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Record Information
Version3.6
Creation Date2006-08-13 03:12:33 UTC
Update Date2013-02-09 00:12:43 UTC
HMDB IDHMDB03681
Secondary Accession Numbers
  • HMDB06238
Metabolite Identification
Common Name4-Acetamidobutanoic acid
Description4-Acetamidobutanoic acid is a GABA derivative, product of the Urea cycle and metabolism of amino groups, the product of NAD-linked aldehyde dehydrogenase (EC 1.2.1.3) (KEGG).
Structure
Thumb
Synonyms
  1. 4-(Acetylamino)butanoate
  2. 4-(Acetylamino)butanoic acid
  3. 4-Acetamidobutyric acid
  4. N-Acetyl-4-aminobutanoate
  5. N-Acetyl-4-aminobutanoic acid
  6. N-Acetyl-4-aminobutyric acid
  7. N-Acetyl-GABA
  8. N-Acetyl-gamma-amino-N-butyric acid
  9. N-Acetyl-gamma-aminobutyrate
  10. N4-Acetylaminobutanoate
  11. N4-Acetylaminobutanoic acid
Chemical FormulaC6H11NO3
Average Molecular Weight145.1564
Monoisotopic Molecular Weight145.073893223
IUPAC Name4-acetamidobutanoic acid
Traditional Name4-acetamidobutyrate
CAS Registry Number3025-96-5
SMILES
CC(=O)NCCCC(O)=O
InChI Identifier
InChI=1S/C6H11NO3/c1-5(8)7-4-2-3-6(9)10/h2-4H2,1H3,(H,7,8)(H,9,10)
InChI KeyUZTFMUBKZQVKLK-UHFFFAOYSA-N
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassLipids
ClassFatty Acids and Conjugates
Sub ClassAmino Fatty Acids
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Organic Compounds
  • Straight Chain Fatty Acids
  • aza fatty acid(ChEBI)
  • short-chain fatty acid(ChEBI)
  • straight-chain saturated fatty acid(ChEBI)
Substituents
  • Carboxamide Group
  • Carboxylic Acid
  • Secondary Carboxylic Acid Amide
Direct ParentAmino Fatty Acids
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
  • Protein synthesis, amino acid biosynthesis
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
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 Solubility19.9ALOGPS
logP-0.48ALOGPS
logP-0.8ChemAxon
logS-0.86ALOGPS
pKa (Strongest Acidic)4.49ChemAxon
pKa (Strongest Basic)-0.63ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity34.9 m3·mol-1ChemAxon
Polarizability14.8 Å3ChemAxon
Spectra
SpectraGC-MS
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Prostate
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.5 (0.0-1.0) uMAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.03 (0.0-0.065) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023214
KNApSAcK IDNot Available
Chemspider ID17180
KEGG Compound IDC02946
BioCyc IDCPD-570
BiGG ID1446095
Wikipedia LinkNot Available
NuGOwiki LinkHMDB03681
Metagene LinkHMDB03681
METLIN IDNot Available
PubChem Compound18189
PDB IDNot Available
ChEBI ID17645
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. Pubmed: 19212411

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Converts gamma-trimethylaminobutyraldehyde into gamma-butyrobetaine. Catalyzes the irreversible oxidation of a broad range of aldehydes to the corresponding acids in an NAD-dependent reaction.
Gene Name:
ALDH9A1
Uniprot ID:
P49189
Molecular weight:
56291.485
Reactions
N4-Acetylaminobutanal + NAD + Water → 4-Acetamidobutanoic acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Multifunctional enzyme mediating important protective effects. Metabolizes betaine aldehyde to betaine, an important cellular osmolyte and methyl donor. Protects cells from oxidative stress by metabolizing a number of lipid peroxidation-derived aldehydes. Involved in lysine catabolism.
Gene Name:
ALDH7A1
Uniprot ID:
P49419
Molecular weight:
58486.74
Reactions
N4-Acetylaminobutanal + NAD + Water → 4-Acetamidobutanoic acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:
ALDH1A3
Uniprot ID:
P47895
Molecular weight:
56107.995
General function:
Involved in oxidoreductase activity
Specific function:
Not Available
Gene Name:
ALDH2
Uniprot ID:
P05091
Molecular weight:
56380.93
Reactions
N4-Acetylaminobutanal + NAD + Water → 4-Acetamidobutanoic acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidation of long-chain aliphatic aldehydes to fatty acids. Active on a variety of saturated and unsaturated aliphatic aldehydes between 6 and 24 carbons in length. Responsible for conversion of the sphingosine 1-phosphate (S1P) degradation product hexadecenal to hexadecenoic acid.
Gene Name:
ALDH3A2
Uniprot ID:
P51648
Molecular weight:
54847.36
Reactions
N4-Acetylaminobutanal + NAD + Water → 4-Acetamidobutanoic acid + NADH + Hydrogen Iondetails
General function:
Involved in oxidoreductase activity
Specific function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation.
Gene Name:
ALDH1B1
Uniprot ID:
P30837
Molecular weight:
57248.96
Reactions
N4-Acetylaminobutanal + NAD + Water → 4-Acetamidobutanoic acid + NADH + Hydrogen Iondetails