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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-13 03:12:33 UTC
Update Date2020-02-26 21:24:46 UTC
HMDB IDHMDB0003681
Secondary Accession Numbers
  • HMDB0006238
  • HMDB0060265
  • HMDB03681
  • HMDB06238
  • HMDB60265
Metabolite Identification
Common Name4-Acetamidobutanoic acid
Description4-Acetamidobutanoic acid, also known as 4-acetamidobutanoate or N-acetyl-4-aminobutyric acid, is a member of the class of compounds known as gamma amino acids and derivatives. These compounds are amino acids having an -NH2 group attached to the gamma carbon atom. 4-Acetamidobutanoic acid is soluble (in water) and a weakly acidic compound (based on its pKa). 4-Acetamidobutanoic acid can be found in a number of food items such as Rubus species (blackberry, raspberry), cassava, pepper (C. frutescens), and napa cabbage, which makes 4-acetamidobutanoic acid a potential biomarker for the consumption of these food products. 4-Acetamidobutanoic acid can be found in blood, feces, and urine, as well as in human prostate tissue. 4-Acetamidobutanoic acid exists in all eukaryotes, ranging from yeast to humans. 4-Acetamidobutanoic acid is a GABA derivative, a product of the urea cycle and the metabolism of amino groups, and the product of NAD-linked aldehyde dehydrogenase (EC 1.2.1.3) (KEGG).
Structure
Data?1582752286
Synonyms
ValueSource
4-Acetamidobutyric acidChEBI
N-Acetyl-4-aminobutanoic acidChEBI
N-Acetyl-4-aminobutyric acidChEBI
N4-Acetylaminobutanoic acidChEBI
N4-AcetylaminobutanoateKegg
4-AcetamidobutyrateGenerator
N-Acetyl-4-aminobutanoateGenerator
N-Acetyl-4-aminobutyrateGenerator
4-AcetamidobutanoateGenerator
4-(Acetylamino)butanoateHMDB
4-(Acetylamino)butanoic acidHMDB
N-Acetyl-gabaHMDB
N-Acetyl-gamma-amino-N-butyric acidHMDB
N-Acetyl-gamma-aminobutyrateHMDB
4-Acetamidobutanoic acidGenerator
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
Description belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentGamma amino acids and derivatives
Alternative Parents
Substituents
  • Gamma amino acid or derivatives
  • Straight chain fatty acid
  • Fatty acid
  • Fatty acyl
  • Carboximidic acid
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboximidic acid derivative
  • Hydrocarbon derivative
  • Carbonyl group
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

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 Solubility19.9 g/LALOGPS
logP-0.48ALOGPS
logP-0.8ChemAxon
logS-0.86ALOGPS
pKa (Strongest Acidic)4.49ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area66.4 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity34.9 m³·mol⁻¹ChemAxon
Polarizability14.8 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (2 TMS)splash10-0ab9-5910000000-616492abfabb6439af40Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-000i-8900000000-9c41d4816e53d2df1696Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0ab9-5910000000-616492abfabb6439af40Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000i-8900000000-9c41d4816e53d2df1696Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0ab9-5910000000-616492abfabb6439af40Spectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000i-8900000000-9c41d4816e53d2df1696Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0a4i-0900000000-5bd8cc559b90a64af1a4Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000i-5910000000-392be10f3144349f0934Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9000000000-1d251bd6acc9a9656032Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-006x-9200000000-801b38a728ac351762e3Spectrum
LC-MS/MSLC-MS/MS Spectrum - , negativesplash10-0udi-1900000000-2b55924041c3b349dcb9Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000j-0900000000-9b0713f455b5092ea5b0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004r-4900000000-61610846c38b08a1c362Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-9300000000-34ef78b671c3a4979c55Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-979b40d7d5bb3012fba3Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0f6x-2900000000-a4f5296fa5b6b4439356Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pdl-8900000000-08e05706af59b90ee5aeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-7586f2859664a58f822dSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Placenta
  • Prostate
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified0.5 (0.0-1.0) uMAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>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
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothBladder cancer details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023214
KNApSAcK IDNot Available
Chemspider ID17180
KEGG Compound IDC02946
BioCyc IDNot Available
BiGG ID1446095
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound18189
PDB IDNot Available
ChEBI ID17645
Food Biomarker OntologyNot Available
VMH ID4AABUTN
MarkerDB ID
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. doi: 10.1038/nature07762. [PubMed:19212411 ]
  2. Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 May;31(5):419-25. doi: 10.1038/nbt.2488. Epub 2013 Mar 3. [PubMed:23455439 ]
  3. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

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