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Record Information
Version1.0
Created at2006-05-22 14:17:34 UTC
Updated at2021-08-19 23:58:04 UTC
NP-MRD IDNP0000382
Secondary Accession NumbersNone
Natural Product 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
Thumb
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
Omega hydroxy dodecanoateHMDB
Omega hydroxy dodecanoic acidHMDB
Omega-hydroxylauric acidHMDB
SabinateHMDB
12-Hydroxydodecanoic acidChEBI
Chemical FormulaC12H24O3
Average Mass216.3172 Da
Monoisotopic Mass216.17254 Da
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
Spectra
Spectrum TypeDescriptionDepositor IDDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart Lab2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Wishart Lab2021-06-20View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Pinus radiataKNApSAcK Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Trypanosoma bruceiLOTUS Database
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
Physical Properties
StateSolid
Experimental 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
Predicted 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
HMDB IDHMDB0002059
DrugBank IDDB03704
Phenol Explorer Compound IDNot Available
FoodDB 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
Good Scents IDrw1157251
References
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 ]
  2. Ichihara K, Yamakawa I, Kusunose E, Kusunose M: Fatty acid omega and (omega-1)-Hydroxylation in rabbit intestinal mucosa microsomes. J Biochem. 1979 Jul;86(1):139-46. [PubMed:113393 ]
  3. Crespi CL, Chang TK, Waxman DJ: Determination of CYP4A11-catalyzed lauric acid 12-hydroxylation by high-performance liquid chromatography with radiometric detection. Methods Mol Biol. 2006;320:143-7. doi: 10.1385/1-59259-998-2:143. [PubMed:16719385 ]
  4. Gotoh Y, Sumimoto H, Minakami S: Formation of 20-oxoleukotriene B4 by an alcohol dehydrogenase isolated from human neutrophils. Biochim Biophys Acta. 1990 Mar 12;1043(1):52-6. doi: 10.1016/0005-2760(90)90109-b. [PubMed:2155662 ]
  5. Chaurasia CS, Alterman MA, Lu P, Hanzlik RP: Biochemical characterization of lauric acid omega-hydroxylation by a CYP4A1/NADPH-cytochrome P450 reductase fusion protein. Arch Biochem Biophys. 1995 Feb 20;317(1):161-9. doi: 10.1006/abbi.1995.1149. [PubMed:7872779 ]