Structure

Physi-Chem Properties

Molecular Weight:  118.04
Volume:  128.056
LogP:  2.578
LogD:  2.802
LogS:  -2.684
# Rotatable Bonds:  0
TPSA:  13.14
# H-Bond Aceptor:  1
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  1

MedChem Properties

QED Drug-Likeness Score:  0.517
Synthetic Accessibility Score:  1.804
Fsp3:  0.0
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Rejected
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.214
MDCK Permeability:  2.6851521397475153e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.162
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.967
30% Bioavailability (F30%):  0.335

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.48
Plasma Protein Binding (PPB):  93.63190460205078%
Volume Distribution (VD):  1.57
Pgp-substrate:  8.825794219970703%

ADMET: Metabolism

CYP1A2-inhibitor:  0.989
CYP1A2-substrate:  0.84
CYP2C19-inhibitor:  0.841
CYP2C19-substrate:  0.195
CYP2C9-inhibitor:  0.156
CYP2C9-substrate:  0.383
CYP2D6-inhibitor:  0.139
CYP2D6-substrate:  0.624
CYP3A4-inhibitor:  0.031
CYP3A4-substrate:  0.257

ADMET: Excretion

Clearance (CL):  12.144
Half-life (T1/2):  0.682

ADMET: Toxicity

hERG Blockers:  0.083
Human Hepatotoxicity (H-HT):  0.058
Drug-inuced Liver Injury (DILI):  0.573
AMES Toxicity:  0.311
Rat Oral Acute Toxicity:  0.891
Maximum Recommended Daily Dose:  0.031
Skin Sensitization:  0.198
Carcinogencity:  0.821
Eye Corrosion:  0.912
Eye Irritation:  0.995
Respiratory Toxicity:  0.832

Download Data

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  Natural Product: NPC206007

Natural Product ID:  NPC206007
Common Name*:   Benzofuran
IUPAC Name:   1-benzofuran
Synonyms:   Benzofuran
Standard InCHIKey:  IANQTJSKSUMEQM-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C8H6O/c1-2-4-8-7(3-1)5-6-9-8/h1-6H
SMILES:  c1ccc2c(c1)occ2
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL363614
PubChem CID:   9223
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000002] Organoheterocyclic compounds
      • [CHEMONTID:0000301] Benzofurans

*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
NPO21707 Trichosanthes kirilowii Species Cucurbitaceae Eukaryota n.a. seed n.a. DOI[10.1016/S0031-9422(00)97029-8]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. rhizome n.a. DOI[10.1021/np100392m]
NPO29221 Sarcandra glabra Species Chloranthaceae Eukaryota Whole plant n.a. n.a. PMID[16643038]
NPO21707 Trichosanthes kirilowii Species Cucurbitaceae Eukaryota seeds n.a. n.a. PMID[18603435]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. root n.a. PMID[18975262]
NPO29221 Sarcandra glabra Species Chloranthaceae Eukaryota n.a. n.a. n.a. PMID[20038159]
NPO21707 Trichosanthes kirilowii Species Cucurbitaceae Eukaryota Seeds n.a. n.a. PMID[20469887]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota Rhizomes n.a. n.a. PMID[20879743]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[21807513]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. root n.a. PMID[23738470]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. rhizome n.a. PMID[23738470]
NPO18068 Curcuma phaeocaulis Species Zingiberaceae Eukaryota rhizomes n.a. n.a. PMID[23755850]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. PMID[24333010]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota Rhizomes n.a. n.a. PMID[25275213]
NPO29221 Sarcandra glabra Species Chloranthaceae Eukaryota aerial part n.a. n.a. PMID[25442304]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. PMID[9868158]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO8516 Dipsacus asperoides Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29221 Sarcandra glabra Species Chloranthaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17262 Polygala caudata Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO11301 Ulmus glabra Species Ulmaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO5949 Pericarpium arecae n.a. n.a. n.a. n.a. n.a. n.a. Database[HerDing]
NPO21707 Trichosanthes kirilowii Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO30762 Melilotus suaveolens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5949 Pericarpium arecae n.a. n.a. n.a. n.a. n.a. n.a. Database[TCMID]
NPO11301 Ulmus glabra Species Ulmaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17262 Polygala caudata Species Polygalaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO8516 Dipsacus asperoides Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO19849.1 Melilotus officinalis subsp. suaveolens Subspecies Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO21707 Trichosanthes kirilowii Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO463 Moschus berezovskii Species Moschidae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO23265 Dianthus caryophyllus Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO29221 Sarcandra glabra Species Chloranthaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO463 Moschus berezovskii Species Moschidae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO21707 Trichosanthes kirilowii Species Cucurbitaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO8516 Dipsacus asperoides Species Caprifoliaceae 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]
NPO30762 Melilotus suaveolens Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29221 Sarcandra glabra Species Chloranthaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO21707 Trichosanthes kirilowii Species Cucurbitaceae 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]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO18068 Curcuma phaeocaulis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO8516 Dipsacus asperoides Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7929 Curcuma zedoaria Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO463 Moschus berezovskii Species Moschidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO11301 Ulmus glabra Species Ulmaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29221 Sarcandra glabra Species Chloranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO10577 Loranthus glaber Species Loranthaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO23265 Dianthus caryophyllus Species Caryophyllaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO8516 Dipsacus asperoides Species Caprifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9997 Pandanus dubius Species Pandanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18176 Ephedra sinica Species Ephedraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22741 Curcuma kwangsiensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2618 Curcuma wenyujin Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO18068 Curcuma phaeocaulis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO19849.1 Melilotus officinalis subsp. suaveolens Subspecies Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO9210 Desmodium uncinatum Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17262 Polygala caudata Species Polygalaceae 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
