Structure

Physi-Chem Properties

Molecular Weight:  150.07
Volume:  162.698
LogP:  2.691
LogD:  2.81
LogS:  -2.479
# Rotatable Bonds:  3
TPSA:  26.3
# H-Bond Aceptor:  2
# H-Bond Donor:  0
# Rings:  1
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.601
Synthetic Accessibility Score:  1.135
Fsp3:  0.222
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:  -4.225
MDCK Permeability:  3.5445533285383135e-05
Pgp-inhibitor:  0.002
Pgp-substrate:  0.0
Human Intestinal Absorption (HIA):  0.003
20% Bioavailability (F20%):  0.03
30% Bioavailability (F30%):  0.978

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.309
Plasma Protein Binding (PPB):  90.48834228515625%
Volume Distribution (VD):  1.765
Pgp-substrate:  7.0591630935668945%

ADMET: Metabolism

CYP1A2-inhibitor:  0.982
CYP1A2-substrate:  0.674
CYP2C19-inhibitor:  0.831
CYP2C19-substrate:  0.161
CYP2C9-inhibitor:  0.296
CYP2C9-substrate:  0.27
CYP2D6-inhibitor:  0.043
CYP2D6-substrate:  0.187
CYP3A4-inhibitor:  0.023
CYP3A4-substrate:  0.214

ADMET: Excretion

Clearance (CL):  11.339
Half-life (T1/2):  0.81

ADMET: Toxicity

hERG Blockers:  0.077
Human Hepatotoxicity (H-HT):  0.011
Drug-inuced Liver Injury (DILI):  0.468
AMES Toxicity:  0.009
Rat Oral Acute Toxicity:  0.014
Maximum Recommended Daily Dose:  0.007
Skin Sensitization:  0.42
Carcinogencity:  0.087
Eye Corrosion:  0.331
Eye Irritation:  0.993
Respiratory Toxicity:  0.075

Download Data

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

  Natural Product: NPC249912

Natural Product ID:  NPC249912
Common Name*:   Ethyl Benzoate
IUPAC Name:   ethyl benzoate
Synonyms:   Ethyl Benzoate
Standard InCHIKey:  MTZQAGJQAFMTAQ-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C9H10O2/c1-2-11-9(10)8-6-4-3-5-7-8/h3-7H,2H2,1H3
SMILES:  CCOC(=O)c1ccccc1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL510714
PubChem CID:   7165
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0002448] Benzenoids
      • [CHEMONTID:0002279] Benzene and substituted derivatives
        • [CHEMONTID:0000176] Benzoic acids and derivatives
          • [CHEMONTID:0001350] Benzoic acid esters

