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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2008-10-15 12:12:16 UTC
Update Date2021-09-14 15:00:41 UTC
HMDB IDHMDB0010728
Secondary Accession Numbers
  • HMDB10728
Metabolite Identification
Common Name(R)-3-Hydroxydodecanoic acid
Description(R)-3-Hydroxydodecanoic acid, also known as (3R)-3-hydroxylauric acid or (R)-beta-OH lauric acid, belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain (R)-3-Hydroxydodecanoic acid exists in all eukaryotes, ranging from yeast to plants to humans. In humans, (R)-3-hydroxydodecanoic acid is involved in the fatty acid biosynthesis pathway (R)-3-Hydroxydodecanoic acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make (R)-3-hydroxydodecanoic acid a potential biomarker for the consumption of these foods (R)-3-Hydroxydodecanoic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on (R)-3-Hydroxydodecanoic acid.
Structure
Data?1582752866
Synonyms
ValueSource
(3R)-3-Hydroxydodecanoic acidChEBI
(3R)-3-Hydroxylauric acidChEBI
(R)-3-OH Dodecanoic acidChEBI
(R)-3-OH Lauric acidChEBI
(R)-beta-Hydroxydodecanoic acidChEBI
(R)-beta-Hydroxylauric acidChEBI
(R)-beta-OH Dodecanoic acidChEBI
(R)-beta-OH Lauric acidChEBI
D-(-)-3-Hydroxydodecanoic acidChEBI
D-3-Hydroxydodecanoic acidChEBI
(3R)-3-HydroxydodecanoateGenerator
(3R)-3-HydroxylaateGenerator
(3R)-3-Hydroxylaic acidGenerator
(R)-3-OH DodecanoateGenerator
(R)-3-OH LaateGenerator
(R)-3-OH Laic acidGenerator
(R)-b-HydroxydodecanoateGenerator
(R)-b-Hydroxydodecanoic acidGenerator
(R)-beta-HydroxydodecanoateGenerator
(R)-Β-hydroxydodecanoateGenerator
(R)-Β-hydroxydodecanoic acidGenerator
(R)-b-HydroxylaateGenerator
(R)-b-Hydroxylaic acidGenerator
(R)-beta-HydroxylaateGenerator
(R)-beta-Hydroxylaic acidGenerator
(R)-Β-hydroxylaateGenerator
(R)-Β-hydroxylaic acidGenerator
(R)-b-OH DodecanoateGenerator
(R)-b-OH Dodecanoic acidGenerator
(R)-beta-OH DodecanoateGenerator
(R)-Β-OH dodecanoateGenerator
(R)-Β-OH dodecanoic acidGenerator
(R)-b-OH LaateGenerator
(R)-b-OH Laic acidGenerator
(R)-beta-OH LaateGenerator
(R)-beta-OH Laic acidGenerator
(R)-Β-OH laateGenerator
(R)-Β-OH laic acidGenerator
D-(-)-3-HydroxydodecanoateGenerator
D-3-HydroxydodecanoateGenerator
(R)-3-HydroxydodecanoateGenerator
Chemical FormulaC12H24O3
Average Molecular Weight216.3172
Monoisotopic Molecular Weight216.172544634
IUPAC Name(3R)-3-hydroxydodecanoic acid
Traditional Name(R)-3-hydroxydodecanoic acid
CAS Registry NumberNot Available
SMILES
[H][C@@](O)(CCCCCCCCC)CC(O)=O
InChI Identifier
InChI=1S/C12H24O3/c1-2-3-4-5-6-7-8-9-11(13)10-12(14)15/h11,13H,2-10H2,1H3,(H,14,15)/t11-/m1/s1
InChI KeyMUCMKTPAZLSKTL-LLVKDONJSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain hydroxy acids and derivatives. These are hydroxy acids with a 6 to 12 carbon atoms long side chain.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassMedium-chain hydroxy acids and derivatives
Direct ParentMedium-chain hydroxy acids and derivatives
Alternative Parents
Substituents
  • Medium-chain hydroxy acid
  • Medium-chain fatty acid
  • Beta-hydroxy acid
  • Hydroxy fatty acid
  • Fatty acyl
  • Fatty acid
  • Secondary alcohol
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Alcohol
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.34 g/LALOGPS
logP3.63ALOGPS
logP3.25ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)4.67ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity60.2 m³·mol⁻¹ChemAxon
Polarizability26.59 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available154.2131661259
DarkChem[M-H]-PredictedNot Available151.82831661259

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
(R)-3-Hydroxydodecanoic acid,1TMS,#11780.9321https://arxiv.org/abs/1905.12712
(R)-3-Hydroxydodecanoic acid,1TMS,#21767.3688https://arxiv.org/abs/1905.12712
(R)-3-Hydroxydodecanoic acid,2TMS,#11855.4991https://arxiv.org/abs/1905.12712
(R)-3-Hydroxydodecanoic acid,1TBDMS,#12007.2114https://arxiv.org/abs/1905.12712
(R)-3-Hydroxydodecanoic acid,1TBDMS,#22000.8281https://arxiv.org/abs/1905.12712
(R)-3-Hydroxydodecanoic acid,2TBDMS,#12314.8667https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000f-9500000000-ce0e4abc46c623ad50532016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00bc-9042000000-0d213d881baf293e004c2017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-0930000000-57fa523571a510c849402016-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0f7k-3900000000-db0ac4f7e5c200e8ffe92016-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052f-9200000000-af4ea991e8885d84f4d22016-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-1790000000-438c129b69517f0cd6f12016-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0q29-3920000000-f4f68c93f91c4519ee512016-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9600000000-05e66928d4652560bee32016-09-14View Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB07930
Phenol Explorer Compound IDNot Available
FooDB IDFDB027875
KNApSAcK IDNot Available
Chemspider ID4472229
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5312804
PDB IDHXD
ChEBI ID43197
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in transferase activity
Specific function:
Fatty acid synthetase catalyzes the formation of long-chain fatty acids from acetyl-CoA, malonyl-CoA and NADPH. This multifunctional protein has 7 catalytic activities and an acyl carrier protein.
Gene Name:
FASN
Uniprot ID:
P49327
Molecular weight:
273424.06