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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:03:31 UTC
Update Date2022-03-07 02:55:31 UTC
HMDB IDHMDB0037798
Secondary Accession Numbers
  • HMDB37798
Metabolite Identification
Common Name(S)-10,16-Dihydroxyhexadecanoic acid
Description(S)-10,16-Dihydroxyhexadecanoic acid 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. Based on a literature review a significant number of articles have been published on (S)-10,16-Dihydroxyhexadecanoic acid.
Structure
Data?1563863090
Synonyms
ValueSource
(S)-10,16-DihydroxyhexadecanoateGenerator
10,16-DHHAMeSH, HMDB
(R)-10,16-Dihydroxyhexadecanoic acidMeSH, HMDB
10,16-Dihydroxy-palmitateGenerator
(S)-10,16-Dihydroxyhexadecanoic acidMeSH
10,16-Dihydroxyhexadecanoic acidMeSH
10,16-DihydroxyhexadecanoateGenerator
Chemical FormulaC16H32O4
Average Molecular Weight288.4229
Monoisotopic Molecular Weight288.230059512
IUPAC Name10,16-dihydroxyhexadecanoic acid
Traditional Name10,16-dihydroxy-palmitic acid
CAS Registry Number69232-67-3
SMILES
OCCCCCCC(O)CCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C16H32O4/c17-14-10-6-5-8-12-15(18)11-7-3-1-2-4-9-13-16(19)20/h15,17-18H,1-14H2,(H,19,20)
InChI KeyVJZBXAQGWLMYMS-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
  • Secondary alcohol
  • 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
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point74 - 75 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility6.66 mg/L @ 25 °C (est)The Good Scents Company Information System
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.078 g/LALOGPS
logP4.34ALOGPS
logP3.43ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
pKa (Strongest Basic)-1.2ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity80.68 m³·mol⁻¹ChemAxon
Polarizability35.85 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]+173.25431661259
DarkChem[M-H]-171.70931661259
DeepCCS[M+H]+175.6930932474
DeepCCS[M-H]-171.6730932474
DeepCCS[M-2H]-208.99230932474
DeepCCS[M+Na]+184.84630932474
AllCCS[M+H]+174.832859911
AllCCS[M+H-H2O]+171.832859911
AllCCS[M+NH4]+177.532859911
AllCCS[M+Na]+178.332859911
AllCCS[M-H]-175.032859911
AllCCS[M+Na-2H]-175.932859911
AllCCS[M+HCOO]-177.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
(S)-10,16-Dihydroxyhexadecanoic acidOCCCCCCC(O)CCCCCCCCC(O)=O3685.6Standard polar33892256
(S)-10,16-Dihydroxyhexadecanoic acidOCCCCCCC(O)CCCCCCCCC(O)=O2255.6Standard non polar33892256
(S)-10,16-Dihydroxyhexadecanoic acidOCCCCCCC(O)CCCCCCCCC(O)=O2457.1Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
(S)-10,16-Dihydroxyhexadecanoic acid,1TMS,isomer #1C[Si](C)(C)OCCCCCCC(O)CCCCCCCCC(=O)O2515.7Semi standard non polar33892256
(S)-10,16-Dihydroxyhexadecanoic acid,1TMS,isomer #2C[Si](C)(C)OC(CCCCCCO)CCCCCCCCC(=O)O2479.8Semi standard non polar33892256
(S)-10,16-Dihydroxyhexadecanoic acid,1TMS,isomer #3C[Si](C)(C)OC(=O)CCCCCCCCC(O)CCCCCCO2452.6Semi standard non polar33892256
(S)-10,16-Dihydroxyhexadecanoic acid,2TMS,isomer #1C[Si](C)(C)OCCCCCCC(CCCCCCCCC(=O)O)O[Si](C)(C)C2531.8Semi standard non polar33892256
(S)-10,16-Dihydroxyhexadecanoic acid,2TMS,isomer #2C[Si](C)(C)OCCCCCCC(O)CCCCCCCCC(=O)O[Si](C)(C)C2540.1Semi standard non polar33892256
(S)-10,16-Dihydroxyhexadecanoic acid,2TMS,isomer #3C[Si](C)(C)OC(=O)CCCCCCCCC(CCCCCCO)O[Si](C)(C)C2478.5Semi standard non polar33892256
(S)-10,16-Dihydroxyhexadecanoic acid,3TMS,isomer #1C[Si](C)(C)OCCCCCCC(CCCCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2552.2Semi standard non polar33892256
(S)-10,16-Dihydroxyhexadecanoic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCCCCCC(O)CCCCCCCCC(=O)O2736.2Semi standard non polar33892256