*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
NPO17774 Hemerocallis fulva Species Xanthorrhoeaceae Eukaryota Flowers n.a. n.a. DOI[10.1016/j.lwt.2014.11.023]
NPO26266 Isodon japonicus Species Lamiaceae Eukaryota n.a. n.a. n.a. DOI[10.1039/C39730000707]
NPO25769 Heterotheca inuloides Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[11473412]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[1402962]
NPO26927 Salacia madagascariensis Species Celastraceae Eukaryota n.a. root n.a. PMID[15730255]
NPO26927 Salacia madagascariensis Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[15730255]
NPO25870 Vaccinium vitis-idaea Species Ericaceae Eukaryota n.a. fruit n.a. PMID[16417304]
NPO15095 Hippophae rhamnoides Species Elaeagnaceae Eukaryota n.a. fruit n.a. PMID[16417304]
NPO26834 Eutypella scoparia Species Diatrypaceae Eukaryota n.a. n.a. n.a. PMID[16724861]
NPO15095 Hippophae rhamnoides Species Elaeagnaceae Eukaryota n.a. branch n.a. PMID[17202693]
NPO26211 Knightia excelsa Species Proteaceae Eukaryota n.a. n.a. n.a. PMID[17315967]
NPO16194 Morus bombycis Species Moraceae Eukaryota n.a. root n.a. PMID[17396934]
NPO26266 Isodon japonicus Species Lamiaceae Eukaryota n.a. n.a. n.a. PMID[18491868]
NPO26507 Galenia africana Species Aizoaceae Eukaryota leaf n.a. n.a. PMID[20035557]
NPO26654 Penicillium citreonigrum Species Aspergillaceae Eukaryota n.a. atlantic-forest-soil n.a. PMID[20450206]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. PMID[20815207]
NPO26834 Eutypella scoparia Species Diatrypaceae Eukaryota n.a. n.a. n.a. PMID[21302965]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. leaf n.a. PMID[21319773]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. bark n.a. PMID[21319773]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. root n.a. PMID[21319773]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. leaf n.a. PMID[22207282]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. root n.a. PMID[23806866]
NPO28265 Morus alba Species Moraceae Eukaryota root bark University of Veterinary and Pharmaceutical Sciences Brno (UVPS Brno), Brno, Czech Republic 2011-APR PMID[24901948]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. Konya, Turkey 2007-APR PMID[24901948]
NPO28265 Morus alba Species Moraceae Eukaryota leaves Chungbuk, Korea n.a. PMID[25935644]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. root n.a. PMID[25981820]
NPO25769 Heterotheca inuloides Species Asteraceae Eukaryota n.a. n.a. n.a. PMID[26566007]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota Flower Buds n.a. n.a. PMID[26977531]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. latex n.a. PMID[27294120]
NPO26451 Ophiocoma scolopendrina Species Ophiocomidae Eukaryota n.a. n.a. n.a. PMID[27684202]
NPO28265 Morus alba Species Moraceae Eukaryota Root barks n.a. n.a. PMID[3097265]
NPO26927 Salacia madagascariensis Species Celastraceae Eukaryota n.a. n.a. n.a. PMID[7288445]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. n.a. PMID[8904847]
NPO16194 Morus bombycis Species Moraceae Eukaryota n.a. n.a. n.a. PMID[9544568]
NPO15095 Hippophae rhamnoides Species Elaeagnaceae Eukaryota Bark n.a. n.a. Database[FooDB]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota Bark n.a. n.a. Database[FooDB]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota Essential Oil n.a. n.a. Database[FooDB]
NPO15095 Hippophae rhamnoides Species Elaeagnaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota Fruit n.a. n.a. Database[FooDB]
NPO15095 Hippophae rhamnoides Species Elaeagnaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota Leaf n.a. n.a. Database[FooDB]
NPO15095 Hippophae rhamnoides Species Elaeagnaceae Eukaryota Root n.a. n.a. Database[FooDB]
NPO15095 Hippophae rhamnoides Species Elaeagnaceae Eukaryota Seed n.a. n.a. Database[FooDB]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota Stem n.a. n.a. Database[FooDB]
NPO15095 Hippophae rhamnoides Species Elaeagnaceae Eukaryota n.a. n.a. Database[FooDB]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25870 Vaccinium vitis-idaea Species Ericaceae Eukaryota Fruits n.a. Database[FooDB]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. Database[FooDB]
NPO25870 Vaccinium vitis-idaea Species Ericaceae Eukaryota n.a. n.a. Database[FooDB]
NPO26134 Epimedium davidii Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO15095 Hippophae rhamnoides Species Elaeagnaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO16194 Morus bombycis Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO25870 Vaccinium vitis-idaea Species Ericaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO17774 Hemerocallis fulva Species Xanthorrhoeaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO22505 Bombax ceiba Species Malvaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO17774 Hemerocallis fulva Species Xanthorrhoeaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO16194 Morus bombycis Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26699 Leonurus glaucescens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5510 Lepidium draba Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO15095 Hippophae rhamnoides Species Elaeagnaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26349 Frullania tamarisci Species Frullaniaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO25870 Vaccinium vitis-idaea Species Ericaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO26134 Epimedium davidii Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO5510 Lepidium draba Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO16194 Morus bombycis Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO15095 Hippophae rhamnoides Species Elaeagnaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO25972 Eupolyphaga sinensis Species Corydiidae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17774 Hemerocallis fulva Species Xanthorrhoeaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO17774 Hemerocallis fulva Species Xanthorrhoeaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO15095 Hippophae rhamnoides Species Elaeagnaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO16194 Morus bombycis Species Moraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO26654 Penicillium citreonigrum Species Aspergillaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26834 Eutypella scoparia Species Diatrypaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO22505 Bombax ceiba Species Malvaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26184 Diphasia angolensis Species Rutaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25949 Streptomyces griseovariabilis Species Streptomycetaceae Bacteria n.a. n.a. n.a. Database[UNPD]
NPO25972 Eupolyphaga sinensis Species Corydiidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26406 Saussurea carthamoides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO3987 Syzygium aromaticum Species Myrtaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO17774 Hemerocallis fulva Species Xanthorrhoeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26584 Gnidia lamprantha Species Thymelaeaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25769 Heterotheca inuloides Species Asteraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26052 Swertia delavayi Species Gentianaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26624 Ilex amara Species Aquifoliaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26134 Epimedium davidii Species Berberidaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25739 Erysimum odoratum Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO2898 Quercus sessiliflora Species Fagaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25896 Bragantia wallichii n.a. n.a. n.a. n.a. n.a. n.a. Database[UNPD]
NPO25870 Vaccinium vitis-idaea Species Ericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25792 Delphinium andersoni Species Ranunculaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26023 Angelica tarokoensis Species Apiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26161 Globba malaccensis Species Zingiberaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26451 Ophiocoma scolopendrina Species Ophiocomidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26266 Isodon japonicus Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26927 Salacia madagascariensis Species Celastraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26607 Colobocentrotus atratus Species Echinidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26950 Maba buxifolia Species Ebenaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25923 Vismia jefensis Species Hypericaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO28265 Morus alba Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26287 Spodoptera eridania Species 0ctuidae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26374 Alangium premnifolium Species Cornaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26319 Solanum acaule Species Solanaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26211 Knightia excelsa Species Proteaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26699 Leonurus glaucescens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO25995 Laurencia distichophylla