NPASS Compound

Structure

CID58137 OpenBabel06191715392D 22 26 0 0 1 0 0 0 0 0999 V2000 5.1176 0.9675 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 2.5183 1.4526 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6792 0.9684 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3569 -0.0008 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6788 -1.9379 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -1.6784 0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6785 -1.9386 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.0093 -0.9683 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 3.3571 0.9680 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.6789 -0.0003 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8392 -1.4536 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8392 -1.4540 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 2.5178 -0.4849 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.8390 -0.4843 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5177 -1.4533 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5175 -0.4839 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.8394 -0.4846 0.0000 C 0 0 2 0 0 0 0 0 0 0 0 0 4.2375 1.4760 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 2.5176 -1.4543 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4396 -1.7527 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -3.4393 -0.1842 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 18 1 0 0 0 0 2 3 2 0 0 0 0 2 9 1 0 0 0 0 3 10 1 0 0 0 0 4 9 2 0 0 0 0 4 13 1 0 0 0 0 5 11 2 0 0 0 0 5 15 1 0 0 0 0 6 14 2 0 0 0 0 6 16 1 0 0 0 0 7 19 1 0 0 0 0 8 20 1 0 0 0 0 8 21 1 0 0 0 0 9 18 1 0 0 0 0 10 13 2 0 0 0 0 11 12 1 0 0 0 0 11 14 1 0 0 0 0 12 7 1 6 0 0 0 12 17 1 0 0 0 0 13 19 1 0 0 0 0 14 22 1 0 0 0 0 15 16 2 0 0 0 0 15 20 1 0 0 0 0 16 21 1 0 0 0 0 17 10 1 6 0 0 0 17 22 1 0 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	298.08
Volume:	287.938
LogP:	3.683
LogD:	3.328
LogS:	-5.524
# Rotatable Bonds:	1
TPSA:	46.15
# H-Bond Aceptor:	5
# H-Bond Donor:	0
# Rings:	5
# Heavy Atoms:	5

MedChem Properties

QED Drug-Likeness Score:	0.81
Synthetic Accessibility Score:	3.245
Fsp3:	0.294
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Rejected
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	0
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-4.962
MDCK Permeability:	7.843222556402907e-05
Pgp-inhibitor:	0.369
Pgp-substrate:	0.001
Human Intestinal Absorption (HIA):	0.002
20% Bioavailability (F20%):	0.002
30% Bioavailability (F30%):	0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.114
Plasma Protein Binding (PPB):	94.010986328125%
Volume Distribution (VD):	1.057
Pgp-substrate:	3.578479528427124%

ADMET: Metabolism

CYP1A2-inhibitor:	0.938
CYP1A2-substrate:	0.887
CYP2C19-inhibitor:	0.977
CYP2C19-substrate:	0.813
CYP2C9-inhibitor:	0.892
CYP2C9-substrate:	0.911
CYP2D6-inhibitor:	0.942
CYP2D6-substrate:	0.933
CYP3A4-inhibitor:	0.959
CYP3A4-substrate:	0.58

ADMET: Excretion

Clearance (CL):	16.287
Half-life (T1/2):	0.119

ADMET: Toxicity

hERG Blockers:	0.131
Human Hepatotoxicity (H-HT):	0.371
Drug-inuced Liver Injury (DILI):	0.921
AMES Toxicity:	0.909
Rat Oral Acute Toxicity:	0.175
Maximum Recommended Daily Dose:	0.673
Skin Sensitization:	0.523
Carcinogencity:	0.87
Eye Corrosion:	0.004
Eye Irritation:	0.473
Respiratory Toxicity:	0.805

Download Data

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

Natural Product: NPC58137

Natural Product ID:	NPC58137
*Common Name:**	YLZYAUCOYZKLMA-SJKOYZFVSA-N
IUPAC Name:	n.a.
Synonyms:
Standard InCHIKey:	YLZYAUCOYZKLMA-SJKOYZFVSA-N
Standard InCHI:	InChI=1S/C17H14O5/c1-18-9-2-3-10-13(4-9)19-7-12-11-5-15-16(21-8-20-15)6-14(11)22-17(10)12/h2-6,12,17H,7-8H2,1H3/t12-,17-/m1/s1
SMILES:	COc1ccc2c(c1)OC[C@H]1[C@@H]2Oc2c1cc1c(c2)OCO1
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL1983713
PubChem CID:	373519
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0000261] Phenylpropanoids and polyketides [CHEMONTID:0002506] Isoflavonoids [CHEMONTID:0002617] Furanoisoflavonoids [CHEMONTID:0001608] Pterocarpans

*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	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	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]
NPO20598	Lythrum salicaria	Species	Lythraceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO18286	Lycogala epidendrum	Species	Enteridiidae	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]
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]
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]
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]
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]
NPO19231	Sophora flavescens	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
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]
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]
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]
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]
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]
NPO9968	Shigella dysenteriae	Species	Enterobacteriaceae	Bacteria	n.a.	n.a.	n.a.	Database[UNPD]
NPO19810	Myxococcus stipitatus	Species	Myxococcaceae	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]
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]
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]
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]
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]
NPO5903	Conus mus	Species	Conidae	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]
NPO3152	Morella rubra	Species	Myricaceae	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]
NPO20879	Clerodendrum bungei	Species	Lamiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19667	Hypericum styphelioides	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20142	Embelia schimperi	Species	Primulaceae	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]
NPO20421	Aplophyllum alberti-regelii	n.a.	n.a.	n.a.	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]
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]
NPO20489	Epilobium hirsutum	Species	Onagraceae	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]
NPO17849	Centaurea maculosa	Species	Asteraceae	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]
NPO13449	Syzygium polycephaloides	Species	Myrtaceae	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]
NPO14241	Planchonia grandis	Species	Asterolecaniidae	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]

☑ 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	53

Activity Type	# Activity
Cell Line	53

Target ID	Target Type	Target Name	Target Organism	Activity Type	Activity Relation	Value	Unit	Reference
NPT370	Cell Line	NCI-H23	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT369	Cell Line	ACHN	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT371	Cell Line	UO-31	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT116	Cell Line	HL-60	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT372	Cell Line	HOP-92	Homo sapiens	GI50	n.a.	69984.2	nM	PMID[528374]
NPT374	Cell Line	SF-539	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT375	Cell Line	Malme-3M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT373	Cell Line	SK-MEL-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT111	Cell Line	K562	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT377	Cell Line	OVCAR-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT376	Cell Line	A498	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT379	Cell Line	HOP-62	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT112	Cell Line	MOLT-4	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT380	Cell Line	U-251	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT381	Cell Line	OVCAR-8	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT382	Cell Line	OVCAR-5	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT572	Cell Line	DMS-273	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT383	Cell Line	SNB-19	Homo sapiens	GI50	n.a.	30408.85	nM	PMID[528374]
NPT384	Cell Line	TK-10	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT323	Cell Line	SW-620	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT455	Cell Line	NCI-H522	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT387	Cell Line	M14	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT574	Cell Line	XF498	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT386	Cell Line	KM12	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT388	Cell Line	NCI-H322M	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT389	Cell Line	RPMI-8226	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT456	Cell Line	OVCAR-4	Homo sapiens	GI50	n.a.	35727.28	nM	PMID[528374]
NPT390	Cell Line	LOX IMVI	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT147	Cell Line	SK-MEL-2	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT575	Cell Line	KM-20L2	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT81	Cell Line	A549	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT391	Cell Line	HCC 2998	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT392	Cell Line	SNB-75	Homo sapiens	GI50	n.a.	11587.77	nM	PMID[528374]
NPT148	Cell Line	HCT-15	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT395	Cell Line	SF-268	Homo sapiens	GI50	n.a.	74989.42	nM	PMID[528374]
NPT393	Cell Line	HCT-116	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT394	Cell Line	EKVX	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT731	Cell Line	LXFL 529	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT576	Cell Line	DMS-114	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT146	Cell Line	SK-OV-3	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT397	Cell Line	NCI-H460	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT308	Cell Line	CAKI-1	Homo sapiens	GI50	n.a.	58479.01	nM	PMID[528374]
NPT399	Cell Line	SF-295	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT578	Cell Line	SNB-78	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT401	Cell Line	786-0	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT579	Cell Line	DLD-1	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT404	Cell Line	CCRF-CEM	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT405	Cell Line	NCI-H226	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT139	Cell Line	HT-29	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT170	Cell Line	SK-MEL-28	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT406	Cell Line	RXF 393	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT407	Cell Line	COLO 205	Homo sapiens	GI50	n.a.	100000.0	nM	PMID[528374]
NPT732	Cell Line	HOP-18	Homo sapiens	GI50	n.a.	37153.52	nM	PMID[528374]

