Structure

Physi-Chem Properties

Molecular Weight:  224.08
Volume:  247.372
LogP:  2.63
LogD:  2.709
LogS:  -4.07
# Rotatable Bonds:  4
TPSA:  34.14
# H-Bond Aceptor:  2
# H-Bond Donor:  0
# Rings:  2
# Heavy Atoms:  2

MedChem Properties

QED Drug-Likeness Score:  0.59
Synthetic Accessibility Score:  1.477
Fsp3:  0.067
Lipinski Rule-of-5:  Accepted
Pfizer Rule:  Accepted
GSK Rule:  Accepted
BMS Rule:  0
Golden Triangle Rule:  Accepted
Chelating Alert:  0
PAINS Alert:  0

ADMET Properties (ADMETlab2.0)

ADMET: Absorption

Caco-2 Permeability:  -4.545
MDCK Permeability:  2.9701495805056766e-05
Pgp-inhibitor:  0.043
Pgp-substrate:  0.001
Human Intestinal Absorption (HIA):  0.005
20% Bioavailability (F20%):  0.377
30% Bioavailability (F30%):  0.005

ADMET: Distribution

Blood-Brain-Barrier Penetration (BBB):  0.751
Plasma Protein Binding (PPB):  87.40111541748047%
Volume Distribution (VD):  0.309
Pgp-substrate:  5.142519474029541%

ADMET: Metabolism

CYP1A2-inhibitor:  0.979
CYP1A2-substrate:  0.134
CYP2C19-inhibitor:  0.95
CYP2C19-substrate:  0.065
CYP2C9-inhibitor:  0.877
CYP2C9-substrate:  0.102
CYP2D6-inhibitor:  0.016
CYP2D6-substrate:  0.08
CYP3A4-inhibitor:  0.079
CYP3A4-substrate:  0.178

ADMET: Excretion

Clearance (CL):  7.349
Half-life (T1/2):  0.665

ADMET: Toxicity

hERG Blockers:  0.052
Human Hepatotoxicity (H-HT):  0.04
Drug-inuced Liver Injury (DILI):  0.963
AMES Toxicity:  0.481
Rat Oral Acute Toxicity:  0.215
Maximum Recommended Daily Dose:  0.012
Skin Sensitization:  0.84
Carcinogencity:  0.408
Eye Corrosion:  0.792
Eye Irritation:  0.987
Respiratory Toxicity:  0.867

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

  Natural Product: NPC273758

Natural Product ID:  NPC273758
Common Name*:   Dibenzoylmethane
IUPAC Name:   1,3-diphenylpropane-1,3-dione
Synonyms:   Dibenzoylmethane
Standard InCHIKey:  NZZIMKJIVMHWJC-UHFFFAOYSA-N
Standard InCHI:  InChI=1S/C15H12O2/c16-14(12-7-3-1-4-8-12)11-15(17)13-9-5-2-6-10-13/h1-10H,11H2
SMILES:  O=C(c1ccccc1)CC(=O)c1ccccc1
Synthetic Gene Cluster:   n.a.
ChEMBL Identifier:   CHEMBL371523
PubChem CID:   8433
Chemical Classification**:  
  • CHEMONTID:0000000 [Organic compounds]
    • [CHEMONTID:0000261] Phenylpropanoids and polyketides
      • [CHEMONTID:0003467] Linear 1,3-diarylpropanoids
        • [CHEMONTID:0001630] Chalcones and dihydrochalcones
          • [CHEMONTID:0003475] Retro-dihydrochalcones

