC112755
0.956	High Similarity	NPC105283
0.956	High Similarity	NPC43587
0.9557	High Similarity	NPC67037
0.9557	High Similarity	NPC255615
0.9557	High Similarity	NPC254306
0.9542	High Similarity	NPC83283
0.9542	High Similarity	NPC143851
0.9542	High Similarity	NPC210003
0.9542	High Similarity	NPC39360
0.9542	High Similarity	NPC29763
0.9503	High Similarity	NPC169977
0.9503	High Similarity	NPC42773
0.9503	High Similarity	NPC208668
0.9503	High Similarity	NPC204693
0.9503	High Similarity	NPC101026
0.9503	High Similarity	NPC472993
0.9503	High Similarity	NPC21666
0.9503	High Similarity	NPC4390
0.9503	High Similarity	NPC45522
0.9503	High Similarity	NPC24043
0.95	High Similarity	NPC224462
0.95	High Similarity	NPC149011
0.95	High Similarity	NPC204937
0.95	High Similarity	NPC183357
0.95	High Similarity	NPC44328
0.95	High Similarity	NPC79056
0.95	High Similarity	NPC471416
0.95	High Similarity	NPC22195
0.95	High Similarity	NPC21190
0.95	High Similarity	NPC34287
0.95	High Similarity	NPC105511
0.95	High Similarity	NPC105095
0.95	High Similarity	NPC177731
0.9497	High Similarity	NPC48640
0.9497	High Similarity	NPC149244
0.9497	High Similarity	NPC477502
0.9497	High Similarity	NPC116745
0.9494	High Similarity	NPC34531
0.9494	High Similarity	NPC475366
0.9494	High Similarity	NPC475497
0.9494	High Similarity	NPC284277
0.9484	High Similarity	NPC313163
0.9484	High Similarity	NPC161749
0.9484	High Similarity	NPC258035
0.9484	High Similarity	NPC197896
0.9484	High Similarity	NPC156457
0.9481	High Similarity	NPC95090
0.9481	High Similarity	NPC27408
0.9444	High Similarity	NPC214621
0.9444	High Similarity	NPC223426
0.9444	High Similarity	NPC81042
0.9444	High Similarity	NPC43211
0.9444	High Similarity	NPC101191
0.9444	High Similarity	NPC210094
0.9444	High Similarity	NPC16194
0.9444	High Similarity	NPC34267
0.9444	High Similarity	NPC115760
0.9444	High Similarity	NPC477848
0.9444	High Similarity	NPC472607
0.9444	High Similarity	NPC198199
0.9444	High Similarity	NPC294629

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 NPC77660 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	414
0.1-0.2	929
0.2-0.3	1905
0.3-0.4	2694
0.4-0.5	1797
0.5-0.6	934
0.6-0.7	295
0.7-0.8	135
0.8-0.85	20
0.85-0.9	17
0.9-0.95	9
0.95-1	1

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9684	High Similarity	NPD7054	Approved
0.9623	High Similarity	NPD7472	Approved
0.9563	High Similarity	NPD6797	Phase 2
0.9503	High Similarity	NPD7251	Discontinued
0.95	High Similarity	NPD7074	Phase 3
0.9497	High Similarity	NPD3818	Discontinued
0.9484	High Similarity	NPD4381	Clinical (unspecified phase)
0.9444	High Similarity	NPD4338	Clinical (unspecified phase)
0.9325	High Similarity	NPD7808	Phase 3
0.9103	High Similarity	NPD1934	Approved
0.9045	High Similarity	NPD2393	Clinical (unspecified phase)
0.9012	High Similarity	NPD6166	Phase 2
0.9012	High Similarity	NPD6167	Clinical (unspecified phase)
0.9012	High Similarity	NPD6168	Clinical (unspecified phase)
0.8963	High Similarity	NPD7804	Clinical (unspecified phase)
0.8954	High Similarity	NPD1511	Approved
0.8924	High Similarity	NPD2801	Approved
0.8854	High Similarity	NPD4380	Phase 2
0.8839	High Similarity	NPD1512	Approved
0.8812	High Similarity	NPD4868	Clinical (unspecified phase)
0.875	High Similarity	NPD3817	Phase 2
0.858	High Similarity	NPD3882	Suspended
0.858	High Similarity	NPD6559	Discontinued
0.8442	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8442	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8415	Intermediate Similarity	NPD7075	Discontinued
0.8412	Intermediate Similarity	NPD7993	Clinical (unspecified phase)
0.8405	Intermediate Similarity	NPD5402	Approved
0.8387	Intermediate Similarity	NPD1549	Phase 2
0.8375	Intermediate Similarity	NPD1653	Approved
0.8313	Intermediate Similarity	NPD5403	Approved
0.8302	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8282	Intermediate Similarity	NPD6801	Discontinued
0.8232	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8204	Intermediate Similarity	NPD5494	Approved
0.8194	Intermediate Similarity	NPD1510	Phase 2
0.8187	Intermediate Similarity	NPD5401	Approved
0.8182	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.8141	Intermediate Similarity	NPD2796	Approved
0.8125	Intermediate Similarity	NPD6799	Approved
0.8121	Intermediate Similarity	NPD7819	Suspended
0.8121	Intermediate Similarity	NPD1465	Phase 2
0.811	Intermediate Similarity	NPD7411	Suspended
0.8081	Intermediate Similarity	NPD5844	Phase 1
0.8075	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8052	Intermediate Similarity	NPD1613	Approved
0.8047	Intermediate Similarity	NPD6959	Discontinued
0.8046	Intermediate Similarity	NPD7685	Pre-registration
0.8023	Intermediate Similarity	NPD3751	Discontinued
0.8	Intermediate Similarity	NPD6232	Discontinued
0.8	Intermediate Similarity	NPD3787	Discontinued
0.7975	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7965	Intermediate Similarity	NPD7473	Discontinued
0.7955	Intermediate Similarity	NPD8312	Approved
0.7955	Intermediate Similarity	NPD8313	Approved
0.7944	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.7941	Intermediate Similarity	NPD7199	Phase 2
0.7919	Intermediate Similarity	NPD7228	Approved
0.7862	Intermediate Similarity	NPD7266	Discontinued
0.7831	Intermediate Similarity	NPD6599	Discontinued
0.7826	Intermediate Similarity	NPD3750	Approved
0.7826	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7824	Intermediate Similarity	NPD6234	Discontinued
0.7821	Intermediate Similarity	NPD943	Approved
0.7821	Intermediate Similarity	NPD1240	Approved
0.7812	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7803	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7792	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7778	Intermediate Similarity	NPD7584	Approved
0.7746	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7738	Intermediate Similarity	NPD37	Approved
0.7735	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7727	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7722	Intermediate Similarity	NPD1607	Approved
0.7706	Intermediate Similarity	NPD4965	Approved
0.7706	Intermediate Similarity	NPD4966	Approved
0.7706	Intermediate Similarity	NPD4967	Phase 2
0.7692	Intermediate Similarity	NPD8455	Phase 2
0.7688	Intermediate Similarity	NPD1551	Phase 2
0.7683	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7669	Intermediate Similarity	NPD6190	Approved
0.7667	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7661	Intermediate Similarity	NPD3749	Approved
0.7658	Intermediate Similarity	NPD230	Phase 1
0.7658	Intermediate Similarity	NPD1933	Approved
0.7647	Intermediate Similarity	NPD6777	Approved
0.7647	Intermediate Similarity	NPD6781	Approved
0.7647	Intermediate Similarity	NPD6778	Approved
0.7647	Intermediate Similarity	NPD6776	Approved
0.7647	Intermediate Similarity	NPD6782	Approved
0.7647	Intermediate Similarity	NPD6779	Approved
0.7647	Intermediate Similarity	NPD6780	Approved
0.7628	Intermediate Similarity	NPD3027	Phase 3
0.7616	Intermediate Similarity	NPD919	Approved
0.7607	Intermediate Similarity	NPD4628	Phase 3
0.7604	Intermediate Similarity	NPD8151	Discontinued
0.7602	Intermediate Similarity	NPD7768	Phase 2
0.758	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7543	Intermediate Similarity	NPD3926	Phase 2
0.7529	Intermediate Similarity	NPD1247	Approved
0.7526	Intermediate Similarity	NPD7435	Discontinued
0.7516	Intermediate Similarity	NPD3748	Approved
0.7469	Intermediate Similarity	NPD2935	Discontinued
0.7451	Intermediate Similarity	NPD1091	Approved
0.7444	Intermediate Similarity	NPD7240	Approved
0.7439	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7438	Intermediate Similarity	NPD447	Suspended
0.7436	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7436	Intermediate Similarity	NPD7783	Phase 2
0.7435	Intermediate Similarity	NPD7697	Approved
0.7435	Intermediate Similarity	NPD7698	Approved
0.7435	Intermediate Similarity	NPD7696	Phase 3
0.7425	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7425	Intermediate Similarity	NPD2532	Approved
0.7425	Intermediate Similarity	NPD2534	Approved
0.7425	Intermediate Similarity	NPD2533	Approved
0.7407	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7396	Intermediate Similarity	NPD7870	Phase 2
0.7396	Intermediate Similarity	NPD7871	Phase 2
0.7394	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7382	Intermediate Similarity	NPD6823	Phase 2
0.738	Intermediate Similarity	NPD6535	Approved
0.738	Intermediate Similarity	NPD6534	Approved
0.7371	Intermediate Similarity	NPD7585	Approved
0.7371	Intermediate Similarity	NPD7701	Phase 2
0.7337	Intermediate Similarity	NPD920	Approved
0.7333	Intermediate Similarity	NPD2800	Approved
0.7321	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.732	Intermediate Similarity	NPD7583	Approved
0.7308	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7301	Intermediate Similarity	NPD7033	Discontinued
0.7296	Intermediate Similarity	NPD7874	Approved
0.7296	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7293	Intermediate Similarity	NPD5953	Discontinued
0.7287	Intermediate Similarity	NPD4363	Phase 3
0.7287	Intermediate Similarity	NPD4360	Phase 2
0.7277	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.7263	Intermediate Similarity	NPD7699	Phase 2
0.7263	Intermediate Similarity	NPD7700	Phase 2
0.7261	Intermediate Similarity	NPD1203	Approved
0.7259	Intermediate Similarity	NPD7801	Approved
0.7256	Intermediate Similarity	NPD6099	Approved
0.7256	Intermediate Similarity	NPD6100	Approved
0.7251	Intermediate Similarity	NPD7458	Discontinued
0.7251	Intermediate Similarity	NPD3226	Approved
0.725	Intermediate Similarity	NPD2313	Discontinued
0.7233	Intermediate Similarity	NPD6832	Phase 2
0.7233	Intermediate Similarity	NPD4908	Phase 1
0.7229	Intermediate Similarity	NPD1243	Approved
0.7229	Intermediate Similarity	NPD1652	Phase 2
0.7229	Intermediate Similarity	NPD6674	Discontinued
0.7226	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7225	Intermediate Similarity	NPD6844	Discontinued
0.7215	Intermediate Similarity	NPD2798	Approved
0.719	Intermediate Similarity	NPD1548	Phase 1
0.7182	Intermediate Similarity	NPD7286	Phase 2
0.7178	Intermediate Similarity	NPD6651	Approved
0.717	Intermediate Similarity	NPD9494	Approved
0.716	Intermediate Similarity	NPD7390	Discontinued
0.7151	Intermediate Similarity	NPD8150	Discontinued
0.7151	Intermediate Similarity	NPD8434	Phase 2
0.7151	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6212	Phase 3
0.7143	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6213	Phase 3
0.7135	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7134	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7128	Intermediate Similarity	NPD8320	Phase 1
0.7128	Intermediate Similarity	NPD8319	Approved
0.7117	Intermediate Similarity	NPD5124	Phase 1
0.7117	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7117	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7115	Intermediate Similarity	NPD1610	Phase 2
0.7111	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD2346	Discontinued
0.7108	Intermediate Similarity	NPD2344	Approved
0.7091	Intermediate Similarity	NPD2799	Discontinued
0.7089	Intermediate Similarity	NPD3225	Approved
0.7083	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7077	Intermediate Similarity	NPD7680	Approved
0.707	Intermediate Similarity	NPD9269	Phase 2
0.7045	Intermediate Similarity	NPD5353	Approved
0.7037	Intermediate Similarity	NPD6798	Discontinued
0.7037	Intermediate Similarity	NPD3268	Approved
0.7018	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD422	Phase 1
0.7	Intermediate Similarity	NPD5710	Approved
0.7	Intermediate Similarity	NPD5711	Approved
0.6994	Remote Similarity	NPD6233	Phase 2
0.6988	Remote Similarity	NPD1509	Clinical (unspecified phase)
0.698	Remote Similarity	NPD7930	Approved
0.6971	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6962	Remote Similarity	NPD9717	Approved
0.6961	Remote Similarity	NPD5242	Approved
0.6957	Remote Similarity	NPD2861	Phase 2
0.6949	Remote Similarity	NPD4288	Approved
0.6944	Remote Similarity	NPD8127	Discontinued

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