NPASS Compound

Structure

CID311256 OpenBabel06191716122D 27 29 0 0 1 0 0 0 0 0999 V2000 -6.0622 2.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 1.7321 0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -4.3301 1.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -0.0000 1.0000 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 -0.8660 2.5000 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 -1.2321 3.8660 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -3.4641 1.0000 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 -1.7321 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 2.5000 0.0000 C 0 0 2 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 -0.8660 -0.5000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -5.1962 1.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 0.0000 -0.0000 0.0000 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.5981 1.5000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -1.7321 3.0000 0.0000 C 0 0 1 0 0 0 0 0 0 0 0 0 -3.4641 4.0000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.2321 3.8660 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 -6.0622 -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 -2.2321 3.8660 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 0.8660 -0.5000 0.0000 O 0 0 0 0 0 0 0 0 0 0 0 0 1 26 1 0 0 0 0 2 27 1 0 0 0 0 3 4 2 0 0 0 0 3 11 1 0 0 0 0 4 15 1 0 0 0 0 5 11 2 0 0 0 0 5 17 1 0 0 0 0 6 12 2 0 0 0 0 6 18 1 0 0 0 0 7 13 2 0 0 0 0 7 16 1 0 0 0 0 8 12 1 0 0 0 0 8 20 1 0 0 0 0 9 14 1 0 0 0 0 9 21 1 0 0 0 0 10 20 1 0 0 0 0 10 22 1 0 0 0 0 12 13 1 0 0 0 0 13 19 1 0 0 0 0 14 19 1 0 0 0 0 14 20 1 1 0 0 0 15 17 2 0 0 0 0 15 23 1 0 0 0 0 16 18 2 0 0 0 0 16 24 1 0 0 0 0 17 26 1 0 0 0 0 18 27 1 0 0 0 0 19 11 1 6 0 0 0 20 25 1 1 0 0 0 M END $$$$

Physi-Chem Properties

Molecular Weight:	376.15
Volume:	374.52
LogP:	0.961
LogD:	1.369
LogS:	-2.183
# Rotatable Bonds:	5
TPSA:	119.61
# H-Bond Aceptor:	7
# H-Bond Donor:	5
# Rings:	3
# Heavy Atoms:	7

MedChem Properties

QED Drug-Likeness Score:	0.531
Synthetic Accessibility Score:	3.787
Fsp3:	0.4
Lipinski Rule-of-5:	Accepted
Pfizer Rule:	Accepted
GSK Rule:	Accepted
BMS Rule:	0
Golden Triangle Rule:	Accepted
Chelating Alert:	1
PAINS Alert:	0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:	-5.37
MDCK Permeability:	4.118064680369571e-05
Pgp-inhibitor:	0.003
Pgp-substrate:	0.993
Human Intestinal Absorption (HIA):	0.119
20% Bioavailability (F20%):	0.343
30% Bioavailability (F30%):	0.118

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):	0.237
Plasma Protein Binding (PPB):	93.89234924316406%
Volume Distribution (VD):	0.963
Pgp-substrate:	8.68431568145752%

ADMET: Metabolism

CYP1A2-inhibitor:	0.038
CYP1A2-substrate:	0.796
CYP2C19-inhibitor:	0.018
CYP2C19-substrate:	0.504
CYP2C9-inhibitor:	0.031
CYP2C9-substrate:	0.669
CYP2D6-inhibitor:	0.05
CYP2D6-substrate:	0.619
CYP3A4-inhibitor:	0.333
CYP3A4-substrate:	0.726

ADMET: Excretion

Clearance (CL):	13.762
Half-life (T1/2):	0.727

ADMET: Toxicity

hERG Blockers:	0.046
Human Hepatotoxicity (H-HT):	0.413
Drug-inuced Liver Injury (DILI):	0.21
AMES Toxicity:	0.108
Rat Oral Acute Toxicity:	0.103
Maximum Recommended Daily Dose:	0.264
Skin Sensitization:	0.352
Carcinogencity:	0.043
Eye Corrosion:	0.003
Eye Irritation:	0.073
Respiratory Toxicity:	0.294

Download Data

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

Natural Product: NPC311256

Natural Product ID:	NPC311256
*Common Name:**	(+)-Cycloolivil
IUPAC Name:	(2S,3S,4S)-4-(4-hydroxy-3-methoxyphenyl)-2,3-bis(hydroxymethyl)-7-methoxy-3,4-dihydro-1H-naphthalene-2,6-diol
Synonyms:	(+)-Cycloolivil
Standard InCHIKey:	KCIQZCNOUZCRGH-VOBQZIQPSA-N
Standard InCHI:	InChI=1S/C20H24O7/c1-26-17-5-11(3-4-15(17)23)19-13-7-16(24)18(27-2)6-12(13)8-20(25,10-22)14(19)9-21/h3-7,14,19,21-25H,8-10H2,1-2H3/t14-,19+,20-/m1/s1
SMILES:	COc1cc(ccc1O)[C@H]1c2cc(c(cc2C[C@@](CO)([C@@H]1CO)O)OC)O
Synthetic Gene Cluster:	n.a.
ChEMBL Identifier:	CHEMBL516536
PubChem CID:	5316262
Chemical Classification:**	CHEMONTID:0000000 [Organic compounds] [CHEMONTID:0001392] Lignans, neolignans and related compounds [CHEMONTID:0003425] Aryltetralin lignans [CHEMONTID:0003426] 9,9p-dihydroxyaryltetralin lignans

*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
NPO19975	Pycnandra acuminata	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	DOI[10.1016/j.phytochem.2007.07.001]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12081149]
NPO5140	Dipteryx odorata	Species	Fabaceae	Eukaryota	seeds	n.a.	n.a.	PMID[12762787]
NPO5140	Dipteryx odorata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[12762809]
NPO9587	Saussurea laniceps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[15921425]
NPO6412	Echinacea pallida	Species	Asteraceae	Eukaryota	root	n.a.	n.a.	PMID[15921428]
NPO10745	Stereospermum personatum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[16309309]
NPO19434	Securinega suffruticosa	Species	Phyllanthaceae	Eukaryota	n.a.	callus	n.a.	PMID[16327202]
NPO17434	Sambucus williamsii	Species	Adoxaceae	Eukaryota	n.a.	stem	n.a.	PMID[16651764]
NPO1743	Neurospora terricola	Species	Sordariaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[19795843]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	root	n.a.	PMID[22051934]
NPO1689	Epimedium pubescens	Species	Berberidaceae	Eukaryota	n.a.	leaf	n.a.	PMID[24066589]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	aerial parts	herbal garden of Chungbuk National University, Cheongju, Korea	2012-Oct	PMID[24963714]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26767291]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	bark	n.a.	PMID[26767291]
NPO17434	Sambucus williamsii	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	PMID[26988298]
NPO12498	Carpesium cernuum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	PMID[27668963]
NPO19434	Securinega suffruticosa	Species	Phyllanthaceae	Eukaryota	Twigs	n.a.	n.a.	PMID[31082231]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	leaf	n.a.	PMID[8699184]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	aerial part	n.a.	Database[Article]
NPO20569	Psychotria serpens	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19403	Epimedium grandiflorum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO17434	Sambucus williamsii	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO1689	Epimedium pubescens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO633	Mesembryanthemum expansum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO19434	Securinega suffruticosa	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11886	Hemerocallis citrina	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO5140	Dipteryx odorata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[HerDing]
NPO11886	Hemerocallis citrina	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO6856.1	Artemisia ludoviciana subsp. mexicana	Subspecies	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9587	Saussurea laniceps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO4957	Epimedium brevicornu	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19434	Securinega suffruticosa	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO633	Mesembryanthemum expansum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1689	Epimedium pubescens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO19403	Epimedium grandiflorum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO5140	Dipteryx odorata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO10745	Stereospermum personatum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO20569	Psychotria serpens	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO17434	Sambucus williamsii	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCMID]
NPO1689	Epimedium pubescens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO19434	Securinega suffruticosa	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO20569	Psychotria serpens	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TCM_Taiwan]
NPO4957	Epimedium brevicornu	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16314.1	Clematis terniflora var. mandshurica	Varieties	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO13384	Epimedium sempervirens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO19403	Epimedium grandiflorum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO1689	Epimedium pubescens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17434	Sambucus williamsii	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[TM-MC]
NPO17434	Sambucus williamsii	Species	Adoxaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6514	Desmotrichum fimbriatum	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO10298	Symbiodinium microadriaticum	Species	Symbiodiniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12828	Dysidea tupha	Species	Dysideidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5534	Alternaria kikuchiana	Species	Pleosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO14870	Cytisus austriacus	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4759	Helleborus multifidus	Species	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16314.1	Clematis terniflora var. mandshurica	Varieties	Ranunculaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13458	Acarospora montana	Species	Acarosporaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18598	Languas galanga	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO6856.1	Artemisia ludoviciana subsp. mexicana	Subspecies	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8525	Pinus torreyana	Species	Pinaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19975	Pycnandra acuminata	Species	Sapotaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19403	Epimedium grandiflorum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12736	Galleria mellonella	Species	Pyralidae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10970	Osmorhiza aristata	Species	Apiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9587	Saussurea laniceps	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1695	Monascus pilosus	Species	Aspergillaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO143.1	Tephrosia purpurea subsp. apollinea	Subspecies	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10825	Nerine sarniensis	Species	Amaryllidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6861	Galium dasypodum	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8129	Inocybe geophylla	Species	Inocybaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO35	Zanthoxylum dinklagei	Species	Rutaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO8609	Hopea utilis	Species	Dipterocarpaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9141	Epimedium wushanense	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO5140	Dipteryx odorata	Species	Fabaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO218	Acer carpinifolium	Species	Sapindaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1743	Neurospora terricola	Species	Sordariaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9871.1	Ficus benghalensis var. krishnae	Varieties	Moraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11506	Stipa vaseyi	Species	Poaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10745	Stereospermum personatum	Species	Bignoniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO7874	Helichrysum lepidissimum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6412	Echinacea pallida	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4322	Scabiosa succisa	Species	Caprifoliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12118	Cleistopholis staudtii	Species	Annonaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1619	Lactuca triangulata	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO633	Mesembryanthemum expansum	Species	Aizoaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO3455	Picramnia lindeniana	Species	Picramniaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO19434	Securinega suffruticosa	Species	Phyllanthaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO9577	Triclisia dictyophylla	Species	Menispermaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO26095	Hypericum revolutum	Species	Hypericaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO13384	Epimedium sempervirens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO18302	Chondrostereum purpureum	Species	Schizophyllaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11339	Litsea salicifolia	Species	Lauraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO16850	Eucommia ulmoides	Species	Eucommiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10969	Epimedium sagittatum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO20569	Psychotria serpens	Species	Rubiaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO4957	Epimedium brevicornu	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12498	Carpesium cernuum	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO12602	Leuzea centauroides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO11886	Hemerocallis citrina	Species	Asphodelaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO1689	Epimedium pubescens	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO6012	Dumoria heckelii	n.a.	n.a.	n.a.	n.a.	n.a.	n.a.	Database[UNPD]
NPO23024	Epimedium koreanum	Species	Berberidaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO940	Vernonia anisochaetoides	Species	Asteraceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]
NPO10010	Evernia vulpina	Species	Parmeliaceae	Eukaryota	n.a.	n.a.	n.a.	Database[UNPD]