*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
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota Leaves n.a. n.a. PMID[12713396]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. root n.a. PMID[16441081]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[16675659]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota roots n.a. n.a. PMID[20022509]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[21123068]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[21866899]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[22074222]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. root n.a. PMID[22074222]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[23325115]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota Roots n.a. n.a. PMID[23541646]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. rhizome n.a. PMID[23867078]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. root n.a. PMID[23867078]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[24479468]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota roots n.a. n.a. PMID[24957203]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[25445757]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[25744461]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[26841168]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[28140583]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[28522265]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[29641206]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[32196343]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. PMID[7381508]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[HerDing]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCMID]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TCM_Taiwan]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO7154 Glycyrrhiza uralensis Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[TM-MC]
NPO1698 Glycyrrhiza inflata Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO29384 Glycyrrhiza glabra Species Fabaceae Eukaryota n.a. n.a. n.a. Database[UNPD]
NPO7154 Glycyrrhiza uralensis Species Fabaceae 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
NPT203 Individual Protein Carboxylesterase 2 Homo sapiens Ki > 100000.0 nM PMID[466603]
NPT166 Individual Protein Acyl coenzyme A:cholesterol acyltransferase Homo sapiens Ki = 26000.0 nM PMID[466603]
NPT2610 Individual Protein Acyl coenzyme A:cholesterol acyltransferase Oryctolagus cuniculus Ki = 3950.0 nM PMID[466603]
NPT204 Individual Protein Acetylcholinesterase Homo sapiens Ki > 100000.0 nM PMID[466603]
NPT439 Individual Protein Butyrylcholinesterase Homo sapiens Ki > 100000.0 nM PMID[466603]
NPT111 Cell Line K562 Homo sapiens IC50 = 30900.0 nM PMID[466604]
NPT4064 Individual Protein Hormone-sensitive lipase Rattus norvegicus Inhibition = 28.0 % PMID[466605]
NPT48 Individual Protein Lysine-specific demethylase 4D-like Homo sapiens Potency = 28183.8 nM PMID[466606]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency = 22387.2 nM PMID[466606]
NPT531 Individual Protein Nuclear receptor ROR-gamma Mus musculus Potency = 7943.3 nM PMID[466606]
NPT51 Individual Protein Microtubule-associated protein tau Homo sapiens Potency = 8912.5 nM PMID[466606]
NPT282 Individual Protein MAP kinase ERK2 Homo sapiens Potency = 6309.6 nM PMID[466606]
NPT151 Individual Protein 15-hydroxyprostaglandin dehydrogenase [NAD+] Homo sapiens Potency = 39810.7 nM PMID[466606]
NPT109 Individual Protein Cytochrome P450 3A4 Homo sapiens Potency = 12589.3 nM PMID[466606]
NPT531 Individual Protein Nuclear receptor ROR-gamma Mus musculus Potency = 3981.1 nM PMID[466606]
NPT61 Individual Protein Beta-glucocerebrosidase Homo sapiens Potency n.a. 39810.7 nM PMID[466606]
NPT532 Individual Protein Lysine-specific demethylase 4A Homo sapiens Potency n.a. 70794.6 nM PMID[466607]
NPT135 Individual Protein Chromobox protein homolog 1 Homo sapiens Potency n.a. 89125.1 nM PMID[466607]
NPT65 Cell Line HepG2 Homo sapiens Potency n.a. 35481.3 nM PMID[466607]
NPT71 Cell Line HEK293 Homo sapiens Potency n.a. 10000.0 nM PMID[466607]
NPT444 Individual Protein Ubiquitin carboxyl-terminal hydrolase 1 Homo sapiens Potency n.a. 50118.7 nM PMID[466606]
NPT101 Individual Protein Glucagon-like peptide 1 receptor Homo sapiens Potency n.a. 11220.2 nM PMID[466607]
NPT11 Individual Protein Guanine nucleotide-binding protein G(s), subunit alpha Homo sapiens Potency n.a. 35481.3 nM PMID[466607]
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 14125.4 nM PMID[466607]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 20596.2 nM PMID[466606]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 29092.9 nM PMID[466607]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 18356.4 nM PMID[466607]
NPT50 Individual Protein Tyrosyl-DNA phosphodiesterase 1 Homo sapiens Potency n.a. 18356.4 nM PMID[466606]
NPT83 Cell Line MCF7 Homo sapiens Activity = 84.0 % PMID[466609]
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 29581.6 nM PubChem BioAssay data set
NPT153 Individual Protein Androgen Receptor Homo sapiens Potency n.a. 26150.3 nM PubChem BioAssay data set
NPT152 Individual Protein Nuclear factor erythroid 2-related factor 2 Homo sapiens Potency n.a. 23306.5 nM PubChem BioAssay data set
NPT163 Individual Protein Nuclear factor NF-kappa-B p105 subunit Homo sapiens Potency n.a. 37241 nM PubChem BioAssay data set
NPT93 Individual Protein Survival motor neuron protein Homo sapiens Potency = 12589.3 nM PMID[466606]
NPT791 Individual Protein Cruzipain Trypanosoma cruzi Potency = 39810.7 nM PMID[466606]
NPT792 Individual Protein Arachidonate 15-lipoxygenase Homo sapiens Potency = 10000.0 nM PMID[466606]
NPT197 Protein-Protein Interaction Menin/Histone-lysine N-methyltransferase MLL Homo sapiens Potency = 25118.9 nM PMID[466606]
NPT2 Others Unspecified Potency n.a. 3548.1 nM PMID[466607]
NPT2 Others Unspecified AbsAC40_uM n.a. 2.47 uM PMID[466607]
NPT73 Individual Protein Solute carrier organic anion transporter family member 1B1 Homo sapiens Inhibition = 129.7 % PMID[466608]
NPT72 Individual Protein Solute carrier organic anion transporter family member 1B3 Homo sapiens Inhibition = 118.37 % PMID[466608]
NPT2 Others Unspecified Potency n.a. 5011.9 nM PMID[466606]
NPT2 Others Unspecified Potency n.a. 15848.9 nM PMID[466607]
NPT2 Others Unspecified Potency n.a. 1778.3 nM PMID[466606]
NPT2 Others Unspecified Potency n.a. 5623.4 nM PMID[466606]
NPT2 Others Unspecified Potency n.a. 3981.1 nM PMID[466607]
NPT2 Others Unspecified Potency n.a. 11680.9 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 74616.9 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 927.8 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 65686.7 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 4650.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 26150.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 66224.9 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 1650 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 36938.3 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 23306.5 nM PubChem BioAssay data set
NPT74 Individual Protein Proto-oncogene c-JUN Homo sapiens Potency n.a. 59023 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 29581.6 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 8269.5 nM PubChem BioAssay data set
NPT2 Others Unspecified Potency n.a. 3693.8 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 NPC273758 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
0.974 High Similarity NPC273033
0.974 High Similarity NPC12936
0.961 High Similarity NPC71664
0.9359 High Similarity NPC164086
0.9268 High Similarity NPC69057
0.9231 High Similarity NPC300205
0.9221 High Similarity NPC245966
0.9114 High Similarity NPC190567
0.9114 High Similarity NPC95868
0.9103 High Similarity NPC36342
0.9103 High Similarity NPC285470
0.9103 High Similarity NPC2785
0.9 High Similarity NPC145053
0.8987 High Similarity NPC151405
0.8987 High Similarity NPC139901
0.8987 High Similarity NPC272260
0.8941 High Similarity NPC19256
0.8929 High Similarity NPC267262
0.8824 High Similarity NPC113307
0.8824 High Similarity NPC418308
0.878 High Similarity NPC215008
0.8765 High Similarity NPC73978
0.8734 High Similarity NPC9796
0.8734 High Similarity NPC179726
0.8721 High Similarity NPC277277
0.8706 High Similarity NPC157778
0.8642 High Similarity NPC477703
0.8636 High Similarity NPC289883
0.8588 High Similarity NPC43945
0.8523 High Similarity NPC59677
0.8506 High Similarity NPC173413
0.8471 Intermediate Similarity NPC160339
0.8471 Intermediate Similarity NPC307
0.8462 Intermediate Similarity NPC285679
0.8409 Intermediate Similarity NPC133461
0.8409 Intermediate Similarity NPC284475
0.8391 Intermediate Similarity NPC325709
0.8353 Intermediate Similarity NPC123476
0.8333 Intermediate Similarity NPC324624
0.8333 Intermediate Similarity NPC74458
0.8333 Intermediate Similarity NPC197581
0.8333 Intermediate Similarity NPC472880
0.8315 Intermediate Similarity NPC153885
0.8315 Intermediate Similarity NPC188844
0.8315 Intermediate Similarity NPC155232
0.8315 Intermediate Similarity NPC1682
0.8261 Intermediate Similarity NPC49994
0.8222 Intermediate Similarity NPC238219
0.8202 Intermediate Similarity NPC103346
0.8193 Intermediate Similarity NPC285716
0.8193 Intermediate Similarity NPC17408
0.8152 Intermediate Similarity NPC239185
0.8148 Intermediate Similarity NPC78500
0.814 Intermediate Similarity NPC252067
0.8132 Intermediate Similarity NPC260233
0.8118 Intermediate Similarity NPC39600
0.8111 Intermediate Similarity NPC323420
0.8095 Intermediate Similarity NPC100039
0.8085 Intermediate Similarity NPC472879
0.8077 Intermediate Similarity NPC98880
0.8065 Intermediate Similarity NPC134882
0.8043 Intermediate Similarity NPC219573
0.8043 Intermediate Similarity NPC185208
0.7975 Intermediate Similarity NPC95289
0.7957 Intermediate Similarity NPC240042
0.7957 Intermediate Similarity NPC265220
0.7952 Intermediate Similarity NPC76455
0.7952 Intermediate Similarity NPC103488
0.7952 Intermediate Similarity NPC137847
0.7949 Intermediate Similarity NPC311343
0.7917 Intermediate Similarity NPC329556
0.7917 Intermediate Similarity NPC474866
0.7917 Intermediate Similarity NPC472691
0.7917 Intermediate Similarity NPC475939
0.7917 Intermediate Similarity NPC471829
0.7901 Intermediate Similarity NPC208075
0.7895 Intermediate Similarity NPC476993
0.7895 Intermediate Similarity NPC109514
0.7889 Intermediate Similarity NPC110420
0.7889 Intermediate Similarity NPC303967
0.7889 Intermediate Similarity NPC67585
0.7872 Intermediate Similarity NPC75724
0.7865 Intermediate Similarity NPC477704
0.7865 Intermediate Similarity NPC473345
0.7865 Intermediate Similarity NPC153308
0.7865 Intermediate Similarity NPC477693
0.7849 Intermediate Similarity NPC12695
0.7835 Intermediate Similarity NPC249067
0.7831 Intermediate Similarity NPC329318
0.7826 Intermediate Similarity NPC34243
0.7826 Intermediate Similarity NPC261181
0.7802 Intermediate Similarity NPC110704
0.7778 Intermediate Similarity NPC231591
0.7778 Intermediate Similarity NPC271437
0.7755 Intermediate Similarity NPC134120
0.7755 Intermediate Similarity NPC167336
0.7701 Intermediate Similarity NPC149263
0.7692 Intermediate Similarity NPC58872
0.7677 Intermediate Similarity NPC472700
0.7677 Intermediate Similarity NPC472699
0.764 Intermediate Similarity NPC164526
0.7634 Intermediate Similarity NPC246757
0.7634 Intermediate Similarity NPC291070
0.7619 Intermediate Similarity NPC298023
0.7609 Intermediate Similarity NPC141607
0.7609 Intermediate Similarity NPC187725
0.7609 Intermediate Similarity NPC476484
0.76 Intermediate Similarity NPC472695
0.76 Intermediate Similarity NPC472696
0.76 Intermediate Similarity NPC203732
0.76 Intermediate Similarity NPC472683
0.76 Intermediate Similarity NPC472701
0.7579 Intermediate Similarity NPC289201
0.7579 Intermediate Similarity NPC156021
0.7579 Intermediate Similarity NPC103048
0.7556 Intermediate Similarity NPC194326
0.7551 Intermediate Similarity NPC247976
0.7551 Intermediate Similarity NPC274443
0.7551 Intermediate Similarity NPC255676
0.7528 Intermediate Similarity NPC95965
0.7527 Intermediate Similarity NPC77273
0.7526 Intermediate Similarity NPC42211
0.7526 Intermediate Similarity NPC112552
0.7475 Intermediate Similarity NPC329282
0.7449 Intermediate Similarity NPC244427
0.7449 Intermediate Similarity NPC222390
0.7449 Intermediate Similarity NPC25458
0.7444 Intermediate Similarity NPC318107
0.7439 Intermediate Similarity NPC326200
0.7426 Intermediate Similarity NPC141523
0.7423 Intermediate Similarity NPC118343
0.7407 Intermediate Similarity NPC16190
0.7407 Intermediate Similarity NPC235059
0.7407 Intermediate Similarity NPC169222
0.7403 Intermediate Similarity NPC246588
0.74 Intermediate Similarity NPC474910
0.74 Intermediate Similarity NPC105899
0.74 Intermediate Similarity NPC172483
0.7391 Intermediate Similarity NPC298115
0.7391 Intermediate Similarity NPC9822
0.7368 Intermediate Similarity NPC206764
0.7356 Intermediate Similarity NPC157055
0.7356 Intermediate Similarity NPC127343
0.7353 Intermediate Similarity NPC470252
0.7353 Intermediate Similarity NPC17525
0.7327 Intermediate Similarity NPC100767
0.732 Intermediate Similarity NPC329387
0.732 Intermediate Similarity NPC145052
0.732 Intermediate Similarity NPC317280
0.7308 Intermediate Similarity NPC218855
0.7308 Intermediate Similarity NPC186128
0.7303 Intermediate Similarity NPC285773
0.7303 Intermediate Similarity NPC288903
0.7303 Intermediate Similarity NPC44830
0.7273 Intermediate Similarity NPC320891
0.7255 Intermediate Similarity NPC470007
0.7255 Intermediate Similarity NPC211439
0.7245 Intermediate Similarity NPC476042
0.7245 Intermediate Similarity NPC54647
0.7245 Intermediate Similarity NPC217621
0.7238 Intermediate Similarity NPC471481
0.7216 Intermediate Similarity NPC270654
0.7215 Intermediate Similarity NPC113670
0.7212 Intermediate Similarity NPC265513
0.7212 Intermediate Similarity NPC116842
0.7191 Intermediate Similarity NPC230068
0.7188 Intermediate Similarity NPC172925
0.7188 Intermediate Similarity NPC130398
0.7184 Intermediate Similarity NPC318327
0.7184 Intermediate Similarity NPC192577
0.7176 Intermediate Similarity NPC206800
0.7176 Intermediate Similarity NPC32203
0.7174 Intermediate Similarity NPC322387
0.7172 Intermediate Similarity NPC473325
0.717 Intermediate Similarity NPC67377
0.717 Intermediate Similarity NPC234637
0.717 Intermediate Similarity NPC196673
0.717 Intermediate Similarity NPC130591
0.7143 Intermediate Similarity NPC294134
0.7143 Intermediate Similarity NPC268388
0.7143 Intermediate Similarity NPC36357
0.7143 Intermediate Similarity NPC229242
0.7143 Intermediate Similarity NPC280789
0.7143 Intermediate Similarity NPC114327
0.7129 Intermediate Similarity NPC114594
0.7128 Intermediate Similarity NPC62765
0.7115 Intermediate Similarity NPC88141
0.7111 Intermediate Similarity NPC208183
0.7111 Intermediate Similarity NPC243289
0.71 Intermediate Similarity NPC304873
0.7097 Intermediate Similarity NPC329064
0.7089 Intermediate Similarity NPC22786
0.7087 Intermediate Similarity NPC470391
0.7079 Intermediate Similarity NPC71795
0.7075 Intermediate Similarity NPC470253
0.7075 Intermediate Similarity NPC93287
0.7071 Intermediate Similarity NPC325497
0.7059 Intermediate Similarity NPC209632
0.7059 Intermediate Similarity NPC269457
0.7048 Intermediate Similarity NPC210089