Species Rhodomelaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26561 Micromeria pineolens Species Lamiaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26507 Galenia africana Species Aizoaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26806 Nidula candida Species Nidulariaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO16194 Morus bombycis Species Moraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO15095 Hippophae rhamnoides Species Elaeagnaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26349 Frullania tamarisci Species Frullaniaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7447 Nemalion vermiculare Species Liagoraceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO5510 Lepidium draba Species Brassicaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO26900 Vallota purpurea n.a. n.a. n.a. 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
NPT591 Individual Protein Glycogen synthase kinase-3 beta Homo sapiens IC50 > 100000.0 nM PMID[567110]
NPT27 Others Unspecified log Ks = 2.73 n.a. PMID[567109]
NPT1280 Organism Thrips tabaci Thrips tabaci Ratio = 2.1 n.a. PMID[567111]
NPT1281 Organism Thrips obscuratus Thrips obscuratus Ratio = 24.8 n.a. PMID[567111]
NPT1281 Organism Thrips obscuratus Thrips obscuratus Ratio = 35.4 n.a. PMID[567111]
NPT29 Organism Rattus norvegicus Rattus norvegicus pLD50 = 7.65 n.a. PMID[567112]
NPT35 Others n.a. LogD = 2.4 n.a. PMID[567114]
NPT35 Others n.a. LogP = 2.6 n.a. PMID[567114]
NPT2 Others Unspecified Potency n.a. 27306 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 21689.9 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 76958.8 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 NPC249912 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 NPC276775
1.0 High Similarity NPC92754
0.989 High Similarity NPC35448
0.989 High Similarity NPC225060
0.989 High Similarity NPC78701
0.9783 High Similarity NPC146351
0.9778 High Similarity NPC130398
0.9677 High Similarity NPC70624
0.957 High Similarity NPC118343
0.9474 High Similarity NPC474365
0.9474 High Similarity NPC301943
0.9468 High Similarity NPC42211
0.9368 High Similarity NPC188895
0.9362 High Similarity NPC203925
0.9362 High Similarity NPC325497
0.9222 High Similarity NPC173443
0.9184 High Similarity NPC119271
0.9091 High Similarity NPC56493
0.9082 High Similarity NPC269457
0.9072 High Similarity NPC89886
0.9 High Similarity NPC265407
0.9 High Similarity NPC83628
0.9 High Similarity NPC10251
0.9 High Similarity NPC469636
0.9 High Similarity NPC89377
0.9 High Similarity NPC474364
0.9 High Similarity NPC17417
0.898 High Similarity NPC31786
0.8911 High Similarity NPC93084
0.8911 High Similarity NPC196246
0.8911 High Similarity NPC251854
0.8911 High Similarity NPC174099
0.8911 High Similarity NPC214067
0.8889 High Similarity NPC209632
0.8889 High Similarity NPC318107
0.8878 High Similarity NPC60679
0.8824 High Similarity NPC474157
0.8824 High Similarity NPC210089
0.8824 High Similarity NPC476003
0.8824 High Similarity NPC1082
0.8824 High Similarity NPC305912
0.8824 High Similarity NPC260818
0.8804 High Similarity NPC220893
0.88 High Similarity NPC30594
0.88 High Similarity NPC37622
0.8788 High Similarity NPC114594
0.8778 High Similarity NPC58616
0.8776 High Similarity NPC45613
0.8738 High Similarity NPC82899
0.8738 High Similarity NPC321852
0.8738 High Similarity NPC270699
0.8654 High Similarity NPC128368
0.8654 High Similarity NPC272524
0.8654 High Similarity NPC161611
0.8641 High Similarity NPC167504
0.8632 High Similarity NPC261181
0.8627 High Similarity NPC85493
0.8627 High Similarity NPC269023
0.8627 High Similarity NPC99846
0.8617 High Similarity NPC119631
0.8571 High Similarity NPC153053
0.8571 High Similarity NPC307651
0.8571 High Similarity NPC294134
0.8571 High Similarity NPC308744
0.8571 High Similarity NPC474363
0.8558 High Similarity NPC79496
0.8558 High Similarity NPC158282
0.8558 High Similarity NPC474314
0.8557 High Similarity NPC253423
0.8557 High Similarity NPC270654
0.8511 High Similarity NPC62765
0.8495 Intermediate Similarity NPC304760
0.8491 Intermediate Similarity NPC210092
0.8491 Intermediate Similarity NPC474685
0.8476 Intermediate Similarity NPC474176
0.8469 Intermediate Similarity NPC229242
0.8411 Intermediate Similarity NPC149691
0.8384 Intermediate Similarity NPC217621
0.8352 Intermediate Similarity NPC288903
0.8318 Intermediate Similarity NPC306740
0.8265 Intermediate Similarity NPC61944
0.8257 Intermediate Similarity NPC45104
0.8257 Intermediate Similarity NPC217423
0.8241 Intermediate Similarity NPC100353
0.8224 Intermediate Similarity NPC237366
0.8218 Intermediate Similarity NPC25458
