NPASS Compound

Structure

CID229687 OpenBabel06191716022D 41 44 0 0 1 0 0 0 0 0999 V2000 6.9282 -3.0000 0.0000 C 0 0 0 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 2.5981 -1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 4.3301 -4.5000 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 -5.1962 0.0000 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 3.4641 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -1.0000 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 -2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 5.1962 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 -1.0000 0.0000 C 0 0 2 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 0.5000 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5981 -4.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 -4.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -1.5000 0.0000 C 0 0 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 0.0000 2.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 -1.0000 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 -3.4641 0.0000 0.0000 C 0 0 1 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 -0.0000 -3.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 6.0622 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -1.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5981 -5.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8660 -4.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -2.5000 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 -2.5981 -1.5000 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 6.0622 -2.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 0.5000 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 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 37 1 0 0 0 0 2 5 2 0 0 0 0 2 10 1 0 0 0 0 3 4 2 0 0 0 0 3 11 1 0 0 0 0 4 12 1 0 0 0 0 5 16 1 0 0 0 0 6 10 2 0 0 0 0 6 14 1 0 0 0 0 7 11 2 0 0 0 0 7 13 1 0 0 0 0 8 15 1 0 0 0 0 8 38 1 0 0 0 0 9 39 1 0 0 0 0 10 18 1 0 0 0 0 11 40 1 0 0 0 0 12 13 2 0 0 0 0 12 19 1 0 0 0 0 13 27 1 0 0 0 0 14 16 2 0 0 0 0 14 28 1 0 0 0 0 15 20 1 0 0 0 0 15 29 1 6 0 0 0 16 37 1 0 0 0 0 17 9 1 6 0 0 0 17 21 1 0 0 0 0 17 41 1 0 0 0 0 18 19 1 0 0 0 0 18 30 2 0 0 0 0 19 31 2 0 0 0 0 20 23 1 0 0 0 0 20 32 1 1 0 0 0 21 22 1 0 0 0 0 21 33 1 1 0 0 0 22 24 1 0 0 0 0 22 34 1 6 0 0 0 23 25 1 0 0 0 0 23 35 1 6 0 0 0 24 26 1 0 0 0 0 24 36 1 1 0 0 0 25 38 1 0 0 0 0 25 39 1 1 0 0 0 26 40 1 6 0 0 0 26 41 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	582.16
Volume:	534.788
LogP:	-0.234
LogD:	-0.079
LogS:	-3.381
# Rotatable Bonds:	9
TPSA:	242.13
# H-Bond Aceptor:	15
# H-Bond Donor:	8
# Rings:	4
# Heavy Atoms:	15

MedChem Properties

QED Drug-Likeness Score:	0.116
Synthetic Accessibility Score:	4.557
Fsp3:	0.462
Lipinski Rule-of-5:	Rejected
Pfizer Rule:	Accepted
GSK Rule:	Rejected
BMS Rule:	1
Golden Triangle Rule:	Rejected
Chelating Alert:	1
PAINS Alert:	1

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-6.519
MDCK Permeability:	2.1687847038265318e-05
Pgp-inhibitor:	0.137
Pgp-substrate:	0.996
Human Intestinal Absorption (HIA):	0.903
20% Bioavailability (F20%):	0.004
30% Bioavailability (F30%):	1.0

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.143
Plasma Protein Binding (PPB):	93.90967559814453%
Volume Distribution (VD):	0.463
Pgp-substrate:	6.164453506469727%

ADMET: Metabolism

CYP1A2-inhibitor:	0.111
CYP1A2-substrate:	0.059
CYP2C19-inhibitor:	0.044
CYP2C19-substrate:	0.053
CYP2C9-inhibitor:	0.013
CYP2C9-substrate:	0.113
CYP2D6-inhibitor:	0.078
CYP2D6-substrate:	0.148
CYP3A4-inhibitor:	0.028
CYP3A4-substrate:	0.023

ADMET: Excretion

Clearance (CL):	1.009
Half-life (T1/2):	0.526

ADMET: Toxicity

hERG Blockers:	0.494
Human Hepatotoxicity (H-HT):	0.05
Drug-inuced Liver Injury (DILI):	0.95
AMES Toxicity:	0.653
Rat Oral Acute Toxicity:	0.032
Maximum Recommended Daily Dose:	0.006
Skin Sensitization:	0.89
Carcinogencity:	0.637
Eye Corrosion:	0.003
Eye Irritation:	0.382
Respiratory Toxicity:	0.011

Download Data

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

Natural Product: NPC229687

Natural Product ID:	NPC229687
*Common Name:**	2',3''-Dihydroxy-4''-Methoxydibenzoyl-4'-O-Beta-D-Xylopyranosyl-(1->6)-Beta-D-Glucopyranoside
IUPAC Name:	1-(3-hydroxy-4-methoxyphenyl)-2-[2-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxyphenyl]ethane-1,2-dione
Synonyms:
Standard InCHIKey:	UMKKAPDEEXWINW-ZHVPDQJESA-N
Standard InCHI:	InChI=1S/C26H30O15/c1-37-16-5-2-10(6-14(16)28)18(30)19(31)12-4-3-11(7-13(12)27)40-26-24(36)22(34)21(33)17(41-26)9-39-25-23(35)20(32)15(29)8-38-25/h2-7,15,17,20-29,32-36H,8-9H2,1H3/t15-,17-,20+,21-,22+,23-,24-,25+,26-/m1/s1
SMILES:	COc1ccc(cc1O)C(=O)C(=O)c1ccc(cc1O)O[C@H]1[C@@H]([C@H]([C@@H]([C@@H](CO[C@H]2[C@@H]([C@H]([C@@H](CO2)O)O)O)O1)O)O)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL3092850
PubChem CID:	73603972
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0000253] Stilbenes [CHEMONTID:0000142] Stilbene 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]
NPO18668	Asimina parviflora	Species	Annonaceae	Eukaryota	twigs	n.a.	n.a.	PMID[1453182]
NPO19667	Hypericum styphelioides	Species	Hypericaceae	Eukaryota	leaves	n.a.	n.a.	PMID[15165152]
NPO19667	Hypericum styphelioides	Species	Hypericaceae	Eukaryota	n.a.	leaf	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	roots	Hualien Hsien, Taiwan	2003-JUL	PMID[16933887]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	root	n.a.	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]
NPO12056	Chondrodendron tomentosum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO21375	Euphorbia nematocypha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO20598	Lythrum salicaria	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19231	Sophora flavescens	Species	Fabaceae	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]
NPO21170	Embelia parviflora	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18668	Asimina parviflora	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20879	Clerodendrum bungei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO3152	Morella rubra	Species	Myricaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21170	Embelia parviflora	Species	Primulaceae	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]
NPO17334	Onopordum acanthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO21375	Euphorbia nematocypha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19231	Sophora flavescens	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]
NPO20489	Epilobium hirsutum	Species	Onagraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO12056	Chondrodendron tomentosum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20598	Lythrum salicaria	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19231	Sophora flavescens	Species	Fabaceae	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]
NPO18176	Ephedra sinica	Species	Ephedraceae	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]
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]
NPO17334	Onopordum acanthium	Species	Asteraceae	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]
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]
NPO19667	Hypericum styphelioides	Species	Hypericaceae	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]
NPO18143	Dendronephthya griffini	Species	Nephtheidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20142	Embelia schimperi	Species	Primulaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20598	Lythrum salicaria	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16569	Gymnocalycium schickendantzii	Species	Cactaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19995	Baccharis neglecta	Species	Asteraceae	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]
NPO20489	Epilobium hirsutum	Species	Onagraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11523	Erysimum leptophyllum	Species	Brassicaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21375	Euphorbia nematocypha	Species	Euphorbiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17849	Centaurea maculosa	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO28072	Theonella conica	Species	Theonellidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18176	Ephedra sinica	Species	Ephedraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20680	Erythrina melanacantha	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]
NPO4051	Tricholoma columbetta	Species	Tricholomataceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21108	Eria anomala	Species	Orchidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12313	Haplophyllum obtusifolium	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13449	Syzygium polycephaloides	Species	Myrtaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16141	Piper regnellii	Species	Piperaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12056	Chondrodendron tomentosum	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO21562	Diospyros assimilis	Species	Ebenaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14241	Planchonia grandis	Species	Asterolecaniidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17560	Pancratium sickenbergeri	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17258	Rhinella marina	Species	Bufonidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18866	Pteridium esculentum	Species	Dennstaedtiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19810	Myxococcus stipitatus	Species	Myxococcaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO9968	Shigella dysenteriae	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO21495	Abelia chinensis	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18668	Asimina parviflora	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20843	Monsonia senegalensis	Species	Geraniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20624	Simarouba glauca	Species	Simaroubaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO17334	Onopordum acanthium	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO27367	Latrunculia magnifica	Species	Latrunculiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18473	Plathymenia reticulata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19036	Esenbeckia leiocarpa	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19511	Dolabella californica	Species	Aplysiidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22961	Cordia leucocephala	Species	Cordiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO22937	Vernonia fagifolia	Species	Asteraceae	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]
NPO19912	Vellozia nanuzae	Species	Velloziaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5903	Conus mus	Species	Conidae	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
Others	2