NPT1066 Individual Protein Lysozyme Enterobacteria phage T4 Kd = 112000.0 nM PMID[490300]
NPT108 Individual Protein Estrogen receptor alpha Homo sapiens Potency n.a. 1258925.4 nM PMID[490302]
NPT46 Individual Protein Thyroid hormone receptor beta-1 Homo sapiens Potency n.a. 6.3 nM PMID[490303]
NPT249 Individual Protein Glucocorticoid receptor Homo sapiens Potency n.a. 12.6 nM PMID[490304]
NPT540 Individual Protein Bile acid receptor FXR Homo sapiens Potency n.a. 0.7 nM PMID[490304]
NPT155 Individual Protein Aryl hydrocarbon receptor Homo sapiens Potency n.a. 25118.9 nM PMID[490303]
NPT155 Individual Protein Aryl hydrocarbon receptor Homo sapiens Potency n.a. 1258925.4 nM PMID[490302]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 48557.7 nM PMID[490303]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 1000000.0 nM PMID[490302]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 66824.2 nM PMID[490304]
NPT11 Individual Protein Guanine nucleotide-binding protein G(s), subunit alpha Homo sapiens Potency n.a. 50118.7 nM PMID[490305]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 1258925.4 nM PMID[490302]
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 54941 nM PubChem BioAssay data set
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 15355.3 nM PubChem BioAssay data set
NPT106 Individual Protein Peroxisome proliferator-activated receptor delta Homo sapiens Potency n.a. 54941 nM PubChem BioAssay data set
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 43641.2 nM PubChem BioAssay data set
NPT162 Individual Protein Heat shock protein beta-1 Homo sapiens Potency n.a. 48966.2 nM PubChem BioAssay data set
NPT106 Individual Protein Peroxisome proliferator-activated receptor delta Homo sapiens Potency n.a. 61644.8 nM PubChem BioAssay data set
NPT163 Individual Protein Nuclear factor NF-kappa-B p105 subunit Homo sapiens Potency n.a. 61644.8 nM PubChem BioAssay data set
NPT191 Organism Hepatitis C virus Hepatitis C virus FC = 10.0 n.a. PMID[490301]
NPT99 Individual Protein Peroxisome proliferator-activated receptor gamma Homo sapiens Potency n.a. 1122018.5 nM PMID[490302]
NPT610 Others Molecular identity unknown Potency n.a. 794328.2 nM PMID[490302]
NPT2 Others Unspecified Ac50 n.a. 2.818 uM PMID[490306]
NPT2 Others Unspecified Ac50 n.a. 1.585 uM PMID[490306]
NPT2 Others Unspecified Ac50 n.a. 5.623 uM PMID[490306]
NPT2 Others Unspecified AC50 n.a. 10000.0 nM PMID[490306]
NPT2 Others Unspecified AC50 n.a. 5623.4 nM PMID[490306]
NPT2 Others Unspecified Potency n.a. 97.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 4896.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 54941 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 76958.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 12299.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 19.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 544.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 7.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 306.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 61130.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 34376.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 38570.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 13685.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 43277.1 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 309 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 21872.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 4897.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 4364.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 48557.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 68589.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 48966.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 245.4 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 19331.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 2.2 nM PubChem BioAssay data set
NPT74 Individual Protein Proto-oncogene c-JUN Homo sapiens Potency n.a. 54941 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 61644.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 4855.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 38895.2 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 123 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 30637.9 nM PubChem BioAssay data set

☑ 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 NPC206007 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
0.9138 High Similarity NPC246214
0.9091 High Similarity NPC50583
0.9052 High Similarity NPC137710
0.8689 High Similarity NPC83301
0.8618 High Similarity NPC141059
0.8583 High Similarity NPC115859
0.8571 High Similarity NPC42471
0.8547 High Similarity NPC205523
0.8534 High Similarity NPC53953
0.8534 High Similarity NPC279916
0.8525 High Similarity NPC11799
0.8525 High Similarity NPC141252
0.8516 High Similarity NPC209858
0.8512 High Similarity NPC314329
0.8487 Intermediate Similarity NPC32298
0.8475 Intermediate Similarity NPC316062
0.8475 Intermediate Similarity NPC59035
0.8475 Intermediate Similarity NPC79202
0.8462 Intermediate Similarity NPC252004
0.8417 Intermediate Similarity NPC54243
0.8417 Intermediate Similarity NPC35744
0.8403 Intermediate Similarity NPC217180
0.8403 Intermediate Similarity NPC312525
0.8387 Intermediate Similarity NPC470858
0.8372 Intermediate Similarity NPC324117
0.8372 Intermediate Similarity NPC265793
0.8346 Intermediate Similarity NPC475092
0.8333 Intermediate Similarity NPC59502
0.8306 Intermediate Similarity NPC471074
0.8306 Intermediate Similarity NPC473885
0.8291 Intermediate Similarity NPC22678
0.8264 Intermediate Similarity NPC201284
0.8258 Intermediate Similarity NPC233707
0.825 Intermediate Similarity NPC45104
0.8244 Intermediate Similarity NPC64157
0.8244 Intermediate Similarity NPC278832
0.8235 Intermediate Similarity NPC28054
0.8226 Intermediate Similarity NPC118853
0.8205 Intermediate Similarity NPC23332
0.8205 Intermediate Similarity NPC54626
0.8205 Intermediate Similarity NPC57879
0.8182 Intermediate Similarity NPC243704
0.8182 Intermediate Similarity NPC130976
0.8148 Intermediate Similarity NPC27220
0.814 Intermediate Similarity NPC473982
0.813 Intermediate Similarity NPC97566
0.8125 Intermediate Similarity NPC156768
0.8125 Intermediate Similarity NPC66246
0.8125 Intermediate Similarity NPC170546
0.8125 Intermediate Similarity NPC939
0.812 Intermediate Similarity NPC183648
0.8108 Intermediate Similarity NPC95755
0.8099 Intermediate Similarity NPC217423
0.8095 Intermediate Similarity NPC2771
0.8088 Intermediate Similarity NPC51146
0.8088 Intermediate Similarity NPC166858
0.8083 Intermediate Similarity NPC150895
0.808 Intermediate Similarity NPC93730
0.8062 Intermediate Similarity NPC183348
0.8062 Intermediate Similarity NPC282230
0.8053 Intermediate Similarity NPC84325
0.8049 Intermediate Similarity NPC230951
0.8033 Intermediate Similarity NPC187547
0.8033 Intermediate Similarity NPC171023
0.8033 Intermediate Similarity NPC152159
0.8033 Intermediate Similarity NPC21831
0.8017 Intermediate Similarity NPC45536
0.8017 Intermediate Similarity NPC470860
0.8016 Intermediate Similarity NPC193805
0.8016 Intermediate Similarity NPC107846
0.8 Intermediate Similarity NPC470976
0.8 Intermediate Similarity NPC15083
0.8 Intermediate Similarity NPC196979
0.8 Intermediate Similarity NPC470977
0.7971 Intermediate Similarity NPC246903
0.797 Intermediate Similarity NPC163029
0.7969 Intermediate Similarity NPC298884
0.7953 Intermediate Similarity NPC224657
0.7951 Intermediate Similarity NPC227660
0.7951 Intermediate Similarity NPC469954
0.7939 Intermediate Similarity NPC470859
0.7937 Intermediate Similarity NPC178382
0.7937 Intermediate Similarity NPC188377
0.7937 Intermediate Similarity NPC472888
0.7937 Intermediate Similarity NPC65735
0.7934 Intermediate Similarity NPC188907
0.7928 Intermediate Similarity NPC146316
0.7923 Intermediate Similarity NPC477645
0.7914 Intermediate Similarity NPC308799
0.7914 Intermediate Similarity NPC190572
0.7913 Intermediate Similarity NPC38209
0.791 Intermediate Similarity NPC29638
0.7907 Intermediate Similarity NPC125887
0.7899 Intermediate Similarity NPC290038
0.7886 Intermediate Similarity NPC293424
0.7869 Intermediate Similarity NPC474987
0.7869 Intermediate Similarity NPC476031
0.7869 Intermediate Similarity NPC476014
0.7863 Intermediate Similarity NPC279596
0.7863 Intermediate Similarity NPC11173
0.7857 Intermediate Similarity NPC113428
0.7857 Intermediate Similarity NPC198427
0.7857 Intermediate Similarity NPC61284
0.7852 Intermediate Similarity NPC62735
0.7851 Intermediate Similarity NPC292036
0.7842 Intermediate Similarity NPC208584
0.7836 Intermediate Similarity NPC215109
0.7836 Intermediate Similarity NPC307401
0.7836 Intermediate Similarity NPC170604
0.7829 Intermediate Similarity NPC22783
0.7829 Intermediate Similarity NPC41721
0.7829 Intermediate Similarity NPC161322
0.7826 Intermediate Similarity NPC158871
0.7826 Intermediate Similarity NPC117674
0.7826 Intermediate Similarity NPC298224
0.7823 Intermediate Similarity NPC473969
0.7812 Intermediate Similarity NPC52035
0.7801 Intermediate Similarity NPC306788
0.7801 Intermediate Similarity NPC266743
0.7794 Intermediate Similarity NPC112757
0.7786 Intermediate Similarity NPC228184
0.7786 Intermediate Similarity NPC245395
0.777 Intermediate Similarity NPC93241
0.777 Intermediate Similarity NPC469642
0.777 Intermediate Similarity NPC27798
0.7769 Intermediate Similarity NPC196034
0.7769 Intermediate Similarity NPC90903
0.7761 Intermediate Similarity NPC204592
0.776 Intermediate Similarity NPC470092
0.7752 Intermediate Similarity NPC474264
0.7752 Intermediate Similarity NPC237868
0.775 Intermediate Similarity NPC105249
0.775 Intermediate Similarity NPC233238
0.7746 Intermediate Similarity NPC88445
0.7742 Intermediate Similarity NPC291619
0.7742 Intermediate Similarity NPC254958
0.7734 Intermediate Similarity NPC255073
0.7734 Intermediate Similarity NPC56332
0.7734 Intermediate Similarity NPC4012
0.7731 Intermediate Similarity NPC259554
0.773 Intermediate Similarity NPC74539
0.773 Intermediate Similarity NPC304443
0.7727 Intermediate Similarity NPC324488
0.7727 Intermediate Similarity NPC301717
0.7721 Intermediate Similarity NPC202260
0.7717 Intermediate Similarity NPC311219
0.7717 Intermediate Similarity NPC291189
0.7717 Intermediate Similarity NPC69403
0.771 Intermediate Similarity NPC238309
0.7698 Intermediate Similarity NPC53192
0.7698 Intermediate Similarity NPC79557
0.7692 Intermediate Similarity NPC139891
0.7692 Intermediate Similarity NPC135303
0.7692 Intermediate Similarity NPC329707
0.7692 Intermediate Similarity NPC472406
0.7692 Intermediate Similarity NPC191104
0.7692 Intermediate Similarity NPC148423
0.7687 Intermediate Similarity NPC247743
0.768 Intermediate Similarity NPC4898
0.7676 Intermediate Similarity NPC95526
0.7674 Intermediate Similarity NPC88403
0.7674 Intermediate Similarity NPC473626
0.7674 Intermediate Similarity NPC165556
0.7674 Intermediate Similarity NPC4164
0.7669 Intermediate Similarity NPC284424
0.7669 Intermediate Similarity NPC293253
0.7664 Intermediate Similarity NPC473983
0.7664 Intermediate Similarity NPC201370
0.7661 Intermediate Similarity NPC208906
0.7661 Intermediate Similarity NPC131801
0.7661 Intermediate Similarity NPC144745
0.766 Intermediate Similarity NPC281398
0.7656 Intermediate Similarity NPC182646
0.7652 Intermediate Similarity NPC278787
0.7652 Intermediate Similarity NPC7569
0.7652 Intermediate Similarity NPC13755
0.7647 Intermediate Similarity NPC473356
0.7647 Intermediate Similarity NPC471521
0.7643 Intermediate Similarity NPC17262
0.7643 Intermediate Similarity NPC302181
0.7642 Intermediate Similarity NPC220540
0.7639 Intermediate Similarity NPC156244
0.7639 Intermediate Similarity NPC116604
0.7639 Intermediate Similarity NPC472407
0.763 Intermediate Similarity NPC125269
0.763 Intermediate Similarity NPC217914
0.7627 Intermediate Similarity NPC1065
0.7626 Intermediate Similarity NPC254010
0.7622 Intermediate Similarity NPC472298
0.7615 Intermediate Similarity NPC184391
0.7612 Intermediate Similarity NPC106247
0.7609 Intermediate Similarity NPC262635
0.76 Intermediate Similarity NPC87466
0.76 Intermediate Similarity NPC166591
0.7597 Intermediate Similarity NPC221798
0.7594 Intermediate Similarity NPC141549
0.7589 Intermediate Similarity NPC98926
0.7589 Intermediate Similarity NPC233791
0.7589 Intermediate Similarity NPC230943
0.7589 Intermediate Similarity NPC478166

  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 NPC206007 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
0.8512 High Similarity NPD1547 Clinical (unspecified phase)
0.8376 Intermediate Similarity NPD1241 Discontinued
0.8258 Intermediate Similarity NPD2343 Clinical (unspecified phase)
0.8088 Intermediate Similarity NPD643 Clinical (unspecified phase)
0.7971 Intermediate Similarity NPD642 Clinical (unspecified phase)
0.7907 Intermediate Similarity NPD6832 Phase 2
0.7852 Intermediate Similarity NPD2344 Approved
0.7752 Intermediate Similarity NPD1019 Discontinued
0.773 Intermediate Similarity NPD920 Approved
0.7717 Intermediate Similarity NPD9717 Approved
0.7692 Intermediate Similarity NPD9697 Approved
0.7674 Intermediate Similarity NPD1203 Approved
0.7626 Intermediate Similarity NPD2309 Approved
0.7609 Intermediate Similarity NPD1243 Approved
0.7597 Intermediate Similarity NPD1876 Approved
0.7578 Intermediate Similarity NPD3972 Approved
0.7519 Intermediate Similarity NPD2313 Discontinued
0.7518 Intermediate Similarity NPD1551 Phase 2
0.7518 Intermediate Similarity NPD2796 Approved
0.7483 Intermediate Similarity NPD5616 Clinical (unspecified phase)
0.7481 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7481 Intermediate Similarity NPD2798 Approved
0.7464 Intermediate Similarity NPD1471 Phase 3
0.741 Intermediate Similarity NPD1549 Phase 2
0.7407 Intermediate Similarity NPD3140 Approved
0.7407 Intermediate Similarity NPD4307 Phase 2
0.7407 Intermediate Similarity NPD3142 Approved
0.7405 Intermediate Similarity NPD3266 Approved
0.7405 Intermediate Similarity NPD3267 Approved
0.7357 Intermediate Similarity NPD7421 Clinical (unspecified phase)
0.7353 Intermediate Similarity NPD1933 Approved
0.7347 Intermediate Similarity NPD6280 Approved
0.7347 Intermediate Similarity NPD6279 Approved
0.7338 Intermediate Similarity NPD1550 Clinical (unspecified phase)
0.7338 Intermediate Similarity NPD1552 Clinical (unspecified phase)
0.7333 Intermediate Similarity NPD919 Approved
0.7323 Intermediate Similarity NPD1894 Discontinued
0.7319 Intermediate Similarity NPD3748 Approved
0.7319 Intermediate Similarity NPD2799 Discontinued
0.7302 Intermediate Similarity NPD9493 Approved
0.7279 Intermediate Similarity NPD1240 Approved
0.7273 Intermediate Similarity NPD2797 Approved
0.7265 Intermediate Similarity NPD1238 Approved
0.7259 Intermediate Similarity NPD411 Approved
0.7241 Intermediate Similarity NPD3869 Phase 3
0.7241 Intermediate Similarity NPD3873 Phase 3
0.7237 Intermediate Similarity NPD1247 Approved
0.7227 Intermediate Similarity NPD9261 Approved
0.7209 Intermediate Similarity NPD17 Approved
0.7194 Intermediate Similarity NPD4308 Phase 3
0.7194 Intermediate Similarity NPD1510 Phase 2
0.719 Intermediate Similarity NPD3134 Approved
0.7188 Intermediate Similarity NPD9545 Approved
0.7174 Intermediate Similarity NPD1607 Approved
0.7164 Intermediate Similarity NPD9494 Approved
0.7153 Intermediate Similarity NPD6799 Approved
0.7143 Intermediate Similarity NPD1049 Clinical (unspecified phase)
0.7132 Intermediate Similarity NPD3268 Approved
0.7132 Intermediate Similarity NPD1651 Approved
0.7131 Intermediate Similarity NPD1358 Approved
0.7131 Intermediate Similarity NPD290 Approved
0.7109 Intermediate Similarity NPD9092 Discovery
0.7103 Intermediate Similarity NPD5401 Approved