0.8218 Intermediate Similarity NPC304873
0.8182 Intermediate Similarity NPC27633
0.8182 Intermediate Similarity NPC94298
0.8182 Intermediate Similarity NPC94637
0.8148 Intermediate Similarity NPC81808
0.8125 Intermediate Similarity NPC240108
0.8125 Intermediate Similarity NPC213156
0.8119 Intermediate Similarity NPC473325
0.8113 Intermediate Similarity NPC243355
0.8111 Intermediate Similarity NPC78517
0.8111 Intermediate Similarity NPC167577
0.8108 Intermediate Similarity NPC90522
0.8108 Intermediate Similarity NPC328459
0.8091 Intermediate Similarity NPC469574
0.8073 Intermediate Similarity NPC220540
0.8073 Intermediate Similarity NPC188907
0.8056 Intermediate Similarity NPC196075
0.8056 Intermediate Similarity NPC477411
0.8043 Intermediate Similarity NPC323103
0.8039 Intermediate Similarity NPC284477
0.8036 Intermediate Similarity NPC72977
0.8036 Intermediate Similarity NPC473243
0.8022 Intermediate Similarity NPC121800
0.8021 Intermediate Similarity NPC9822
0.802 Intermediate Similarity NPC228435
0.802 Intermediate Similarity NPC472318
0.802 Intermediate Similarity NPC98911
0.8 Intermediate Similarity NPC131192
0.8 Intermediate Similarity NPC128825
0.8 Intermediate Similarity NPC176228
0.8 Intermediate Similarity NPC470391
0.7981 Intermediate Similarity NPC105899
0.7965 Intermediate Similarity NPC50872
0.7961 Intermediate Similarity NPC255676
0.7961 Intermediate Similarity NPC234305
0.7961 Intermediate Similarity NPC160382
0.7959 Intermediate Similarity NPC77273
0.7957 Intermediate Similarity NPC270507
0.7941 Intermediate Similarity NPC282895
0.7938 Intermediate Similarity NPC185501
0.7935 Intermediate Similarity NPC89950
0.7935 Intermediate Similarity NPC303245
0.7928 Intermediate Similarity NPC240664
0.7912 Intermediate Similarity NPC170484
0.7909 Intermediate Similarity NPC226093
0.7905 Intermediate Similarity NPC1065
0.7895 Intermediate Similarity NPC26285
0.789 Intermediate Similarity NPC53953
0.7889 Intermediate Similarity NPC3672
0.7889 Intermediate Similarity NPC287790
0.7885 Intermediate Similarity NPC85977
0.7876 Intermediate Similarity NPC230951
0.7876 Intermediate Similarity NPC233282
0.787 Intermediate Similarity NPC212415
0.787 Intermediate Similarity NPC57879
0.787 Intermediate Similarity NPC23332
0.787 Intermediate Similarity NPC54626
0.7857 Intermediate Similarity NPC110704
0.7849 Intermediate Similarity NPC106313
0.7849 Intermediate Similarity NPC103387
0.7838 Intermediate Similarity NPC470860
0.783 Intermediate Similarity NPC249811
0.7826 Intermediate Similarity NPC472703
0.7826 Intermediate Similarity NPC223351
0.7826 Intermediate Similarity NPC291189
0.7826 Intermediate Similarity NPC69403
0.7822 Intermediate Similarity NPC325499
0.7818 Intermediate Similarity NPC474095
0.7818 Intermediate Similarity NPC252004
0.7812 Intermediate Similarity NPC96625
0.78 Intermediate Similarity NPC5472
0.7798 Intermediate Similarity NPC13784
0.7788 Intermediate Similarity NPC61779
0.7788 Intermediate Similarity NPC179686
0.7778 Intermediate Similarity NPC183648
0.7778 Intermediate Similarity NPC175393
0.7768 Intermediate Similarity NPC228318
0.7766 Intermediate Similarity NPC308619
0.7766 Intermediate Similarity NPC324835
0.7766 Intermediate Similarity NPC127491
0.7766 Intermediate Similarity NPC285773
0.7759 Intermediate Similarity NPC472704
0.7757 Intermediate Similarity NPC281604
0.7748 Intermediate Similarity NPC135730
0.7745 Intermediate Similarity NPC160548
0.7745 Intermediate Similarity NPC210529
0.7745 Intermediate Similarity NPC175852
0.7742 Intermediate Similarity NPC165212
0.7736 Intermediate Similarity NPC475203
0.7736 Intermediate Similarity NPC474376
0.7736 Intermediate Similarity NPC472316
0.7736 Intermediate Similarity NPC472315
0.7714 Intermediate Similarity NPC249067
0.7714 Intermediate Similarity NPC269644
0.77 Intermediate Similarity NPC23453
0.7699 Intermediate Similarity NPC293424
0.7692 Intermediate Similarity NPC295664
0.7692 Intermediate Similarity NPC221798
0.7692 Intermediate Similarity NPC246166
0.7692 Intermediate Similarity NPC184219
0.7692 Intermediate Similarity NPC125053
0.7685 Intermediate Similarity NPC234639
0.7672 Intermediate Similarity NPC475692
0.7672 Intermediate Similarity NPC474283
0.7658 Intermediate Similarity NPC228936
0.7642 Intermediate Similarity NPC128730
0.7636 Intermediate Similarity NPC17693
0.7632 Intermediate Similarity NPC204784
0.7629 Intermediate Similarity NPC286608
0.7629 Intermediate Similarity NPC169050
0.7629 Intermediate Similarity NPC322387
0.7627 Intermediate Similarity NPC49938
0.7627 Intermediate Similarity NPC470765
0.7627 Intermediate Similarity NPC476599

  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 NPC249912 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
0.957 High Similarity NPD1238 Approved
0.9 High Similarity NPD2182 Approved
0.898 High Similarity NPD164 Approved
0.8889 High Similarity NPD9259 Approved
0.8889 High Similarity NPD9257 Approved
0.8824 High Similarity NPD2181 Clinical (unspecified phase)
0.8632 High Similarity NPD1202 Approved
0.8511 High Similarity NPD9258 Approved
0.8511 High Similarity NPD9256 Approved
0.8182 Intermediate Similarity NPD9545 Approved
0.8163 Intermediate Similarity NPD9260 Approved
0.8 Intermediate Similarity NPD9493 Approved
0.7912 Intermediate Similarity NPD9490 Approved
0.787 Intermediate Similarity NPD1609 Clinical (unspecified phase)
0.7818 Intermediate Similarity NPD690 Clinical (unspecified phase)
0.7766 Intermediate Similarity NPD9491 Approved
0.7757 Intermediate Similarity NPD6831 Clinical (unspecified phase)
0.7745 Intermediate Similarity NPD9495 Approved
0.7739 Intermediate Similarity NPD6287 Discontinued
0.7727 Intermediate Similarity NPD1241 Discontinued
0.7723 Intermediate Similarity NPD1989 Approved
0.7714 Intermediate Similarity NPD1237 Approved
0.7692 Intermediate Similarity NPD2198 Approved
0.7692 Intermediate Similarity NPD2199 Approved
0.7685 Intermediate Similarity NPD2067 Discontinued
0.7629 Intermediate Similarity NPD1282 Approved
0.7629 Intermediate Similarity NPD1087 Approved
0.7627 Intermediate Similarity NPD552 Approved
0.7627 Intermediate Similarity NPD9567 Approved
0.7627 Intermediate Similarity NPD553 Approved
0.7619 Intermediate Similarity NPD9261 Approved
0.7609 Intermediate Similarity NPD225 Approved
0.7609 Intermediate Similarity NPD227 Approved
0.7586 Intermediate Similarity NPD518 Clinical (unspecified phase)
0.7576 Intermediate Similarity NPD3673 Approved
0.7576 Intermediate Similarity NPD3672 Approved
0.757 Intermediate Similarity NPD3134 Approved
0.7563 Intermediate Similarity NPD1019 Discontinued
0.7521 Intermediate Similarity NPD9717 Approved
0.75 Intermediate Similarity NPD1358 Approved
0.7477 Intermediate Similarity NPD5277 Phase 2
0.7475 Intermediate Similarity NPD800 Approved
0.7453 Intermediate Similarity NPD1930 Approved
0.7453 Intermediate Similarity NPD1931 Clinical (unspecified phase)
0.7453 Intermediate Similarity NPD1929 Approved
0.7438 Intermediate Similarity NPD6832 Phase 2
0.74 Intermediate Similarity NPD1090 Approved
0.74 Intermediate Similarity NPD1086 Approved
0.74 Intermediate Similarity NPD1089 Approved
0.7387 Intermediate Similarity NPD9508 Approved
0.7383 Intermediate Similarity NPD5909 Discontinued
0.7377 Intermediate Similarity NPD5952 Clinical (unspecified phase)
0.7368 Intermediate Similarity NPD226 Approved
0.7345 Intermediate Similarity NPD5951 Approved
0.7339 Intermediate Similarity NPD9265 Clinical (unspecified phase)
0.7339 Intermediate Similarity NPD9264 Approved
0.7339 Intermediate Similarity NPD9263 Approved
0.7339 Intermediate Similarity NPD9267 Approved
0.7333 Intermediate Similarity NPD2066 Phase 3
0.7304 Intermediate Similarity NPD2347 Approved
0.729 Intermediate Similarity NPD6647 Phase 2
0.7288 Intermediate Similarity NPD1547 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD74 Approved
0.7273 Intermediate Similarity NPD9266 Approved
0.7265 Intermediate Similarity NPD3412 Clinical (unspecified phase)
0.7255 Intermediate Similarity NPD1088 Approved
0.7238 Intermediate Similarity NPD5926 Approved
0.7236 Intermediate Similarity NPD7008 Discontinued
0.72 Intermediate Similarity NPD3373 Approved
0.7193 Intermediate Similarity NPD2629 Approved
0.719 Intermediate Similarity NPD1203 Approved
0.7184 Intermediate Similarity NPD1563 Approved
0.7157 Intermediate Similarity NPD1239 Approved
0.7156 Intermediate Similarity NPD9697 Approved
0.7143 Intermediate Similarity NPD1899 Clinical (unspecified phase)
0.7129 Intermediate Similarity NPD689 Discontinued
0.7115 Intermediate Similarity NPD1693 Approved
0.7097 Intermediate Similarity NPD9716 Approved
0.7094 Intermediate Similarity NPD1894 Discontinued
0.7083 Intermediate Similarity NPD3972 Approved
0.708 Intermediate Similarity NPD969 Suspended
0.7037 Intermediate Similarity NPD1932 Approved
0.7031 Intermediate Similarity NPD2670 Approved
0.7031 Intermediate Similarity NPD2567 Approved
0.7031 Intermediate Similarity NPD2569 Approved
0.7019 Intermediate Similarity NPD5122 Clinical (unspecified phase)
0.701 Intermediate Similarity NPD942 Approved
0.7008 Intermediate Similarity NPD230 Phase 1
0.7008 Intermediate Similarity NPD1933 Approved
0.6992 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6981 Remote Similarity NPD1566 Phase 3
0.6981 Remote Similarity NPD1564 Approved
0.6981 Remote Similarity NPD1565 Approved
0.6977 Remote Similarity NPD3170 Approved
0.6977 Remote Similarity NPD1109 Approved
0.6977 Remote Similarity NPD1110 Approved
0.6975 Remote Similarity NPD17 Approved
0.6975 Remote Similarity NPD7163 Clinical (unspecified phase)
0.6975 Remote Similarity NPD1362 Clinical (unspecified phase)
0.6975 Remote Similarity NPD1104 Approved
0.6967 Remote Similarity NPD1876 Approved
0.6967 Remote Similarity NPD5667 Approved
0.6961 Remote Similarity NPD5346 Phase 2
0.6961 Remote Similarity NPD5347 Phase 2
0.696 Remote Similarity NPD6039 Approved
0.6953 Remote Similarity NPD1654 Clinical (unspecified phase)
0.6953 Remote Similarity NPD3528 Clinical (unspecified phase)
0.6952 Remote Similarity NPD688 Clinical (unspecified phase)
0.6947 Remote Similarity NPD9294 Approved
0.6931 Remote Similarity NPD650 Approved
0.6931 Remote Similarity NPD4793 Discontinued
0.6929 Remote Similarity NPD4307 Phase 2
0.6905 Remote Similarity NPD411 Approved
0.6905 Remote Similarity NPD2313 Discontinued
0.6905 Remote Similarity NPD3764 Approved
0.6903 Remote Similarity NPD5237 Approved
0.6903 Remote Similarity NPD5236 Approved
0.6903 Remote Similarity NPD4234 Approved
0.6903 Remote Similarity NPD5235 Approved
0.6903 Remote Similarity NPD1752 Approved
0.6903 Remote Similarity NPD4233 Approved
0.6903 Remote Similarity NPD1756 Approved
0.6903 Remote Similarity NPD5239 Approved
0.6903 Remote Similarity NPD5240 Approved
0.6897 Remote Similarity NPD9281 Approved
0.6891 Remote Similarity NPD5585 Approved
0.6875 Remote Similarity NPD447 Suspended
0.687 Remote Similarity NPD2343 Clinical (unspecified phase)
0.687 Remote Similarity NPD7702 Clinical (unspecified phase)
0.686 Remote Similarity NPD1281 Approved
