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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-05-22 22:04:33 UTC
Update Date2022-03-07 02:49:31 UTC
HMDB IDHMDB0006294
Secondary Accession Numbers
  • HMDB0155887
  • HMDB06294
Metabolite Identification
Common Name16-Hydroxyhexadecanoic acid
Description16-Hydroxyhexadecanoic acid, also known as 16-hydroxypalmitic acid, is a hydroxylated fatty acid where the terminal (omega) carbon has been hydroxylated. In animal tissues, a family of enzymes termed cytochromes P450s are involved in fatty acid oxidation, hydroxylating with high specificity at the energetically unfavourable terminal (omega) or omega-1 carbons. Hydroxy fatty acids primarily come from the consumption of plant products (vegetables or fruits) or cow’s milk. Omega hydroxy fatty acids are found in the structure of suberin, a lipid polyester present in plant cell walls, and of cutin, a lipid polyester which is a component of the plant cuticle. These apoplastic structures are important plant-environment interfaces that act as barriers limiting water and nutrient loss and protecting plants from radiation and pathogens. 16-Hydroxyhexadecanoic acid and 18-hydroxystearic acid are particularly abundant in cutin in the plant cuticle. 16-Hydroxyhexadecanoic acid has been proposed as a biomarker of beer consumption.
Structure
Data?1600461531
Synonyms
ValueSource
16-Hydroxy-hexadecanoic acidChEBI
16-Hydroxypalmitic acidChEBI
16-OH 16:0ChEBI
Juniperic acidChEBI
Omega-hydroxypalmitic acidChEBI
16-Hydroxy-hexadecanoateGenerator
16-HydroxypalmitateGenerator
JuniperateGenerator
Omega-hydroxypalmitateGenerator
16-HydroxyhexadecanoateGenerator
16-Hydroxy hexadecanoateHMDB
FA(16:0(16-OH))HMDB
Lanopalmitic acidHMDB
Omega-hydroxyhexadecanoic acidHMDB
Ω-hydroxyhexadecanoic acidHMDB
Ω-hydroxypalmitic acidHMDB
16-Hydroxyhexadecanoic acidChEBI, HMDB
Chemical FormulaC16H32O3
Average Molecular Weight272.4235
Monoisotopic Molecular Weight272.23514489
IUPAC Name16-hydroxyhexadecanoic acid
Traditional Name16-hydroxyhexadecanoic acid
CAS Registry Number506-13-8
SMILES
OCCCCCCCCCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C16H32O3/c17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16(18)19/h17H,1-15H2,(H,18,19)
InChI KeyUGAGPNKCDRTDHP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Hydroxy fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point94.00 to 98.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Boiling Point414.00 to 415.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility2.87 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP4.904 (est)The Good Scents Company Information System
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg168.98830932474
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.001 g/LALOGPS
logP5.77ALOGPS
logP4.82ChemAxon
logS-4.9ALOGPS
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 Count15ChemAxon
Refractivity79.01 m³·mol⁻¹ChemAxon
Polarizability35.41 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]+172.02531661259
DarkChem[M-H]-170.31131661259
DeepCCS[M+H]+167.02130932474
DeepCCS[M-H]-163.00130932474
DeepCCS[M-2H]-200.59430932474
DeepCCS[M+Na]+176.29430932474
AllCCS[M+H]+171.132859911
AllCCS[M+H-H2O]+168.132859911
AllCCS[M+NH4]+173.932859911
AllCCS[M+Na]+174.732859911
AllCCS[M-H]-173.032859911
AllCCS[M+Na-2H]-174.032859911
AllCCS[M+HCOO]-175.232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
16-Hydroxyhexadecanoic acidOCCCCCCCCCCCCCCCC(O)=O3310.4Standard polar33892256
16-Hydroxyhexadecanoic acidOCCCCCCCCCCCCCCCC(O)=O2142.8Standard non polar33892256
16-Hydroxyhexadecanoic acidOCCCCCCCCCCCCCCCC(O)=O2256.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
16-Hydroxyhexadecanoic acid,1TMS,isomer #1C[Si](C)(C)OCCCCCCCCCCCCCCCC(=O)O2354.8Semi standard non polar33892256
16-Hydroxyhexadecanoic acid,1TMS,isomer #2C[Si](C)(C)OC(=O)CCCCCCCCCCCCCCCO2312.2Semi standard non polar33892256
16-Hydroxyhexadecanoic acid,2TMS,isomer #1C[Si](C)(C)OCCCCCCCCCCCCCCCC(=O)O[Si](C)(C)C2404.5Semi standard non polar33892256
16-Hydroxyhexadecanoic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCCCCCCCCCCCCCCC(=O)O2579.6Semi standard non polar33892256
16-Hydroxyhexadecanoic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCCCCCCCCCO2563.8Semi standard non polar33892256
16-Hydroxyhexadecanoic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCCCCCCCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2921.0Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 16-Hydroxyhexadecanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-7930000000-ad8cf0089b491fa1e5cd2018-04-09Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 16-Hydroxyhexadecanoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Hydroxyhexadecanoic acid 10V, Positive-QTOFsplash10-0a4i-0090000000-468101d8a11af1e19fb22015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Hydroxyhexadecanoic acid 20V, Positive-QTOFsplash10-0a4i-1390000000-b96e5d9bf93a0533f50a2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Hydroxyhexadecanoic acid 40V, Positive-QTOFsplash10-001l-7910000000-de85d9f11917d3bd2f542015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Hydroxyhexadecanoic acid 10V, Negative-QTOFsplash10-00di-0090000000-355bea410e278c7b034e2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Hydroxyhexadecanoic acid 20V, Negative-QTOFsplash10-0uk9-1090000000-a82fa5c9114086d0e61e2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Hydroxyhexadecanoic acid 40V, Negative-QTOFsplash10-0a4l-9250000000-93d26870cf342252967f2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Hydroxyhexadecanoic acid 10V, Positive-QTOFsplash10-0ab9-2290000000-578204c997b44c45b07a2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Hydroxyhexadecanoic acid 20V, Positive-QTOFsplash10-0a4i-9440000000-a06fb9b2d3c16ea9e8142021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Hydroxyhexadecanoic acid 40V, Positive-QTOFsplash10-0a4m-9000000000-9ad19ca2f1345bd8f8122021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Hydroxyhexadecanoic acid 10V, Negative-QTOFsplash10-00di-0090000000-09835f7bfaa31d64d09c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Hydroxyhexadecanoic acid 20V, Negative-QTOFsplash10-0fk9-0090000000-9e380c8ffde0c8460bc62021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 16-Hydroxyhexadecanoic acid 40V, Negative-QTOFsplash10-0006-9320000000-be3d31d993db22a6eb072021-09-23Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • 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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB001611
KNApSAcK IDC00007430
Chemspider ID10034
KEGG Compound IDC18218
BioCyc ID16-HYDROXYPALMITATE
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound10466
PDB IDNot Available
ChEBI ID55328
Food Biomarker OntologyNot Available
VMH IDWHHDCA
MarkerDB IDNot Available
Good Scents IDrw1157321
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available