0.7103 Intermediate Similarity NPD4661 Approved
0.7103 Intermediate Similarity NPD4662 Approved
0.7101 Intermediate Similarity NPD447 Suspended
0.7097 Intermediate Similarity NPD2181 Clinical (unspecified phase)
0.7092 Intermediate Similarity NPD2346 Discontinued
0.7077 Intermediate Similarity NPD1778 Approved
0.7063 Intermediate Similarity NPD3750 Approved
0.7049 Intermediate Similarity NPD968 Approved
0.7045 Intermediate Similarity NPD1608 Approved
0.7045 Intermediate Similarity NPD1481 Phase 2
0.7023 Intermediate Similarity NPD3496 Discontinued
0.702 Intermediate Similarity NPD2296 Approved
0.7014 Intermediate Similarity NPD3887 Approved
0.7014 Intermediate Similarity NPD3295 Clinical (unspecified phase)
0.7007 Intermediate Similarity NPD6859 Clinical (unspecified phase)
0.7007 Intermediate Similarity NPD5403 Approved
0.7007 Intermediate Similarity NPD6798 Discontinued
0.7 Intermediate Similarity NPD5585 Approved
0.6992 Remote Similarity NPD9263 Approved
0.6992 Remote Similarity NPD9267 Approved
0.6992 Remote Similarity NPD9264 Approved
0.6978 Remote Similarity NPD4618 Approved
0.6978 Remote Similarity NPD6355 Discontinued
0.6978 Remote Similarity NPD4622 Approved
0.6974 Remote Similarity NPD4947 Clinical (unspecified phase)
0.6972 Remote Similarity NPD2353 Approved
0.6972 Remote Similarity NPD2355 Clinical (unspecified phase)
0.697 Remote Similarity NPD1281 Approved
0.697 Remote Similarity NPD1535 Discovery
0.6968 Remote Similarity NPD5668 Clinical (unspecified phase)
0.6968 Remote Similarity NPD6808 Phase 2
0.6953 Remote Similarity NPD2557 Approved
0.6944 Remote Similarity NPD4628 Phase 3
0.694 Remote Similarity NPD3225 Approved
0.6935 Remote Similarity NPD74 Approved
0.6935 Remote Similarity NPD9266 Approved
0.6935 Remote Similarity NPD2684 Approved
0.6928 Remote Similarity NPD3749 Approved
0.6913 Remote Similarity NPD5808 Clinical (unspecified phase)
0.6912 Remote Similarity NPD454 Approved
0.6905 Remote Similarity NPD1609 Clinical (unspecified phase)
0.6901 Remote Similarity NPD2935 Discontinued
0.6899 Remote Similarity NPD405 Clinical (unspecified phase)
0.6884 Remote Similarity NPD1296 Phase 2
0.6879 Remote Similarity NPD5688 Approved
0.6879 Remote Similarity NPD4575 Clinical (unspecified phase)
0.6879 Remote Similarity NPD5689 Approved
0.6871 Remote Similarity NPD4378 Clinical (unspecified phase)
0.687 Remote Similarity NPD5691 Approved
0.6867 Remote Similarity NPD6599 Discontinued
0.6863 Remote Similarity NPD3882 Suspended
0.685 Remote Similarity NPD5535 Approved
0.6849 Remote Similarity NPD7440 Discontinued
0.6846 Remote Similarity NPD5536 Phase 2
0.6839 Remote Similarity NPD710 Clinical (unspecified phase)
0.6832 Remote Similarity NPD6559 Discontinued
0.6828 Remote Similarity NPD1878 Clinical (unspecified phase)
0.6828 Remote Similarity NPD7003 Approved
0.6824 Remote Similarity NPD6273 Approved
0.6821 Remote Similarity NPD7411 Suspended
0.6815 Remote Similarity NPD3926 Phase 2
0.6815 Remote Similarity NPD1283 Approved
0.6806 Remote Similarity NPD2897 Discontinued
0.6803 Remote Similarity NPD1511 Approved
0.68 Remote Similarity NPD2651 Approved
0.68 Remote Similarity NPD2182 Approved
0.68 Remote Similarity NPD2649 Approved
0.6794 Remote Similarity NPD1548 Phase 1
0.6792 Remote Similarity NPD7893 Clinical (unspecified phase)
0.6792 Remote Similarity NPD2163 Approved
