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Human Metabolome Database Version 3.5

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Showing metabocard for 4-Trimethylammoniobutanoic acid (HMDB01161)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:10:00 -0700
HMDB ID HMDB01161
Secondary Accession Numbers None
Metabolite Identification
Common Name 4-Trimethylammoniobutanoic acid
Description 4-Trimethylammoniobutanoic acid is a substrate for Gamma-butyrobetaine dioxygenase, Aldehyde dehydrogenase (dimeric NADP-preferring), Aldehyde dehydrogenase family 7 member A1, Aldehyde dehydrogenase 1A3, Aldehyde dehydrogenase (mitochondrial), Fatty aldehyde dehydrogenase, Aldehyde dehydrogenase X (mitochondrial) and 4-trimethylaminobutyraldehyde dehydrogenase.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. 4-(N-Trimethylamino)butyrate
  2. 4-Butyrobetaine
  3. 4-Trimethylammoniobutanoate
  4. 4-Trimethylammoniobutanoic acid
  5. Actinine
  6. Butyrobetaine
  7. Deoxycarnitine
  8. gamma-Butyrobetaine
Chemical Formula C7H16NO2
Average Molecular Weight 146.2074
Monoisotopic Molecular Weight 146.118103761
IUPAC Name (3-carboxypropyl)trimethylazanium
Traditional IUPAC Name (3-carboxypropyl)trimethylazanium
CAS Registry Number 407-64-7
SMILES C[N+](C)(C)CCCC(O)=O
InChI Identifier InChI=1S/C7H15NO2/c1-8(2,3)6-4-5-7(9)10/h4-6H2,1-3H3/p+1
InChI Key JHPNVNIEXXLNTR-UHFFFAOYSA-O
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
  • quaternary ammonium ion(ChEBI)
Substituents
  • Carboxylic Acid
  • Quaternary Ammonium Salt
Direct Parent Amino Fatty Acids
Ontology
Status Detected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Lipid catabolism, Fatty acid transport, Energy production
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Cytoplasm
  • 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 0.33 g/L ALOGPS
LogP -3.01 ALOGPS
LogP -4 ChemAxon
LogS -2.74 ALOGPS
pKa (strongest acidic) 4.46 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 1 ChemAxon
Polar Surface Area 37.3 A2 ChemAxon
Rotatable Bond Count 4 ChemAxon
Refractivity 51.44 ChemAxon
Polarizability 16.63 ChemAxon
Formal Charge 1 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Carnitine Synthesis SMP00465 Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Comments
Blood Detected and Quantified
Article_icon
10.0 (0.5-20.0) uM Adult (>18 years old) Both Normal Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022456
KNApSAcK ID Not Available
Chemspider ID 131 Link_out
KEGG Compound ID C01181 Link_out
BioCyc ID 4-TRIMETHYLAMMONIOBUTANOATE Link_out
BiGG ID 53567 Link_out
Wikipedia Link Not Available
NuGOwiki Link HMDB01161 Link_out
Metagene Link HMDB01161 Link_out
METLIN ID 6043 Link_out
PubChem Compound 134 Link_out
PDB ID NM2 Link_out
ChEBI ID 1941 Link_out
References
Synthesis Reference Kawamura, Masao; Akutsu, Seiichi; Fukuda, Hirosuke; Hata, Hiroyuki; Morishita, Tsuyoshi; Kano, Kenji; Nishimori, Hirokuni. Manufacture of g-butyrobetaine by fermentation. Jpn. Kokai Tokkyo Koho (1987), 6 pp.
Material Safety Data Sheet (MSDS) Not Available
General References
  1. Hewawasam P, Ding M, Chen N, King D, Knipe J, Pajor L, Ortiz A, Gribkoff VK, Starrett J: Synthesis of water-soluble prodrugs of BMS-191011: a maxi-K channel opener targeted for post-stroke neuroprotection. Bioorg Med Chem Lett. 2003 May 19;13(10):1695-8. Pubmed: 12729644 Link_out
  2. Siliprandi N, Ciman M, Sartorelli L: Myocardial carnitine transport. Basic Res Cardiol. 1987;82 Suppl 1:53-62. Pubmed: 3311009 Link_out
  3. Rebouche CJ, Engel AG: Significance of renal gamma-butyrobetaine hydroxylase for carnitine biosynthesis in man. J Biol Chem. 1980 Sep 25;255(18):8700-5. Pubmed: 6773946 Link_out
  4. Terada N, Inoue F, Okochi M, Nakajima H, Kizaki Z, Kinugasa A, Sawada T: Measurement of carnitine precursors, epsilon-trimethyllysine and gamma-butyrobetaine in human serum by tandem mass spectrometry. J Chromatogr B Biomed Sci Appl. 1999 Aug 6;731(1):89-95. Pubmed: 10491993 Link_out
  5. Rebouche CJ, Chenard CA: Metabolic fate of dietary carnitine in human adults: identification and quantification of urinary and fecal metabolites. J Nutr. 1991 Apr;121(4):539-46. Pubmed: 2007906 Link_out
Enzymes
Name: 4-trimethylaminobutyraldehyde dehydrogenase
Reactions:
  • 4-trimethylammoniobutanal + NAD+ + H2O = 4-trimethylammoniobutanoate + NADH + 2 H+ [RN:R03283]
Gene Name: ALDH9A1
Uniprot ID: P49189 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Alpha-aminoadipic semialdehyde dehydrogenase
Reactions:
  • L-2-aminoadipate 6-semialdehyde + NAD(P)+ + H2O = L-2-aminoadipate + NAD(P)H + H+ [RN:R03102 R03103]
Gene Name: ALDH7A1
Uniprot ID: P49419 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldehyde dehydrogenase family 1 member A3
Reactions:
  • an aldehyde + NAD(P)+ + H2O = an acid + NAD(P)H + H+ [RN:R00538 R00634]
Gene Name: ALDH1A3
Uniprot ID: P47895 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldehyde dehydrogenase, mitochondrial
Reactions:
  • an aldehyde + NAD+ + H2O = an acid + NADH + H+ [RN:R00538]
Gene Name: ALDH2
Uniprot ID: P05091 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Fatty aldehyde dehydrogenase
Reactions:
  • an aldehyde + NAD+ + H2O = an acid + NADH + H+ [RN:R00538]
Gene Name: ALDH3A2
Uniprot ID: P51648 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldehyde dehydrogenase X, mitochondrial
Reactions:
  • an aldehyde + NAD+ + H2O = an acid + NADH + H+ [RN:R00538]
Gene Name: ALDH1B1
Uniprot ID: P30837 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Gamma-butyrobetaine dioxygenase
Reactions:
  • 4-trimethylammoniobutanoate + 2-oxoglutarate + O2 = 3-hydroxy-4-trimethylammoniobutanoate + succinate + CO2 [RN:R02397]
Gene Name: BBOX1
Uniprot ID: O75936 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA