Details of Metabolite

General Information of MET (ID: META00007)
Name 3-Hydroxyoctanoic acid
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(3S)-3-Hydroxy-octanoate; (3S)-3-Hydroxy-octanoic acid; (3S)-3-Hydroxyoctanoate; (S)-3-Hydroxycaprylate; (S)-3-Hydroxycaprylic acid; (S)-3-Hydroxyoctanoate; (S)-3-OH Octanoate; (S)-3-OH Octanoic acid; (S)-3-OH-Caprylate; (S)-3-OH-Caprylic acid; (S)-b-Hydroxycaprylate; (S)-b-Hydroxycaprylic acid; (S)-b-Hydroxyoctanoate; (S)-b-Hydroxyoctanoic acid; (S)-b-OH-Caprylate; (S)-b-OH-Caprylic acid; (S)-b-OH-Octanoate; (S)-b-OH-Octanoic acid; (S)-beta-Hydroxycaprylic acid; (S)-beta-Hydroxyoctanoic acid; (S)-beta-OH-Caprylic acid; (S)-beta-OH-Octanoic acid; 3-Hydroxycaprylate; 3-Hydroxycaprylic acid; 3-Hydroxyoctanoate; 3-Hydroxyoctanoic acid; 3-Hydroxyoctanoic acid, (S)-isomer; FA(8:0(3-OH)); FA(8:0(3S-OH)); S-3-Hydroxyoctanoate; S-3-Hydroxyoctanoic acid; beta-Hydroxycaprylate; beta-Hydroxycaprylic acid; beta-Hydroxyoctanoate
Source Endogenous;Fatty acyls;Food
Structure Type   Medium-chain hydroxy acids and derivatives  (Click to Show/Hide the Complete Structure Type Hierarchy)
Organic acids and derivatives
Hydroxy acids and derivatives
Medium-chain hydroxy acids and derivatives
PubChem CID
11367166
HMDB ID
HMDB0001954
Formula
C8H16O3
Structure
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3D MOL 2D MOL
  Click to Show/Hide the Molecular/Functional Data (External Links/Property/Function) of This Metabolite
ChEBI ID
37100
FooDB ID
FDB022761
ChemSpider ID
9542083
Physicochemical Properties Molecular Weight 160.21 Topological Polar Surface Area 57.5
XlogP 1.4 Complexity 112
Heavy Atom Count 11 Rotatable Bond Count 6
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Function
3-Hydroxyoctanoic acid (CAS: 14292-27-4) is an organic 3-hydroxy dicarboxylic acid, a metabolite of medium-chain fatty acid oxidation found in human urine. It is believed that urinary 3-hydroxy dicarboxylic acids are derived from the omega-oxidation of 3-hydroxy fatty acids and the subsequent beta-oxidation of longer-chain 3-hydroxy dicarboxylic acids. 3-Hydroxyoctanoic acid has been identified in the human placenta.
Regulatory Network
Full List of Protein(s) Regulated by This Metabolite
      GPCR rhodopsin (GPCR-1)
            Hydroxycarboxylic acid receptor 3 (HCAR3) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [1]
                      Introduced Variation 3-Hydroxyoctanoic acid addition (1 hours)
                      Induced Change HCAR3 protein activity levels: increase
                      Summary Introduced Variation         Induced Change 
                      Disease Status Diabetic acidosis [ICD-11: 5A22]
                      Details It is reported that 3-hydroxyoctanoic acid addition causes the increase of HCAR3 protein activity compared with control group.
Full List of Protein(s) Regulating This Metabolite
      Transferases (EC 2)
            Arylamine N-acetyltransferase 1 (NAT1) Click to Show/Hide the Full List of Regulating Pair(s):   1 Pair(s)
               Detailed Information Protein   Info click to show the details of this protein
               Regulating Pair Experim Info click to show the details of experiment for validating this pair [2]
                      Introduced Variation Knockout of NAT1
                      Induced Change 3-Hydroxyoctanoic acid concentration: increase (FC = 3.3)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Breast cancer [ICD-11: 2C60]
                      Details It is reported that knockout of NAT1 leads to the increase of 3-hydroxyoctanoic acid levels compared with control group.
References
1 Deorphanization of GPR109B as a receptor for the beta-oxidation intermediate 3-OH-octanoic acid and its role in the regulation of lipolysis. J Biol Chem. 2009 Aug 14;284(33):21928-21933.
2 CRISPR/Cas9 knockout of human arylamine N-acetyltransferase 1 in MDA-MB-231 breast cancer cells suggests a role in cellular metabolism. Sci Rep. 2020 Jun 17;10(1):9804.

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