  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 NPC273758 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
0.974 High Similarity NPD942 Approved
0.9114 High Similarity NPD1507 Clinical (unspecified phase)
0.8953 High Similarity NPD1508 Approved
0.8652 High Similarity NPD1843 Approved
0.8588 High Similarity NPD650 Approved
0.8409 Intermediate Similarity NPD7609 Phase 3
0.8315 Intermediate Similarity NPD7631 Approved
0.8161 Intermediate Similarity NPD506 Clinical (unspecified phase)
0.8152 Intermediate Similarity NPD3495 Discontinued
0.8 Intermediate Similarity NPD1932 Approved
0.7917 Intermediate Similarity NPD1930 Approved
0.7917 Intermediate Similarity NPD1931 Clinical (unspecified phase)
0.7917 Intermediate Similarity NPD1929 Approved
0.7835 Intermediate Similarity NPD1237 Approved
0.7826 Intermediate Similarity NPD1202 Approved
0.7604 Intermediate Similarity NPD2066 Phase 3
0.7529 Intermediate Similarity NPD227 Approved
0.7529 Intermediate Similarity NPD225 Approved
0.7525 Intermediate Similarity NPD2329 Discontinued
0.7449 Intermediate Similarity NPD2193 Phase 2
0.7449 Intermediate Similarity NPD2648 Phase 3
0.7447 Intermediate Similarity NPD5122 Clinical (unspecified phase)
0.7444 Intermediate Similarity NPD9257 Approved
0.7444 Intermediate Similarity NPD9259 Approved
0.7442 Intermediate Similarity NPD9490 Approved
0.7423 Intermediate Similarity NPD1238 Approved
0.7419 Intermediate Similarity NPD1239 Approved
0.7396 Intermediate Similarity NPD1099 Approved
0.7396 Intermediate Similarity NPD1100 Approved
0.7368 Intermediate Similarity NPD4094 Approved
0.7303 Intermediate Similarity NPD9491 Approved
0.73 Intermediate Similarity NPD2577 Clinical (unspecified phase)
0.7273 Intermediate Similarity NPD2196 Discontinued
0.7273 Intermediate Similarity NPD2171 Approved
0.7273 Intermediate Similarity NPD226 Approved
0.7263 Intermediate Similarity NPD1563 Approved
0.7216 Intermediate Similarity NPD4657 Approved
0.7216 Intermediate Similarity NPD4655 Approved
0.7215 Intermediate Similarity NPD675 Discontinued
0.7188 Intermediate Similarity NPD688 Clinical (unspecified phase)
0.7176 Intermediate Similarity NPD9716 Approved
0.7174 Intermediate Similarity NPD1087 Approved
0.7128 Intermediate Similarity NPD9256 Approved
0.7128 Intermediate Similarity NPD9258 Approved
0.7113 Intermediate Similarity NPD1989 Approved
0.7059 Intermediate Similarity NPD1677 Discontinued
0.7059 Intermediate Similarity NPD2192 Approved
0.7059 Intermediate Similarity NPD2197 Approved
0.7048 Intermediate Similarity NPD4141 Clinical (unspecified phase)
0.7041 Intermediate Similarity NPD1565 Approved
0.7041 Intermediate Similarity NPD1566 Phase 3
0.7041 Intermediate Similarity NPD1564 Approved
0.7021 Intermediate Similarity NPD800 Approved
0.701 Intermediate Similarity NPD1693 Approved
0.6989 Remote Similarity NPD4793 Discontinued
0.6981 Remote Similarity NPD1609 Clinical (unspecified phase)
0.6961 Remote Similarity NPD5909 Discontinued
0.6952 Remote Similarity NPD1317 Discontinued
0.6952 Remote Similarity NPD664 Approved
0.6947 Remote Similarity NPD1089 Approved
0.6947 Remote Similarity NPD1086 Approved
0.6947 Remote Similarity NPD1090 Approved
