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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 23:05:22 UTC
Update Date2022-03-07 02:55:31 UTC
HMDB IDHMDB0037831
Secondary Accession Numbers
  • HMDB37831
Metabolite Identification
Common Namexi-8-Hydroxyhexadecanedioic acid
Descriptionxi-8-Hydroxyhexadecanedioic acid, also known as 9-hydroxy-hexadecan-1,16-dioate, 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 small amount of articles have been published on xi-8-Hydroxyhexadecanedioic acid.
Structure
Data?1563863095
Synonyms
ValueSource
XI-8-hydroxyhexadecanedioateGenerator
9-Hydroxy-hexadecan-1,16-dioateHMDB
Chemical FormulaC16H30O5
Average Molecular Weight302.4064
Monoisotopic Molecular Weight302.20932407
IUPAC Name8-hydroxyhexadecanedioic acid
Traditional Name8-hydroxyhexadecanedioic acid
CAS Registry NumberNot Available
SMILES
OC(CCCCCCCC(O)=O)CCCCCCC(O)=O
InChI Identifier
InChI=1S/C16H30O5/c17-14(11-7-4-5-9-13-16(20)21)10-6-2-1-3-8-12-15(18)19/h14,17H,1-13H2,(H,18,19)(H,20,21)
InChI KeyGZQVGXLMHGPBET-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
  • Dicarboxylic acid or derivatives
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.13 g/LALOGPS
logP2.59ALOGPS
logP3.55ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)4.36ChemAxon
pKa (Strongest Basic)-1.3ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity80.42 m³·mol⁻¹ChemAxon
Polarizability36.15 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]+177.26931661259
DarkChem[M-H]-173.75131661259
DeepCCS[M+H]+176.19330932474
DeepCCS[M-H]-172.17830932474
DeepCCS[M-2H]-209.29830932474
DeepCCS[M+Na]+185.14230932474
AllCCS[M+H]+177.032859911
AllCCS[M+H-H2O]+174.232859911
AllCCS[M+NH4]+179.732859911
AllCCS[M+Na]+180.432859911
AllCCS[M-H]-176.832859911
AllCCS[M+Na-2H]-177.732859911
AllCCS[M+HCOO]-178.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
xi-8-Hydroxyhexadecanedioic acidOC(CCCCCCCC(O)=O)CCCCCCC(O)=O3835.1Standard polar33892256
xi-8-Hydroxyhexadecanedioic acidOC(CCCCCCCC(O)=O)CCCCCCC(O)=O2231.3Standard non polar33892256
xi-8-Hydroxyhexadecanedioic acidOC(CCCCCCCC(O)=O)CCCCCCC(O)=O2536.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
xi-8-Hydroxyhexadecanedioic acid,1TMS,isomer #1C[Si](C)(C)OC(CCCCCCCC(=O)O)CCCCCCC(=O)O2581.8Semi standard non polar33892256
xi-8-Hydroxyhexadecanedioic acid,1TMS,isomer #2C[Si](C)(C)OC(=O)CCCCCCCC(O)CCCCCCC(=O)O2591.7Semi standard non polar33892256
xi-8-Hydroxyhexadecanedioic acid,1TMS,isomer #3C[Si](C)(C)OC(=O)CCCCCCC(O)CCCCCCCC(=O)O2590.9Semi standard non polar33892256
xi-8-Hydroxyhexadecanedioic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)CCCCCCCC(CCCCCCC(=O)O)O[Si](C)(C)C2603.6Semi standard non polar33892256
xi-8-Hydroxyhexadecanedioic acid,2TMS,isomer #2C[Si](C)(C)OC(=O)CCCCCCC(CCCCCCCC(=O)O)O[Si](C)(C)C2604.0Semi standard non polar33892256
xi-8-Hydroxyhexadecanedioic acid,2TMS,isomer #3C[Si](C)(C)OC(=O)CCCCCCCC(O)CCCCCCC(=O)O[Si](C)(C)C2629.6Semi standard non polar33892256
xi-8-Hydroxyhexadecanedioic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)CCCCCCCC(CCCCCCC(=O)O[Si](C)(C)C)O[Si](C)(C)C2659.2Semi standard non polar33892256
xi-8-Hydroxyhexadecanedioic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(CCCCCCCC(=O)O)CCCCCCC(=O)O2851.9Semi standard non polar33892256
xi-8-Hydroxyhexadecanedioic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCC(O)CCCCCCC(=O)O2833.9Semi standard non polar33892256
xi-8-Hydroxyhexadecanedioic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)CCCCCCC(O)CCCCCCCC(=O)O2832.8Semi standard non polar33892256
xi-8-Hydroxyhexadecanedioic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCC(CCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C3142.3Semi standard non polar33892256
xi-8-Hydroxyhexadecanedioic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)CCCCCCC(CCCCCCCC(=O)O)O[Si](C)(C)C(C)(C)C3143.0Semi standard non polar33892256
xi-8-Hydroxyhexadecanedioic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCC(O)CCCCCCC(=O)O[Si](C)(C)C(C)(C)C3129.6Semi standard non polar33892256
xi-8-Hydroxyhexadecanedioic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCCCCCC(CCCCCCC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C3387.6Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - xi-8-Hydroxyhexadecanedioic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-1790000000-b89b00078d51a13395cc2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - xi-8-Hydroxyhexadecanedioic acid GC-MS (3 TMS) - 70eV, Positivesplash10-0fb9-5309320000-514840ec8246b1a5260c2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - xi-8-Hydroxyhexadecanedioic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - xi-8-Hydroxyhexadecanedioic 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 - xi-8-Hydroxyhexadecanedioic acid 10V, Negative-QTOFsplash10-0udi-0069000000-cb2627432cee11e6a2052016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-8-Hydroxyhexadecanedioic acid 20V, Negative-QTOFsplash10-0pc9-1193000000-456fb4bd3466fd20302f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-8-Hydroxyhexadecanedioic acid 40V, Negative-QTOFsplash10-0a4i-9440000000-c6f2009a600c77a7051f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-8-Hydroxyhexadecanedioic acid 10V, Negative-QTOFsplash10-0ue9-0089000000-854ac4fd55ba0fa6a1742021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-8-Hydroxyhexadecanedioic acid 20V, Negative-QTOFsplash10-0kar-1092000000-e3b10fc48849d93bf5992021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-8-Hydroxyhexadecanedioic acid 40V, Negative-QTOFsplash10-0536-5790000000-17f4343d71ae7e248c612021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-8-Hydroxyhexadecanedioic acid 10V, Positive-QTOFsplash10-00kr-0091000000-f5a286539843964cb9d02016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-8-Hydroxyhexadecanedioic acid 20V, Positive-QTOFsplash10-000i-0290000000-137d01ff4393e607cab82016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-8-Hydroxyhexadecanedioic acid 40V, Positive-QTOFsplash10-000t-7960000000-3be1c224b6d2a682531d2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-8-Hydroxyhexadecanedioic acid 10V, Positive-QTOFsplash10-000i-0191000000-3d6b4f2dc26b2adbf0c42021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-8-Hydroxyhexadecanedioic acid 20V, Positive-QTOFsplash10-00kr-0490000000-5dde8f6f333560416ac22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - xi-8-Hydroxyhexadecanedioic acid 40V, Positive-QTOFsplash10-0a4i-9620000000-7d4fdc452f9dd031a6dc2021-09-23Wishart 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 IDFDB016980
KNApSAcK IDNot Available
Chemspider ID17220725
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound16061042
PDB IDNot Available
ChEBI IDNot Available
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.