Activity Type	# Activity
CELL-LINE	1
NON-MOLECULAR	1

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT20529	NON-MOLECULAR	NON-PROTEIN TARGET	n.a.	Inhibition	=	27.1	%	PMID[474757]
NPT21742	CELL-LINE	L02	Homo sapiens	Survival	=	61.3	%	PMID[474757]

☑ 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 NPC229687 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	423
0.1-0.2	1685
0.2-0.3	3767
0.3-0.4	8919
0.4-0.5	9084
0.5-0.6	4449
0.6-0.7	4983
0.7-0.8	5869
0.8-0.85	2165
0.85-0.9	841
0.9-0.95	480
0.95-1	32

Similarity Score	Similarity Level	Natural Product ID
0.9937	High Similarity	NPC45400
0.9873	High Similarity	NPC5778
0.9873	High Similarity	NPC236934
0.9812	High Similarity	NPC183357
0.9812	High Similarity	NPC231194
0.9812	High Similarity	NPC21190
0.9812	High Similarity	NPC44558
0.9812	High Similarity	NPC474434
0.9812	High Similarity	NPC22195
0.9812	High Similarity	NPC471416
0.9812	High Similarity	NPC34287
0.9812	High Similarity	NPC51326
0.9811	High Similarity	NPC229729
0.981	High Similarity	NPC165720
0.9752	High Similarity	NPC205076
0.9752	High Similarity	NPC307518
0.9752	High Similarity	NPC48773
0.975	High Similarity	NPC170675
0.975	High Similarity	NPC472381
0.975	High Similarity	NPC210042
0.975	High Similarity	NPC183036
0.975	High Similarity	NPC471457
0.975	High Similarity	NPC95855
0.975	High Similarity	NPC472383
0.975	High Similarity	NPC112755
0.9747	High Similarity	NPC88043
0.9747	High Similarity	NPC29830
0.9691	High Similarity	NPC239549
0.9691	High Similarity	NPC236191
0.9691	High Similarity	NPC51774
0.9689	High Similarity	NPC105095
0.9689	High Similarity	NPC44328
0.9689	High Similarity	NPC224462
0.9689	High Similarity	NPC105511
0.9689	High Similarity	NPC177731
0.9689	High Similarity	NPC212748
0.9689	High Similarity	NPC79056
0.9688	High Similarity	NPC93099
0.9688	High Similarity	NPC477502
0.9688	High Similarity	NPC116745
0.9686	High Similarity	NPC311830
0.9686	High Similarity	NPC22832
0.9684	High Similarity	NPC300537
0.9684	High Similarity	NPC127782
0.963	High Similarity	NPC235575
0.963	High Similarity	NPC301683
0.963	High Similarity	NPC261254
0.963	High Similarity	NPC472386
0.963	High Similarity	NPC267254
0.963	High Similarity	NPC256760
0.9627	High Similarity	NPC195257
0.9627	High Similarity	NPC226294
0.9627	High Similarity	NPC52382
0.9627	High Similarity	NPC61791
0.9627	High Similarity	NPC43587
0.9627	High Similarity	NPC201292
0.9627	High Similarity	NPC58053
0.9627	High Similarity	NPC209296
0.9627	High Similarity	NPC270578
0.9627	High Similarity	NPC475942
0.9627	High Similarity	NPC293629
0.9627	High Similarity	NPC186807
0.9627	High Similarity	NPC93337
0.9627	High Similarity	NPC469931
0.9627	High Similarity	NPC45638
0.9627	High Similarity	NPC105025
0.9625	High Similarity	NPC210073
0.9625	High Similarity	NPC115674
0.9623	High Similarity	NPC284960
0.9623	High Similarity	NPC309025
0.9623	High Similarity	NPC19709
0.9623	High Similarity	NPC270335
0.9623	High Similarity	NPC191306
0.9623	High Similarity	NPC168822
0.9623	High Similarity	NPC222936
0.9623	High Similarity	NPC243930
0.9623	High Similarity	NPC88023
0.9571	High Similarity	NPC204693
0.9571	High Similarity	NPC208668
0.9571	High Similarity	NPC172033
0.9571	High Similarity	NPC175230
0.9571	High Similarity	NPC88560
0.9568	High Similarity	NPC149011
0.9568	High Similarity	NPC150767
0.9568	High Similarity	NPC206123
0.9568	High Similarity	NPC204937
0.9568	High Similarity	NPC78734
0.9565	High Similarity	NPC92565
0.9565	High Similarity	NPC135345
0.9565	High Similarity	NPC160156
0.9565	High Similarity	NPC58716
