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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-12-19 16:05:52 UTC
Update Date2020-02-26 21:26:03 UTC
HMDB IDHMDB0005767
Secondary Accession Numbers
  • HMDB05767
Metabolite Identification
Common NameHomoanserine
DescriptionHomoanserine belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond. Homoanserine is a very strong basic compound (based on its pKa).
Structure
Data?1582752363
Synonyms
ValueSource
L-N-(4-Aminobutyryl)-3-methyl-histidineHMDB
N-(4-Amino-1-oxobutyl)-3-methyl-L-histidineHMDB
N-(4-Aminobutyryl)-1-methyl-imidazole-5-alanineHMDB
(2S)-2-[(4-Amino-1-hydroxybutylidene)amino]-3-(1-methyl-1H-imidazol-5-yl)propanoateGenerator
Chemical FormulaC11H18N4O3
Average Molecular Weight254.2856
Monoisotopic Molecular Weight254.137890462
IUPAC Name(2S)-2-(4-aminobutanamido)-3-(1-methyl-1H-imidazol-5-yl)propanoic acid
Traditional Name(2S)-2-(4-aminobutanamido)-3-(3-methylimidazol-4-yl)propanoic acid
CAS Registry Number20314-38-9
SMILES
CN1C=NC=C1C[C@H](NC(=O)CCCN)C(O)=O
InChI Identifier
InChI=1S/C11H18N4O3/c1-15-7-13-6-8(15)5-9(11(17)18)14-10(16)3-2-4-12/h6-7,9H,2-5,12H2,1H3,(H,14,16)(H,17,18)/t9-/m0/s1
InChI KeyHXBKNURIXGGFCX-VIFPVBQESA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hybrid peptides. Hybrid peptides are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassPeptidomimetics
Sub ClassHybrid peptides
Direct ParentHybrid peptides
Alternative Parents
Substituents
  • Hybrid peptide
  • Histidine or derivatives
  • N-acyl-alpha-amino acid
  • N-acyl-alpha amino acid or derivatives
  • N-acyl-l-alpha-amino acid
  • Gamma amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Imidazolyl carboxylic acid derivative
  • Fatty amide
  • N-acyl-amine
  • N-substituted imidazole
  • Fatty acyl
  • Heteroaromatic compound
  • Azole
  • Imidazole
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Amino acid
  • Amino acid or derivatives
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Azacycle
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Primary aliphatic amine
  • Carbonyl group
  • Primary amine
  • Hydrocarbon derivative
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

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 Solubility3.19 g/LALOGPS
logP-2.8ALOGPS
logP-4ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)3.52ChemAxon
pKa (Strongest Basic)9.99ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area110.24 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity65.21 m³·mol⁻¹ChemAxon
Polarizability26.24 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-053r-9120000000-c0689e57c6ec53c2e597Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9720000000-c14e517b33cc2655eb94Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-1290000000-1f1ab504467a3c930addSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dr-5940000000-492142f7755fb16b7ae9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0596-9500000000-01c7cab0f39bf390066fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0090000000-cd2b55a04c9a5c299632Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0zfr-3980000000-566caaf49a2f490f6cecSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udl-9600000000-f0d3bbd19cbdf23bd211Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023757
KNApSAcK IDNot Available
Chemspider ID17216339
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound20849429
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kunze N, Kleinkauf H, Bauer K: Characterization of two carnosine-degrading enzymes from rat brain. Partial purification and characterization of a carnosinase and a beta-alanyl-arginine hydrolase. Eur J Biochem. 1986 Nov 3;160(3):605-13. [PubMed:3780724 ]
  2. Nakajima T, Wolfgram F, Clark WG: The isolation of homoanserine from bovine brain. J Neurochem. 1967 Dec;14(12):1107-12. [PubMed:6078589 ]
  3. Bauer K, Schulz M: Biosynthesis of carnosine and related peptides by skeletal muscle cells in primary culture. Eur J Biochem. 1994 Jan 15;219(1-2):43-7. [PubMed:8307008 ]