2,3-diphenyl-1H-indole-7-carboxylic acid

Identification

Generic Name
2,3-diphenyl-1H-indole-7-carboxylic acid
DrugBank Accession Number
DB08709
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 313.3493
Monoisotopic: 313.110278729
Chemical Formula
C21H15NO2
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
USerine/threonine-protein kinase pim-1Not AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 2-phenylindoles. These are indoles substituted at the 2-position with a phenyl group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
Indoles
Direct Parent
2-phenylindoles
Alternative Parents
Phenylpyrroles / Benzene and substituted derivatives / Vinylogous amides / Heteroaromatic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds
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Substituents
2-phenylindole / 2-phenylpyrrole / 3-phenylpyrrole / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carboxylic acid / Carboxylic acid derivative / Heteroaromatic compound / Hydrocarbon derivative
show 11 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
5BFF2LV9EF
CAS number
Not Available
InChI Key
OLUDUXWVPIEHDA-UHFFFAOYSA-N
InChI
InChI=1S/C21H15NO2/c23-21(24)17-13-7-12-16-18(14-8-3-1-4-9-14)19(22-20(16)17)15-10-5-2-6-11-15/h1-13,22H,(H,23,24)
IUPAC Name
2,3-diphenyl-1H-indole-7-carboxylic acid
SMILES
OC(=O)C1=CC=CC2=C1NC(=C2C1=CC=CC=C1)C1=CC=CC=C1

References

General References
Not Available
PubChem Compound
5003498
PubChem Substance
99445180
ChemSpider
4183181
BindingDB
26670
ChEMBL
CHEMBL406652
ZINC
ZINC000001506669
PDBe Ligand
VX3
PDB Entries
3bgz

Clinical Trials

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PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000692 mg/mLALOGPS
logP5.01ALOGPS
logP4.94Chemaxon
logS-5.7ALOGPS
pKa (Strongest Acidic)3.53Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area53.09 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity94.55 m3·mol-1Chemaxon
Polarizability34.39 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9375
Caco-2 permeable-0.546
P-glycoprotein substrateNon-substrate0.7839
P-glycoprotein inhibitor INon-inhibitor0.9545
P-glycoprotein inhibitor IINon-inhibitor0.8328
Renal organic cation transporterNon-inhibitor0.884
CYP450 2C9 substrateNon-substrate0.7414
CYP450 2D6 substrateNon-substrate0.8484
CYP450 3A4 substrateNon-substrate0.7319
CYP450 1A2 substrateInhibitor0.853
CYP450 2C9 inhibitorInhibitor0.7038
CYP450 2D6 inhibitorNon-inhibitor0.8429
CYP450 2C19 inhibitorInhibitor0.5518
CYP450 3A4 inhibitorNon-inhibitor0.7681
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5284
Ames testNon AMES toxic0.8815
CarcinogenicityNon-carcinogens0.8831
BiodegradationNot ready biodegradable0.8247
Rat acute toxicity2.6026 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9872
hERG inhibition (predictor II)Non-inhibitor0.8091
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0292-0091000000-5783ada7d5d7165767e0
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0039000000-a05c7181690a9d6c0d4d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-02t9-0094000000-f7c7051456c928f85114
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-0049000000-d86b1bf897f12e58575f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-02t9-0096000000-2476b1eb66e21b526892
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0091000000-69d9231302925e754471
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0gb9-0090000000-9d4a90f9848101e5841a
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-187.5655462
predicted
DarkChem Lite v0.1.0
[M-H]-164.90251
predicted
DeepCCS 1.0 (2019)
[M+H]+167.26051
predicted
DeepCCS 1.0 (2019)
[M+Na]+174.08372
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Proto-oncogene with serine/threonine kinase activity involved in cell survival and cell proliferation and thus providing a selective advantage in tumorigenesis (PubMed:15528381, PubMed:1825810, PubMed:31548394). Exerts its oncogenic activity through: the regulation of MYC transcriptional activity, the regulation of cell cycle progression and by phosphorylation and inhibition of proapoptotic proteins (BAD, MAP3K5, FOXO3) (PubMed:18593906). Phosphorylation of MYC leads to an increase of MYC protein stability and thereby an increase of transcriptional activity (By similarity). The stabilization of MYC exerted by PIM1 might explain partly the strong synergism between these two oncogenes in tumorigenesis (By similarity). Mediates survival signaling through phosphorylation of BAD, which induces release of the anti-apoptotic protein Bcl-X(L)/BCL2L1 (By similarity). Phosphorylation of MAP3K5, another proapoptotic protein, by PIM1, significantly decreases MAP3K5 kinase activity and inhibits MAP3K5-mediated phosphorylation of JNK and JNK/p38MAPK subsequently reducing caspase-3 activation and cell apoptosis (PubMed:19749799). Stimulates cell cycle progression at the G1-S and G2-M transitions by phosphorylation of CDC25A and CDC25C (PubMed:16356754). Phosphorylation of CDKN1A, a regulator of cell cycle progression at G1, results in the relocation of CDKN1A to the cytoplasm and enhanced CDKN1A protein stability (PubMed:12431783). Promotes cell cycle progression and tumorigenesis by down-regulating expression of a regulator of cell cycle progression, CDKN1B, at both transcriptional and post-translational levels (PubMed:18593906). Phosphorylation of CDKN1B, induces 14-3-3 proteins binding, nuclear export and proteasome-dependent degradation (PubMed:18593906). May affect the structure or silencing of chromatin by phosphorylating HP1 gamma/CBX3 (PubMed:10664448). Acts also as a regulator of homing and migration of bone marrow cells involving functional interaction with the CXCL12-CXCR4 signaling axis (By similarity). Acts as a positive regulator of mTORC1 signaling by mediating phosphorylation and inhibition of DEPDC5 component of the GATOR1 complex (PubMed:31548394). Acts as a negative regulator of innate immunity by mediating phosphorylation and inactivation of GBP1 in absence of infection: phosphorylation of GBP1 induces interaction with 14-3-3 protein sigma (SFN) and retention in the cytosol (PubMed:37797010). Also phosphorylates and activates the ATP-binding cassette transporter ABCG2, allowing resistance to drugs through their excretion from cells (PubMed:18056989). Promotes brown adipocyte differentiation (By similarity)
Specific Function
ATP binding
Gene Name
PIM1
Uniprot ID
P11309
Uniprot Name
Serine/threonine-protein kinase pim-1
Molecular Weight
35685.44 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at September 15, 2010 21:34 / Updated at June 12, 2020 16:52