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Bovine Rumen Metabolome Database



Showing metabocard for 4-Hydroxybutyric acid (RMDB00710)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-07-03 11:34:31
Accession Number RMDB00710
Common Name 4-Hydroxybutyric acid
Description 4-hydroxybutyric acid may cause bradycardia and dyskinesias. The precise function of GHB in the body is not clear. It is an immediate precursor to GABA, a neurotransmitter which regulates awakeness, physical activity and sleep. As GABA cannot cross the blood-brain barrier, GHB obtained from food may be used for converting to GABA. GHB protects cells from oxygen starvation, which might explain presence of the compound in vital organs. GHB was also found to have neuroprotective capabilities.
Synonyms
  1. Oxybate sodium
  2. 4-hydroxy-Butanoic acid
  3. monosodium salt
  4. gamma-hydroxybutyric acid
  5. 4-hydroxy-butyric acid
  6. 4-Hydroxybutyric acid
  7. gamma-hydroxy butyrate
  8. 4-Hydroxybutanoate
  9. gamma-hydroxy sodium butyrate
  10. Sodium gamma-hydroxybutyrate
  11. gamma-hydroxybutyrate sodium
  12. 4-Hydroxybutanoic acid
  13. Hydroxybutyric acid
  14. Sodium oxybate
  15. 4-Hydroxybutyric acid monosodium salt
  16. Sodium gamma-oxybutyrate
  17. 4-Hydroxybutyrate sodium
  18. 4-hydroxy-Butanoate
Chemical IUPAC Name 4-hydroxy-butanoic acid
Chemical Formula C4H8O3
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Organic acids
Class
  • Hydroxy Acids; Fatty Acids
Sub Class
  • Short chain hydroxy acids
Family
  • Microbial_Metabolite
Species
  • primary alcohol; carboxylic acid
Biofunction
Application
Source
  • Endogenous
Average Molecular Weight 104.104
Monoisotopic Molecular Weight 104.047340
Isomeric SMILES OCCCC(O)=O
Canonical SMILES OCCCC(O)=O
KEGG Compound ID C00989 Link Image
BioCyc ID CPD-3193 Link Image
BiGG ID Not Available
Wikipedia Link gamma-hydroxybutyric acid Link Image
METLIN ID 5678 Link Image
PubChem Compound 10413 Link Image
PubChem Substance 8157522 Link Image
ChEBI ID 30830 Link Image
CAS Registry Number 591-81-1
InChI Identifier InChI=1/C4H8O3/c5-3-1-2-4(6)7/h5H,1-3H2,(H,6,7)
Synthesis Reference Takigawa, Shinichiro; Araya, Shuzo. Process for the preparation of g-hydroxybutyric acid as a synthetic intermediate. Jpn. Kokai Tokkyo Koho (1988), 3 pp.
Melting Point (Experimental) Not Available
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 494.0 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity -0.63 [Predicted by ALOGPS]; -0.6 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
MOL File Show Link Image
SDF File Show Link Image
PDB File Show Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Not Available
Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Not Available
Predicted 1H NMR Spectrum Show Image
Show Peaklist
Predicted 13C NMR Spectrum Show Image
Show Peaklist
Mass Spectrum Not Available
Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location Not Available
Biofluid Location
  • Rumen
Tissue Location Not Available
Concentrations (Normal)
Biofluid Rumen
Value 206.16 +/- 81.77 uM
Age 4-5 years old
Sex Female (lactating)
Condition Normal (0% barley grain in dry matter (DM) basis)
Breed Holstein-Friesian
Experimental Condition Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800.
Comments Not Available
References
  • The rumen metabolome (in preparation)
Concentrations (Abnormal)
Biofluid Rumen
Value 217 +/- 22 uM
Age 4-5 years old
Sex Female (lactating)
Condition 15% barley grain in dry matter (DM) basis
Breed Holstein-Friesian
Experimental Condition Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800.
Comments Not Available
References
  • The rumen metabolome (in preparation)
Biofluid Rumen
Value 253 +/- 94 uM
Age 4-5 years old
Sex Female (lactating)
Condition 30% barley grain in dry matter (DM) basis
Breed Holstein-Friesian
Experimental Condition Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800.
Comments Not Available
References
  • The rumen metabolome (in preparation)
Biofluid Rumen
Value 239 +/- 48 uM
Age 4-5 years old
Sex Female (lactating)
Condition 45% barley grain in dry matter (DM) basis
Breed Holstein-Friesian
Experimental Condition Rumen fluid for the analysis was collected 15-20 minutes before the morning feeding on days 12 and 21 of each experimental period. Cows were fed once daily at 0800.
Comments Not Available
References
  • The rumen metabolome (in preparation)
Pathway Names Not Available
HMDB Pathways Not Available
KEGG Pathways Not Available
SimCell Pathways Not Available
General References
  1. Wikipedia Link Image
Metabolic Enzymes
  1. Hydroxyacid-oxoacid transhydrogenase, mitochondrial
Enzyme 1 [top]
Enzyme 1 ID 595
Enzyme 1 Name Hydroxyacid-oxoacid transhydrogenase, mitochondrial
Enzyme 1 Synonyms
  1. HOT
  2. Alcohol dehydrogenase iron-containing protein 1
Enzyme 1 Gene Name ADHFE1
Enzyme 1 Protein Sequence >Hydroxyacid-oxoacid transhydrogenase, mitochondrial
MAAARSRVVHLLRLLQRAACQCPSHSHTYSQAPGLSPSGKTTDYAFEMAVSTIRYGAGVT
KEVGMDLQSMGAKNVCLMTDKNLSQLPPVQTVMDSLVKNGINFKVYDHVRVEPTDTSFME
AIEFAKKGAFDAFLAVGGGSTIDTCKAANLYSSSPDSDFLDYVNAPIGKGKPVTVPLKPL
IAVPTTSGTGSETTGVAIFDYEHLKVKTGIASRAIKPTLGLIDPLHTLHMPERVVANSGF
DVLCHALESYTALPYHMRSPCPSSPITRPAYQGSNPISDIWAVHALRIVAKYLKRAIRNP
DDLEARSNMHLASAFAGIGFGNAGVHLCHGMSYPISGLVKTYKAKDYNVDHPLVPHGLSV
VLTSPAVFTFTSQMFPERHLEVAEILGADTRTARRPDAGPVLADTLRKFLFDLDVDDGLA
AIGYSKADIPELVKGTLPQERVTKLAPRPQSEEDLSALFEASMKLY
Enzyme 1 Number of Residues 466
Enzyme 1 Molecular Weight 50342.2
Enzyme 1 Theoretical pI 7.65
Enzyme 1 GO Classification
Function
Process
Component
Enzyme 1 General Function Energy production and conversion
Enzyme 1 Specific Function Catalyzes the cofactor-independent reversible oxidation of gamma-hydroxybutyrate (GHB) to succinic semialdehyde (SSA) coupled to reduction of 2-ketoglutarate (2-KG) to D-2- hydroxyglutarate (D-2-HG). L-3-hydroxybutyrate (L-3-OHB) is also a substrate for HOT when using 2-KG as hydrogen acceptor, resulting in the formation of D-2-HG
Enzyme 1 Pathways Not Available
Enzyme 1 Reactions Not Available
Enzyme 1 Pfam Domain Function
Enzyme 1 Signals
  • None
Enzyme 1 Transmembrane Regions
  • None
Enzyme 1 Essentiality Not Available
Enzyme 1 GenBank ID Protein 151553907 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID A6QP15 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name HOT_BOVIN Link Image
Enzyme 1 PDB ID Not Available
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence >1401 bp
ATGGCCGCCGCTCGCTCTCGGGTAGTGCACTTGCTGAGGCTTCTGCAACGCGCAGCATGC
CAGTGCCCGAGTCATTCTCATACTTATTCCCAAGCTCCTGGACTTTCACCTTCTGGGAAA
ACAACAGATTATGCCTTCGAGATGGCTGTTTCAACTATTAGATATGGAGCAGGAGTTACA
AAGGAAGTGGGCATGGACCTACAAAGCATGGGTGCTAAAAATGTTTGTTTGATGACAGAC
AAGAACCTCTCCCAACTCCCTCCTGTACAGACAGTGATGGATTCCCTAGTGAAGAATGGC
ATAAACTTTAAGGTTTATGATCATGTGAGAGTGGAACCAACTGATACAAGCTTCATGGAA
GCCATTGAATTTGCCAAAAAGGGAGCTTTCGATGCCTTCCTGGCCGTGGGTGGCGGTTCC
ACCATAGACACCTGTAAAGCCGCTAATCTGTATTCATCCAGCCCTGACTCTGACTTCCTA
GACTACGTCAATGCCCCCATTGGGAAGGGAAAGCCTGTGACTGTGCCTCTGAAACCTCTG
ATCGCAGTTCCAACTACCTCAGGCACTGGGAGCGAAACTACCGGAGTTGCCATTTTTGAC
TACGAACACTTGAAAGTAAAAACTGGCATTGCTTCGCGAGCCATCAAACCCACACTCGGC
CTGATTGATCCTCTACACACCCTGCACATGCCTGAGCGGGTGGTCGCCAACAGTGGCTTC
GATGTGCTCTGCCACGCCCTGGAGTCCTACACTGCCCTCCCATATCACATGCGGAGCCCC
TGCCCTTCAAGCCCTATCACTCGGCCAGCCTACCAGGGCAGCAACCCCATCAGTGACATC
TGGGCAGTCCACGCACTGCGGATCGTTGCCAAGTATCTGAAGAGGGCTATCAGAAATCCT
GATGATCTTGAAGCAAGGTCTAATATGCACTTGGCAAGTGCTTTTGCTGGCATTGGCTTT
GGAAATGCTGGTGTTCATCTATGCCATGGAATGTCTTACCCAATTTCTGGCTTAGTGAAG
ACTTATAAAGCAAAGGATTACAATGTGGATCATCCCCTGGTGCCTCATGGCCTTTCTGTG
GTGCTCACCTCCCCAGCAGTGTTCACATTTACATCACAGATGTTTCCTGAGCGGCACTTG
GAAGTGGCAGAAATATTGGGAGCTGACACCCGCACTGCCAGGAGGCCAGATGCTGGGCCT
GTCTTGGCAGACACGCTGCGGAAATTCTTATTCGATCTGGATGTGGATGACGGCCTGGCT
GCCATTGGCTACTCCAAGGCCGACATCCCCGAGCTGGTGAAAGGAACGCTGCCCCAGGAA
AGAGTCACCAAGCTTGCACCACGCCCTCAGTCAGAAGAGGATCTATCTGCTCTGTTTGAA
GCATCAATGAAACTGTATTAA
Enzyme 1 GenBank Gene ID BC149097 Link Image
Enzyme 1 GeneCard ID ADHFE1 Link Image
Enzyme 1 GenAtlas ID Not Available
Enzyme 1 HGNC ID Not Available
Enzyme 1 Chromosome Location Chromosome:8
Enzyme 1 Locus 8q13.1
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References Not Available
Enzyme 1 Metabolite References Not Available