Human Metabolome Database Version 3.5

Showing metabocard for 4-Acetamidobutanoic acid (HMDB03681)

Record Information
Version 3.5
Creation Date 2006-08-12 21:12:33 -0600
Update Date 2013-02-08 17:12:43 -0700
HMDB ID HMDB03681
Secondary Accession Numbers
  • HMDB06238
Metabolite Identification
Common Name 4-Acetamidobutanoic acid
Description 4-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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C6H11NO3
Average Molecular Weight 145.1564
Monoisotopic Molecular Weight 145.073893223
IUPAC Name 4-acetamidobutanoic acid
Traditional IUPAC Name 4-acetamidobutyrate
CAS Registry Number 3025-96-5
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 Key UZTFMUBKZQVKLK-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Acids and Conjugates
Sub Class Amino 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 Parent Amino Fatty Acids
Ontology
Status Detected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 19.9 g/L ALOGPS
LogP -0.48 ALOGPS
LogP -0.8 ChemAxon
LogS -0.86 ALOGPS
pKa (strongest acidic) 4.49 ChemAxon
pKa (strongest basic) -0.63 ChemAxon
Hydrogen Acceptor Count 3 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 66.4 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 34.9 ChemAxon
Polarizability 14.8 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
MS/MS Spectrum GC-MS
MS/MS Spectrum GC-MS
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue Location
  • Prostate
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Blood Detected and Quantified
0.5 (0.0-1.0) uM Adult (>18 years old) Both Comment Normal
Urine Detected and Quantified
0.03 (0.0-0.065) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023214
KNApSAcK ID Not Available
Chemspider ID 17180 Link_out
KEGG Compound ID C02946 Link_out
BioCyc ID CPD-570 Link_out
BiGG ID 1446095 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB03681 Link_out
Metagene Link HMDB03681 Link_out
METLIN ID Not Available
PubChem Compound 18189 Link_out
PDB ID Not Available
ChEBI ID 17645 Link_out
References
Synthesis Reference Not 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 Link_out

Enzymes
Name: 4-trimethylaminobutyraldehyde dehydrogenase
Reactions:
N4-Acetylaminobutanal + NAD + Water unknown 4-Acetamidobutanoic acid + NADH + Hydrogen Ion details
Gene Name: ALDH9A1
Uniprot ID: P49189 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Alpha-aminoadipic semialdehyde dehydrogenase
Reactions:
N4-Acetylaminobutanal + NAD + Water unknown 4-Acetamidobutanoic acid + NADH + Hydrogen Ion details
Gene Name: ALDH7A1
Uniprot ID: P49419 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldehyde dehydrogenase family 1 member A3
Reactions: Not Available
Gene Name: ALDH1A3
Uniprot ID: P47895 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldehyde dehydrogenase, mitochondrial
Reactions:
N4-Acetylaminobutanal + NAD + Water unknown 4-Acetamidobutanoic acid + NADH + Hydrogen Ion details
Gene Name: ALDH2
Uniprot ID: P05091 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Fatty aldehyde dehydrogenase
Reactions:
N4-Acetylaminobutanal + NAD + Water unknown 4-Acetamidobutanoic acid + NADH + Hydrogen Ion details
Gene Name: ALDH3A2
Uniprot ID: P51648 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldehyde dehydrogenase X, mitochondrial
Reactions:
N4-Acetylaminobutanal + NAD + Water unknown 4-Acetamidobutanoic acid + NADH + Hydrogen Ion details
Gene Name: ALDH1B1
Uniprot ID: P30837 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA