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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2006-05-22 14:17:34 UTC
Update Date2022-03-07 02:49:12 UTC
HMDB IDHMDB0002059
Secondary Accession Numbers
  • HMDB02059
Metabolite Identification
Common Name12-Hydroxydodecanoic acid
Description12-hydroxydodecanoic acid is the substrate of the human glutathione-dependent formaldehyde dehydrogenase (EC1.1.1.1). The enzyme that catalyzes the conversion of alcohols to aldehydes is a zinc-containing dimeric enzyme responsible for the oxidation of long-chain alcohols and omega-hydroxy fatty acids. (OMIM). The human glutathione-dependent formaldehyde dehydrogenase is unique among the structurally studied members of the alcohol dehydrogenase family in that it follows a random bi kinetic mechanism forming a binary complex, and a ternary complex with NAD+. (PMID 12196016 ).
Structure
Data?1582752226
Synonyms
ValueSource
12-Hydroxy lauric acidChEBI
2-Hydroxy-dodecanoic acidChEBI
Omega-hydroxy lauric acidChEBI
Omega-hydroxydodecanoic acidChEBI
Omega-OH dodecanoic acidChEBI
Omega-OH lauric acidChEBI
12-Hydroxy laateGenerator
12-Hydroxy laic acidGenerator
2-Hydroxy-dodecanoateGenerator
Omega-hydroxy laateGenerator
Omega-hydroxy laic acidGenerator
Omega-hydroxydodecanoateGenerator
Omega-OH dodecanoateGenerator
Omega-OH laateGenerator
Omega-OH laic acidGenerator
12-HydroxydodecanoateGenerator
12-HydroxylaurateHMDB
12-Hydroxylauric acidHMDB, MeSH
Omega hydroxy dodecanoateHMDB
Omega hydroxy dodecanoic acidHMDB
Omega-hydroxylauric acidMeSH, HMDB
12-Hydroxydodecanoic acidChEBI
SabinateGenerator, HMDB
Chemical FormulaC12H24O3
Average Molecular Weight216.3172
Monoisotopic Molecular Weight216.172544634
IUPAC Name12-hydroxydodecanoic acid
Traditional Name12-hydroxydodecanoic acid
CAS Registry Number505-95-3
SMILES
OCCCCCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C12H24O3/c13-11-9-7-5-3-1-2-4-6-8-10-12(14)15/h13H,1-11H2,(H,14,15)
InChI KeyZDHCZVWCTKTBRY-UHFFFAOYSA-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
  • Hydroxy fatty acid
  • Straight chain fatty acid
  • Fatty acyl
  • Fatty acid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Organooxygen compound
  • Primary alcohol
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point85.00 to 88.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point359.00 to 360.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility278 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.866 (est)The Good Scents Company Information System
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Not Available152.8http://allccs.zhulab.cn/database/detail?ID=AllCCS00002077
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.21 g/LALOGPS
logP3.5ALOGPS
logP3.04ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
pKa (Strongest Basic)-2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count11ChemAxon
Refractivity60.61 m³·mol⁻¹ChemAxon
Polarizability26.85 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+154.5931661259
DarkChem[M-H]-151.57431661259
DeepCCS[M+H]+151.51630932474
DeepCCS[M-H]-147.49230932474
DeepCCS[M-2H]-184.75830932474
DeepCCS[M+Na]+160.44430932474
AllCCS[M+H]+152.132859911
AllCCS[M+H-H2O]+148.632859911
AllCCS[M+NH4]+155.332859911
AllCCS[M+Na]+156.232859911
AllCCS[M-H]-155.832859911
AllCCS[M+Na-2H]-156.932859911
AllCCS[M+HCOO]-158.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
12-Hydroxydodecanoic acidOCCCCCCCCCCCC(O)=O2947.9Standard polar33892256
12-Hydroxydodecanoic acidOCCCCCCCCCCCC(O)=O1781.2Standard non polar33892256
12-Hydroxydodecanoic acidOCCCCCCCCCCCC(O)=O1868.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
12-Hydroxydodecanoic acid,1TMS,isomer #1C[Si](C)(C)OCCCCCCCCCCCC(=O)O1948.5Semi standard non polar33892256
12-Hydroxydodecanoic acid,1TMS,isomer #2C[Si](C)(C)OC(=O)CCCCCCCCCCCO1908.6Semi standard non polar33892256
12-Hydroxydodecanoic acid,2TMS,isomer #1C[Si](C)(C)OCCCCCCCCCCCC(=O)O[Si](C)(C)C2010.2Semi standard non polar33892256
12-Hydroxydodecanoic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCCCCCCCCCCC(=O)O2179.0Semi standard non polar33892256
12-Hydroxydodecanoic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCCCCCO2151.7Semi standard non polar33892256
12-Hydroxydodecanoic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCCCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2489.8Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 12-Hydroxydodecanoic acid EI-B (Non-derivatized)splash10-053v-9100000000-a92cb682b3bdad87a6b82017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 12-Hydroxydodecanoic acid EI-B (Non-derivatized)splash10-000t-9600000000-80739833ebc1d91a8f412017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 12-Hydroxydodecanoic acid EI-B (Non-derivatized)splash10-053v-9100000000-a92cb682b3bdad87a6b82018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 12-Hydroxydodecanoic acid EI-B (Non-derivatized)splash10-000t-9600000000-80739833ebc1d91a8f412018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 12-Hydroxydodecanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-8900000000-cca19c514cbd27e8ceb02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 12-Hydroxydodecanoic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00di-9661000000-4b85552e5625e377c6ba2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 12-Hydroxydodecanoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 12-Hydroxydodecanoic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-014i-1790000000-86939bdc2617444c93912012-07-25HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 12-Hydroxydodecanoic acid 40V, Negative-QTOFsplash10-052f-9200000000-897a99eb6e667c5ecef12021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 12-Hydroxydodecanoic acid 10V, Negative-QTOFsplash10-014i-0090000000-bf2f637495ab7368ab082021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 12-Hydroxydodecanoic acid 10V, Positive-QTOFsplash10-001i-9500000000-8b9aea66eb0e0ded6c6b2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 12-Hydroxydodecanoic acid 40V, Positive-QTOFsplash10-052f-9000000000-9dcbfcf4beef873ee06a2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 12-Hydroxydodecanoic acid 20V, Negative-QTOFsplash10-014i-0190000000-472d75ec2602139f5cc62021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 12-Hydroxydodecanoic acid 20V, Positive-QTOFsplash10-0a59-9200000000-6ad7fc879c5d723218a02021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Hydroxydodecanoic acid 10V, Positive-QTOFsplash10-0002-0910000000-844a5190b2e310ec626f2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Hydroxydodecanoic acid 20V, Positive-QTOFsplash10-000t-1900000000-499d158a0890694b2f7d2015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Hydroxydodecanoic acid 40V, Positive-QTOFsplash10-07gv-9600000000-cc905025c302321c2c332015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Hydroxydodecanoic acid 10V, Negative-QTOFsplash10-014i-0790000000-ba75e81dad07b4533bfa2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Hydroxydodecanoic acid 20V, Negative-QTOFsplash10-00kb-1920000000-64041ca2f1e9970c6e5e2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Hydroxydodecanoic acid 40V, Negative-QTOFsplash10-0a4m-9600000000-2c68993598743f556da62015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Hydroxydodecanoic acid 10V, Negative-QTOFsplash10-014i-0190000000-9d7bab7f261095aca2802021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Hydroxydodecanoic acid 20V, Negative-QTOFsplash10-014j-2890000000-c7f539a275c9a02bb82b2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Hydroxydodecanoic acid 40V, Negative-QTOFsplash10-002f-9400000000-276cebbd2318c8b4ae1d2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Hydroxydodecanoic acid 10V, Positive-QTOFsplash10-0671-9410000000-b1c59c70e8e4ae8d9b2f2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Hydroxydodecanoic acid 20V, Positive-QTOFsplash10-0avi-9100000000-b3eb89584383f43928512021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 12-Hydroxydodecanoic acid 40V, Positive-QTOFsplash10-0a4l-9000000000-c3285b34ced442e30df52021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-05Wishart LabView Spectrum
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)2012-12-05Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane (predicted from logP)
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 IDDB03704
Phenol Explorer Compound IDNot Available
FooDB IDFDB022822
KNApSAcK IDC00001219
Chemspider ID71366
KEGG Compound IDC08317
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6465
PubChem Compound79034
PDB IDNot Available
ChEBI ID39567
Food Biomarker OntologyNot Available
VMH IDWHDDCA
MarkerDB IDNot Available
Good Scents IDrw1157251
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Sanghani PC, Robinson H, Bosron WF, Hurley TD: Human glutathione-dependent formaldehyde dehydrogenase. Structures of apo, binary, and inhibitory ternary complexes. Biochemistry. 2002 Sep 3;41(35):10778-86. [PubMed:12196016 ]