☑ 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 NPC58137 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	547
0.1-0.2	1769
0.2-0.3	4997
0.3-0.4	12244
0.4-0.5	5675
0.5-0.6	4845
0.6-0.7	7929
0.7-0.8	3556
0.8-0.85	846
0.85-0.9	246
0.9-0.95	32
0.95-1	11

Similarity Score	Similarity Level	Natural Product ID
1.0	High Similarity	NPC300798
0.9925	High Similarity	NPC80326
0.9778	High Similarity	NPC174522
0.9632	High Similarity	NPC472562
0.9565	High Similarity	NPC205316
0.9565	High Similarity	NPC474749
0.9565	High Similarity	NPC42716
0.9565	High Similarity	NPC178014
0.9565	High Similarity	NPC11422
0.95	High Similarity	NPC301961
0.95	High Similarity	NPC166584
0.9496	High Similarity	NPC162193
0.9403	High Similarity	NPC474478
0.9362	High Similarity	NPC71726
0.9357	High Similarity	NPC226540
0.9328	High Similarity	NPC266848
0.9328	High Similarity	NPC136750
0.9265	High Similarity	NPC78047
0.9254	High Similarity	NPC261812
0.9254	High Similarity	NPC72046
0.9254	High Similarity	NPC7744
0.9254	High Similarity	NPC65183
0.9231	High Similarity	NPC238140
0.9209	High Similarity	NPC311057
0.9191	High Similarity	NPC189474
0.9179	High Similarity	NPC192255
0.9161	High Similarity	NPC240521
0.9149	High Similarity	NPC180953
0.9149	High Similarity	NPC307466
0.9143	High Similarity	NPC474808
0.9137	High Similarity	NPC312199
0.913	High Similarity	NPC292487
0.9118	High Similarity	NPC31530
0.9118	High Similarity	NPC170779
0.9118	High Similarity	NPC90083
0.911	High Similarity	NPC159922
0.9065	High Similarity	NPC27495
0.9065	High Similarity	NPC103448
0.9065	High Similarity	NPC216434
0.9051	High Similarity	NPC49235
0.9051	High Similarity	NPC148893
0.9051	High Similarity	NPC25333
0.8993	High Similarity	NPC9068
0.8986	High Similarity	NPC121651
0.8963	High Similarity	NPC237169
0.8963	High Similarity	NPC470624
0.8958	High Similarity	NPC270751
0.8955	High Similarity	NPC165128
0.8955	High Similarity	NPC57119
0.8955	High Similarity	NPC31707
0.8955	High Similarity	NPC82862
0.8955	High Similarity	NPC222127
0.8955	High Similarity	NPC226862
0.8955	High Similarity	NPC158471
0.8936	High Similarity	NPC474295
0.8936	High Similarity	NPC107161
0.8929	High Similarity	NPC226547
0.8921	High Similarity	NPC196420
0.8921	High Similarity	NPC185908
0.8913	High Similarity	NPC474139
0.8897	High Similarity	NPC51328
0.8897	High Similarity	NPC82111
0.8897	High Similarity	NPC55158
0.8897	High Similarity	NPC286235
0.8897	High Similarity	NPC227160
0.8881	High Similarity	NPC8050
0.8881	High Similarity	NPC473092
0.8881	High Similarity	NPC473093
0.8873	High Similarity	NPC81638
0.8865	High Similarity	NPC247291
0.8857	High Similarity	NPC236306
0.8857	High Similarity	NPC471388
0.8857	High Similarity	NPC113550
0.8857	High Similarity	NPC473739
0.8857	High Similarity	NPC232164
0.8849	High Similarity	NPC197166
0.8849	High Similarity	NPC11453
0.8849	High Similarity	NPC32189
0.8849	High Similarity	NPC173660
0.8828	High Similarity	NPC248132
0.8828	High Similarity	NPC175976
0.8828	High Similarity	NPC130449
0.8824	High Similarity	NPC271208
0.8824	High Similarity	NPC233224
0.8819	High Similarity	NPC33832
0.8815	High Similarity	NPC54321
0.8815	High Similarity	NPC328682
0.8815	High Similarity	NPC281864
0.8811	High Similarity	NPC12641
0.8811	High Similarity	NPC93323
0.8811	High Similarity	NPC45257
0.8811	High Similarity	NPC280092
0.8806	High Similarity	NPC50683
0.8806	High Similarity	NPC285725
0.8806	High Similarity	NPC112571
