Record Information
Version1.0
Creation date2011-09-21 01:51:34 UTC
Update date2015-07-21 06:59:39 UTC
Primary IDFDB029196
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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. [HMDB]
CAS Number56353-15-2
Structure
Thumb
Synonyms
SynonymSource
N-Acetylcarnosinehmdb
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC11H16N4O4
IUPAC name(2R)-2-(3-acetamidopropanamido)-3-(1H-imidazol-5-yl)propanoic acid
InChI IdentifierInChI=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 KeyInChIKey=BKAYIFDRRZZKNF-SECBINFHSA-N
Isomeric SMILES[H]OC(=O)[C@]([H])(N([H])C(=O)C([H])([H])C([H])([H])N([H])C(=O)C([H])([H])[H])C([H])([H])C1=C([H])N=C([H])N1[H]
Average Molecular Weight268
Monoisotopic Molecular Weight268
Classification
DescriptionThis compound belongs to the class of chemical entities known as hybrid peptides. These are compounds containing at least two different types of amino acids (alpha, beta, gamma, delta) linked to each other through a peptide bond.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassPeptidomimetics
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
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
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-022c-9340000000-84836a85524168a8642dView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-9221000000-de2fd1c2648a58838decView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0n4i-1390000000-a4eff96c8b8a51ef137aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0bvi-6960000000-617fa10b46b58704d909View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-06r6-9600000000-98bf8559c9f43dce2cbfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0190000000-398790fb46688699d48fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0l59-6970000000-7df29e865cf688e6b8a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9200000000-66887a850db8f75f875cView in MoNA
ChemSpider ID8396518
ChEMBL IDNot Available
KEGG Compound IDNot Available
Pubchem Compound ID10221026
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB12881
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG IDNot Available
KNApSAcK IDNot Available
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDacetylcarnosine
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
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference