Details of Metabolite

General Information of MET (ID: META00476)
Name 3-Hydroxycapric acid
Synonyms   Click to Show/Hide Synonyms of This Metabolite
(+)-3-Hydroxydecanoate; (+)-3-Hydroxydecanoic acid; (3S)-3-Hydroxydecanoate; (S)-3-Hydroxydecanoate; 3(S)-Hydroxydecanoate; 3(S)-Hydroxydecanoic acid; 3-Hydroxidecanoate; 3-Hydroxidecanoic acid; 3-Hydroxycaprate; 3-Hydroxycapric acid; 3-Hydroxydecanoate; 3-Hydroxydecanoic acid; FA(10:0(3-OH)); FA(10:0(3S-OH)); L-beta-Hydroxydecanoate; S-3-Hydroxydecanoate; S-3-Hydroxydecanoic acid; beta-Hydroxycaprate; beta-Hydroxycapric acid; beta-Hydroxydecanoate
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
5312799
HMDB ID
HMDB0002203
Formula
C10H20O3
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
37371
FooDB ID
FDB022904
ChemSpider ID
4472224
METLIN ID
6544
Physicochemical Properties Molecular Weight 188.26 Topological Polar Surface Area 57.5
XlogP 2.5 Complexity 134
Heavy Atom Count 13 Rotatable Bond Count 8
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 3
Function
3-Hydroxycapric acid (CAS: 14292-26-3) is a normally occurring carboxylic acid in human blood plasma. Medium- and long-chain 3-hydroxymonocarboxylic acids represent intermediates in the beta-oxidation of fatty acids. They accumulate in the plasma of patients with an inherited deficiency of long-chain 3-hydroxyacyl-CoA dehydrogenase (EC 1.1.1.35). 3-Hydroxyacyl-CoA dehydrogenase (HADH) deficiency has been described in diverse clinical cases: juvenile-onset recurrent myoglobinuria, hypoketotic hypoglycemic encephalopathy, hypertrophic/dilatative cardiomyopathy, sudden infant death, and fulminant hepatic failure (OMIM: 231530). 3-Hydroxycapric acid has some shape-transforming action on the membrane of intact human erythrocytes.
Regulatory Network
Full List of Protein(s) Regulating This Metabolite
      Hydrolases (EC 3)
            Sulfatase sulf-1 (SULF1) 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 Knockdown (shRNA) of SULF1
                      Induced Change 3-Hydroxycapric acid concentration: increase (FC = 1.93)
                      Summary Introduced Variation         Induced Change 
                      Disease Status Ovarian cancer [ICD-11: 2C73]
                      Details It is reported that knockdown of SULF1 leads to the increase of 3-hydroxycapric acid levels compared with control group.
      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-Hydroxycapric 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-hydroxycapric acid levels compared with control group.
References
1 Erratum to: Loss of HSulf-1 promotes altered lipid metabolism in ovarian cancer. Cancer Metab. 2014 Nov 4;2:24.
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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