(S)-10,16-Dihydroxyhexadecanoic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(CCCCCCO)CCCCCCCCC(=O)O2725.4Semi standard non polar33892256
(S)-10,16-Dihydroxyhexadecanoic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCCC(O)CCCCCCO2699.2Semi standard non polar33892256
(S)-10,16-Dihydroxyhexadecanoic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCCCCCC(CCCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C3039.0Semi standard non polar33892256
(S)-10,16-Dihydroxyhexadecanoic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OCCCCCCC(O)CCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C3018.8Semi standard non polar33892256
(S)-10,16-Dihydroxyhexadecanoic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCCC(CCCCCCO)O[Si](C)(C)C(C)(C)C2980.8Semi standard non polar33892256
(S)-10,16-Dihydroxyhexadecanoic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCCCCCCC(CCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3265.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - (S)-10,16-Dihydroxyhexadecanoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-059x-2960000000-2eaabc8702e2f4a5e61e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-10,16-Dihydroxyhexadecanoic acid GC-MS (3 TMS) - 70eV, Positivesplash10-00vr-9774800000-ec2aa22ffd38d50ea18b2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - (S)-10,16-Dihydroxyhexadecanoic 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 - (S)-10,16-Dihydroxyhexadecanoic acid 10V, Positive-QTOFsplash10-0fk9-0090000000-465e7a338a58c2a3de1c2015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-10,16-Dihydroxyhexadecanoic acid 20V, Positive-QTOFsplash10-0uk9-2290000000-9073cde6e77c8f10440e2015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-10,16-Dihydroxyhexadecanoic acid 40V, Positive-QTOFsplash10-07bg-9540000000-7ddf031597711d9586f02015-05-26Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-10,16-Dihydroxyhexadecanoic acid 10V, Negative-QTOFsplash10-00kr-0090000000-ac8fa3ff7d152e1fa5b32015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-10,16-Dihydroxyhexadecanoic acid 20V, Negative-QTOFsplash10-014r-1190000000-e325664d06a4406780572015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-10,16-Dihydroxyhexadecanoic acid 40V, Negative-QTOFsplash10-0a4l-9540000000-222e6592a223044f033c2015-05-27Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-10,16-Dihydroxyhexadecanoic acid 10V, Positive-QTOFsplash10-0fk9-0190000000-67c90c18a24e681cd7962021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-10,16-Dihydroxyhexadecanoic acid 20V, Positive-QTOFsplash10-0uki-6980000000-81be362580046b5068ab2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-10,16-Dihydroxyhexadecanoic acid 40V, Positive-QTOFsplash10-0a4i-9100000000-e9d2d3f3fd3cb3ccc0a62021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-10,16-Dihydroxyhexadecanoic acid 10V, Negative-QTOFsplash10-000i-0090000000-18e9d8e8ec7c021c55172021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-10,16-Dihydroxyhexadecanoic acid 20V, Negative-QTOFsplash10-00kr-1090000000-37ade3e214aa7e62cf8c2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (S)-10,16-Dihydroxyhexadecanoic acid 40V, Negative-QTOFsplash10-05mo-8970000000-b958bbb62074ba6a7c372021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • 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 IDFDB021203
KNApSAcK IDC00007440
Chemspider ID390182
KEGG Compound IDC08285
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound441449
PDB IDNot Available
ChEBI ID692
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1439041
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.