☑ Note for Reference:
In addition to directly collecting NP source organism data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated them from below databases:
☉ UNPD: Universal Natural Products Database [PMID: 23638153].
☉ StreptomeDB: a database of streptomycetes natural products [PMID: 33051671].
☉ TM-MC: a database of medicinal materials and chemical compounds in Northeast Asian traditional medicine [PMID: 26156871].
☉ TCM@Taiwan: a Traditional Chinese Medicine database [PMID: 21253603].
☉ TCMID: a Traditional Chinese Medicine database [PMID: 29106634].
☉ TCMSP: The traditional Chinese medicine systems pharmacology database and analysis platform [PMID: 24735618].
☉ HerDing: a herb recommendation system to treat diseases using genes and chemicals [PMID: 26980517].
☉ MetaboLights: a metabolomics database [PMID: 27010336].
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

NP Quantity Composition/Concentration

Organism ID	NP ID	Organism Material Preparation	Organism Part	NP Quantity (Standard)	NP Quantity (Minimum)	NP Quantity (Maximum)	Quantity Unit	Reference

☑ Note for Reference:
In addition to directly collecting NP quantitative data from primary literature (where reference will provided as NCBI PMID or DOI links), NPASS also integrated NP quantitative records for specific NP domains (e.g., NPS from foods or herbs) from domain-specific databases. These databases include:
☉ DUKE: Dr. Duke's Phytochemical and Ethnobotanical Databases.
☉ PHENOL EXPLORER: is the first comprehensive database on polyphenol content in foods [PMID: 24103452], its homepage can be accessed at here.
☉ FooDB: a database of constituents, chemistry and biology of food species [www.foodb.ca].

Biological Activity

Activity Type	# Activity
IC50	1
Others	1

Activity Type	# Activity
Individual Protein	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.	SC50	=	17.38	uM	PMID[558385]
NPT967	Individual Protein	Xanthine dehydrogenase	Homo sapiens	IC50	=	101380.0	nM	PMID[558385]

☑ 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 NPC311256 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	408
0.1-0.2	1438
0.2-0.3	3637
0.3-0.4	9691
0.4-0.5	9076
0.5-0.6	4010
0.6-0.7	8631
0.7-0.8	4444
0.8-0.85	792
0.85-0.9	505
0.9-0.95	60
0.95-1	5

Similarity Score	Similarity Level	Natural Product ID
0.9545	High Similarity	NPC184613
0.9528	High Similarity	NPC307050
0.9528	High Similarity	NPC277458
0.9449	High Similarity	NPC5428
0.9398	High Similarity	NPC230124
0.9398	High Similarity	NPC114171
0.9398	High Similarity	NPC6300
0.9389	High Similarity	NPC471942
0.9318	High Similarity	NPC313081
0.9297	High Similarity	NPC165045
0.9297	High Similarity	NPC118533
0.9291	High Similarity	NPC228771
0.9291	High Similarity	NPC266705
0.9291	High Similarity	NPC29008
0.9248	High Similarity	NPC202846
0.9248	High Similarity	NPC143139
0.9237	High Similarity	NPC14224
0.9237	High Similarity	NPC161958
0.9173	High Similarity	NPC158142
0.9173	High Similarity	NPC294884
0.9173	High Similarity	NPC10314
0.9173	High Similarity	NPC200557
0.9173	High Similarity	NPC69029
0.9173	High Similarity	NPC108198
0.916	High Similarity	NPC277804
0.9141	High Similarity	NPC148627
0.9141	High Similarity	NPC9067
0.9134	High Similarity	NPC280704
0.9111	High Similarity	NPC212942
0.9111	High Similarity	NPC29868
0.9111	High Similarity	NPC79622
0.9104	High Similarity	NPC68292
0.9098	High Similarity	NPC160697
0.9098	High Similarity	NPC209199
0.9098	High Similarity	NPC125649
0.9091	High Similarity	NPC228843
0.9084	High Similarity	NPC64201
0.9084	High Similarity	NPC187998
0.9084	High Similarity	NPC77040
0.9084	High Similarity	NPC242807
0.9084	High Similarity	NPC174495
0.9084	High Similarity	NPC153739
0.9084	High Similarity	NPC143483
0.9084	High Similarity	NPC42300
0.9084	High Similarity	NPC145305
0.9084	High Similarity	NPC92164
0.9084	High Similarity	NPC241522
0.9084	High Similarity	NPC257582
0.9077	High Similarity	NPC252307
0.9077	High Similarity	NPC245826
0.9077	High Similarity	NPC472968
0.9077	High Similarity	NPC474178
0.9055	High Similarity	NPC85488
0.9044	High Similarity	NPC308768
0.9044	High Similarity	NPC12668
0.9037	High Similarity	NPC56329
0.9037	High Similarity	NPC242715
0.903	High Similarity	NPC241241
0.9015	High Similarity	NPC474017
0.9008	High Similarity	NPC475875
0.9007	High Similarity	NPC44452
0.9	High Similarity	NPC21563
0.9	High Similarity	NPC106511
0.8993	High Similarity	NPC286245
0.8993	High Similarity	NPC272619
0.8984	High Similarity	NPC471693
0.8971	High Similarity	NPC218131
0.8971	High Similarity	NPC132804
0.8971	High Similarity	NPC105847
0.8971	High Similarity	NPC220344
0.8971	High Similarity	NPC243759
0.8971	High Similarity	NPC243996
0.8971	High Similarity	NPC275061
0.8963	High Similarity	NPC209985
0.8963	High Similarity	NPC205442
0.8963	High Similarity	NPC177160
0.8963	High Similarity	NPC30632
0.8963	High Similarity	NPC54743
0.8963	High Similarity	NPC263367
0.8963	High Similarity	NPC156502
0.8963	High Similarity	NPC10737
0.8963	High Similarity	NPC477939
0.8963	High Similarity	NPC29799
0.8955	High Similarity	NPC478085
0.8947	High Similarity	NPC181049
0.8947	High Similarity	NPC207400
0.8939	High Similarity	NPC126836
0.8931	High Similarity	NPC282703
0.8931	High Similarity	NPC470084
0.8931	High Similarity	NPC129570
0.8931	High Similarity	NPC11258
0.8931	High Similarity	NPC45774
0.8931	High Similarity	NPC184733
0.8931	High Similarity	NPC128208
0.8931	High Similarity	NPC21867
0.8929	High Similarity	NPC112251
0.8921	High Similarity	NPC253015
0.8921	High Similarity	NPC471065
0.8913	High Similarity	NPC175838
0.8906	High Similarity	NPC30462
0.8897	High Similarity	NPC46277
0.8897	High Similarity	NPC22902
0.8897	High Similarity	NPC3072
0.8897	High Similarity	NPC156948
0.8897	High Similarity	NPC151656
0.8897	High Similarity	NPC230919
0.8897	High Similarity	NPC266453
0.8897	High Similarity	NPC86605
0.8897	High Similarity	NPC301765
0.8897	High Similarity	NPC266006
0.8897	High Similarity	NPC200935
0.8889	High Similarity	NPC240279
0.8889	High Similarity	NPC55239
0.8889	High Similarity	NPC214853
0.8889	High Similarity	NPC180602
0.8889	High Similarity	NPC256262
0.8881	High Similarity	NPC227719
0.8872	High Similarity	NPC40432
0.8872	High Similarity	NPC27843
0.8872	High Similarity	NPC161557
0.8872	High Similarity	NPC115207
0.8872	High Similarity	NPC228346
0.8872	High Similarity	NPC158079
0.8872	High Similarity	NPC7171
0.8865	High Similarity	NPC474397
0.8864	High Similarity	NPC476968
0.8864	High Similarity	NPC86030
0.8864	High Similarity	NPC170844
0.8864	High Similarity	NPC5851
0.8855	High Similarity	NPC127587
0.8855	High Similarity	NPC183181
0.8855	High Similarity	NPC118787
0.8855	High Similarity	NPC163332
0.8855	High Similarity	NPC41706
0.8855	High Similarity	NPC111247
0.8855	High Similarity	NPC319625
0.8855	High Similarity	NPC147821
0.8855	High Similarity	NPC292056
0.8849	High Similarity	NPC469630
0.8832	High Similarity	NPC70682
0.8832	High Similarity	NPC260741
0.8828	High Similarity	NPC113865
0.8828	High Similarity	NPC54872
0.8828	High Similarity	NPC476343
0.8828	High Similarity	NPC312675
0.8828	High Similarity	NPC324571
0.8828	High Similarity	NPC470212
0.8828	High Similarity	NPC343720
0.8828	High Similarity	NPC184651
0.8828	High Similarity	NPC473853
0.8828	High Similarity	NPC262156
0.8824	High Similarity	NPC270456
0.8824	High Similarity	NPC162659
0.8824	High Similarity	NPC248727
0.8824	High Similarity	NPC77861
0.8824	High Similarity	NPC133025
0.8824	High Similarity	NPC265433
0.8819	High Similarity	NPC165133
0.8819	High Similarity	NPC56214
0.8819	High Similarity	NPC242885
0.8819	High Similarity	NPC95614
0.8819	High Similarity	NPC227217
0.8819	High Similarity	NPC232316
0.8819	High Similarity	NPC117780
0.8815	High Similarity	NPC188378
0.8815	High Similarity	NPC193026
0.8815	High Similarity	NPC287745
0.8815	High Similarity	NPC555
0.8815	High Similarity	NPC469659
0.8815	High Similarity	NPC206737
0.8815	High Similarity	NPC187616
0.8815	High Similarity	NPC289258
0.8815	High Similarity	NPC7515
0.8815	High Similarity	NPC49603
0.8815	High Similarity	NPC56764
0.8815	High Similarity	NPC276026
0.8806	High Similarity	NPC303144
0.8806	High Similarity	NPC6451
0.8806	High Similarity	NPC4940
0.8806	High Similarity	NPC201587
0.8806	High Similarity	NPC227002
0.8806	High Similarity	NPC253105
0.8797	High Similarity	NPC470727
0.8794	High Similarity	NPC233980
0.8788	High Similarity	NPC98631
0.8788	High Similarity	NPC72529
0.8788	High Similarity	NPC470213
0.8788	High Similarity	NPC206615
0.8788	High Similarity	NPC186843
0.8786	High Similarity	NPC469795
0.8786	High Similarity	NPC473108
0.8779	High Similarity	NPC191037
0.8779	High Similarity	NPC58607
0.8779	High Similarity	NPC470724
0.8779	High Similarity	NPC76451
0.8779	High Similarity	NPC206882
0.8779	High Similarity	NPC178284
0.8777	High Similarity	NPC183709
0.8777	High Similarity	NPC204347
0.8777	High Similarity	NPC475891

