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

Identification

Name
5-(3-carbamoylbenzyl)-5,6,7,8,9,10-hexahydrocyclohepta[b]indole-4-carboxylic acid
Accession Number
DB07945
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 362.4217
Monoisotopic: 362.16304258
Chemical Formula
C22H22N2O3
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

Pharmacology

Indication
Not Available
Structured Indications
Not Available
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
9863791
PubChem Substance
99444416
ChemSpider
8039485
BindingDB
50248245
ChEMBL
CHEMBL516023
HET
I4A
PDB Entries
3fr5

Clinical Trials

Clinical Trials
Not Available

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)3.09ChemAxon
pKa (Strongest Basic)-0.96ChemAxon
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/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
N-alkylindole / 3-alkylindole / Benzamide / Benzoic acid or derivatives / Indole / Benzoyl / Monocyclic benzene moiety / Substituted pyrrole / Benzenoid / Pyrrole
show 16 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Carriers

Kind
Protein
Organism
Human
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. [PubMed:10592235]

Drug created on September 15, 2010 15:27 / Updated on December 01, 2017 15:58