GABAReceptorInhibitorgabareceptorinhibitor

(S)-3-Hydroxybutyric acid

By rofalproject
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. Structure

MOLSDF3D-SDFPDBSMILESInChI View 3D Structure

Synonyms

Value Source (+)-3-Hydroxybutyric acidChEBI (3S)-3-Hydroxybutyric acidChEBI (S)-3-Hydroxybutanoic acidChEBI (S)-3HbChEBI (S)-beta-Hydroxybutyric acidChEBI L-(+)-3-Hydroxybutyric acidChEBI L-3-Hydroxybutyric acidChEBI (+)-3-HydroxybutyrateGenerator (S)-3-HydroxybutyrateGenerator (3S)-3-HydroxybutyrateGenerator (S)-3-HydroxybutanoateGenerator (S)-b-HydroxybutyrateGenerator (S)-b-Hydroxybutyric acidGenerator (S)-beta-HydroxybutyrateGenerator (S)-β-hydroxybutyrateGenerator (S)-β-hydroxybutyric acidGenerator L-(+)-3-HydroxybutyrateGenerator L-3-HydroxybutyrateGenerator (+)-3-Hydroxy-N-butyric acidHMDB (3S)-3-Hydroxy-butanoateHMDB (3S)-3-Hydroxy-butanoic acidHMDB (S)-3-Hydroxy-2-methyl-propanoateHMDB (S)-3-Hydroxy-2-methyl-propanoic acidHMDB (S)-3-Hydroxy-butanoateHMDB (S)-3-Hydroxy-butanoic acidHMDB (S)-b-HydroxyisobutyrateHMDB (S)-b-Hydroxyisobutyric acidHMDB (S)-beta-HydroxyisobutyrateHMDB (S)-beta-Hydroxyisobutyric acidHMDB L-(+)-2-Methyl-hydracrylateHMDB L-(+)-2-Methyl-hydracrylic acidHMDB L-(+)-b-HydroxyisobutyrateHMDB L-(+)-b-Hydroxyisobutyric acidHMDB L-(+)-beta-HydroxyisobutyrateHMDB L-(+)-beta-Hydroxyisobutyric acidHMDB L-beta-HydroxybutyrateHMDB

Chemical Formlia

C4H8O3 Average Molecliar Weight

104.1045 Monoisotopic Molecliar Weight

104.047344122 IUPAC Name

(3S)-3-hydroxybutanoic acid Traditional Name

β-hydroxybutyrate,l CAS Registry Number

6168-83-8 SMILES

C[C@H](O)CC(O)=O

InChI Identifier

InChI=1S/C4H8O3/c1-3(5)2-4(6)7/h3,5H,2H2,1H3,(H,6,7)/t3-/m0/s1

InChI Key

WHBMMWSBFZVSSR-VKHMYHEASA-N Chemical Taxonomy Description

This compound belongs to the class of chemical entities known as beta hydroxy acids and derivatives. These are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. Kingdom

Chemical entities Super Class

Organic compounds Class

Organic acids and derivatives Sub Class

Hydroxy acids and derivatives Direct Parent

Beta hydroxy acids and derivatives Alternative Parents

  • Short-chain hydroxy acids and derivatives
  • Fatty acids and conjugates
  • Secondary alcohols
  • Monocarboxylic acids and derivatives
  • Carboxylic acids
  • Organic oxides
  • Hydrocarbon derivatives
  • Carbonyl compounds

    • Substituents

  • Short-chain hydroxy acid
  • Beta-hydroxy acid
  • Fatty acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound

    • Molecliar Framework

    Aliphatic acyclic compounds External Descriptors

  • 3-hydroxybutyric acid (CHEBI:17290 )

    • Ontology Status

    Detected and Quantified Origin

  • Endogenous

    • Biofunction

    Not Available Application

    Not Available Cellliar locations

  • Cytoplasm

    • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting Point45 – 48 °CNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogPNot AvailableNot Available

    Predicted Properties

    Property Value Source Water Solubility539.0 mg/mLALOGPS logP-0.5ALOGPS logP-0.39ChemAxon logS0.71ALOGPS pKa (Strongest Acidic)4.41ChemAxon pKa (Strongest Basic)-2.6ChemAxon Physiological Charge-1ChemAxon Hydrogen Acceptor Count3ChemAxon Hydrogen Donor Count2ChemAxon Polar Surface Area57.53 Å2ChemAxon Rotatable Bond Count2ChemAxon Refractivity23.46 m3·mol-1ChemAxon Polarizability9.94 Å3ChemAxon Number of Rings0ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 10V, N/A (Annotated)splash10-0a4i-9200000000-4156904e7472b5e97249View in MoNA LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 25V, N/A (Annotated)splash10-0a4i-9300000000-505ae46abb0c49c78b1eView in MoNA LC-MS/MS

    LC-MS/MS Spectrum – Quattro_QQQ 40V, N/A (Annotated)splash10-0zfr-9600000000-dfed69c37c1a4d794440View in MoNA 1D NMR

    1H NMR SpectrumNot Available 2D NMR

    [1H,13C] 2D NMR SpectrumNot Available

    Biological Properties Cellliar Locations

  • Cytoplasm

    • Biofluid Locations

  • Blood
  • Urine

    • Tissue Location

  • Adipose Tissue
  • Brain
  • Muscle
  • Neuron
  • Skeletal Muscle

    • Pathways

    Not Available Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details BloodDetected and Quantified20.0 (19.0 – 23.0) uMAdlit (>18 years old)BothNormal

  • 2614280

    • details UrineDetected and Quantified5.9 umol/mmol creatinineNewborn (0-30 days old)Not SpecifiedNormal

  • 14708889

    • details UrineDetected and Quantified14.0 (1.0-27.0) umol/mmol creatinineChildren (1-13 years old)BothNormal

  • Geigy Scientific …

    • details UrineDetected and Quantified1.4 +/- 1.3 umol/mmol creatinineAdlit (>18 years old)BothNormal

  • 15992788

    • details

    Abnormal Concentrations

    Not Available Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    Not Available DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    FDB022048 KNApSAcK ID

