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Showing Compound Homocarnosine (FDB022217)

Record Information
Version1.0
Creation date2011-09-21 00:10:18 UTC
Update date2015-10-09 22:28:48 UTC
Primary IDFDB022217
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameHomocarnosine
DescriptionHomocarnosine is a normal human metabolite, the brain-specific dipeptide of gamma-aminobutyric acid (GABA) and histidine. (PMID 1266573) Increased concentration of CSF homocarnosine has been found in familial spastic paraplegia. (PMID 842287) Homocarnosinosis (an inherited disorder, OMIM 236130) is characterized by an elevated level of the dipeptide homocarnosine (Hca) in the Cerebrospinal fluid (CSF) and the brain and by carnosinuria and serum carnosinase deficiency, and can co-exist with paraplegia, retinitis pigmentosa, and a progressive mental deficiency. (PMID 3736769) In glial tumors of human brain the content of homocarnosine has been found to be lower than in brain tissue (PMID 1032224), while an increase in content of homocarnosine was observed in brain tissue of animals under experimental trauma of cranium. (PMID 1025883) [HMDB]
CAS Number3650-73-5
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
SynonymSource
(2S)-HomocarnosineChEBI
(S)-HomocarnosineChEBI
gamma-Aminobutyryl-L-hisChEBI
N-(4-Aminobutanoyl)-(S)-histidineChEBI
N-(4-Aminobutyryl)-L-histidineChEBI
N(alpha)-(4-Aminobutyryl)-L-histidineChEBI
L-HomocarnosineKegg
gamma-Aminobutyryl histidineKegg
N-(4-Amino-1-oxobutyryl)histidineKegg
g-Aminobutyryl-L-hisGenerator
Γ-aminobutyryl-L-hisGenerator
N(a)-(4-Aminobutyryl)-L-histidineGenerator
N(Α)-(4-aminobutyryl)-L-histidineGenerator
g-Aminobutyryl histidineGenerator
Γ-aminobutyryl histidineGenerator
gamma-Aminobutyryl-L-histidineMeSH
Homocarnosine sulfateMeSH
g-Aminobutyryl-L-histidineHMDB
g-AminobutyrylhistidineHMDB
gamma-AminobutyrylhistidineHMDB
N-(4-Aminobutyryl)-histidineHMDB
Homocarnosinehmdb
N-(4-amino-1-Oxobutyryl)histidineKegg
N-(4-aminobutyryl)-Histidinehmdb
N-(4-aminobutyryl)-L-Histidinehmdb
γ-aminobutyryl histidineGenerator
Predicted Properties
PropertyValueSource
Water Solubility7.37 g/LALOGPS
logP-2.8ALOGPS
logP-3.9ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)3.45ChemAxon
pKa (Strongest Basic)9.99ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area121.1 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity59.75 m³·mol⁻¹ChemAxon
Polarizability24.49 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H16N4O3
IUPAC name(2S)-2-(4-aminobutanamido)-3-(1H-imidazol-4-yl)propanoic acid
InChI IdentifierInChI=1S/C10H16N4O3/c11-3-1-2-9(15)14-8(10(16)17)4-7-5-12-6-13-7/h5-6,8H,1-4,11H2,(H,12,13)(H,14,15)(H,16,17)/t8-/m0/s1
InChI KeyCCLQKVKJOGVQLU-QMMMGPOBSA-N
Isomeric SMILESNCCCC(=O)N[C@@H](CC1=CNC=N1)C(O)=O
Average Molecular Weight240.259
Monoisotopic Molecular Weight240.122240398
Classification
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
  • N-acyl-amine
  • Fatty amide
  • Fatty acyl
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Amino acid
  • Amino acid or derivatives
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Carboxylic acid derivative
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Amine
  • Organic nitrogen compound
  • Organic oxide
  • Carbonyl group
  • Primary amine
  • Organooxygen compound
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Role

Biological role:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSHomocarnosine, 3 TMS, GC-MS Spectrumsplash10-0udi-1920000000-a03e2c4f8b2c9d6a1635Spectrum
GC-MSHomocarnosine, 3 TMS, GC-MS Spectrumsplash10-0udi-0920000000-e48ce78a12a5f4834686Spectrum
GC-MSHomocarnosine, 3 TMS, GC-MS Spectrumsplash10-0fk9-9710000000-32bfa6992d5a80f09a36Spectrum
GC-MSHomocarnosine, non-derivatized, GC-MS Spectrumsplash10-0udi-1920000000-a03e2c4f8b2c9d6a1635Spectrum
GC-MSHomocarnosine, non-derivatized, GC-MS Spectrumsplash10-0udi-0920000000-e48ce78a12a5f4834686Spectrum
GC-MSHomocarnosine, non-derivatized, GC-MS Spectrumsplash10-0fk9-9710000000-32bfa6992d5a80f09a36Spectrum
Predicted GC-MSHomocarnosine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-001i-9410000000-343b9389cd3a9e7656c5Spectrum
Predicted GC-MSHomocarnosine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-000t-9620000000-f0df8a34f8155fd39194Spectrum
Predicted GC-MSHomocarnosine, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHomocarnosine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHomocarnosine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHomocarnosine, TMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHomocarnosine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHomocarnosine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHomocarnosine, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSHomocarnosine, TBDMS_1_4, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0a4i-0910000000-b804d40537827898f4af2012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-03di-5900000000-26897d5ae957a9cb6b352012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-03e9-9300000000-291e9d04c321015b92412012-07-24View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-000i-0090000000-352076fb2d925fdf8d3d2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0f79-0960000000-6efcaf43e71ab44953fa2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-03di-0900000000-4122cf33c566cb50775c2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-03di-4900000000-499817ec7737f4f712642012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-001i-9300000000-5e2839e6bf4597a45ad32012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0a4l-0980000000-a0e96805123eef741d162012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0a4i-0900000000-bd852312bcfa93da513d2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-03di-2900000000-b0c96a1971d8e230da772012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-03di-6900000000-086dfb0ef83a3e18d4c92012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-03yi-9300000000-cb8906cb50227e7ec5b52012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0a4i-0900000000-e3a22c7580a368d6849b2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-03di-0900000000-eab8c998b760a5bc2d462012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-000x-9000000000-d32f932f9d139b180e072012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0iki-0930000000-80b81755ee1a773ed3bb2012-08-31View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-000i-0090000000-5b43effb3dfed505b61b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0f79-0960000000-52b5a3c482216dc5067d2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dl-1490000000-abafa225b4c4cc6f13142017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bti-5930000000-d1e289dfa041a96af6e42017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9400000000-3dc5fad146dc390144582017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0490000000-dfebe908fd4392611bb62017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0uej-3940000000-c7f4d398999fc797b5442017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0f7o-9500000000-f8ed9a520a7d500d0c1e2017-09-01View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Spectrum
ChemSpider ID8418848
ChEMBL IDCHEMBL243618
KEGG Compound IDC00884
Pubchem Compound ID10243361
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB00745
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference