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Bovine Metabolome Database



Showing metabocard for (R)-3-Hydroxybutyric acid (BMDB00011)

Legend: metabolite field enzyme field

Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-05 20:57:37
Accession Number BMDB00011
Common Name (R)-3-Hydroxybutyric acid
Description (R)-3-Hydroxybutyric acid is a butyric acid substituted with a hydroxyl group in the beta or 3 position. It is involved in the synthesis and degradation of ketone bodies. Like the other ketone bodies (acetoacetate and acetone), levels of beta-hydroxybutyrate are raised in the blood and urine in ketosis. This acid is metabolized by 3-hydroxybutyrate dehydrogenase (catalyzes the oxidation of D-3-hydroxybutyrate to form acetoacetate, using NAD+ as an electron acceptor). The enzyme functions in nervous tissues and muscles, enabling the use of circulating hydroxybutyrate as a fuel. In the liver mitochondrial matrix, the enzyme can also catalyze the reverse reaction, a step in ketogenesis. 3-Hydroxybutyric acid is a chiral compound having two enantiomers, D-3-hydroxybutyric acid and L-3-hydroxybutyric acid. In humans, beta-hydroxybutyrate is synthesized in the liver from acetyl-CoA, and can be used as an energy source by the brain when blood glucose is low. It can also be used for the synthesis of biodegradable plastics (Wikipedia).
Synonyms
  1. (R)-(-)-b-Hydroxybutyrate
  2. (R)-(-)-b-Hydroxybutyric acid
  3. (R)-3-Hydroxybutanoate
  4. (R)-3-Hydroxybutanoic acid
  5. (R)-3-Hydroxybutyrate
  6. D-(-)-3-hydroxybutyrate
  7. D-3-hydroxybutyrate
  8. D-3-hydroxybutyric acid
  9. D-beta-hydroxybutyrate
  10. (R)-(-)-beta-Hydroxybutyrate
  11. (R)-(-)-beta-Hydroxybutyric acid
  12. delta-(-)-3-hydroxybutyrate
  13. delta-3-hydroxybutyrate
  14. delta-3-hydroxybutyric acid
  15. delta-beta-hydroxybutyrate
  16. 3-D-hydroxybutyrate
  17. 3-D-hydroxybutyric acid
  18. 3-delta-hydroxybutyrate
  19. 3-delta-hydroxybutyric acid
Chemical IUPAC Name (3R)-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
  • Component of Butanoate metabolism
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 C01089 Link Image
BioCyc ID CPD-335 Link Image
BiGG ID 36784 Link Image
Wikipedia Link Not Available
METLIN ID Not Available
PubChem Compound 92135 Link Image
PubChem Substance 4324 Link Image
ChEBI ID 17066 Link Image
CAS Registry Number 625-72-9
InChI Identifier InChI=1/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m1/s1
Synthesis Reference Le Sann, Christine; Munoz, Dulce M.; Saunders, Natalie; Simpson, Thomas J.; Smith, David I.; Soulas, Florilene; Watts, Paul; Willis, Christine L. Assembly intermediates in polyketide biosynthesis: enantioselective syntheses of b-hydroxycarbonyl compounds
Melting Point (Experimental) 49-50 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)
MOL File Show
SDF File Show
PDB File Show
2D Structure
3D Structure
Experimental PDB ID Not Available