0.6783 Remote Similarity NPD4477 Approved
0.6783 Remote Similarity NPD4476 Approved
0.6781 Remote Similarity NPD2354 Approved
0.6779 Remote Similarity NPD5586 Clinical (unspecified phase)
0.6776 Remote Similarity NPD6844 Discontinued
0.6763 Remote Similarity NPD3764 Approved
0.6759 Remote Similarity NPD2654 Approved
0.6757 Remote Similarity NPD7410 Clinical (unspecified phase)
0.675 Remote Similarity NPD3050 Clinical (unspecified phase)
0.6748 Remote Similarity NPD1237 Approved
0.6748 Remote Similarity NPD164 Approved
0.6742 Remote Similarity NPD3444 Approved
0.6742 Remote Similarity NPD3445 Approved
0.6742 Remote Similarity NPD3049 Approved
0.6742 Remote Similarity NPD3443 Approved
0.6741 Remote Similarity NPD4359 Approved
0.6738 Remote Similarity NPD1184 Approved
0.6732 Remote Similarity NPD1006 Clinical (unspecified phase)
0.6732 Remote Similarity NPD7096 Clinical (unspecified phase)
0.6732 Remote Similarity NPD7819 Suspended
0.6731 Remote Similarity NPD5494 Approved
0.672 Remote Similarity NPD9265 Clinical (unspecified phase)
0.6719 Remote Similarity NPD821 Approved
0.6719 Remote Similarity NPD7843 Approved
0.6716 Remote Similarity NPD1611 Approved
0.6716 Remote Similarity NPD422 Phase 1
0.6715 Remote Similarity NPD5647 Approved
0.6714 Remote Similarity NPD4062 Phase 3
0.6714 Remote Similarity NPD6233 Phase 2
0.6713 Remote Similarity NPD7033 Discontinued
0.6711 Remote Similarity NPD5049 Phase 3
0.6711 Remote Similarity NPD5889 Approved
0.6711 Remote Similarity NPD5890 Approved
0.6711 Remote Similarity NPD1512 Approved
0.6709 Remote Similarity NPD644 Clinical (unspecified phase)
0.6692 Remote Similarity NPD2556 Approved
0.6692 Remote Similarity NPD2554 Approved
0.6689 Remote Similarity NPD3226 Approved
0.6688 Remote Similarity NPD5402 Approved
0.6667 Remote Similarity NPD1934 Approved
0.6667 Remote Similarity NPD9257 Approved
0.6667 Remote Similarity NPD6801 Discontinued
0.6667 Remote Similarity NPD1182 Approved
0.6667 Remote Similarity NPD9259 Approved
0.6667 Remote Similarity NPD592 Approved
0.6667 Remote Similarity NPD594 Approved
0.6667 Remote Similarity NPD2979 Phase 3
0.6645 Remote Similarity NPD7768 Phase 2
0.6645 Remote Similarity NPD4380 Phase 2
0.6644 Remote Similarity NPD7004 Clinical (unspecified phase)
0.6643 Remote Similarity NPD743 Approved
0.6641 Remote Similarity NPD3596 Phase 2
0.6623 Remote Similarity NPD957 Approved
0.6623 Remote Similarity NPD2393 Clinical (unspecified phase)
0.6621 Remote Similarity NPD6003 Clinical (unspecified phase)
0.6621 Remote Similarity NPD6002 Phase 3
0.6621 Remote Similarity NPD6006 Clinical (unspecified phase)
0.6621 Remote Similarity NPD6005 Phase 3
0.6621 Remote Similarity NPD6004 Phase 3
0.6615 Remote Similarity NPD9281 Approved
0.6615 Remote Similarity NPD690 Clinical (unspecified phase)
0.6603 Remote Similarity NPD4381 Clinical (unspecified phase)
0.6603 Remote Similarity NPD7075 Discontinued
0.6596 Remote Similarity NPD8032 Phase 2
0.6593 Remote Similarity NPD1201 Approved
0.6593 Remote Similarity NPD1610 Phase 2
0.6587 Remote Similarity NPD6040 Clinical (unspecified phase)

  Bioactivity similarity: Similar Natural Products in NPASS

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

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

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