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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:40:46 UTC
Update Date2019-07-23 06:07:57 UTC
HMDB IDHMDB0031068
Secondary Accession Numbers
  • HMDB31068
Metabolite Identification
Common NameIsopalmitic acid
DescriptionIsopalmitic acid, also known as isopalmitate, 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 Isopalmitic acid.
Structure
Data?1563862077
Synonyms
ValueSource
IsopalmitateGenerator
3,4-Dihydroxyphenyl thiocyanateHMDB
4-ThiocyanatopyrocatecholHMDB
Thiocyanic acid, 3,4-dihydroxyphenyl esterHMDB
Iso-C16:0PhytoBank
Isohexadecanoic acidPhytoBank
Isopalmitic acidPhytoBank
FA(i-16:0)PhytoBank
Chemical FormulaC16H32O2
Average Molecular Weight256.4241
Monoisotopic Molecular Weight256.240230268
IUPAC Name14-methylpentadecanoic acid
Traditional Nameisopalmitic acid
CAS Registry Number4669-02-7
SMILES
CC(C)CCCCCCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C16H32O2/c1-15(2)13-11-9-7-5-3-4-6-8-10-12-14-16(17)18/h15H,3-14H2,1-2H3,(H,17,18)
InChI KeyZONJATNKKGGVSU-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
  • Methyl-branched fatty acid
  • Branched fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point61.8 - 62.4 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00026 g/LALOGPS
logP10(7.04) g/LALOGPS
logP10(6.1) g/LChemAxon
logS10(-6) g/LALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count13ChemAxon
Refractivity77.03 m³·mol⁻¹ChemAxon
Polarizability34.08 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+161.38431661259
DarkChem[M-H]-165.59731661259
DeepCCS[M+H]+164.56930932474
DeepCCS[M-H]-160.54930932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Isopalmitic acidCC(C)CCCCCCCCCCCCC(O)=O2847.1Standard polar33892256
Isopalmitic acidCC(C)CCCCCCCCCCCCC(O)=O1863.9Standard non polar33892256
Isopalmitic acidCC(C)CCCCCCCCCCCCC(O)=O1945.6Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Isopalmitic acid,1TMS,isomer #1CC(C)CCCCCCCCCCCCC(=O)O[Si](C)(C)C2009.4Semi standard non polar33892256
Isopalmitic acid,1TBDMS,isomer #1CC(C)CCCCCCCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2258.4Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Isopalmitic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9510000000-0d06bf46220ef14e0bcf2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isopalmitic acid GC-MS (1 TMS) - 70eV, Positivesplash10-01y6-9330000000-5b3e93f280ae71ac62552017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Isopalmitic 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 - Isopalmitic acid 10V, Negative-QTOFsplash10-0a4i-0090000000-ee7714d6cd5a622bb73c2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isopalmitic acid 20V, Negative-QTOFsplash10-0a4i-0190000000-d5a6c38eea9fffffe17d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Isopalmitic acid 40V, Negative-QTOFsplash10-0002-5940000000-33bf33d9792bf8201f7e2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopalmitic acid 10V, Positive-QTOFsplash10-0a4r-0190000000-33d807f3cab7056ed9252016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopalmitic acid 20V, Positive-QTOFsplash10-0bti-6980000000-0a8e71b9f000705649362016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopalmitic acid 40V, Positive-QTOFsplash10-0a4i-9500000000-348a5914e488834ee8962016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopalmitic acid 10V, Negative-QTOFsplash10-0a4i-0090000000-64b91bef636787fb8a822016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopalmitic acid 20V, Negative-QTOFsplash10-0a4i-1090000000-53943f08df2971d688662016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopalmitic acid 40V, Negative-QTOFsplash10-0a4i-9320000000-a46de522dbb50d5bff3d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopalmitic acid 10V, Negative-QTOFsplash10-0a4i-0090000000-9437efc32cf6544653e12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopalmitic acid 20V, Negative-QTOFsplash10-0a4r-0090000000-9a2057664dde47a0e7dd2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopalmitic acid 40V, Negative-QTOFsplash10-0006-9410000000-5b9357da386b83b3dc982021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopalmitic acid 10V, Positive-QTOFsplash10-0a4r-6590000000-89791213cc212a7ebbcf2021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopalmitic acid 20V, Positive-QTOFsplash10-0a4r-9200000000-58a774bcd6fa17984c912021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Isopalmitic acid 40V, Positive-QTOFsplash10-0a4i-9000000000-587bbbd8bcbc7e16ff2a2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothColorectal Cancer details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer
details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  3. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003070
KNApSAcK IDC00052561
Chemspider ID33331
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound36247
PDB IDNot Available
ChEBI ID84890
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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.