0.6855 Remote Similarity NPD2798 Approved
0.6852 Remote Similarity NPD7798 Approved
0.685 Remote Similarity NPD7713 Phase 3
0.6842 Remote Similarity NPD2201 Approved
0.6838 Remote Similarity NPD4198 Discontinued
0.6833 Remote Similarity NPD1778 Approved
0.6833 Remote Similarity NPD5306 Approved
0.6833 Remote Similarity NPD5305 Approved
0.6814 Remote Similarity NPD2329 Discontinued
0.6803 Remote Similarity NPD1608 Approved
0.68 Remote Similarity NPD9494 Approved
0.6797 Remote Similarity NPD3142 Approved
0.6797 Remote Similarity NPD3140 Approved
0.6794 Remote Similarity NPD1551 Phase 2
0.678 Remote Similarity NPD694 Clinical (unspecified phase)
0.6777 Remote Similarity NPD4136 Approved
0.6777 Remote Similarity NPD1889 Phase 1
0.6777 Remote Similarity NPD7457 Clinical (unspecified phase)
0.6777 Remote Similarity NPD4106 Approved
0.6777 Remote Similarity NPD4135 Approved
0.6774 Remote Similarity NPD2797 Approved
0.6774 Remote Similarity NPD3266 Approved
0.6774 Remote Similarity NPD3267 Approved
0.6772 Remote Similarity NPD9471 Clinical (unspecified phase)
0.6767 Remote Similarity NPD7421 Clinical (unspecified phase)
0.6765 Remote Similarity NPD506 Clinical (unspecified phase)
0.6754 Remote Similarity NPD1317 Discontinued
0.6754 Remote Similarity NPD3646 Clinical (unspecified phase)
0.6752 Remote Similarity NPD1246 Approved
0.675 Remote Similarity NPD5691 Approved
0.6748 Remote Similarity NPD182 Clinical (unspecified phase)
0.6724 Remote Similarity NPD2607 Approved
0.6721 Remote Similarity NPD4806 Approved
0.6721 Remote Similarity NPD4807 Approved
0.6719 Remote Similarity NPD520 Approved
0.6718 Remote Similarity NPD4308 Phase 3
0.6718 Remote Similarity NPD2799 Discontinued
0.6716 Remote Similarity NPD4628 Phase 3
0.6694 Remote Similarity NPD1283 Approved
0.6692 Remote Similarity NPD6414 Clinical (unspecified phase)
0.6667 Remote Similarity NPD2650 Approved
0.6667 Remote Similarity NPD6637 Approved
0.6667 Remote Similarity NPD2935 Discontinued
0.6667 Remote Similarity NPD454 Approved
0.6667 Remote Similarity NPD3887 Approved
0.6667 Remote Similarity NPD7609 Phase 3
0.6667 Remote Similarity NPD9250 Approved
0.6667 Remote Similarity NPD2652 Approved
0.6667 Remote Similarity NPD1481 Phase 2
0.6639 Remote Similarity NPD3496 Discontinued
0.6639 Remote Similarity NPD5291 Approved
0.6639 Remote Similarity NPD5292 Approved
0.6636 Remote Similarity NPD2550 Approved
0.6636 Remote Similarity NPD2552 Approved
0.6636 Remote Similarity NPD2553 Approved
0.6636 Remote Similarity NPD2549 Approved
0.6636 Remote Similarity NPD2558 Approved
0.6636 Remote Similarity NPD2555 Approved
0.6618 Remote Similarity NPD7236 Approved
0.6617 Remote Similarity NPD2346 Discontinued
0.6617 Remote Similarity NPD2355 Clinical (unspecified phase)
0.6617 Remote Similarity NPD7611 Approved
0.6617 Remote Similarity NPD2353 Approved
0.6613 Remote Similarity NPD4359 Approved
0.6613 Remote Similarity NPD5157 Phase 1
0.6613 Remote Similarity NPD5158 Clinical (unspecified phase)
0.6613 Remote Similarity NPD5159 Phase 2
0.6612 Remote Similarity NPD4105 Approved
0.6612 Remote Similarity NPD4102 Approved
0.661 Remote Similarity NPD4766 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