0.6931 Remote Similarity NPD6027 Approved
0.6931 Remote Similarity NPD6024 Approved
0.6923 Remote Similarity NPD3971 Phase 1
0.6875 Remote Similarity NPD1007 Discontinued
0.6857 Remote Similarity NPD6831 Clinical (unspecified phase)
0.6842 Remote Similarity NPD5347 Phase 2
0.6842 Remote Similarity NPD5346 Phase 2
0.6837 Remote Similarity NPD9260 Approved
0.6804 Remote Similarity NPD1088 Approved
0.6796 Remote Similarity NPD164 Approved
0.6789 Remote Similarity NPD5951 Approved
0.6789 Remote Similarity NPD1246 Approved
0.6771 Remote Similarity NPD3673 Approved
0.6771 Remote Similarity NPD3672 Approved
0.6768 Remote Similarity NPD5206 Clinical (unspecified phase)
0.6765 Remote Similarity NPD813 Approved
0.6757 Remote Similarity NPD7610 Discontinued
0.6733 Remote Similarity NPD7798 Approved
0.6729 Remote Similarity NPD2181 Clinical (unspecified phase)
0.6726 Remote Similarity NPD2345 Approved
0.6726 Remote Similarity NPD5836 Discontinued
0.6699 Remote Similarity NPD3357 Discontinued
0.6696 Remote Similarity NPD7009 Phase 2
0.6696 Remote Similarity NPD3972 Approved
0.6667 Remote Similarity NPD4879 Approved
0.6609 Remote Similarity NPD6287 Discontinued
0.6609 Remote Similarity NPD1547 Clinical (unspecified phase)
0.6596 Remote Similarity NPD5734 Clinical (unspecified phase)
0.6581 Remote Similarity NPD1876 Approved
0.6552 Remote Similarity NPD4878 Approved
0.6542 Remote Similarity NPD2182 Approved
0.6538 Remote Similarity NPD9261 Approved
0.6522 Remote Similarity NPD7457 Clinical (unspecified phase)
0.6505 Remote Similarity NPD3135 Clinical (unspecified phase)
0.6496 Remote Similarity NPD5157 Phase 1
0.6496 Remote Similarity NPD5158 Clinical (unspecified phase)
0.6496 Remote Similarity NPD5159 Phase 2
0.6491 Remote Similarity NPD1245 Approved
0.6471 Remote Similarity NPD9495 Approved
0.6471 Remote Similarity NPD466 Approved
0.6471 Remote Similarity NPD5926 Approved
0.6466 Remote Similarity NPD1201 Approved
0.6458 Remote Similarity NPD1282 Approved
0.6455 Remote Similarity NPD7094 Approved
0.6455 Remote Similarity NPD6858 Approved
0.6441 Remote Similarity NPD1574 Approved
0.6435 Remote Similarity NPD7163 Clinical (unspecified phase)
0.6435 Remote Similarity NPD1727 Approved
0.6415 Remote Similarity NPD5048 Discontinued
0.6408 Remote Similarity NPD742 Approved
0.6396 Remote Similarity NPD1241 Discontinued
0.6396 Remote Similarity NPD1175 Approved
0.6395 Remote Similarity NPD9497 Clinical (unspecified phase)
0.6387 Remote Similarity NPD1470 Approved
0.6387 Remote Similarity NPD1593 Approved
0.6381 Remote Similarity NPD6647 Phase 2
0.6372 Remote Similarity NPD405 Clinical (unspecified phase)
0.6339 Remote Similarity NPD1075 Approved
0.6339 Remote Similarity NPD1073 Approved
0.6339 Remote Similarity NPD690 Clinical (unspecified phase)
0.6339 Remote Similarity NPD1074 Approved
0.6337 Remote Similarity NPD6048 Clinical (unspecified phase)
0.6337 Remote Similarity NPD6049 Phase 2
0.6333 Remote Similarity NPD4980 Approved
0.6333 Remote Similarity NPD2798 Approved
0.6311 Remote Similarity NPD253 Approved
0.631 Remote Similarity NPD173 Clinical (unspecified phase)
0.6303 Remote Similarity NPD6330 Clinical (unspecified phase)
0.6296 Remote Similarity NPD9265 Clinical (unspecified phase)
