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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-16 18:04:07 UTC
NP-MRD IDNP0000588
Secondary Accession NumbersNone
Natural Product Identification
Common NameIsovalerylalanine
DescriptionIsovalerylalanine, also known as isopentanoylalanine, belongs to the class of organic compounds known as N-acyl-L-alpha-amino acids. These are N-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom. Isovalerylalanine results from the formal condensation of the carboxy group of isovaleric acid with the amino group of L-alanine. Isovalerylalanine is one of the constituents of the organic acid profile in isovaleric acidemia, it is believed to be formed by the action of the enzyme glycine N-acylase on alanine, using isovaleryl-CoA as a substrate (PMID: 6197208 ). Isovaleric acidemia was the first organic acid acidemia to be documented in humans. It is an autosomal recessive inborn error in the metabolism of leucine, caused by a deficiency of the mitochondrial enzyme isovaleryl-CoA dehydrogenase (IVD) that results in the accumulation isovaleryl-CoA derivatives (PMID: 16602101). The excess of isovaleryl-CoA in plasma allows for the formation of condensation derivatives, such as isovalerylalanine which makes it one of the biomarkers for this condition.
Structure
Thumb
Synonyms
ValueSource
(2S)-2-(3-Methylbutanamido)propanoic acidChEBI
IsopentanoylalanineChEBI
N-Isopentanoyl-L-alanineChEBI
N-IsopentanoylalanineChEBI
N-IsovalerylalanineChEBI
(2S)-2-(3-Methylbutanamido)propanoateGenerator
N-Isovaleryl-L-alanineHMDB
IsovalerylalanineChEBI
Chemical FormulaC8H15NO3
Average Mass173.2096 Da
Monoisotopic Mass173.10519 Da
IUPAC Name(2S)-2-(3-methylbutanamido)propanoic acid
Traditional Nameisovalerylalanine
CAS Registry Number68219-63-6
SMILES
CC(C)CC(=O)N[C@@H](C)C(O)=O
InChI Identifier
InChI=1S/C8H15NO3/c1-5(2)4-7(10)9-6(3)8(11)12/h5-6H,4H2,1-3H3,(H,9,10)(H,11,12)/t6-/m0/s1
InChI KeyOJPSNARFDYTAEN-LURJTMIESA-N
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 5%_DMSO, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as n-acyl-l-alpha-amino acids. These are n-acylated alpha amino acids which have the L-configuration of the alpha-carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentN-acyl-L-alpha-amino acids
Alternative Parents
Substituents
  • N-acyl-l-alpha-amino acid
  • Alanine or derivatives
  • Fatty amide
  • N-acyl-amine
  • Fatty acyl
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Organic oxide
  • Organopnictogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility11 g/LALOGPS
logP0.8ALOGPS
logP0.67ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)4.21ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity43.72 m³·mol⁻¹ChemAxon
Polarizability18.28 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000747
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022219
KNApSAcK IDNot Available
Chemspider ID114516
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5715
PubChem Compound129285
PDB IDNot Available
ChEBI ID136818
Good Scents IDNot Available
References
General References
  1. Lehnert W: N-Isovalerylalanine and N-isovalerylsarcosine: two new minor metabolites in isovaleric acidemia. Clin Chim Acta. 1983 Oct 31;134(1-2):207-12. [PubMed:6197208 ]
  2. Authors unspecified: Cancer Therapy Interactions With Foods and Dietary Supplements (PDQ(R)): Patient Version. 2002. [PubMed:34403226 ]
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  5. Authors unspecified: Adult Soft Tissue Sarcoma Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389481 ]
  6. Authors unspecified: Testicular Cancer Screening (PDQ(R)): Health Professional Version. 2002. [PubMed:26389404 ]
  7. Authors unspecified: Rectal Cancer Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389402 ]
  8. Authors unspecified: Childhood Astrocytomas Treatment (PDQ(R)): Patient Version. 2002. [PubMed:26389391 ]
  9. Authors unspecified: Colon Cancer Treatment (PDQ(R)): Health Professional Version. 2002. [PubMed:26389297 ]
  10. Authors unspecified: Childhood Craniopharyngioma Treatment (PDQ(R)): Patient Version. 2002. [PubMed:26389237 ]
  11. Authors unspecified: Childhood Hodgkin Lymphoma Treatment (PDQ(R)): Patient Version. 2002. [PubMed:26389224 ]
  12. Authors unspecified: Langerhans Cell Histiocytosis Treatment (PDQ(R)): Patient Version. 2002. [PubMed:26389196 ]
  13. Karikalan M, Chander V, Mahajan S, Deol P, Agrawal RK, Nandi S, Rai SK, Mathur A, Pawde A, Singh KP, Sharma GK: Natural infection of Delta mutant of SARS-CoV-2 in Asiatic Lions of India. Transbound Emerg Dis. 2021 Aug 17. doi: 10.1111/tbed.14290. [PubMed:34404118 ]