(3e)-3-[(4-Hydroxyphenyl)Imino]-1h-Indol-2(3h)-One

Overview

DrugBank ID
DB03650
Type
Small Molecule
US Approved
NO
Other Approved
NO
Clinical Trials
Phase 0
0
Phase 1
0
Phase 2
0
Phase 3
0
Phase 4
0

Identification

Generic Name
(3e)-3-[(4-Hydroxyphenyl)Imino]-1h-Indol-2(3h)-One
DrugBank Accession Number
DB03650
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 238.2414
Monoisotopic: 238.074227574
Chemical Formula
C14H10N2O2
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 alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Alpha amino acids and derivatives
Alternative Parents
Indoles and derivatives / p-Aminophenols / Aniline and substituted anilines / Secondary alkylarylamines / 1-hydroxy-2-unsubstituted benzenoids / N-acylimines / Azacyclic compounds / Organopnictogen compounds / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
1-hydroxy-2-unsubstituted benzenoid / Alpha-amino acid or derivatives / Amine / Aminophenol / Aniline or substituted anilines / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonyl group / Hydrocarbon derivative
show 14 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
ZJASRZFZRYISET-UHFFFAOYSA-N
InChI
InChI=1S/C14H10N2O2/c17-10-7-5-9(6-8-10)15-13-11-3-1-2-4-12(11)16-14(13)18/h1-8,17H,(H,15,16,18)
IUPAC Name
(3Z)-3-[(4-hydroxyphenyl)imino]-2,3-dihydro-1H-indol-2-one
SMILES
OC1=CC=C(C=C1)\N=C1/C(=O)NC2=CC=CC=C12

References

General References
Not Available
PubChem Compound
611002
PubChem Substance
46509196
ChemSpider
531133
ZINC
ZINC000018137759
PDBe Ligand
LI7
PDB Entries
1yxx

Clinical Trials

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 Solubility0.222 mg/mLALOGPS
logP2.36ALOGPS
logP2.81Chemaxon
logS-3ALOGPS
pKa (Strongest Acidic)8.15Chemaxon
pKa (Strongest Basic)-0.45Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area61.69 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity71.2 m3·mol-1Chemaxon
Polarizability24.78 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9911
Blood Brain Barrier+0.9526
Caco-2 permeable+0.551
P-glycoprotein substrateNon-substrate0.6048
P-glycoprotein inhibitor INon-inhibitor0.8945
P-glycoprotein inhibitor IINon-inhibitor0.6174
Renal organic cation transporterNon-inhibitor0.7987
CYP450 2C9 substrateNon-substrate0.7224
CYP450 2D6 substrateNon-substrate0.7586
CYP450 3A4 substrateNon-substrate0.5098
CYP450 1A2 substrateInhibitor0.9703
CYP450 2C9 inhibitorNon-inhibitor0.5278
CYP450 2D6 inhibitorNon-inhibitor0.7985
CYP450 2C19 inhibitorNon-inhibitor0.6105
CYP450 3A4 inhibitorNon-inhibitor0.9013
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.7454
Ames testAMES toxic0.7001
CarcinogenicityNon-carcinogens0.8166
BiodegradationNot ready biodegradable0.9953
Rat acute toxicity2.4817 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9872
hERG inhibition (predictor II)Non-inhibitor0.8246
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-MSsplash10-0bt9-1590000000-23765108717142781316
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0090000000-d06e6dee24f9c50897b5
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-1090000000-01d9f786515f1b984c65
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0290000000-6328399a30ea6a818159
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000l-6090000000-8ea3c40d4f6c80542490
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f89-9500000000-e3ffcc726bab15b20aa6
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9300000000-6ceb255ed47773b6363c
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]-153.55527
predicted
DeepCCS 1.0 (2019)
[M+H]+155.926
predicted
DeepCCS 1.0 (2019)
[M+Na]+162.00642
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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. 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 June 13, 2005 13:24 / Updated at June 12, 2020 16:52