0.9565	High Similarity	NPC146792
0.9565	High Similarity	NPC45618
0.956	High Similarity	NPC77660
0.956	High Similarity	NPC148273
0.956	High Similarity	NPC189142
0.956	High Similarity	NPC473043
0.9515	High Similarity	NPC476621
0.9515	High Similarity	NPC476623
0.9515	High Similarity	NPC476620
0.9515	High Similarity	NPC472387
0.9515	High Similarity	NPC476618
0.9515	High Similarity	NPC476619
0.9515	High Similarity	NPC476622
0.9512	High Similarity	NPC102028
0.9512	High Similarity	NPC108202
0.9512	High Similarity	NPC142996
0.9509	High Similarity	NPC259152
0.9509	High Similarity	NPC475155
0.9509	High Similarity	NPC67134
0.9509	High Similarity	NPC47140
0.9509	High Similarity	NPC476405
0.9509	High Similarity	NPC254540
0.9509	High Similarity	NPC172807
0.9509	High Similarity	NPC211594
0.9509	High Similarity	NPC156977
0.9509	High Similarity	NPC3583
0.9509	High Similarity	NPC117260
0.9506	High Similarity	NPC86008
0.9506	High Similarity	NPC225434
0.9506	High Similarity	NPC203050
0.9506	High Similarity	NPC223747
0.9506	High Similarity	NPC105283
0.9506	High Similarity	NPC120099
0.9506	High Similarity	NPC219904
0.9503	High Similarity	NPC21100
0.9503	High Similarity	NPC197285
0.9503	High Similarity	NPC99957
0.9503	High Similarity	NPC181616
0.9503	High Similarity	NPC8856
0.95	High Similarity	NPC127415
0.9497	High Similarity	NPC182045
0.9455	High Similarity	NPC268533
0.9455	High Similarity	NPC472380
0.9455	High Similarity	NPC472384
0.9455	High Similarity	NPC169733
0.9455	High Similarity	NPC472382
0.9451	High Similarity	NPC101026
0.9451	High Similarity	NPC42773
0.9451	High Similarity	NPC4390
0.9451	High Similarity	NPC472993
0.9451	High Similarity	NPC45522
0.9451	High Similarity	NPC24043
0.9451	High Similarity	NPC21666
0.9451	High Similarity	NPC169977
0.9448	High Similarity	NPC67105
0.9448	High Similarity	NPC245014
0.9448	High Similarity	NPC293004
0.9448	High Similarity	NPC282987
0.9448	High Similarity	NPC218488
0.9448	High Similarity	NPC84265
0.9448	High Similarity	NPC72249
0.9448	High Similarity	NPC95866
0.9448	High Similarity	NPC285197
0.9444	High Similarity	NPC84362
0.9444	High Similarity	NPC317489
0.9444	High Similarity	NPC325555
0.9444	High Similarity	NPC52550
0.9444	High Similarity	NPC223424
0.9444	High Similarity	NPC265530
0.9444	High Similarity	NPC226304
0.9444	High Similarity	NPC127546
0.9444	High Similarity	NPC173637
0.9441	High Similarity	NPC475497
0.9441	High Similarity	NPC475366
0.9441	High Similarity	NPC277205
0.9441	High Similarity	NPC284277
0.9434	High Similarity	NPC110349
0.9398	High Similarity	NPC168584
0.9398	High Similarity	NPC241196
0.9394	High Similarity	NPC16194
0.9394	High Similarity	NPC472607
0.9394	High Similarity	NPC19108
0.9394	High Similarity	NPC294815
0.9394	High Similarity	NPC473327
0.9394	High Similarity	NPC477848
0.9394	High Similarity	NPC198199
0.9394	High Similarity	NPC294629
0.9394	High Similarity	NPC220173
0.9394	High Similarity	NPC476472
0.939	High Similarity	NPC155877
0.939	High Similarity	NPC134532
0.939	High Similarity	NPC471748
0.939	High Similarity	NPC203259
0.939	High Similarity	NPC176740
0.939	High Similarity	NPC190003
0.939	High Similarity	NPC26230
0.939	High Similarity	NPC153755
0.939	High Similarity	NPC33054
0.939	High Similarity	NPC180918
0.939	High Similarity	NPC175107
0.939	High Similarity	NPC471725
0.939	High Similarity	NPC60735
0.9387	High Similarity	NPC227508
0.9383	High Similarity	NPC113968
0.9383	High Similarity	NPC135599
0.9383	High Similarity	NPC56077
0.9383	High Similarity	NPC118284
0.9383	High Similarity	NPC277174
0.9383	High Similarity	NPC73855

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 NPC229687 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	376
0.1-0.2	909
0.2-0.3	1861
0.3-0.4	2665
0.4-0.5	1875
0.5-0.6	925
0.6-0.7	373
0.7-0.8	129
0.8-0.85	20
0.85-0.9	9
0.9-0.95	5
0.95-1	3

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.9689	High Similarity	NPD7074	Phase 3
0.9627	High Similarity	NPD7054	Approved
0.9568	High Similarity	NPD7472	Approved
0.9565	High Similarity	NPD3818	Discontinued
0.939	High Similarity	NPD6797	Phase 2
0.9333	High Similarity	NPD7251	Discontinued
0.9308	High Similarity	NPD4381	Clinical (unspecified phase)
0.9277	High Similarity	NPD4338	Clinical (unspecified phase)
0.9277	High Similarity	NPD7808	Phase 3
0.9202	High Similarity	NPD6168	Clinical (unspecified phase)
0.9202	High Similarity	NPD6166	Phase 2
0.9202	High Similarity	NPD6167	Clinical (unspecified phase)
0.9177	High Similarity	NPD1934	Approved
0.9	High Similarity	NPD2393	Clinical (unspecified phase)
0.8922	High Similarity	NPD7804	Clinical (unspecified phase)
0.8889	High Similarity	NPD4868	Clinical (unspecified phase)
0.8882	High Similarity	NPD2801	Approved
0.8773	High Similarity	NPD3882	Suspended
0.8696	High Similarity	NPD4380	Phase 2
0.8655	High Similarity	NPD6559	Discontinued
0.8614	High Similarity	NPD5494	Approved
0.8598	High Similarity	NPD3817	Phase 2
0.8596	High Similarity	NPD7993	Clinical (unspecified phase)
0.8553	High Similarity	NPD1511	Approved
0.8494	Intermediate Similarity	NPD7075	Discontinued
0.8447	Intermediate Similarity	NPD1512	Approved
0.8424	Intermediate Similarity	NPD1465	Phase 2
0.8354	Intermediate Similarity	NPD1549	Phase 2
0.8313	Intermediate Similarity	NPD7096	Clinical (unspecified phase)
0.8291	Intermediate Similarity	NPD1550	Clinical (unspecified phase)
0.8291	Intermediate Similarity	NPD1552	Clinical (unspecified phase)
0.8266	Intermediate Similarity	NPD5844	Phase 1
0.8263	Intermediate Similarity	NPD5402	Approved
0.8253	Intermediate Similarity	NPD6801	Discontinued
0.8232	Intermediate Similarity	NPD1653	Approved
0.8208	Intermediate Similarity	NPD7228	Approved
0.8204	Intermediate Similarity	NPD7819	Suspended
0.8193	Intermediate Similarity	NPD7411	Suspended
0.8187	Intermediate Similarity	NPD6232	Discontinued
0.8171	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.816	Intermediate Similarity	NPD4378	Clinical (unspecified phase)
0.8155	Intermediate Similarity	NPD8443	Clinical (unspecified phase)
0.815	Intermediate Similarity	NPD7473	Discontinued
0.8136	Intermediate Similarity	NPD8313	Approved
0.8136	Intermediate Similarity	NPD8312	Approved
0.8129	Intermediate Similarity	NPD6959	Discontinued
0.8125	Intermediate Similarity	NPD7685	Pre-registration
0.8122	Intermediate Similarity	NPD7879	Clinical (unspecified phase)
0.8113	Intermediate Similarity	NPD2796	Approved
0.8098	Intermediate Similarity	NPD6799	Approved
0.8061	Intermediate Similarity	NPD5403	Approved
0.805	Intermediate Similarity	NPD1510	Phase 2
0.8049	Intermediate Similarity	NPD7410	Clinical (unspecified phase)
0.8023	Intermediate Similarity	NPD7199	Phase 2
0.8012	Intermediate Similarity	NPD6234	Discontinued
0.8011	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD3751	Discontinued
0.795	Intermediate Similarity	NPD7266	Discontinued
0.7944	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7939	Intermediate Similarity	NPD5401	Approved
0.7929	Intermediate Similarity	NPD37	Approved
0.7917	Intermediate Similarity	NPD6599	Discontinued
0.7911	Intermediate Similarity	NPD1613	Approved
0.7911	Intermediate Similarity	NPD943	Approved
0.7911	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.7911	Intermediate Similarity	NPD1240	Approved
0.7895	Intermediate Similarity	NPD4966	Approved
0.7895	Intermediate Similarity	NPD4967	Phase 2
0.7895	Intermediate Similarity	NPD4965	Approved
0.7886	Intermediate Similarity	NPD7852	Clinical (unspecified phase)
0.7874	Intermediate Similarity	NPD3787	Discontinued
0.7865	Intermediate Similarity	NPD8151	Discontinued
0.7829	Intermediate Similarity	NPD3926	Phase 2
0.7829	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7819	Intermediate Similarity	NPD6780	Approved
0.7819	Intermediate Similarity	NPD6776	Approved
0.7819	Intermediate Similarity	NPD6779	Approved
0.7819	Intermediate Similarity	NPD6781	Approved
0.7819	Intermediate Similarity	NPD6777	Approved
0.7819	Intermediate Similarity	NPD6778	Approved
0.7819	Intermediate Similarity	NPD6782	Approved
0.7812	Intermediate Similarity	NPD1607	Approved
0.7805	Intermediate Similarity	NPD1878	Clinical (unspecified phase)
0.7771	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.776	Intermediate Similarity	NPD7584	Approved
0.775	Intermediate Similarity	NPD1933	Approved
0.775	Intermediate Similarity	NPD230	Phase 1
0.7746	Intermediate Similarity	NPD3749	Approved
0.7722	Intermediate Similarity	NPD7240	Approved
0.7722	Intermediate Similarity	NPD3027	Phase 3
0.7714	Intermediate Similarity	NPD1247	Approved
0.7701	Intermediate Similarity	NPD919	Approved
0.7697	Intermediate Similarity	NPD4628	Phase 3
0.7697	Intermediate Similarity	NPD3750	Approved
0.7696	Intermediate Similarity	NPD7698	Approved
0.7696	Intermediate Similarity	NPD7435	Discontinued
0.7696	Intermediate Similarity	NPD7697	Approved
0.7696	Intermediate Similarity	NPD7696	Phase 3
0.7688	Intermediate Similarity	NPD7768	Phase 2
0.7674	Intermediate Similarity	NPD8455	Phase 2
0.7658	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.7651	Intermediate Similarity	NPD6190	Approved
0.764	Intermediate Similarity	NPD447	Suspended
0.7629	Intermediate Similarity	NPD7701	Phase 2
0.7602	Intermediate Similarity	NPD7783	Phase 2
0.7602	Intermediate Similarity	NPD7782	Clinical (unspecified phase)
0.7595	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.7576	Intermediate Similarity	NPD970	Clinical (unspecified phase)
0.7565	Intermediate Similarity	NPD7870	Phase 2
0.7565	Intermediate Similarity	NPD7871	Phase 2
0.7561	Intermediate Similarity	NPD2935	Discontinued
0.7561	Intermediate Similarity	NPD1551	Phase 2
0.7553	Intermediate Similarity	NPD6534	Approved
0.7553	Intermediate Similarity	NPD6535	Approved
0.7552	Intermediate Similarity	NPD6823	Phase 2
0.7539	Intermediate Similarity	NPD7501	Clinical (unspecified phase)
0.753	Intermediate Similarity	NPD7421	Clinical (unspecified phase)
0.7526	Intermediate Similarity	NPD7699	Phase 2
0.7526	Intermediate Similarity	NPD7700	Phase 2
0.7515	Intermediate Similarity	NPD2532	Approved
0.7515	Intermediate Similarity	NPD2534	Approved
0.7515	Intermediate Similarity	NPD2533	Approved
0.7473	Intermediate Similarity	NPD5953	Discontinued
0.7462	Intermediate Similarity	NPD7874	Approved
0.7462	Intermediate Similarity	NPD7875	Clinical (unspecified phase)
0.7453	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7442	Intermediate Similarity	NPD3226	Approved
0.7427	Intermediate Similarity	NPD920	Approved
0.7425	Intermediate Similarity	NPD2800	Approved
0.7424	Intermediate Similarity	NPD7801	Approved
0.7396	Intermediate Similarity	NPD7237	Clinical (unspecified phase)
0.7394	Intermediate Similarity	NPD3748	Approved
0.7394	Intermediate Similarity	NPD651	Clinical (unspecified phase)
0.7385	Intermediate Similarity	NPD8320	Phase 1
0.7385	Intermediate Similarity	NPD8319	Approved
0.7382	Intermediate Similarity	NPD8090	Clinical (unspecified phase)
0.7375	Intermediate Similarity	NPD9494	Approved
0.7363	Intermediate Similarity	NPD7286	Phase 2
0.736	Intermediate Similarity	NPD7585	Approved
0.7341	Intermediate Similarity	NPD7458	Discontinued
0.7333	Intermediate Similarity	NPD7680	Approved
0.7326	Intermediate Similarity	NPD8150	Discontinued
0.7326	Intermediate Similarity	NPD8434	Phase 2
0.7321	Intermediate Similarity	NPD6674	Discontinued
0.7316	Intermediate Similarity	NPD6212	Phase 3
0.7316	Intermediate Similarity	NPD6213	Phase 3
0.7316	Intermediate Similarity	NPD6214	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.731	Intermediate Similarity	NPD7583	Approved
0.731	Intermediate Similarity	NPD642	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD2346	Discontinued
0.7305	Intermediate Similarity	NPD2344	Approved
0.7289	Intermediate Similarity	NPD2799	Discontinued
0.7246	Intermediate Similarity	NPD6099	Approved
0.7246	Intermediate Similarity	NPD6100	Approved
0.7239	Intermediate Similarity	NPD2313	Discontinued
0.7238	Intermediate Similarity	NPD5242	Approved
0.7233	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7232	Intermediate Similarity	NPD5353	Approved
0.7222	Intermediate Similarity	NPD6832	Phase 2
0.7222	Intermediate Similarity	NPD4908	Phase 1
0.7219	Intermediate Similarity	NPD1243	Approved
0.7216	Intermediate Similarity	NPD6844	Discontinued
0.7215	Intermediate Similarity	NPD1091	Approved
0.7215	Intermediate Similarity	NPD1547	Clinical (unspecified phase)
0.7205	Intermediate Similarity	NPD2798	Approved
0.7204	Intermediate Similarity	NPD4419	Clinical (unspecified phase)
0.7198	Intermediate Similarity	NPD5619	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD643	Clinical (unspecified phase)
0.7188	Intermediate Similarity	NPD4363	Phase 3
0.7188	Intermediate Similarity	NPD4360	Phase 2
0.7186	Intermediate Similarity	NPD1509	Clinical (unspecified phase)
0.7186	Intermediate Similarity	NPD7033	Discontinued
0.7176	Intermediate Similarity	NPD6398	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD6651	Approved
0.7151	Intermediate Similarity	NPD7390	Discontinued
0.7143	Intermediate Similarity	NPD5808	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD1203	Approved
0.7135	Intermediate Similarity	NPD2309	Approved
0.7134	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7127	Intermediate Similarity	NPD8127	Discontinued
0.711	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.7108	Intermediate Similarity	NPD1899	Clinical (unspecified phase)
0.7107	Intermediate Similarity	NPD5005	Approved
0.7107	Intermediate Similarity	NPD5006	Approved
0.7105	Intermediate Similarity	NPD6842	Approved
0.7105	Intermediate Similarity	NPD6841	Approved
0.7105	Intermediate Similarity	NPD6843	Phase 3
0.7101	Intermediate Similarity	NPD8155	Clinical (unspecified phase)
0.7088	Intermediate Similarity	NPD5710	Approved
0.7088	Intermediate Similarity	NPD5711	Approved
0.7063	Intermediate Similarity	NPD9269	Phase 2
0.7062	Intermediate Similarity	NPD7615	Clinical (unspecified phase)
0.7062	Intermediate Similarity	NPD6385	Approved
0.7062	Intermediate Similarity	NPD6386	Approved
0.7037	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.703	Intermediate Similarity	NPD6798	Discontinued
0.7018	Intermediate Similarity	NPD1652	Phase 2
0.7011	Intermediate Similarity	NPD7784	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD5123	Clinical (unspecified phase)

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