Experimental 1H NMR Spectrum Download Spectrum
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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
  • Extracellular
  • mitochondria
Biofluid Location Not Available
Tissue Location
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Pathway Names
  • Synthesis and Degradation of Ketone Bodies
HMDB Pathways
Name Synthesis and Degradation of Ketone Bodies
Image Show Link Image
KEGG Pathways
Name Synthesis and Degradation of Ketone Bodies
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SimCell Pathways
Name Synthesis and Degradation of Ketone Bodies
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Graph Show Link Image
SBML Download (XML) Link Image
General References Not Available
Metabolic Enzymes
  1. 3-hydroxybutyrate dehydrogenase type 2
  2. D-beta-hydroxybutyrate dehydrogenase, mitochondrial
Enzyme 1 [top]
Enzyme 1 ID 1009
Enzyme 1 Name 3-hydroxybutyrate dehydrogenase type 2
Enzyme 1 Synonyms
  1. R-beta-hydroxybutyrate dehydrogenase
  2. Dehydrogenase/reductase SDR family member 6
Enzyme 1 Gene Name BDH2
Enzyme 1 Protein Sequence >3-hydroxybutyrate dehydrogenase type 2
MGRLDGKVIVLTAAAQGIGRAAALAFAKEGAKVIATDINDSKLQELDKYPGIHTRVLDVT
KKKQIDQFANDIERLDVLFNVAGFVHHGTILDCEETDWDFSMNLNVRSMYLMIKAFLPKM
MAQKSGNIINMSSVASSIKGVVNRCVYSTTKAAVIGLTKSVAADFIQQGIRCNCVCPGTV
DTPSLQERIQARPNPEEALSDFLKRQKTGRFATAEEVALLCVYLASDESAYITGNPVIID
GGWSL
Enzyme 1 Number of Residues 245
Enzyme 1 Molecular Weight 26661.5
Enzyme 1 Theoretical pI 7.30
Enzyme 1 GO Classification
Function
Process
Component
Enzyme 1 General Function Lipid transport and metabolism
Enzyme 1 Specific Function (R)-3-hydroxybutanoate + NAD(+) = acetoacetate + NADH
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 74355014 Link Image
Enzyme 1 UniProtKB/Swiss-Prot ID Q3T046 Link Image
Enzyme 1 UniProtKB/Swiss-Prot Entry Name BDH2_BOVIN Link Image
Enzyme 1 PDB ID Not Available
Enzyme 1 Cellular Location Not Available
Enzyme 1 Gene Sequence >738 bp
ATGGGTCGACTTGATGGGAAGGTCATTGTCCTGACGGCTGCTGCTCAGGGGATCGGCCGG
GCAGCCGCATTGGCTTTTGCAAAAGAAGGTGCCAAAGTCATAGCCACCGATATCAATGAC
TCCAAACTTCAGGAACTGGATAAGTACCCAGGTATTCACACTCGGGTCCTTGATGTCACA
AAGAAGAAGCAAATTGACCAGTTTGCCAATGACATTGAGAGACTTGATGTTCTCTTTAAC
GTTGCTGGTTTCGTCCATCACGGAACCATCCTGGACTGTGAAGAGACAGACTGGGACTTC
TCGATGAACCTCAACGTCCGCAGCATGTACCTGATGATCAAGGCTTTTCTTCCTAAGATG
ATGGCTCAGAAATCTGGCAACATTATCAACATGTCCTCTGTGGCTTCCAGCATCAAAGGC
GTTGTGAACAGGTGCGTGTACAGCACAACCAAGGCGGCCGTGATCGGCCTCACAAAGTCC
GTGGCTGCAGACTTCATCCAGCAGGGTATCCGGTGCAACTGTGTGTGTCCAGGAACAGTT
GATACCCCATCTCTGCAAGAAAGAATACAAGCCAGACCAAATCCTGAAGAGGCACTGAGC
GATTTCCTAAAGAGACAGAAAACAGGAAGATTTGCAACTGCAGAAGAAGTAGCCCTGCTC
TGCGTGTACTTGGCCTCTGATGAATCTGCCTACATCACGGGGAATCCTGTCATCATTGAT
GGAGGCTGGAGTTTGTGA
Enzyme 1 GenBank Gene ID BC102567 Link Image
Enzyme 1 GeneCard ID BDH2 Link Image
Enzyme 1 GenAtlas ID Not Available
Enzyme 1 HGNC ID Not Available
Enzyme 1 Chromosome Location Chromosome:4