0.8803	High Similarity	NPC246947
0.8797	High Similarity	NPC191768
0.8797	High Similarity	NPC283170
0.8797	High Similarity	NPC92869
0.8794	High Similarity	NPC46591
0.8794	High Similarity	NPC160283
0.8794	High Similarity	NPC254759
0.8794	High Similarity	NPC309124
0.8794	High Similarity	NPC184797
0.8794	High Similarity	NPC177868
0.8794	High Similarity	NPC284464
0.8786	High Similarity	NPC283949
0.8777	High Similarity	NPC150534
0.8777	High Similarity	NPC195022
0.8776	High Similarity	NPC474975
0.8768	High Similarity	NPC196937
0.8768	High Similarity	NPC58585
0.8768	High Similarity	NPC1474
0.8767	High Similarity	NPC35877
0.8767	High Similarity	NPC55715
0.8767	High Similarity	NPC95392
0.8759	High Similarity	NPC227902
0.8759	High Similarity	NPC116019
0.8759	High Similarity	NPC39657
0.8759	High Similarity	NPC469698
0.8759	High Similarity	NPC473412
0.8741	High Similarity	NPC298317
0.8741	High Similarity	NPC47633
0.8741	High Similarity	NPC85264
0.8741	High Similarity	NPC255566
0.8741	High Similarity	NPC102044
0.8732	High Similarity	NPC471389
0.8723	High Similarity	NPC6369
0.8723	High Similarity	NPC25966
0.8723	High Similarity	NPC292882
0.8723	High Similarity	NPC245207
0.8723	High Similarity	NPC30951
0.8723	High Similarity	NPC127218
0.8723	High Similarity	NPC319647
0.8716	High Similarity	NPC302610
0.8714	High Similarity	NPC143895
0.8714	High Similarity	NPC25695
0.8714	High Similarity	NPC172818
0.8707	High Similarity	NPC472710
0.8707	High Similarity	NPC472709
0.8705	High Similarity	NPC145722
0.8705	High Similarity	NPC185680
0.8705	High Similarity	NPC256776
0.8696	High Similarity	NPC129687
0.8696	High Similarity	NPC171928
0.8696	High Similarity	NPC33611
0.8696	High Similarity	NPC16830
0.8696	High Similarity	NPC158526
0.8696	High Similarity	NPC100223
0.869	High Similarity	NPC190714
0.869	High Similarity	NPC99515
0.8681	High Similarity	NPC239254
0.8681	High Similarity	NPC471667
0.8681	High Similarity	NPC172171
0.8681	High Similarity	NPC217635
0.8681	High Similarity	NPC79429
0.8681	High Similarity	NPC63879
0.8671	High Similarity	NPC287124
0.8667	High Similarity	NPC186845
0.8667	High Similarity	NPC164152
0.8667	High Similarity	NPC88297
0.8667	High Similarity	NPC9891
0.8662	High Similarity	NPC56091
0.8657	High Similarity	NPC34902
0.8657	High Similarity	NPC256015
0.8657	High Similarity	NPC18449
0.8657	High Similarity	NPC294156
0.8657	High Similarity	NPC121783
0.8652	High Similarity	NPC103976
0.8652	High Similarity	NPC102904
0.8652	High Similarity	NPC326797
0.8652	High Similarity	NPC276490
0.8652	High Similarity	NPC176051
0.8652	High Similarity	NPC477938
0.8652	High Similarity	NPC107551
0.8652	High Similarity	NPC474282
0.8647	High Similarity	NPC211231
0.8643	High Similarity	NPC224941
0.8643	High Similarity	NPC311430
0.8633	High Similarity	NPC263064
0.863	High Similarity	NPC21776
0.863	High Similarity	NPC16269
0.8621	High Similarity	NPC22150
0.8621	High Similarity	NPC476301
0.8621	High Similarity	NPC475868
0.8621	High Similarity	NPC43508
0.8621	High Similarity	NPC38041
0.8621	High Similarity	NPC279298
0.8621	High Similarity	NPC475096
0.8611	High Similarity	NPC76415
0.8611	High Similarity	NPC12728
0.8611	High Similarity	NPC218510
0.8611	High Similarity	NPC252169
0.8611	High Similarity	NPC477616
0.8611	High Similarity	NPC185071
0.8609	High Similarity	NPC189730
0.8603	High Similarity	NPC98745
0.8601	High Similarity	NPC108674
0.8601	High Similarity	NPC311530
0.8592	High Similarity	NPC156376

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 NPC58137 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	435
0.1-0.2	915
0.2-0.3	1991
0.3-0.4	2715
0.4-0.5	1606
0.5-0.6	872
0.6-0.7	536
0.7-0.8	73
0.8-0.85	7
0.85-0.9	0
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8298	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8298	Intermediate Similarity	NPD1613	Approved
0.8162	Intermediate Similarity	NPD3705	Approved
0.8143	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8129	Intermediate Similarity	NPD4965	Approved
0.8129	Intermediate Similarity	NPD4966	Approved
0.8129	Intermediate Similarity	NPD4967	Phase 2
0.8071	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8038	Intermediate Similarity	NPD7199	Phase 2
0.8025	Intermediate Similarity	NPD6234	Discontinued
0.7975	Intermediate Similarity	NPD5494	Approved
0.7958	Intermediate Similarity	NPD3027	Phase 3
0.7943	Intermediate Similarity	NPD2861	Phase 2
0.7937	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7935	Intermediate Similarity	NPD37	Approved
0.7908	Intermediate Similarity	NPD1653	Approved
0.7899	Intermediate Similarity	NPD1610	Phase 2
0.7887	Intermediate Similarity	NPD4908	Phase 1
0.7852	Intermediate Similarity	NPD6674	Discontinued
0.7791	Intermediate Similarity	NPD7228	Approved
0.7778	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7761	Intermediate Similarity	NPD5283	Phase 1
0.7707	Intermediate Similarity	NPD3384	Approved
0.7707	Intermediate Similarity	NPD3383	Approved
0.7707	Intermediate Similarity	NPD3382	Approved
0.7692	Intermediate Similarity	NPD3018	Phase 2
0.7662	Intermediate Similarity	NPD1940	Clinical (unspecified phase)
0.7613	Intermediate Similarity	NPD6980	Clinical (unspecified phase)
0.7605	Intermediate Similarity	NPD7240	Approved
0.7595	Intermediate Similarity	NPD1934	Approved
0.7589	Intermediate Similarity	NPD2981	Phase 2
0.7576	Intermediate Similarity	NPD3818	Discontinued
0.7535	Intermediate Similarity	NPD2982	Phase 2
0.7535	Intermediate Similarity	NPD2983	Phase 2
0.7518	Intermediate Similarity	NPD1091	Approved
0.7485	Intermediate Similarity	NPD7074	Phase 3
0.7482	Intermediate Similarity	NPD1548	Phase 1
0.7425	Intermediate Similarity	NPD7054	Approved
0.7425	Intermediate Similarity	NPD5844	Phase 1
0.7419	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7413	Intermediate Similarity	NPD4749	Approved
0.7405	Intermediate Similarity	NPD6055	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7403	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7381	Intermediate Similarity	NPD7472	Approved
0.7355	Intermediate Similarity	NPD5058	Phase 3
0.7353	Intermediate Similarity	NPD4338	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7351	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7347	Intermediate Similarity	NPD4625	Phase 3
0.7338	Intermediate Similarity	NPD7466	Approved
0.7329	Intermediate Similarity	NPD2801	Approved
0.7329	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7305	Intermediate Similarity	NPD1357	Approved
0.7303	Intermediate Similarity	NPD3454	Phase 3
0.7301	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.7297	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7284	Intermediate Similarity	NPD3817	Phase 2
0.7273	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.7255	Intermediate Similarity	NPD1375	Discontinued
0.7251	Intermediate Similarity	NPD7549	Discontinued
0.7251	Intermediate Similarity	NPD7808	Phase 3
0.7239	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7235	Intermediate Similarity	NPD6797	Phase 2
0.7195	Intermediate Similarity	NPD4381	Clinical (unspecified phase)
0.7193	Intermediate Similarity	NPD6559	Discontinued
0.7193	Intermediate Similarity	NPD7251	Discontinued
0.719	Intermediate Similarity	NPD3539	Phase 1
0.7181	Intermediate Similarity	NPD6859	Clinical (unspecified phase)
0.7178	Intermediate Similarity	NPD6374	Clinical (unspecified phase)
0.7169	Intermediate Similarity	NPD1247	Approved
0.7152	Intermediate Similarity	NPD1933	Approved
0.7143	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD6166	Phase 2
0.7143	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD7266	Discontinued
0.7143	Intermediate Similarity	NPD3540	Phase 1
0.7134	Intermediate Similarity	NPD7124	Phase 2
0.7134	Intermediate Similarity	NPD3882	Suspended
0.7134	Intermediate Similarity	NPD6783	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7126	Intermediate Similarity	NPD3787	Discontinued
0.7107	Intermediate Similarity	NPD7314	Clinical (unspecified phase)
0.7086	Intermediate Similarity	NPD4060	Phase 1
0.7078	Intermediate Similarity	NPD2796	Approved
0.7069	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7055	Intermediate Similarity	NPD5327	Phase 3
0.7051	Intermediate Similarity	NPD1652	Phase 2
0.7048	Intermediate Similarity	NPD919	Approved
0.7039	Intermediate Similarity	NPD6355	Discontinued
0.7039	Intermediate Similarity	NPD5123	Clinical (unspecified phase)
0.7039	Intermediate Similarity	NPD5124	Phase 1
0.7034	Intermediate Similarity	NPD1611	Approved
0.7021	Intermediate Similarity	NPD6671	Approved
0.7019	Intermediate Similarity	NPD4210	Discontinued
0.7013	Intermediate Similarity	NPD5588	Approved
0.7013	Intermediate Similarity	NPD3748	Approved
0.7013	Intermediate Similarity	NPD4108	Discontinued
0.7012	Intermediate Similarity	NPD8455	Phase 2
0.7007	Intermediate Similarity	NPD8651	Approved
0.7006	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7006	Intermediate Similarity	NPD6331	Phase 2
0.7006	Intermediate Similarity	NPD3892	Phase 2
0.7006	Intermediate Similarity	NPD4110	Phase 3
0.6982	Remote Similarity	NPD3926	Phase 2
0.6981	Remote Similarity	NPD1511	Approved
0.6978	Remote Similarity	NPD7237	Clinical (unspecified phase)
0.6959	Remote Similarity	NPD3751	Discontinued
0.6957	Remote Similarity	NPD5006	Approved
0.6957	Remote Similarity	NPD5005	Approved
0.6948	Remote Similarity	NPD4537	Clinical (unspecified phase)
0.6948	Remote Similarity	NPD7097	Phase 1
0.6948	Remote Similarity	NPD6111	Discontinued
0.6948	Remote Similarity	NPD4538	Approved
0.6948	Remote Similarity	NPD4536	Approved
0.6943	Remote Similarity	NPD5177	Phase 3
0.6941	Remote Similarity	NPD4481	Phase 3
0.6937	Remote Similarity	NPD7004	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4675	Approved
0.6933	Remote Similarity	NPD5752	Clinical (unspecified phase)
0.6933	Remote Similarity	NPD4678	Approved
0.6929	Remote Similarity	NPD5535	Approved
0.6928	Remote Similarity	NPD3657	Discovery
0.6928	Remote Similarity	NPD5735	Approved
0.6923	Remote Similarity	NPD1550	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD7229	Phase 3
0.6923	Remote Similarity	NPD1552	Clinical (unspecified phase)
0.6923	Remote Similarity	NPD5762	Approved
0.6923	Remote Similarity	NPD5536	Phase 2
0.6923	Remote Similarity	NPD5763	Approved
0.6919	Remote Similarity	NPD7804	Clinical (unspecified phase)
0.6919	Remote Similarity	NPD7680	Approved
0.6919	Remote Similarity	NPD8156	Discontinued
0.6918	Remote Similarity	NPD422	Phase 1
0.6913	Remote Similarity	NPD6917	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD1465	Phase 2
0.6909	Remote Similarity	NPD7096	Clinical (unspecified phase)
0.6909	Remote Similarity	NPD7819	Suspended
0.6908	Remote Similarity	NPD6233	Phase 2
0.6905	Remote Similarity	NPD5677	Discontinued
0.6901	Remote Similarity	NPD7157	Approved
0.6899	Remote Similarity	NPD6658	Clinical (unspecified phase)
0.6897	Remote Similarity	NPD5125	Phase 3
0.6897	Remote Similarity	NPD5126	Approved
0.6897	Remote Similarity	NPD17	Approved
0.6894	Remote Similarity	NPD1512	Approved
0.689	Remote Similarity	NPD7615	Clinical (unspecified phase)
0.6884	Remote Similarity	NPD2684	Approved
0.6879	Remote Similarity	NPD1549	Phase 2
0.6875	Remote Similarity	NPD7213	Phase 3
0.6875	Remote Similarity	NPD7212	Phase 2
0.6871	Remote Similarity	NPD4005	Discontinued
0.6867	Remote Similarity	NPD5402	Approved
0.6863	Remote Similarity	NPD3620	Phase 2
0.6863	Remote Similarity	NPD3619	Clinical (unspecified phase)
0.686	Remote Similarity	NPD8251	Approved
0.686	Remote Similarity	NPD8099	Discontinued
0.686	Remote Similarity	NPD8252	Approved
0.6859	Remote Similarity	NPD6100	Approved
0.6859	Remote Similarity	NPD2161	Phase 2
0.6859	Remote Similarity	NPD6099	Approved
0.6857	Remote Similarity	NPD228	Approved
0.6854	Remote Similarity	NPD6843	Phase 3
0.6854	Remote Similarity	NPD6841	Approved
0.6854	Remote Similarity	NPD6842	Approved
0.6852	Remote Similarity	NPD5976	Discontinued
0.6849	Remote Similarity	NPD3496	Discontinued
0.6842	Remote Similarity	NPD5110	Phase 2
0.6842	Remote Similarity	NPD6798	Discontinued
0.6842	Remote Similarity	NPD5109	Approved
0.6842	Remote Similarity	NPD5111	Phase 2
0.6839	Remote Similarity	NPD7119	Phase 2
0.6839	Remote Similarity	NPD2200	Suspended
0.6835	Remote Similarity	NPD4236	Phase 3
0.6835	Remote Similarity	NPD4237	Approved
0.6832	Remote Similarity	NPD7447	Phase 1
0.6831	Remote Similarity	NPD4420	Approved
0.6829	Remote Similarity	NPD7028	Phase 2
0.6828	Remote Similarity	NPD5585	Approved
0.6824	Remote Similarity	NPD3051	Approved
0.6824	Remote Similarity	NPD6232	Discontinued
0.6812	Remote Similarity	NPD290	Approved
0.6809	Remote Similarity	NPD7843	Approved
0.6807	Remote Similarity	NPD2977	Approved
0.6807	Remote Similarity	NPD2978	Approved
0.6802	Remote Similarity	NPD7473	Discontinued
0.6797	Remote Similarity	NPD1726	Clinical (unspecified phase)
0.6795	Remote Similarity	NPD5960	Phase 3
0.6792	Remote Similarity	NPD6398	Clinical (unspecified phase)
0.6792	Remote Similarity	NPD3750	Approved
0.6786	Remote Similarity	NPD7075	Discontinued
0.6784	Remote Similarity	NPD2970	Approved
0.6784	Remote Similarity	NPD2969	Approved
0.6779	Remote Similarity	NPD6696	Suspended
0.6776	Remote Similarity	NPD7095	Approved
0.6772	Remote Similarity	NPD1372	Clinical (unspecified phase)
0.677	Remote Similarity	NPD6799	Approved
0.6768	Remote Similarity	NPD7261	Clinical (unspecified phase)
0.6768	Remote Similarity	NPD8158	Clinical (unspecified phase)
0.6766	Remote Similarity	NPD2563	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