0.6296 Remote Similarity NPD9267 Approved
0.6296 Remote Similarity NPD9263 Approved
0.6296 Remote Similarity NPD9264 Approved
0.6293 Remote Similarity NPD3412 Clinical (unspecified phase)
0.6293 Remote Similarity NPD4733 Approved
0.6286 Remote Similarity NPD4803 Discontinued
0.6262 Remote Similarity NPD1018 Approved
0.625 Remote Similarity NPD7077 Approved
0.625 Remote Similarity NPD1164 Approved
0.625 Remote Similarity NPD7076 Approved
0.625 Remote Similarity NPD3097 Clinical (unspecified phase)
0.6239 Remote Similarity NPD9266 Approved
0.6239 Remote Similarity NPD3836 Clinical (unspecified phase)
0.6239 Remote Similarity NPD74 Approved
0.6216 Remote Similarity NPD9508 Approved
0.6214 Remote Similarity NPD9566 Approved
0.6207 Remote Similarity NPD4196 Clinical (unspecified phase)
0.6195 Remote Similarity NPD3867 Phase 2
0.6182 Remote Similarity NPD3646 Clinical (unspecified phase)
0.6182 Remote Similarity NPD2067 Discontinued
0.6179 Remote Similarity NPD6039 Approved
0.6179 Remote Similarity NPD1190 Approved
0.6174 Remote Similarity NPD997 Clinical (unspecified phase)
0.6167 Remote Similarity NPD1482 Clinical (unspecified phase)
0.6162 Remote Similarity NPD1628 Approved
0.6162 Remote Similarity NPD1629 Approved
0.6161 Remote Similarity NPD5277 Phase 2
0.614 Remote Similarity NPD1323 Discontinued
0.614 Remote Similarity NPD1025 Discontinued
0.6134 Remote Similarity NPD3355 Approved
0.6134 Remote Similarity NPD3356 Approved
0.6129 Remote Similarity NPD1475 Approved
0.6129 Remote Similarity NPD2313 Discontinued
0.6129 Remote Similarity NPD5422 Clinical (unspecified phase)
0.6102 Remote Similarity NPD1889 Phase 1
0.6087 Remote Similarity NPD9493 Approved
0.6087 Remote Similarity NPD4574 Approved
0.6087 Remote Similarity NPD4576 Approved
0.6087 Remote Similarity NPD4147 Approved
0.6087 Remote Similarity NPD4144 Approved
0.608 Remote Similarity NPD1541 Approved
0.608 Remote Similarity NPD1874 Clinical (unspecified phase)
0.608 Remote Similarity NPD7713 Phase 3
0.608 Remote Similarity NPD1527 Phase 2
0.6071 Remote Similarity NPD2124 Approved
0.6068 Remote Similarity NPD1217 Clinical (unspecified phase)
0.6067 Remote Similarity NPD294 Approved
0.6067 Remote Similarity NPD292 Approved
0.6066 Remote Similarity NPD6007 Clinical (unspecified phase)
0.6064 Remote Similarity NPD3979 Approved
0.6064 Remote Similarity NPD3904 Approved
0.6064 Remote Similarity NPD3981 Approved
0.6064 Remote Similarity NPD3903 Approved
0.6064 Remote Similarity NPD1617 Discontinued
0.6055 Remote Similarity NPD467 Phase 1
0.6053 Remote Similarity NPD1022 Approved
0.6053 Remote Similarity NPD1711 Phase 2
0.6053 Remote Similarity NPD2629 Approved
0.6053 Remote Similarity NPD1021 Approved
0.6053 Remote Similarity NPD2319 Discontinued
0.6053 Remote Similarity NPD1020 Approved
0.6053 Remote Similarity NPD1023 Approved
0.6048 Remote Similarity NPD7008 Discontinued
0.6048 Remote Similarity NPD5952 Clinical (unspecified phase)
0.6038 Remote Similarity NPD5630 Phase 1
0.6036 Remote Similarity NPD1752 Approved
0.6036 Remote Similarity NPD1756 Approved
0.6034 Remote Similarity NPD2347 Approved
0.6033 Remote Similarity NPD2056 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