NAV

L-Octahydroindole-2-carboxylic acid

Identification

Generic Name
L-Octahydroindole-2-carboxylic acid
DrugBank Accession Number
DB03409
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 169.2209
Monoisotopic: 169.110278729
Chemical Formula
C9H15NO2
Synonyms
  • (2S,3aS,7aS)-2-Carboxyoctahydroindole
  • (2S,3aS,7aS)-Octahydroindole-2-carboxylic acid
  • Perindopril impurity A
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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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 l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
L-alpha-amino acids
Alternative Parents
Indolines / Pyrrolidine carboxylic acids / Quaternary ammonium salts / Carboxylic acid salts / Monocarboxylic acids and derivatives / Dialkylamines / Carboxylic acids / Azacyclic compounds / Organic zwitterions / Organic salts
show 3 more
Substituents
Aliphatic heteropolycyclic compound / Amine / Azacycle / Carbonyl group / Carboxylic acid / Carboxylic acid salt / Dihydroindole / Hydrocarbon derivative / Indole or derivatives / L-alpha-amino acid
show 14 more
Molecular Framework
Aliphatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
9ID44U804I
CAS number
80875-98-5
InChI Key
CQYBNXGHMBNGCG-FXQIFTODSA-N
InChI
InChI=1S/C9H15NO2/c11-9(12)8-5-6-3-1-2-4-7(6)10-8/h6-8,10H,1-5H2,(H,11,12)/t6-,7-,8-/m0/s1
IUPAC Name
(2S,3aS,7aS)-octahydro-1H-indole-2-carboxylic acid
SMILES
[H][C@]12C[C@H](N[C@@]1([H])CCCC2)C(O)=O

References

Synthesis Reference

Mirko Pogutter, Felix Rudolf, Hans-Ulrich Bichsel, Thomas Bader, "Method for producing {n-[1-(s)-carbalkoxy-3-phenylpropyl]-s-alanyl-2s, 3ar, 7as-octahydroindole-2-carboxylic acid} compounds." U.S. Patent US20070135513, issued June 14, 2007.

US20070135513
General References
Not Available
PubChem Compound
7408452
PubChem Substance
46509061
ChemSpider
5731148
ZINC
ZINC000004899687
PDBe Ligand
OIC
PDB Entries
1bdk / 3bv9 / 4wvp / 5vbl / 7az5

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 Solubility10.9 mg/mLALOGPS
logP-1ALOGPS
logP-1.3Chemaxon
logS-1.2ALOGPS
pKa (Strongest Acidic)2.09Chemaxon
pKa (Strongest Basic)11.64Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area49.33 Å2Chemaxon
Rotatable Bond Count1Chemaxon
Refractivity44.28 m3·mol-1Chemaxon
Polarizability18.03 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.987
Blood Brain Barrier+0.9135
Caco-2 permeable-0.6008
P-glycoprotein substrateNon-substrate0.5728
P-glycoprotein inhibitor INon-inhibitor0.9918
P-glycoprotein inhibitor IINon-inhibitor0.9766
Renal organic cation transporterNon-inhibitor0.8334
CYP450 2C9 substrateNon-substrate0.8425
CYP450 2D6 substrateNon-substrate0.7951
CYP450 3A4 substrateNon-substrate0.7081
CYP450 1A2 substrateNon-inhibitor0.8623
CYP450 2C9 inhibitorNon-inhibitor0.9561
CYP450 2D6 inhibitorNon-inhibitor0.9449
CYP450 2C19 inhibitorNon-inhibitor0.9627
CYP450 3A4 inhibitorNon-inhibitor0.9843
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9815
Ames testNon AMES toxic0.9452
CarcinogenicityNon-carcinogens0.9684
BiodegradationNot ready biodegradable0.5488
Rat acute toxicity2.0051 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9291
hERG inhibition (predictor II)Non-inhibitor0.95
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-MSsplash10-0005-9400000000-37d3bcfada595ba379a1
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0900000000-eb46db8321bc9bd31029
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0900000000-7e49244b78e0e94a6f9c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-1900000000-cdadb395628be06ddbdd
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-1900000000-dd121bc21e7952734bae
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-001l-9200000000-2e895f3c7121f0803f63
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-006x-9800000000-d63378194d2978f17de1
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]-138.0009198
predicted
DarkChem Lite v0.1.0
[M-H]-137.61436
predicted
DeepCCS 1.0 (2019)
[M+H]+138.8324198
predicted
DarkChem Lite v0.1.0
[M+H]+139.93239
predicted
DeepCCS 1.0 (2019)
[M+Na]+137.8056198
predicted
DarkChem Lite v0.1.0
[M+Na]+145.8449
predicted
DeepCCS 1.0 (2019)

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52