Structure

Physi-Chem Properties

Molecular Weight:  192.04
Volume:  186.382
LogP:  1.186
LogD:  1.33
LogS:  -2.206
# Rotatable Bonds:  1
TPSA:  59.67
# H-Bond Aceptor:  4
# H-Bond Donor:  1
# Rings:  2
# Heavy Atoms:  4

MedChem Properties

QED Drug-Likeness Score:  0.695
Synthetic Accessibility Score:  2.05
Fsp3:  0.1
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  1
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.727
MDCK Permeability:  1.6060675989137962e-05
Pgp-inhibitor:  0.003
Pgp-substrate:  0.945
Human Intestinal Absorption (HIA):  0.009
20% Bioavailability (F20%):  0.225
30% Bioavailability (F30%):  0.998

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.166
Plasma Protein Binding (PPB):  83.35882568359375%
Volume Distribution (VD):  0.691
Pgp-substrate:  19.470502853393555%

ADMET: Metabolism

CYP1A2-inhibitor:  0.969
CYP1A2-substrate:  0.949
CYP2C19-inhibitor:  0.164
CYP2C19-substrate:  0.076
CYP2C9-inhibitor:  0.05
CYP2C9-substrate:  0.839
CYP2D6-inhibitor:  0.446
CYP2D6-substrate:  0.868
CYP3A4-inhibitor:  0.312
CYP3A4-substrate:  0.3

ADMET: Excretion

Clearance (CL):  13.326
Half-life (T1/2):  0.837

ADMET: Toxicity

hERG Blockers:  0.097
Human Hepatotoxicity (H-HT):  0.25
Drug-inuced Liver Injury (DILI):  0.799
AMES Toxicity:  0.061
Rat Oral Acute Toxicity:  0.068
Maximum Recommended Daily Dose:  0.391
Skin Sensitization:  0.563
Carcinogencity:  0.602
Eye Corrosion:  0.342
Eye Irritation:  0.978
Respiratory Toxicity:  0.22

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

  Natural Product: NPC139548

Natural Product ID:  NPC139548
Common Name*:   Isoscopoletin
IUPAC Name:   6-hydroxy-7-methoxychromen-2-one
Synonyms:   Isoscopoletin; Isoscopoletine
Standard InCHIKey:  SYTYLPHCLSSCOJ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C10H8O4/c1-13-9-5-8-6(4-7(9)11)2-3-10(12)14-8/h2-5,11H,1H3
SMILES:  COc1cc2c(ccc(=O)o2)cc1O
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL390320
PubChem CID:   69894
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0000145] Coumarins and derivatives
        • [CHEMONTID:0002908] Hydroxycoumarins

*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
NPO2768 Berchemia floribunda Species Rhamnaceae Eukaryota n.a. n.a. n.a. DOI[10.1002/cbdv.200690067]
NPO6915 Chloranthus japonicus Species Chloranthaceae Eukaryota n.a. whole plant n.a. DOI[10.1016/j.phytol.2016.01.005]
NPO11979 Bugula neritina Species Bugulidae Eukaryota n.a. n.a. n.a. DOI[10.1021/ja00388a092]
NPO21390 Zanthoxylum integrifoliolum Species Rutaceae Eukaryota fruit Lanyu Island, Taitung County, Taiwan n.a. PMID[10395498]
NPO10467 Resupinatus leightonii Species Tricholomataceae Eukaryota n.a. n.a. n.a. PMID[11000039]
NPO11702 Plexaurella grisea Species Plexauridae Eukaryota n.a. n.a. n.a. PMID[11325216]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. leaf n.a. PMID[11348221]
NPO17377 Pittosporum viridiflorum Species Pittosporaceae Eukaryota n.a. n.a. n.a. PMID[11809069]
NPO17823 Lycium chinense Species Solanaceae Eukaryota fruits n.a. n.a. PMID[12467621]
NPO15579 Mycale laxissima Species Mycalidae Eukaryota n.a. n.a. n.a. PMID[12932129]
NPO25302 Viola philippica Species Violaceae Eukaryota n.a. n.a. n.a. PMID[14519932]
NPO11616 Vibrio parahaemolyticus Species Vibrionaceae Bacteria n.a. North Sea n.a. PMID[14640534]
NPO7587 Mallotus resinosus Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[15387675]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota fruit n.a. n.a. PMID[15844957]
NPO11357 Nephelium lappaceum Species Sapindaceae Eukaryota Seeds n.a. n.a. PMID[16180821]
NPO17823 Lycium chinense Species Solanaceae Eukaryota n.a. root n.a. PMID[16212233]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota fruits n.a. n.a. PMID[16378361]
NPO16634 Sinularia manaarensis Species Alcyoniidae Eukaryota n.a. n.a. n.a. PMID[16933863]
NPO7664 Pseudocedrela kotschyi Species Meliaceae Eukaryota roots n.a. n.a. PMID[17253841]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota fruits Tahiti n.a. PMID[17378609]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota Fruits n.a. n.a. PMID[17480098]
NPO21390 Zanthoxylum integrifoliolum Species Rutaceae Eukaryota n.a. n.a. n.a. PMID[17822293]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota roots n.a. n.a. PMID[18076142]
NPO6915 Chloranthus japonicus Species Chloranthaceae Eukaryota n.a. whole plant n.a. PMID[18451544]
NPO13975 Calanthe arisanensis Species Orchidaceae Eukaryota n.a. n.a. n.a. PMID[18640035]
NPO13975 Calanthe arisanensis Species Orchidaceae Eukaryota n.a. n.a. n.a. PMID[19193043]
NPO5018 Nervilia fordii Species Orchidaceae Eukaryota whole plant n.a. n.a. PMID[19422205]
NPO6915 Chloranthus japonicus Species Chloranthaceae Eukaryota whole plants Suiling district, Heilongjiang Province, China 2008-AUG PMID[21142110]
NPO6915 Chloranthus japonicus Species Chloranthaceae Eukaryota Whole plant Suiling district, Heilongjiang Province, China 2008-AUG PMID[21142110]
NPO6915 Chloranthus japonicus Species Chloranthaceae Eukaryota n.a. whole plant n.a. PMID[21142110]
NPO6915 Chloranthus japonicus Species Chloranthaceae Eukaryota n.a. n.a. n.a. PMID[21650224]
NPO6915 Chloranthus japonicus Species Chloranthaceae Eukaryota n.a. whole plant n.a. PMID[21650224]
NPO5258 Fagara zanthoxyloides n.a. n.a. n.a. n.a. n.a. n.a. PMID[22472691]
NPO17823 Lycium chinense Species Solanaceae Eukaryota root bark n.a. n.a. PMID[23282106]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[24224843]
NPO11979 Bugula neritina Species Bugulidae Eukaryota n.a. South China Sea n.a. PMID[25932671]
NPO18671 Saussurea involucrata Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[26214875]
NPO17823 Lycium chinense Species Solanaceae Eukaryota Root Bark n.a. n.a. PMID[26982999]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. PMID[27196335]
NPO15933 Dysoxylum binectariferum Species Meliaceae Eukaryota leaves n.a. n.a. PMID[27363938]
NPO2722 Humulus japonicus Species Cannabaceae Eukaryota Aerial Parts n.a. n.a. PMID[29254897]
NPO23429 Lycium barbarum Species Solanaceae Eukaryota n.a. n.a. n.a. PMID[31397570]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota Fruits n.a. n.a. PMID[32083868]
NPO26277 Euphorbia hirta Species Euphorbiaceae Eukaryota n.a. n.a. n.a. PMID[32141299]
NPO21322 Plinia cauliflora Species Myrtaceae Eukaryota leaves n.a. n.a. PMID[32706260]
NPO11616 Vibrio parahaemolyticus Species Vibrionaceae Bacteria n.a. n.a. n.a. PMID[7853008]
NPO11979 Bugula neritina Species Bugulidae Eukaryota n.a. Gulf of Aomori, Japan n.a. PMID[8691208]
NPO10969 Epimedium sagittatum Species Berberidaceae Eukaryota n.a. leaf n.a. PMID[8699184]
NPO11979 Bugula neritina Species Bugulidae Eukaryota n.a. n.a. n.a. PMID[8882431]
NPO17823 Lycium chinense Species Solanaceae Eukaryota fruits n.a. n.a. PMID[9090870]
NPO16120 Swertia decora Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[Article]
NPO11616 Vibrio parahaemolyticus Species Vibrionaceae Bacteria n.a. n.a. n.a. DOI[DOI: 10.1111/j.1574-6968.1992.tb05311.x]
NPO11357 Nephelium lappaceum Species Sapindaceae Eukaryota n.a. n.a. Database[FooDB]
NPO15212 Fraxinus chinensis Species Oleaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO14650 Lobelia chinensis Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO2722 Humulus japonicus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15413 Glycyrrhiza pallidiflora Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4307 Canarium album Species Burseraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18671 Saussurea involucrata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO9661 Fraxinus szaboana Species Oleaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO23429 Lycium barbarum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO6915 Chloranthus japonicus Species Chloranthaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3564 Fraxinus stylosa Species Oleaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO10969 Epimedium sagittatum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO26277 Euphorbia hirta Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22524 Ranunculus sceleratus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO24301.1 Buxus microphylla var. sinica Varieties Buxaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO358 Uncaria guianensis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18681 Artemisia scoparia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17823 Lycium chinense Species Solanaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO12755 Siphonostegia chinensis Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18671 Saussurea involucrata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15151 Syringa vulgaris Species Oleaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22524 Ranunculus sceleratus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25302 Viola philippica Species Violaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO12755 Siphonostegia chinensis Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15212.1 Fraxinus chinensis subsp. rhynchophylla Subspecies Oleaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4307 Canarium album Species Burseraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO2722 Humulus japonicus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22541 Channa argus Species Channidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21413 Armillaria tabescens Species Physalacriaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO3564 Fraxinus stylosa Species Oleaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7446 Erythrina eriotriocha Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO6915 Chloranthus japonicus Species Chloranthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15933 Dysoxylum binectariferum Species Meliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21390 Zanthoxylum integrifoliolum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14650 Lobelia chinensis Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15904 Chrysosplenium oppositifolium Species Saxifragaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15413 Glycyrrhiza pallidiflora Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO14127 Veratrum eschscholtzii Species Melanthiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15212 Fraxinus chinensis Species Oleaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17823 Lycium chinense Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15057 Isodon gesneroides Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO24301.1 Buxus microphylla var. sinica Varieties Buxaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26277 Euphorbia hirta Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23429 Lycium barbarum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO18681 Artemisia scoparia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9661 Fraxinus szaboana Species Oleaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO10969 Epimedium sagittatum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO358 Uncaria guianensis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO9964 Aglaia lawii Species Meliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO581 Conyza bonariensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO4307 Canarium album Species Burseraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO12755 Siphonostegia chinensis Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2722 Humulus japonicus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21924 Althaea officinalis Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15413 Glycyrrhiza pallidiflora Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO14650 Lobelia chinensis Species Campanulaceae 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]
NPO9661 Fraxinus szaboana Species Oleaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3564 Fraxinus stylosa Species Oleaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15212 Fraxinus chinensis Species Oleaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18681 Artemisia scoparia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO24301.2 Buxus microphylla sieb. et zucc. var. sinica rehd. et wils. Varieties Buxaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO23429 Lycium barbarum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17823 Lycium chinense Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO18671 Saussurea involucrata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15212 Fraxinus chinensis Species Oleaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15212.1 Fraxinus chinensis subsp. rhynchophylla Subspecies Oleaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO3564 Fraxinus stylosa Species Oleaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO17823 Lycium chinense Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26277 Euphorbia hirta Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO4307 Canarium album Species Burseraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO14650 Lobelia chinensis Species Campanulaceae 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]
NPO12755 Siphonostegia chinensis Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO25302 Viola philippica Species Violaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO9661 Fraxinus szaboana Species Oleaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO23429 Lycium barbarum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8837 Viola mandshurica Species Violaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8298 Sphaeria biglobosa n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO13296 Pinus sitchensis Species Pinaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16526 Papularia sphaerosperma n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO6469 Clematis angustifolia Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6899 Hepialus hecta Species Hepialidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15027 Helianthus divaricatus Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5824 Hygrophila polysperma Species Acanthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29072 Tritomaria quinquedentata Species Scapaniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5473 Streptomyces orinoci Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO15904 Chrysosplenium oppositifolium Species Saxifragaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9964 Aglaia lawii Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO581 Conyza bonariensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15194 Euphorbia balsamifera Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15972 Quercus gilva Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16553 Theonella cupola Species Theonellidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22541 Channa argus Species Channidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7664 Pseudocedrela kotschyi Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26942 Vicoa vestita n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO16888 Sophora davidii Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13773 Eriogonum nudum Species Polygonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14127 Veratrum eschscholtzii Species Melanthiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1354 Myelochroa rhytidodes Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3084 Xylopia brasiliensis Species Annonaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14650 Lobelia chinensis Species Campanulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21322 Plinia cauliflora Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27425 Pseudotaxus chienii Species Taxaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17117 Diaporthe amygdali Species Diaporthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5258 Fagara zanthoxyloides n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO16713 Choisya arizonica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14896 Reaumuria mucronata Species Tamaricaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12034 Dictamnus gymnostylis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO27420 Venidium hirsutum n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO15057 Isodon gesneroides Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13410 Mcneillia graminifolia Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11702 Plexaurella grisea Species Plexauridae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28881 