Enzyme 1 Locus 4q24
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 General References Not Available
Enzyme 1 Metabolite References Not Available
Enzyme 2 [top]
Enzyme 2 ID 1010
Enzyme 2 Name D-beta-hydroxybutyrate dehydrogenase, mitochondrial
Enzyme 2 Synonyms
  1. BDH
  2. 3-hydroxybutyrate dehydrogenase
Enzyme 2 Gene Name BDH1
Enzyme 2 Protein Sequence >D-beta-hydroxybutyrate dehydrogenase, mitochondrial
MLTARLSRPLSQLPRKTLNFSDRENGTRGSLLLYSAPFVPVGRRTYAASVDPVGSKAVLI
TGCDSGFGFSLAKHLHSEGFLVFAGCLMKDKGSDGVKELDSMKSDRLRTVQLNVCKSEEV
DKAAEVIRSSLEDPEKGLWGLVNNAGISTFGDVEFTSMETYKEVAEVNLWGTVRVTKAFL
PLIRRAKGRVVNISSMMGRMANVARSPYCITKFGVEAFSDCLRYEMHPLGVKVSVVEPGN
FIAATSLYGGTERIQAIANKMWEELPEVVRQDYGRKYFDEKVARMESYCTSGSTDTSPVI
KAVTHALTATTPYTRYHPMDYYWWLRMQIMTHFPGAISDRIYIH
Enzyme 2 Number of Residues 344
Enzyme 2 Molecular Weight 38390.8
Enzyme 2 Theoretical pI 8.90
Enzyme 2 GO Classification
Function
Process
Component
Enzyme 2 General Function Lipid transport and metabolism
Enzyme 2 Specific Function (R)-3-hydroxybutanoate + NAD(+) = acetoacetate + NADH
Enzyme 2 Pathways Not Available
Enzyme 2 Reactions Not Available
Enzyme 2 Pfam Domain Function
Enzyme 2 Signals
  • None
Enzyme 2 Transmembrane Regions
  • None
Enzyme 2 Essentiality Not Available
Enzyme 2 GenBank ID Protein 73587365 Link Image
Enzyme 2 UniProtKB/Swiss-Prot ID Q02337 Link Image
Enzyme 2 UniProtKB/Swiss-Prot Entry Name BDH_BOVIN Link Image
Enzyme 2 PDB ID Not Available
Enzyme 2 Cellular Location Not Available
Enzyme 2 Gene Sequence >1035 bp
ATGCTAACAGCCCGCCTCTCCAGACCCCTGTCACAGCTTCCAAGGAAAACCCTGAATTTC
TCTGATAGAGAAAATGGGACAAGAGGCTCGCTGCTGCTTTACTCTGCGCCCTTTGTTCCT
GTTGGCCGTCGGACTTACGCTGCTTCAGTGGACCCGGTTGGCAGCAAAGCTGTCCTGATC
ACGGGCTGTGACTCGGGATTTGGGTTCTCCTTGGCCAAGCATCTGCATTCAGAAGGCTTC
CTTGTGTTTGCTGGCTGTTTGATGAAGGACAAAGGGAGTGATGGGGTCAAAGAGCTGGAC
AGCATGAAGAGTGATCGCTTAAGAACTGTCCAGCTCAACGTCTGCAAAAGCGAAGAGGTG
GATAAAGCGGCGGAGGTCATCCGCTCAAGCCTGGAGGACCCTGAGAAAGGCTTGTGGGGC
CTGGTTAACAATGCGGGCATCTCGACGTTTGGAGACGTGGAGTTCACCAGCATGGAGACC
TACAAGGAGGTGGCGGAAGTGAACCTCTGGGGCACTGTTCGGGTGACGAAAGCCTTCCTC
CCCCTCATCCGGAGGGCAAAAGGCCGCGTTGTTAACATCAGCAGCATGATGGGCCGCATG
GCCAACGTGGCCCGCTCCCCGTACTGCATCACCAAGTTCGGGGTGGAGGCTTTCTCTGAC
TGCCTGCGCTACGAGATGCACCCGCTGGGAGTAAAGGTCAGCGTGGTGGAACCCGGCAAC
TTCATCGCCGCCACCAGCCTCTACGGCGGTACTGAGCGCATCCAGGCCATCGCCAACAAG
ATGTGGGAGGAGCTGCCTGAGGTGGTGCGCCAGGACTACGGCAGGAAGTACTTCGATGAG
AAGGTCGCCAGGATGGAGAGCTACTGCACCAGCGGCTCCACGGACACCTCTCCTGTCATC
AAGGCTGTGACACACGCCCTGACTGCCACCACTCCCTACACTCGCTACCATCCCATGGAC
TACTACTGGTGGCTGCGGATGCAGATCATGACCCACTTCCCCGGAGCCATCTCCGACAGG
ATCTATATTCACTGA
Enzyme 2 GenBank Gene ID BC103051 Link Image
Enzyme 2 GeneCard ID BDH1 Link Image
Enzyme 2 GenAtlas ID Not Available
Enzyme 2 HGNC ID Not Available
Enzyme 2 Chromosome Location Chromosome:3
Enzyme 2 Locus 3q29
Enzyme 2 SNPs SNPJam Report Link Image
Enzyme 2 General References
  1. [PubMed Link Image]
Enzyme 2 Metabolite References Not Available