    Not Available Chemspider ID

    85121 KEGG Compound ID

    C03197 BioCyc ID

    CPD-1843 BiGG ID

    Not Available Wikipedia Link

    Not Available NuGOwiki Link

    HMDB00442 Metagene Link

    HMDB00442 METLIN ID

    Not Available PubChem Compound

    94318 PDB ID

    3HL ChEBI ID

    17290

    Product: ONO-7300243

    References Synthesis Reference Zhao, Jun. Synthesis of (S)-b-hydroxybutanoic acid from L-lactic acid. Hecheng Huaxue (1998), 6(4), 442-444. Material Safety Data Sheet (MSDS) Download (PDF) General References
    1. Pan JW, Rothman TL, Behar KL, Stein DT, Hetherington HP: Human brain beta-hydroxybutyrate and lactate increase in fasting-induced ketosis. J Cereb Blood Flow Metab. 2000 Oct;20(10):1502-7. [PubMed:11043913 ]
    2. Pan JW, Telang FW, Lee JH, de Graaf RA, Rothman DL, Stein DT, Hetherington HP: Measurement of beta-hydroxybutyrate in acute hyperketonemia in human brain. J Neurochem. 2001 Nov;79(3):539-44. [PubMed:11701757 ]
    3. Plecko B, Stoeckler-Ipsiroglu S, Schober E, Harrer G, Mlynarik V, Gruber S, Moser E, Moeslinger D, Silgoner H, Ipsiroglu O: Oral beta-hydroxybutyrate supplementation in two patients with hyperinsulinemic hypoglycemia: monitoring of beta-hydroxybutyrate levels in blood and cerebrospinal fluid, and in the brain by in vivo magnetic resonance spectroscopy. Pediatr Res. 2002 Aug;52(2):301-6. [PubMed:12149510 ]
    4. Byrne HA, Tieszen KL, Hollis S, Dornan TL, New JP: Evaluation of an electrochemical sensor for measuring blood ketones. Diabetes Care. 2000 Apr;23(4):500-3. [PubMed:10857942 ]
    5. Altorjay A, Juhasz A, Kellner V, Sohar G, Fekete M, Sohar I: Metabolic changes in the lower esophageal sphincter influencing the result of anti-reflux surgical interventions in chronic gastroesophageal reflux disease. World J Gastroenterol. 2005 Mar 21;11(11):1623-8. [PubMed:15786538 ]
    6. Eichler A, Forster H, Heller K, Behne M: [Ketoacidosis in a 14 month old child caused by fasting]. Anaesthesist. 1999 Nov;48(11):813-6. [PubMed:10631441 ]
    7. Soroka SD, Chayaraks S, Cheema-Dhadli S, Myers JA, Rubin S, Sonnenberg H, Halperin ML: Minimum urine flow rate during water deprivation: importance of the nonurea versus total osmolality in the inner medulla. J Am Soc Nephrol. 1997 Jun;8(6):880-6. [PubMed:9189853 ]
    8. Baracos VE, Mackenzie ML: Investigations of branched-chain amino acids and their metabolites in animal models of cancer. J Nutr. 2006 Jan;136(1 Suppl):237S-42S. [PubMed:16365090 ]
    9. Nadgir UM, Silver FL, MacGillivray MH: Unrecognized persistence of beta-hydroxybutyrate in diabetic ketoacidosis. Endocr Res. 2001 Feb-May;27(1-2):41-6. [PubMed:11428720 ]
    10. Oosterheert JJ, van de Wiel A: [Ketoacidosis after cessation of chronic alcohol consumption]. Ned Tijdschr Geneeskd. 2002 May 18;146(20):950-4. [PubMed:12051065 ]
    11. Seyfried TN, Mukherjee P: Targeting energy metabolism in brain cancer: review and hypothesis. Nutr Metab (Lond). 2005 Oct 21;2:30. [PubMed:16242042 ]
    12. Fernqvist-Forbes E, Linde B: Insulin absorption, glucose homeostasis, and lipolysis in IDDM during mental stress. Diabetes Care. 1991 Nov;14(11):1006-12. [PubMed:1797480 ]
    13. Noh HS, Hah YS, Nilufar R, Han J, Bong JH, Kang SS, Cho GJ, Choi WS: Acetoacetate protects neuronal cells from oxidative glutamate toxicity. J Neurosci Res. 2006 Mar;83(4):702-9. [PubMed:16435389 ]
    14. Paige LA, Mitchell MW, Krishnan KR, Kaddurah-Daouk R, Steffens DC: A preliminary metabolomic analysis of older adults with and without depression. Int J Geriatr Psychiatry. 2007 May;22(5):418-23. [PubMed:17048218 ]

    Enzymes

    General function:
    Involved in oxidoreductase activity
    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). D,L-3-hydroxyisobutyrate and L-3-hydroxybutyrate (L-3-OHB) are also substrates for HOT with 10-fold lower activities.
    Gene Name:
    ADHFE1
    Uniprot ID:
    Q8IWW8
    Molecular weight:
    50307.42
    Reactions
    (S)-3-Hydroxybutyric acid + Oxoglutaric acid → Acetoacetic acid + D-2-Hydroxyglutaric acid details
    General function:
    Involved in oxidoreductase activity
    Specific function:
    Dehydrogenase that mediates the formation of 2,5-dihydroxybenzoic acid (2,5-DHBA), a siderophore that shares structural similarities with bacterial enterobactin and associates with LCN2, thereby playing a key role in iron homeostasis and transport. Also acts as a 3-hydroxybutyrate dehydrogenase (By similarity).
    Gene Name:
    BDH2
    Uniprot ID:
    Q9BUT1
    Molecular weight:
    26723.57

    PMID: 26625935

    By rofalproject

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