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 NPC311256 and all drugs/candidates.
● The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

range	Tanimoto Coefficient
0-0.1	342
0.1-0.2	861
0.2-0.3	1685
0.3-0.4	2703
0.4-0.5	1764
0.5-0.6	943
0.6-0.7	678
0.7-0.8	164
0.8-0.85	9
0.85-0.9	1
0.9-0.95	0
0.95-1	0

Similarity Score	Similarity Level	Drug ID	Developmental Stage
0.8864	High Similarity	NPD3027	Phase 3
0.8667	High Similarity	NPD3619	Clinical (unspecified phase)
0.8667	High Similarity	NPD3620	Phase 2
0.8394	Intermediate Similarity	NPD1613	Approved
0.8394	Intermediate Similarity	NPD1612	Clinical (unspecified phase)
0.8268	Intermediate Similarity	NPD5283	Phase 1
0.8235	Intermediate Similarity	NPD1529	Clinical (unspecified phase)
0.8182	Intermediate Similarity	NPD6674	Discontinued
0.8162	Intermediate Similarity	NPD1530	Clinical (unspecified phase)
0.8133	Intermediate Similarity	NPD37	Approved
0.811	Intermediate Similarity	NPD228	Approved
0.8105	Intermediate Similarity	NPD6234	Discontinued
0.8056	Intermediate Similarity	NPD5698	Clinical (unspecified phase)
0.8	Intermediate Similarity	NPD4060	Phase 1
0.8	Intermediate Similarity	NPD3600	Clinical (unspecified phase)
0.7986	Intermediate Similarity	NPD4907	Clinical (unspecified phase)
0.7974	Intermediate Similarity	NPD4965	Approved
0.7974	Intermediate Similarity	NPD4967	Phase 2
0.7974	Intermediate Similarity	NPD4966	Approved
0.7971	Intermediate Similarity	NPD4908	Phase 1
0.7953	Intermediate Similarity	NPD3021	Approved
0.7953	Intermediate Similarity	NPD3022	Approved
0.7914	Intermediate Similarity	NPD4625	Phase 3
0.7899	Intermediate Similarity	NPD2861	Phase 2
0.7883	Intermediate Similarity	NPD3094	Phase 2
0.7868	Intermediate Similarity	NPD4379	Clinical (unspecified phase)
0.7862	Intermediate Similarity	NPD7228	Approved
0.7852	Intermediate Similarity	NPD3705	Approved
0.7817	Intermediate Similarity	NPD5735	Approved
0.773	Intermediate Similarity	NPD6410	Clinical (unspecified phase)
0.7721	Intermediate Similarity	NPD1610	Phase 2
0.7721	Intermediate Similarity	NPD3092	Approved
0.7698	Intermediate Similarity	NPD4624	Approved
0.7698	Intermediate Similarity	NPD6917	Clinical (unspecified phase)
0.7692	Intermediate Similarity	NPD3657	Discovery
0.7671	Intermediate Similarity	NPD2029	Clinical (unspecified phase)
0.7643	Intermediate Similarity	NPD3018	Phase 2
0.7622	Intermediate Similarity	NPD2238	Phase 2
0.761	Intermediate Similarity	NPD6232	Discontinued
0.7609	Intermediate Similarity	NPD4749	Approved
0.7609	Intermediate Similarity	NPD2983	Phase 2
0.7609	Intermediate Similarity	NPD2982	Phase 2
0.7578	Intermediate Similarity	NPD7473	Discontinued
0.7556	Intermediate Similarity	NPD3091	Approved
0.7554	Intermediate Similarity	NPD8651	Approved
0.7551	Intermediate Similarity	NPD5763	Approved
0.7551	Intermediate Similarity	NPD7266	Discontinued
0.7551	Intermediate Similarity	NPD5762	Approved
0.755	Intermediate Similarity	NPD4160	Clinical (unspecified phase)
0.7548	Intermediate Similarity	NPD1934	Approved
0.7547	Intermediate Similarity	NPD7199	Phase 2
0.7536	Intermediate Similarity	NPD2981	Phase 2
0.7517	Intermediate Similarity	NPD4097	Suspended
0.75	Intermediate Similarity	NPD4140	Approved
0.75	Intermediate Similarity	NPD1558	Phase 1
0.75	Intermediate Similarity	NPD5261	Clinical (unspecified phase)
0.75	Intermediate Similarity	NPD2393	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD8055	Clinical (unspecified phase)
0.7485	Intermediate Similarity	NPD5844	Phase 1
0.7483	Intermediate Similarity	NPD5109	Approved
0.7483	Intermediate Similarity	NPD5111	Phase 2
0.7483	Intermediate Similarity	NPD5110	Phase 2
0.7482	Intermediate Similarity	NPD5327	Phase 3
0.7468	Intermediate Similarity	NPD4005	Discontinued
0.7467	Intermediate Similarity	NPD5241	Discontinued
0.7466	Intermediate Similarity	NPD4537	Clinical (unspecified phase)
0.7466	Intermediate Similarity	NPD4538	Approved
0.7466	Intermediate Similarity	NPD4536	Approved
0.7463	Intermediate Similarity	NPD7157	Approved
0.7462	Intermediate Similarity	NPD2684	Approved
0.745	Intermediate Similarity	NPD5177	Phase 3
0.745	Intermediate Similarity	NPD3060	Approved
0.7445	Intermediate Similarity	NPD4626	Approved
0.744	Intermediate Similarity	NPD4663	Approved
0.7429	Intermediate Similarity	NPD6696	Suspended
0.7426	Intermediate Similarity	NPD1548	Phase 1
0.7413	Intermediate Similarity	NPD7095	Approved
0.741	Intermediate Similarity	NPD2230	Approved
0.741	Intermediate Similarity	NPD2232	Approved
0.741	Intermediate Similarity	NPD2233	Approved
0.7407	Intermediate Similarity	NPD6168	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD6166	Phase 2
0.7407	Intermediate Similarity	NPD27	Approved
0.7407	Intermediate Similarity	NPD6167	Clinical (unspecified phase)
0.7407	Intermediate Similarity	NPD2489	Approved
0.7397	Intermediate Similarity	NPD6353	Approved
0.7391	Intermediate Similarity	NPD3051	Approved
0.7389	Intermediate Similarity	NPD2801	Approved
0.7372	Intermediate Similarity	NPD1357	Approved
0.7368	Intermediate Similarity	NPD7040	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD6143	Clinical (unspecified phase)
0.7368	Intermediate Similarity	NPD7041	Phase 2
0.7368	Intermediate Similarity	NPD7843	Approved
0.7365	Intermediate Similarity	NPD4578	Approved
0.7365	Intermediate Similarity	NPD7311	Approved
0.7365	Intermediate Similarity	NPD7310	Approved
0.7365	Intermediate Similarity	NPD7312	Approved
0.7365	Intermediate Similarity	NPD7313	Approved
0.7365	Intermediate Similarity	NPD4577	Approved
0.7353	Intermediate Similarity	NPD5536	Phase 2
0.7351	Intermediate Similarity	NPD2677	Approved
0.7351	Intermediate Similarity	NPD6190	Approved
0.7349	Intermediate Similarity	NPD7240	Approved
0.7346	Intermediate Similarity	NPD2970	Approved
0.7346	Intermediate Similarity	NPD7184	Clinical (unspecified phase)
0.7346	Intermediate Similarity	NPD2969	Approved
0.7333	Intermediate Similarity	NPD6671	Approved
0.7329	Intermediate Similarity	NPD8127	Discontinued
0.7324	Intermediate Similarity	NPD6584	Phase 3
0.7321	Intermediate Similarity	NPD7309	Approved
0.7319	Intermediate Similarity	NPD5126	Approved
0.7319	Intermediate Similarity	NPD5846	Approved
0.7319	Intermediate Similarity	NPD6516	Phase 2
0.7319	Intermediate Similarity	NPD5125	Phase 3
0.7319	Intermediate Similarity	NPD3095	Discontinued
0.7305	Intermediate Similarity	NPD1283	Approved
0.7303	Intermediate Similarity	NPD5058	Phase 3
0.7297	Intermediate Similarity	NPD5960	Phase 3
0.7297	Intermediate Similarity	NPD5588	Approved
0.7296	Intermediate Similarity	NPD4868	Clinical (unspecified phase)
0.7294	Intermediate Similarity	NPD7906	Approved
0.729	Intermediate Similarity	NPD1653	Approved
0.7285	Intermediate Similarity	NPD6331	Phase 2
0.7285	Intermediate Similarity	NPD8166	Discontinued
0.7267	Intermediate Similarity	NPD7037	Approved
0.725	Intermediate Similarity	NPD7975	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7831	Phase 2
0.725	Intermediate Similarity	NPD7832	Clinical (unspecified phase)
0.725	Intermediate Similarity	NPD7833	Phase 2
0.7246	Intermediate Similarity	NPD5691	Approved
0.7246	Intermediate Similarity	NPD1651	Approved
0.7244	Intermediate Similarity	NPD3020	Approved
