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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2014-04-16 20:46:46 UTC
Update Date2020-02-26 19:17:41 UTC
HMDB IDHMDB0061714
Secondary Accession Numbers
  • HMDB0062219
  • HMDB61714
  • HMDB62219
Metabolite Identification
Common NameDocosadienoate (22:2n6)
Description(13Z,16Z)-Docosadienoic acid, also known as docosadienoate or C22:2N-6,9, belongs to the class of organic compounds known as very-long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. (13Z,16Z)-Docosadienoic acid is a very hydrophobic molecule that is practically insoluble (in water) and is relatively neutral. (13Z,16Z)-Docosadienoic acid can be found in feces.
Structure
Data?1572453805
Synonyms
ValueSource
(13Z,16Z)-Docosa-13,16-dienoic acidChEBI
13Z,16Z-Docosadienoic acidChEBI
C22:2N-6,9ChEBI
cis-13,16 Docosadienoic acidChEBI
(13Z,16Z)-Docosa-13,16-dienoateGenerator
13Z,16Z-DocosadienoateGenerator
cis-13,16 DocosadienoateGenerator
(13Z,16Z)-DocosadienoateGenerator
(13Z,16Z)-13,16-DocosadienoateHMDB
(13Z,16Z)-13,16-Docosadienoic acidHMDB
(13Z,16Z)-Docosadienoic acidHMDB
DocosadienoateHMDB
Docosadienoic acidHMDB
FA(22:2(13Z,16Z))HMDB
FA(22:2n6)HMDB
all-cis-13,16-DocosadienoateHMDB
all-cis-13,16-Docosadienoic acidHMDB
cis-13,cis-16-DocosadienoateHMDB
cis-13,cis-16-Docosadienoic acidHMDB
Chemical FormulaC22H40O2
Average Molecular Weight336.56
Monoisotopic Molecular Weight336.302830528
IUPAC Name(13Z,16Z)-docosa-13,16-dienoic acid
Traditional Name13,16-docosadienoic acid
CAS Registry Number17735-98-7
SMILES
CCCCC\C=C/C\C=C/CCCCCCCCCCCC(O)=O
InChI Identifier
InChI=1S/C22H40O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h6-7,9-10H,2-5,8,11-21H2,1H3,(H,23,24)/b7-6-,10-9-
InChI KeyHVGRZDASOHMCSK-HZJYTTRNSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentVery long-chain fatty acids
Alternative Parents
Substituents
  • Very long-chain fatty acid
  • Unsaturated fatty acid
  • Straight chain 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

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.8e-05 g/LALOGPS
logP8.54ALOGPS
logP8.2ChemAxon
logS-7.1ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count18ChemAxon
Refractivity106.92 m³·mol⁻¹ChemAxon
Polarizability44.21 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f96-9880000000-ce9c4c0dd6a59a04ea3eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fkc-9663000000-d8ffd9f0c4572ba9306aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0019000000-b16628e7a9d44a0b33a2Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00uf-5594000000-7f184cef096501e49df1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-002f-9870000000-70e24b488e2390b90337Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0019000000-7d55420d63317daf854dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00ku-1039000000-0f578d0228adb9009c04Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9130000000-b28019651a5671beaba3Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)Both
Colorectal cancer
details
FecesDetected but not Quantified Adult (>18 years old)BothColorectal Cancer details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. 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 ]
  2. 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 ]
  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 IDNot Available
KNApSAcK IDNot Available
Chemspider ID4471979
KEGG Compound IDC16533
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound5312554
PDB IDNot Available
ChEBI ID75117
Food Biomarker OntologyNot Available
VMH IDM00021
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. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.