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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2009-07-25 00:09:08 UTC
Update Date2020-02-26 21:37:56 UTC
HMDB IDHMDB0012881
Secondary Accession Numbers
  • HMDB12881
Metabolite Identification
Common NameAcetylcarnosine
DescriptionN-Acetylcarnosine (NAC) is a naturally-occurring compound chemically related to the dipeptide carnosine. Its molecular structure is similar to carnosine with the exception that it carries an additional acetyl group. This makes NAC a more stable molecule which is not easily destroyed by carnosinase, an enzyme that breaks down carnosine to its constituent amino acids, beta-alanine and histidine. NAC is a free-radical scavenger and is particularly active against lipid peroxidation in the different parts of the lens in the eye. It is the active ingredient of eye drops used in order to prevent or treat cataract.
Structure
Data?1582753075
Synonyms
ValueSource
N-AcetylcarnosineHMDB
(2R)-2-({1-hydroxy-3-[(1-hydroxyethylidene)amino]propylidene}amino)-3-(1H-imidazol-5-yl)propanoateGenerator
Chemical FormulaC11H16N4O4
Average Molecular Weight268.2691
Monoisotopic Molecular Weight268.11715502
IUPAC Name(2R)-2-(3-acetamidopropanamido)-3-(1H-imidazol-5-yl)propanoic acid
Traditional Name(2R)-2-(3-acetamidopropanamido)-3-(3H-imidazol-4-yl)propanoic acid
CAS Registry Number56353-15-2
SMILES
CC(=O)NCCC(=O)N[C@H](CC1=CN=CN1)C(O)=O
InChI Identifier
InChI=1S/C11H16N4O4/c1-7(16)13-3-2-10(17)15-9(11(18)19)4-8-5-12-6-14-8/h5-6,9H,2-4H2,1H3,(H,12,14)(H,13,16)(H,15,17)(H,18,19)/t9-/m1/s1
InChI KeyBKAYIFDRRZZKNF-SECBINFHSA-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
  • Beta amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Imidazolyl carboxylic acid derivative
  • Azole
  • Heteroaromatic compound
  • Imidazole
  • Acetamide
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Carboxylic acid
  • Azacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Organic oxide
  • Organic oxygen compound
  • Organopnictogen compound
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • 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 Solubility1.07 g/LALOGPS
logP-0.93ALOGPS
logP-3.2ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)3.61ChemAxon
pKa (Strongest Basic)6.75ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area124.18 ŲChemAxon
Rotatable Bond Count7ChemAxon
Refractivity65.01 m³·mol⁻¹ChemAxon
Polarizability26.1 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, Positivesplash10-022c-9340000000-84836a85524168a8642dSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9221000000-de2fd1c2648a58838decSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0n4i-1390000000-a4eff96c8b8a51ef137aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bvi-6960000000-617fa10b46b58704d909Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06r6-9600000000-98bf8559c9f43dce2cbfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0190000000-398790fb46688699d48fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0l59-6970000000-7df29e865cf688e6b8a3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9200000000-66887a850db8f75f875cSpectrum
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 IDFDB029196
KNApSAcK IDNot Available
Chemspider ID8396518
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAcetylcarnosine
METLIN IDNot Available
PubChem Compound10221026
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 ReferencesNot Available