NAV

5-(3-carbamoylbenzyl)-5,6,7,8,9,10-hexahydrocyclohepta[b]indole-4-carboxylic acid

Identification

Generic Name
5-(3-carbamoylbenzyl)-5,6,7,8,9,10-hexahydrocyclohepta[b]indole-4-carboxylic acid
DrugBank Accession Number
DB07945
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 362.4217
Monoisotopic: 362.16304258
Chemical Formula
C22H22N2O3
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
Not Available
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 n-alkylindoles. These are compounds containing an indole moiety that carries an alkyl chain at the 1-position.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Indoles and derivatives
Sub Class
N-alkylindoles
Direct Parent
N-alkylindoles
Alternative Parents
3-alkylindoles / Benzamides / Benzoyl derivatives / Substituted pyrroles / Vinylogous amides / Heteroaromatic compounds / Primary carboxylic acid amides / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds
show 5 more
Substituents
3-alkylindole / Aromatic heteropolycyclic compound / Azacycle / Benzamide / Benzenoid / Benzoic acid or derivatives / Benzoyl / Carboxamide group / Carboxylic acid / Carboxylic acid derivative
show 16 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
GKBQRPKZHUFGOB-UHFFFAOYSA-N
InChI
InChI=1S/C22H22N2O3/c23-21(25)15-7-4-6-14(12-15)13-24-19-11-3-1-2-8-16(19)17-9-5-10-18(20(17)24)22(26)27/h4-7,9-10,12H,1-3,8,11,13H2,(H2,23,25)(H,26,27)
IUPAC Name
5-[(3-carbamoylphenyl)methyl]-5H,6H,7H,8H,9H,10H-cyclohepta[b]indole-4-carboxylic acid
SMILES
NC(=O)C1=CC=CC(CN2C3=C(CCCCC3)C3=CC=CC(C(O)=O)=C23)=C1

References

General References
Not Available
PubChem Compound
9863791
PubChem Substance
99444416
ChemSpider
8039485
BindingDB
50248245
ChEMBL
CHEMBL516023
ZINC
ZINC000003961887
PDBe Ligand
I4A
PDB Entries
3fr5

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

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 Solubility0.00325 mg/mLALOGPS
logP3.66ALOGPS
logP4.19Chemaxon
logS-5ALOGPS
pKa (Strongest Acidic)3.53Chemaxon
pKa (Strongest Basic)-0.34Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area85.32 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity105.1 m3·mol-1Chemaxon
Polarizability39.39 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9524
Blood Brain Barrier+0.912
Caco-2 permeable-0.657
P-glycoprotein substrateNon-substrate0.5624
P-glycoprotein inhibitor INon-inhibitor0.9044
P-glycoprotein inhibitor IIInhibitor0.5056
Renal organic cation transporterNon-inhibitor0.5869
CYP450 2C9 substrateNon-substrate0.8149
CYP450 2D6 substrateNon-substrate0.6916
CYP450 3A4 substrateNon-substrate0.6176
CYP450 1A2 substrateNon-inhibitor0.6932
CYP450 2C9 inhibitorNon-inhibitor0.838
CYP450 2D6 inhibitorNon-inhibitor0.9366
CYP450 2C19 inhibitorNon-inhibitor0.7742
CYP450 3A4 inhibitorNon-inhibitor0.6615
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6868
Ames testNon AMES toxic0.7274
CarcinogenicityNon-carcinogens0.9236
BiodegradationNot ready biodegradable0.9472
Rat acute toxicity2.3354 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9885
hERG inhibition (predictor II)Non-inhibitor0.5271
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 MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-01ot-0009000000-027c69125dcdd8ec6d33
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-02ta-0039000000-aba62fa79c960c9f4bee
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-02mi-0069000000-3175cb128e30a184288d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01ot-0209000000-dacd3e9608e768632c63
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-014l-3910000000-c287a801def25a373fc8
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-007n-4893000000-a8eff786949da67a33db
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]-193.07957
predicted
DeepCCS 1.0 (2019)
[M+H]+195.43759
predicted
DeepCCS 1.0 (2019)
[M+Na]+202.19353
predicted
DeepCCS 1.0 (2019)

Carriers

Details1. Fatty acid-binding protein, adipocyte
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transporter activity
Specific Function
Lipid transport protein in adipocytes. Binds both long chain fatty acids and retinoic acid. Delivers long-chain fatty acids and retinoic acid to their cognate receptors in the nucleus (By similarity).
Gene Name
FABP4
Uniprot ID
P15090
Uniprot Name
Fatty acid-binding protein, adipocyte
Molecular Weight
14718.815 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 21:27 / Updated at June 12, 2020 16:52