Virola sebifera Species Myristicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12378 Streptomyces blastmyceticus Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO15212 Fraxinus chinensis Species Oleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13257 Euphorbia officinarum Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15212.1 Fraxinus chinensis subsp. rhynchophylla Subspecies Oleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4307 Canarium album Species Burseraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1933 Sideritis nutans Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15151 Syringa vulgaris Species Oleaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11979 Bugula neritina Species Bugulidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16634 Sinularia manaarensis Species Alcyoniidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO14625 Santolina rosmarinifolia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16466 Baccharis santelicis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18671 Saussurea involucrata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16439 Alphitonia macrocarpa Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21924 Althaea officinalis Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9781 Hyphear tanakae n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO21413 Armillaria tabescens Species Physalacriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3619 Ilex hainanensis Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7201 Rhodopila globiformis Species Acetobacteraceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO752 Oligonychus bessardi Species Tetranychidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8782 Arnica sachalinensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15691 Senecio coahuilensis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1660 Ligularia subspicata Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO816 Stenomesson miniatum Species Amaryllidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10396 Pteris australis Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12755 Siphonostegia chinensis Species Orobanchaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5868 Morus rubra Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16313 Ochrocarpos odoratus Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16878 Roldana barba-johannis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4323 Morinda citrifolia Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21773 Rothmannia urcelliformis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9073 Withania frutescens Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9150 Polypodiodes formosana Species Polypodiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9425 Punctelia microsticta Species Parmeliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13130 0tholaena peninsularis Species Pteridaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO358 Uncaria guianensis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16223 Serratula xeranthemoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15452 Senecio othonniformis Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25302 Viola philippica Species Violaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10467 Resupinatus leightonii Species Tricholomataceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15579 Mycale laxissima Species Mycalidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21171 Rubus thibetanus Species Rosaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9728 Quercus acuta Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO4676 Melicope sarcococca Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8216 Garcinia volkensii Species Clusiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3488 Glossocalyx brevipes Species Siparunaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO12087 Amaioua guianensis Species Rubiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11241 Arisarum vulgare Species Araceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10969 Epimedium sagittatum Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1321 Centaurea spruneri Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11413 Incarvillea emodi Species Bignoniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17447 Agathosma betulina Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7446 Erythrina eriotriocha Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2768 Berchemia floribunda Species Rhamnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11117 Xerula melanotricha Species Physalacriaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17377 Pittosporum viridiflorum Species Pittosporaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO13005 Aplophyllum telephioides n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO13975 Calanthe arisanensis Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16789 Erythrina sandwicensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15341 Mucuna sloanei Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15730 Citrus medica Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11478 Aniba duckei Species Lauraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5018 Nervilia fordii Species Orchidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15413 Glycyrrhiza pallidiflora Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3742 Betula maximowicziana Species Betulaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11616 Vibrio parahaemolyticus Species Vibrionaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO22524 Ranunculus sceleratus Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22394 Hyacinthoides hispanica Species Hyacinthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11895 Nama johnstonii Species Namaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17823 Lycium chinense Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26277 Euphorbia hirta Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO6915 Chloranthus japonicus Species Chloranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO21390 Zanthoxylum integrifoliolum Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15933 Dysoxylum binectariferum Species Meliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18681 Artemisia scoparia Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2722 Humulus japonicus Species Cannabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16120 Swertia decora Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23429 Lycium barbarum Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15762 Eucalyptus sieberiana Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO24059 Agathosma recurvifolia Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7587 Mallotus resinosus Species Euphorbiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9827 Indigofera linnaei Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO1780 Sphaeria doliolum n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO11357 Nephelium lappaceum Species Sapindaceae 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

Target ID Target Type Target Name Target Organism Activity Type Activity Relation Value Unit Reference
NPT570 Individual Protein Arachidonate 5-lipoxygenase Homo sapiens IC50 > 100000.0 nM PMID[546207]
NPT257 Individual Protein Arachidonate 15-lipoxygenase Oryctolagus cuniculus IC50 = 15100.0 nM PMID[546207]
NPT31 Individual Protein Cyclooxygenase-2 Homo sapiens IC50 > 100000.0 nM PMID[546207]
NPT2740 Cell Line Neutrophils IC50 = 77520.0 nM PMID[546209]
NPT41 Individual Protein Aldose reductase Homo sapiens IC50 = 56200.0 nM PMID[546211]
NPT1551 Individual Protein Sorbitol dehydrogenase Homo sapiens IC50 > 250000.0 nM PMID[546211]
NPT199 Individual Protein DNA polymerase kappa Homo sapiens Potency n.a. 23778.1 nM PMID[546212]
NPT66 Individual Protein Acetylcholinesterase Electrophorus electricus Inhibition = 28.07 % PMID[546213]
NPT3101 Individual Protein Carbonic anhydrase XIII Homo sapiens Ki = 5270.0 nM PMID[546214]
NPT233 Individual Protein Carbonic anhydrase II Homo sapiens Ki > 100000.0 nM PMID[546214]
NPT43 Individual Protein Tyrosinase Agaricus bisporus Inhibition > 30.0 % PMID[546216]
NPT461 Cell Line PANC-1 Homo sapiens PC50 = 26.9 uM PMID[546217]
NPT57 Individual Protein Induced myeloid leukemia cell differentiation protein Mcl-1 Homo sapiens Ki = 15870.0 nM PMID[546218]
NPT57 Individual Protein Induced myeloid leukemia cell differentiation protein Mcl-1 Homo sapiens IC50 = 51480.0 nM PMID[546218]
NPT967 Individual Protein Xanthine dehydrogenase Homo sapiens IC50 = 138000.0 nM PMID[546208]
NPT2 Others Unspecified Activity = 42.0 % PMID[546210]
NPT2 Others Unspecified Activity = 2.0 % PMID[546210]
NPT2 Others Unspecified Activity = 26.0 % PMID[546210]
NPT2 Others Unspecified Activity = 14.0 % PMID[546210]
NPT2 Others Unspecified IC50 = 101000.0 nM PMID[546211]
NPT2 Others Unspecified Ratio IC50 > 2.48 n.a. PMID[546211]
NPT2 Others Unspecified Ratio IC50 = 0.56 n.a. PMID[546211]
NPT67 Individual Protein Cholinesterase Equus caballus Inhibition = 3.87 % PMID[546213]
NPT955 Individual Protein Carbonic anhydrase VII Homo sapiens Ki = 23800.0 nM PMID[546214]
NPT947 Individual Protein Carbonic anhydrase I Homo sapiens Ki = 14000.0 nM PMID[546214]
NPT948 Individual Protein Carbonic anhydrase IX Homo sapiens Ki = 7370.0 nM PMID[546214]
NPT949 Individual Protein Carbonic anhydrase XII Homo sapiens Ki = 4140.0 nM PMID[546214]
NPT2 Others Unspecified IC50 = 32200000.0 nM PMID[546215]

☑ 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 NPC139548 and all remaining natural products in the NPASS database.
●  The right table: Most similar natural products (Tc>=0.56 or Top200).

Similarity Score Similarity Level Natural Product ID
1.0 High Similarity NPC20511
1.0 High Similarity NPC76336
1.0 High Similarity NPC95162
1.0 High Similarity NPC52086
1.0 High Similarity NPC148835
0.9924 High Similarity NPC13067
0.9923 High Similarity NPC126682
0.9923 High Similarity NPC82271
0.9769 High Similarity NPC92830
0.9692 High Similarity NPC26673
0.9615 High Similarity NPC137949
0.9542 High Similarity NPC277021
0.9538 High Similarity NPC73738
0.9485 High Similarity NPC256555
0.9485 High Similarity NPC110067
0.9485 High Similarity NPC236419
0.9485 High Similarity NPC91492
0.9485 High Similarity NPC7439
0.9485 High Similarity NPC34245
0.9478 High Similarity NPC164148
0.9478 High Similarity NPC43500
0.9462 High Similarity NPC244799
0.9462 High Similarity NPC240722
0.9385 High Similarity NPC27239
0.9385 High Similarity NPC123127
0.9353 High Similarity NPC231149
0.9343 High Similarity NPC230157
0.9338 High Similarity NPC300611
0.9318 High Similarity NPC137669
0.9286 High Similarity NPC139839
0.9259 High Similarity NPC38874
0.9248 High Similarity NPC233018
0.9248 High Similarity NPC36437
0.9248 High Similarity NPC241341
0.922 High Similarity NPC176903
0.922 High Similarity NPC30688
0.9203 High Similarity NPC138212
0.9179 High Similarity NPC309953
0.9179 High Similarity NPC111635
0.9155 High Similarity NPC205727
0.9155 High Similarity NPC120426
0.9155 High Similarity NPC21184
0.9155 High Similarity NPC294522
0.9149 High Similarity NPC48366
0.9137 High Similarity NPC185127
0.9137 High Similarity NPC471763
0.9118 High Similarity NPC474886
0.9104 High Similarity NPC474810
0.9091 High Similarity NPC213197
0.9085 High Similarity NPC313334
0.9085 High Similarity NPC206264
0.9085 High Similarity NPC212670
0.9078 High Similarity NPC178129
0.9078 High Similarity NPC476347
0.9077 High Similarity NPC300326
0.9077 High Similarity NPC58279
0.9065 High Similarity NPC6568
0.9044 High Similarity NPC167517
0.903 High Similarity NPC319969
0.903 High Similarity NPC245120
0.9028 High Similarity NPC120774
0.9028 High Similarity NPC163598
0.9028 High Similarity NPC264875
0.9023 High Similarity NPC19242
0.9015 High Similarity NPC109275
0.9014 High Similarity NPC187398
0.9014 High Similarity NPC476348
0.9007 High Similarity NPC205361
0.8993 High Similarity NPC469564
0.8978 High Similarity NPC20796
0.8971 High Similarity NPC240915
0.8971 High Similarity NPC472521
0.8971 High Similarity NPC234865
0.8955 High Similarity NPC142530
0.8955 High Similarity NPC147317
0.8947 High Similarity NPC45824
0.8947 High Similarity NPC48315
0.8944 High Similarity NPC41844
0.8944 High Similarity NPC15577
0.8936 High Similarity NPC476450
0.8913 High Similarity NPC270256
0.8905 High Similarity NPC309031
0.8905 High Similarity NPC286843
0.8897 High Similarity NPC7163
0.8881 High Similarity NPC214860
0.8881 High Similarity NPC96294
0.8855 High Similarity NPC183446
0.8841 High Similarity NPC476171
0.8841 High Similarity NPC105493
0.8832 High Similarity NPC73071
0.8832 High Similarity NPC252095
0.8824 High Similarity NPC472522
0.8797 High Similarity NPC216836
0.8786 High Similarity NPC279851
0.8786 High Similarity NPC472520
0.8779 High Similarity NPC238810
0.8769 High Similarity NPC310373
0.8759 High Similarity NPC474600
0.8759 High Similarity NPC106215
0.8759 High Similarity NPC114740
0.875 High Similarity NPC123954
0.875 High Similarity NPC5423
0.875 High Similarity NPC474635
0.8731 High Similarity NPC474616
0.8705 High Similarity NPC276328
0.8696 High Similarity NPC472337
0.8692 High Similarity NPC302107
0.8692 High Similarity NPC307253
0.8686 High Similarity NPC168059
0.8686 High Similarity NPC229442
0.8681 High Similarity NPC275125
0.8681 High Similarity NPC170239
0.8681 High Similarity NPC97937
0.8676 High Similarity NPC82503
0.8667 High Similarity NPC10225
0.8667 High Similarity NPC58164
0.8657 High Similarity NPC194841
0.8657 High Similarity NPC474670
0.8647 High Similarity NPC27352
0.8647 High Similarity NPC271985
0.8633 High Similarity NPC26954
0.8633 High Similarity NPC472334
0.8633 High Similarity NPC472336
0.8633 High Similarity NPC38099
0.8626 High Similarity NPC187868
0.8626 High Similarity NPC285289
0.8626 High Similarity NPC52247
0.8623 High Similarity NPC147030
0.8623 High Similarity NPC326600
0.8623 High Similarity NPC50896
0.8623 High Similarity NPC204353
0.8621 High Similarity NPC478237
0.8615 High Similarity NPC247553
0.8615 High Similarity NPC2058
0.8613 High Similarity NPC202762
0.8613 High Similarity NPC161203
0.8613 High Similarity NPC86655
0.8613 High Similarity NPC194277
0.8611 High Similarity NPC40222
0.8611 High Similarity NPC268515
0.8611 High Similarity NPC287275
0.8603 High Similarity NPC299221
0.8603 High Similarity NPC311680
0.8603 High Similarity NPC51840
0.8603 High Similarity NPC220935
0.8603 High Similarity NPC91291
0.8603 High Similarity NPC234488
0.8593 High Similarity NPC474651
0.8593 High Similarity NPC19694
0.8593 High Similarity NPC474623
0.8592 High Similarity NPC472332
0.8592 High Similarity NPC472335
0.8582 High Similarity NPC127604
0.8582 High Similarity NPC476006
0.8582 High Similarity NPC267291
0.8581 High Similarity NPC150442
0.8571 High Similarity NPC281014
0.8571 High Similarity NPC474282
0.8571 High Similarity NPC184861
0.8571 High Similarity NPC126206
0.8571 High Similarity NPC326797
0.8571 High Similarity NPC225106
0.8571 High Similarity NPC212124
0.8571 High Similarity NPC102904
0.8571 High Similarity NPC107551
0.8571 High Similarity NPC294456
0.8571 High Similarity NPC176051
0.8571 High Similarity NPC276490
0.8571 High Similarity NPC103976
0.8562 High Similarity NPC113790
0.8562 High Similarity NPC107636
0.8561 High Similarity NPC33986
0.8561 High Similarity NPC194626
0.8552 High Similarity NPC52740
0.8551 High Similarity NPC36661
0.8551 High Similarity NPC94236
0.8551 High Similarity NPC37196
0.8551 High Similarity NPC163557
0.8551 High Similarity NPC36490
0.8542 High Similarity NPC125617
0.854 High Similarity NPC29734
0.8538 High Similarity NPC298796
0.8523 High Similarity NPC8712
0.8521 High Similarity NPC83375
0.8521 High Similarity NPC224876
0.8519 High Similarity NPC121740
0.8519 High Similarity NPC224774
0.8519 High Similarity NPC258567
0.8519 High Similarity NPC474821
0.8519 High Similarity NPC210355
0.8514 High Similarity NPC169404
0.8514 High Similarity NPC53587
0.8514 High Similarity NPC176186
0.8511 High Similarity NPC25966
0.8511 High Similarity NPC151946
0.8511 High Similarity NPC127218
0.8511 High Similarity NPC245207
0.8511 High Similarity NPC319647
0.8507 High Similarity NPC244495
0.8507 High Similarity NPC93219

  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 NPC139548 and all drugs/candidates.
●  The right table: Most similar clinical/approved drugs (Tc>=0.56 or Top200).

Similarity Score Similarity Level Drug ID Developmental Stage
0.9085 High Similarity NPD1653 Approved
0.8626 High Similarity NPD422 Phase 1
0.8456 Intermediate Similarity NPD1529 Clinical (unspecified phase)
0.8382 Intermediate Similarity NPD1530 Clinical (unspecified phase)
0.8345 Intermediate Similarity NPD1613 Approved
0.8345 Intermediate Similarity NPD1612 Clinical (unspecified phase)
0.8278 Intermediate Similarity NPD2801 Approved
0.8129 Intermediate Similarity NPD3027 Phase 3
0.8041 Intermediate Similarity NPD1511 Approved
0.8028 Intermediate Similarity NPD447 Suspended
0.8028 Intermediate Similarity NPD230 Phase 1
0.8014 Intermediate Similarity NPD1652 Phase 2
0.7974 Intermediate Similarity NPD1934 Approved
0.7935 Intermediate Similarity NPD4868 Clinical (unspecified phase)
0.7933 Intermediate Similarity NPD1512 Approved
0.7922 Intermediate Similarity NPD1465 Phase 2
0.7871 Intermediate Similarity NPD3817 Phase 2
0.7826 Intermediate Similarity NPD4379 Clinical (unspecified phase)
0.7821 Intermediate Similarity NPD3882 Suspended
0.7815 Intermediate Similarity NPD1940 Clinical (unspecified phase)
0.7786 Intermediate Similarity NPD228 Approved
0.7778 Intermediate Similarity NPD5844 Phase 1
0.7778 Intermediate Similarity NPD1548 Phase 1
0.7737 Intermediate Similarity NPD3496 Discontinued
0.7703 Intermediate Similarity NPD970 Clinical (unspecified phase)
0.7697 Intermediate Similarity NPD4338 Clinical (unspecified phase)
0.7697 Intermediate Similarity NPD7549 Discontinued
0.7692 Intermediate Similarity NPD2393 Clinical (unspecified phase)
0.7676 Intermediate Similarity NPD1008 Clinical (unspecified phase)
0.7655 Intermediate Similarity NPD5124 Phase 1
0.7655 Intermediate Similarity NPD5123 Clinical (unspecified phase)
0.7607 Intermediate Similarity NPD3818 Discontinued
0.7606 Intermediate Similarity NPD3018 Phase 2
0.76 Intermediate Similarity NPD3750 Approved
0.7569 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7568 Intermediate Similarity NPD1551 Phase 2
0.7561 Intermediate Similarity NPD7054 Approved
0.7554 Intermediate Similarity NPD1610 Phase 2
0.7532 Intermediate Similarity NPD5402 Approved
0.7518 Intermediate Similarity NPD3225 Approved
0.7517 Intermediate Similarity NPD7266 Discontinued
0.7515 Intermediate Similarity NPD7472 Approved
0.75 Intermediate Similarity NPD919 Approved
0.7485 Intermediate Similarity NPD6167 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD6168 Clinical (unspecified phase)
0.7485 Intermediate Similarity NPD6166 Phase 2
0.7483 Intermediate Similarity NPD6398 Clinical (unspecified phase)
0.7466 Intermediate Similarity NPD4060 Phase 1
0.7462 Intermediate Similarity NPD9697 Approved
0.7451 Intermediate Similarity NPD6799 Approved
0.745 Intermediate Similarity NPD2935 Discontinued
0.7448 Intermediate Similarity NPD1296 Phase 2
0.7447 Intermediate Similarity NPD2983 Phase 2
0.7447 Intermediate Similarity NPD2982 Phase 2
0.7434 Intermediate Similarity NPD6190 Approved
0.7431 Intermediate Similarity NPD4908 Phase 1
0.7429 Intermediate Similarity NPD1091 Approved
0.741 Intermediate Similarity NPD7074 Phase 3
0.7391 Intermediate Similarity NPD6234 Discontinued
0.7376 Intermediate Similarity NPD9717 Approved
0.7376 Intermediate Similarity NPD9269 Phase 2
0.7376 Intermediate Similarity NPD2981 Phase 2
0.7365 Intermediate Similarity NPD7993 Clinical (unspecified phase)
0.7365 Intermediate Similarity NPD6797 Phase 2
0.7362 Intermediate Similarity NPD6232 Discontinued
0.7361 Intermediate Similarity NPD9494 Approved
0.7348 Intermediate Similarity NPD1358 Approved
0.7347 Intermediate Similarity NPD1558 Phase 1
0.7343 Intermediate Similarity NPD1203 Approved
0.7338 Intermediate Similarity NPD4357 Discontinued
0.7329 Intermediate Similarity NPD7075 Discontinued
0.7329 Intermediate Similarity NPD4907 Clinical (unspecified phase)
0.7324 Intermediate Similarity NPD4749 Approved
0.7321 Intermediate Similarity NPD7251 Discontinued
0.7319 Intermediate Similarity NPD5536 Phase 2
0.7301 Intermediate Similarity NPD7199 Phase 2
0.7301 Intermediate Similarity NPD1247 Approved
0.7299 Intermediate Similarity NPD6671 Approved
0.729 Intermediate Similarity NPD4378 Clinical (unspecified phase)
0.7286 Intermediate Similarity NPD1778 Approved
0.7278 Intermediate Similarity NPD7808 Phase 3
0.7267 Intermediate Similarity NPD1510 Phase 2
0.7267 Intermediate Similarity NPD3748 Approved
0.7255 Intermediate Similarity NPD1878 Clinical (unspecified phase)
0.725 Intermediate Similarity NPD7096 Clinical (unspecified phase)
0.7241 Intermediate Similarity NPD2861 Phase 2
0.7239 Intermediate Similarity NPD5494 Approved
0.7237 Intermediate Similarity NPD1549 Phase 2
0.723 Intermediate Similarity NPD1240 Approved
0.7229 Intermediate Similarity NPD7473 Discontinued
0.7226 Intermediate Similarity NPD6143 Clinical (unspecified phase)
0.7222 Intermediate Similarity NPD2797 Approved
0.7222 Intermediate Similarity NPD4381 Clinical (unspecified phase)
0.7218 Intermediate Similarity NPD290 Approved
0.7212 Intermediate Similarity NPD7184 Clinical (unspecified phase)
0.7211 Intermediate Similarity NPD411 Approved
0.7197 Intermediate Similarity NPD6980 Clinical (unspecified phase)
0.7197 Intermediate Similarity NPD5403 Approved
0.7188 Intermediate Similarity NPD6801 Discontinued
0.7188 Intermediate Similarity NPD37 Approved
0.7183 Intermediate Similarity NPD1535 Discovery
0.7183 Intermediate Similarity NPD1611 Approved
0.7181 Intermediate Similarity NPD1933 Approved
0.7181 Intermediate Similarity NPD4340 Discontinued
0.7179 Intermediate Similarity NPD5401 Approved
0.7171 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7171 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.717 Intermediate Similarity NPD4380 Phase 2
0.717 Intermediate Similarity NPD6599 Discontinued
0.7163 Intermediate Similarity NPD4626 Approved
0.7162 Intermediate Similarity NPD6233 Phase 2
0.716 Intermediate Similarity NPD4966 Approved
0.716 Intermediate Similarity NPD4965 Approved
0.716 Intermediate Similarity NPD4967 Phase 2
0.7152 Intermediate Similarity NPD3687 Approved
0.7152 Intermediate Similarity NPD3686 Approved
0.7143 Intermediate Similarity NPD4625 Phase 3
0.7143 Intermediate Similarity NPD968 Approved
0.7143 Intermediate Similarity NPD7819 Suspended
0.7143 Intermediate Similarity NPD4628 Phase 3
0.7134 Intermediate Similarity NPD7314 Clinical (unspecified phase)
0.7133 Intermediate Similarity NPD1481 Phase 2
0.7133 Intermediate Similarity NPD1607 Approved
0.7114 Intermediate Similarity NPD943 Approved
0.7097 Intermediate Similarity NPD2219 Phase 1
0.7095 Intermediate Similarity NPD6410 Clinical (unspecified phase)
0.7095 Intermediate Similarity NPD3268 Approved
0.7092 Intermediate Similarity NPD9268 Approved
0.7089 Intermediate Similarity NPD920 Approved
0.7083 Intermediate Similarity NPD7228 Approved
0.7078 Intermediate Similarity NPD1243 Approved
0.7067 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7063 Intermediate Similarity NPD4678 Approved
0.7063 Intermediate Similarity NPD3705 Approved
0.7063 Intermediate Similarity NPD4675 Approved
0.7059 Intermediate Similarity NPD3540 Phase 1
0.7055 Intermediate Similarity NPD7768 Phase 2
0.7039 Intermediate Similarity NPD4308 Phase 3
0.703 Intermediate Similarity NPD5677 Discontinued
0.7029 Intermediate Similarity NPD5283 Phase 1
0.7027 Intermediate Similarity NPD7095 Approved
0.7021 Intermediate Similarity NPD9545 Approved
0.7019 Intermediate Similarity NPD7411 Suspended
0.7018 Intermediate Similarity NPD6559 Discontinued
0.7015 Intermediate Similarity NPD3134 Approved
0.7014 Intermediate Similarity NPD1608 Approved
0.6994 Remote Similarity NPD5353 Approved
0.6993 Remote Similarity NPD2796 Approved
0.6993 Remote Similarity NPD3539 Phase 1
0.6988 Remote Similarity NPD8127 Discontinued
0.698 Remote Similarity NPD6798 Discontinued
0.6972 Remote Similarity NPD1357 Approved
0.6972 Remote Similarity NPD5691 Approved
0.6968 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6962 Remote Similarity NPD2534 Approved
0.6962 Remote Similarity NPD7410 Clinical (unspecified phase)
0.6962 Remote Similarity NPD2532 Approved
0.6962 Remote Similarity NPD642 Clinical (unspecified phase)
0.6962 Remote Similarity NPD2533 Approved
0.6957 Remote Similarity NPD5535 Approved
0.6954 Remote Similarity NPD6355 Discontinued
0.6954 Remote Similarity NPD8055 Clinical (unspecified phase)
0.6948 Remote Similarity NPD5763 Approved
0.6948 Remote Similarity NPD5762 Approved
0.6943 Remote Similarity NPD643 Clinical (unspecified phase)
0.6939 Remote Similarity NPD1019 Discontinued
0.6932 Remote Similarity NPD8397 Clinical (unspecified phase)
0.6928 Remote Similarity NPD651 Clinical (unspecified phase)
0.6923 Remote Similarity NPD4109 Clinical (unspecified phase)
0.6923 Remote Similarity NPD4110 Phase 3
0.6919 Remote Similarity NPD7685 Pre-registration
0.6914 Remote Similarity NPD5090 Approved
0.6914 Remote Similarity NPD5089 Approved
0.6912 Remote Similarity NPD2684 Approved
0.6909 Remote Similarity NPD3749 Approved
0.6908 Remote Similarity NPD6653 Approved
0.6903 Remote Similarity NPD2424 Discontinued
0.6899 Remote Similarity NPD5297 Approved
0.6894 Remote Similarity NPD3111 Phase 1
0.6894 Remote Similarity NPD1242 Phase 1
0.6883 Remote Similarity NPD6100 Approved
0.6883 Remote Similarity NPD6099 Approved
0.6882 Remote Similarity NPD3751 Discontinued
0.6879 Remote Similarity NPD9493 Approved
0.6871 Remote Similarity NPD3266 Approved
0.6871 Remote Similarity NPD3267 Approved
0.6867 Remote Similarity NPD1048 Approved
0.6859 Remote Similarity NPD6674 Discontinued
0.6846 Remote Similarity NPD6832 Phase 2
0.6842 Remote Similarity NPD291 Approved
0.6842 Remote Similarity NPD846 Approved
0.6842 Remote Similarity NPD7804 Clinical (unspecified phase)
0.6842 Remote Similarity NPD940 Approved
0.6839 Remote Similarity NPD1375 Discontinued
0.6835 Remote Similarity NPD7843 Approved
0.6824 Remote Similarity NPD6917 Clinical (unspecified phase)
0.6818 Remote Similarity NPD7033 Discontinued
0.681 Remote Similarity NPD7615 Clinical (unspecified phase)
0.6809 Remote Similarity NPD7157 Approved
0.6807 Remote Similarity NPD6971 Discontinued

  Bioactivity similarity: Similar Natural Products in NPASS

Bioactivity similarity was calculated based on bioactivity descriptors of compounds. The bioactivity descriptors were calculated by a recently developed AI algorithm Chemical Checker (CC) [Nature Biotechnology, 38:1087–1096, 2020; Nature Communications, 12:3932, 2021], which evaluated bioactivity similarities at five levels:
☉ A: chemistry similarity;
☉ B: biological targets similarity;
☉ C: networks similarity;
☉ D: cell-based bioactivity similarity;
☉ E: similarity based on clinical data.

Those 5 categories of CC bioactivity descriptors were calculated and then subjected to manifold projection using UMAP algorithm, to project all NPs on a 2-Dimensional space. The current NP was highlighted with a small circle in the 2-D map. Below figures: left-to-right, A-to-E.

A: chemistry similarity
B: biological targets similarity
C: networks similarity
D: cell-based bioactivity similarity
E: similarity based on clinical data