0.7239	Intermediate Similarity	NPD7635	Approved
0.7237	Intermediate Similarity	NPD5307	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD7090	Clinical (unspecified phase)
0.7219	Intermediate Similarity	NPD4236	Phase 3
0.7219	Intermediate Similarity	NPD4237	Approved
0.7214	Intermediate Similarity	NPD1091	Approved
0.7208	Intermediate Similarity	NPD7422	Clinical (unspecified phase)
0.72	Intermediate Similarity	NPD1375	Discontinued
0.7194	Intermediate Similarity	NPD4059	Approved
0.7192	Intermediate Similarity	NPD2674	Phase 3
0.7188	Intermediate Similarity	NPD3882	Suspended
0.7181	Intermediate Similarity	NPD4108	Discontinued
0.7181	Intermediate Similarity	NPD6029	Clinical (unspecified phase)
0.7181	Intermediate Similarity	NPD6028	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD4628	Phase 3
0.7171	Intermediate Similarity	NPD4109	Clinical (unspecified phase)
0.7171	Intermediate Similarity	NPD4110	Phase 3
0.717	Intermediate Similarity	NPD2978	Approved
0.717	Intermediate Similarity	NPD5929	Approved
0.717	Intermediate Similarity	NPD2977	Approved
0.717	Intermediate Similarity	NPD6818	Clinical (unspecified phase)
0.7162	Intermediate Similarity	NPD4579	Clinical (unspecified phase)
0.7153	Intermediate Similarity	NPD7340	Approved
0.7151	Intermediate Similarity	NPD8397	Clinical (unspecified phase)
0.7143	Intermediate Similarity	NPD2979	Phase 3
0.7143	Intermediate Similarity	NPD5451	Approved
0.7143	Intermediate Similarity	NPD1511	Approved
0.7133	Intermediate Similarity	NPD6099	Approved
0.7133	Intermediate Similarity	NPD6100	Approved
0.7133	Intermediate Similarity	NPD2438	Suspended
0.7126	Intermediate Similarity	NPD7074	Phase 3
0.7125	Intermediate Similarity	NPD2563	Approved
0.7125	Intermediate Similarity	NPD2560	Approved
0.7124	Intermediate Similarity	NPD5084	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD6812	Clinical (unspecified phase)
0.7123	Intermediate Similarity	NPD3144	Approved
0.7123	Intermediate Similarity	NPD6798	Discontinued
0.7123	Intermediate Similarity	NPD3145	Approved
0.7121	Intermediate Similarity	NPD2342	Discontinued
0.7121	Intermediate Similarity	NPD290	Approved
0.7114	Intermediate Similarity	NPD7097	Phase 1
0.7113	Intermediate Similarity	NPD1669	Approved
0.7113	Intermediate Similarity	NPD6582	Phase 2
0.7113	Intermediate Similarity	NPD6583	Phase 3
0.7108	Intermediate Similarity	NPD3818	Discontinued
0.7097	Intermediate Similarity	NPD4123	Phase 3
0.7097	Intermediate Similarity	NPD7004	Clinical (unspecified phase)
0.7097	Intermediate Similarity	NPD7446	Clinical (unspecified phase)
0.7095	Intermediate Similarity	NPD6355	Discontinued
0.7092	Intermediate Similarity	NPD1281	Approved
0.7089	Intermediate Similarity	NPD7028	Phase 2
0.7089	Intermediate Similarity	NPD4380	Phase 2
0.7086	Intermediate Similarity	NPD3540	Phase 1
0.7078	Intermediate Similarity	NPD7124	Phase 2
0.7075	Intermediate Similarity	NPD6233	Phase 2
0.7071	Intermediate Similarity	NPD2667	Approved
0.7071	Intermediate Similarity	NPD3019	Approved
0.7071	Intermediate Similarity	NPD2668	Approved
0.7066	Intermediate Similarity	NPD7054	Approved
0.7063	Intermediate Similarity	NPD1465	Phase 2
0.7059	Intermediate Similarity	NPD6658	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD3892	Phase 2
0.7059	Intermediate Similarity	NPD4869	Clinical (unspecified phase)
0.7059	Intermediate Similarity	NPD1398	Phase 1
0.7055	Intermediate Similarity	NPD4666	Phase 3
0.7051	Intermediate Similarity	NPD1512	Approved
0.705	Intermediate Similarity	NPD7741	Discontinued
0.7045	Intermediate Similarity	NPD968	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