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Bovine Metabolome Database



Showing metabocard for (S)-3-Hydroxybutyric acid (BMDB00442)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-05 20:57:59
Accession Number BMDB00442
Common Name (S)-3-Hydroxybutyric acid
Description (S)-3-Hydroxybutyric acid is a normal human metabolite, that has been found elevated in geriatric patients remitting from depression. (PMID 17048218) 3-Hydroxybutyric acid is a ketone body. Like the other ketone bodies (acetoacetate and acetone), levels of 3-Hydroxybutyric acid are raised in ketosis. In humans, 3-Hydroxybutyric acid is synthesized in the liver from acetyl-CoA, and can be used as an energy source by the brain when blood glucose is low.
Synonyms
  1. (S)-3-hydroxy-Butanoic acid
  2. (3S)-3-hydroxy-Butanoate
  3. (3S)-3-hydroxy-Butanoic acid
  4. (S)-3-Hydroxybutyrate
  5. (S)-3-hydroxy-2-methyl-Propanoate
  6. (S)-3-hydroxy-2-methyl-Propanoic acid
  7. (S)-b-Hydroxyisobutyrate
  8. (S)-b-Hydroxyisobutyric acid
  9. (S)-beta-Hydroxyisobutyric acid
  10. L-(+)-2-methyl-Hydracrylate
  11. L-(+)-2-methyl-Hydracrylic acid
  12. L-(+)-b-Hydroxyisobutyrate
  13. L-(+)-b-Hydroxyisobutyric acid
  14. L-beta-Hydroxybutyrate
  15. L-(+)-beta-Hydroxyisobutyrate
  16. L-(+)-beta-Hydroxyisobutyric acid
  17. (S)-beta-Hydroxyisobutyrate
  18. (+)-3-Hydroxy-n-butyric acid
  19. (3S)-3-Hydroxybutyric acid
  20. (S)-3-Hydroxybutanoic acid
  21. L-(+)-3-Hydroxybutyric acid
  22. L-3-Hydroxybutyric acid
  23. (+)-3-Hydroxybutyric acid
  24. (S)-3-hydroxybutanoate
  25. (S)-3-hydroxy-Butanoate
Chemical IUPAC Name (3S)-3-hydroxybutanoic acid
Chemical Formula C4H8O3
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Organic acids
Class
  • Hydroxy Acids
Sub Class
  • Short chain hydroxy acids
Family
  • Mammalian_Metabolite
Species
  • secondary alcohol; carboxylic acid
Biofunction
Application
Source
  • Endogenous
Average Molecular Weight 104.104
Monoisotopic Molecular Weight 104.047340
Isomeric SMILES C[C@H](O)CC(O)=O
Canonical SMILES CC(O)CC(O)=O
KEGG Compound ID C03197 Link Image
BioCyc ID CPD-1843 Link Image
BiGG ID Not Available
Wikipedia Link Not Available
METLIN ID Not Available
PubChem Compound 94318 Link Image
PubChem Substance 16105121 Link Image
ChEBI ID 17290 Link Image
CAS Registry Number 6168-83-8
InChI Identifier InChI=1/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m0/s1
Synthesis Reference Zhao, Jun. Synthesis of (S)-b-hydroxybutanoic acid from L-lactic acid. Hecheng Huaxue (1998), 6(4), 442-444.
Melting Point (Experimental) 45-48 oC
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 539.0 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge -1
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity -0.50 [Predicted by ALOGPS]; -0.5 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS) Not Available
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Download Spectrum
Download FID (Varian)
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Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
Download FID (Bruker)
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Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum
Low Energy
Download File
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Medium Energy
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High Energy
Download File
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Simplified TOCSY Spectrum Not Available
BMRB Spectrum Not Available
Cellular Location
  • Cytoplasm
Biofluid Location Not Available
Tissue Location
Tissue References
Adipose Tissue
Brain
Muscle
Neuron
Skeletal Muscle
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Pathway Names
  • Butyrate Metabolism
HMDB Pathways
Name Butyrate Metabolism
Image Show Link Image
KEGG Pathways
Name Butyrate Metabolism
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SimCell Pathways
Name Butyrate Metabolism
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Graph
SBML
General References Not Available
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