Hmdb loader
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusDetected and Quantified
Creation Date2017-03-21 06:19:54 UTC
Update Date2022-03-07 03:17:54 UTC
HMDB IDHMDB0062436
Secondary Accession Numbers
  • HMDB62436
Metabolite Identification
Common Name9Z-Eicosenoic acid
Description9Z-Eicosenoic acid, also known as gadoleic acid, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. 9Z-Eicosenoic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). 9Z-Eicosenoic acid can be found in a number of food items such as lemon, sugar, garlic, and mung bean, which makes 9Z-eicosenoic acid a potential biomarker for the consumption of these food products. 9Z-Eicosenoic acid can be found in feces, blood, and urine.
Structure
Data?1563866311
Synonyms
ValueSource
(Z)-Eicos-9-enoic acidChEBI
9C-EicosensaeureChEBI
C20:1CChEBI
cis-9-Eicosenoic acidChEBI
cis-Delta(9)-Eicosenoic acidChEBI
Eicos-9C-enoic acidChEBI
Eicos-9C-ensaeureChEBI
(Z)-Eicos-9-enoateGenerator
cis-9-EicosenoateGenerator
cis-delta(9)-EicosenoateGenerator
cis-Δ(9)-eicosenoateGenerator
cis-Δ(9)-eicosenoic acidGenerator
Eicos-9C-enoateGenerator
9Z-EicosenoateGenerator
GadoleateHMDB
Gadoleic acidHMDB
FA(20:1(9Z))HMDB
cis-GadoleateHMDB
Chemical FormulaC20H38O2
Average Molecular Weight310.522
Monoisotopic Molecular Weight310.287180464
IUPAC Name(9Z)-icos-9-enoic acid
Traditional Namegadoleic acid
CAS Registry Number29204-02-2
SMILES
CCCCCCCCCC\C=C/CCCCCCCC(O)=O
InChI Identifier
InChI=1S/C20H38O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h11-12H,2-10,13-19H2,1H3,(H,21,22)/b12-11-
InChI KeyLQJBNNIYVWPHFW-QXMHVHEDSA-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
  • 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
Not AvailableNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility4.9e-05 g/lALOGPS
LogP8.41ALOGPS
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP8.41ALOGPS
logP7.67ChemAxon
logS-6.8ALOGPS
pKa (Strongest Acidic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count17ChemAxon
Refractivity96.6 m³·mol⁻¹ChemAxon
Polarizability41.32 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]+183.99231661259
DarkChem[M-H]-184.90831661259
DeepCCS[M+H]+187.39530932474
DeepCCS[M-H]-183.37530932474
DeepCCS[M-2H]-220.08630932474
DeepCCS[M+Na]+196.2130932474
AllCCS[M+H]+189.132859911
AllCCS[M+H-H2O]+186.332859911
AllCCS[M+NH4]+191.632859911
AllCCS[M+Na]+192.432859911
AllCCS[M-H]-186.932859911
AllCCS[M+Na-2H]-188.732859911
AllCCS[M+HCOO]-191.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
9Z-Eicosenoic acidCCCCCCCCCC\C=C/CCCCCCCC(O)=O3360.0Standard polar33892256
9Z-Eicosenoic acidCCCCCCCCCC\C=C/CCCCCCCC(O)=O2285.2Standard non polar33892256
9Z-Eicosenoic acidCCCCCCCCCC\C=C/CCCCCCCC(O)=O2346.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
9Z-Eicosenoic acid,1TMS,isomer #1CCCCCCCCCC/C=C\CCCCCCCC(=O)O[Si](C)(C)C2417.0Semi standard non polar33892256
9Z-Eicosenoic acid,1TBDMS,isomer #1CCCCCCCCCC/C=C\CCCCCCCC(=O)O[Si](C)(C)C(C)(C)C2687.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 9Z-Eicosenoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-002f-9770000000-8bafce752dcc0e83c2112017-09-20Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 9Z-Eicosenoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-00vi-9561000000-84617bccb2d2f0e647182017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 9Z-Eicosenoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 9Z-Eicosenoic 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 - 9Z-Eicosenoic acid 10V, Positive-QTOFsplash10-03dl-0197000000-f6093bc2d61dbe668e182016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9Z-Eicosenoic acid 20V, Positive-QTOFsplash10-0uxu-3591000000-835bb134b9d517428e952016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9Z-Eicosenoic acid 40V, Positive-QTOFsplash10-0007-8960000000-fa7ac5e35243596e982c2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9Z-Eicosenoic acid 10V, Negative-QTOFsplash10-0a4i-0029000000-053d5a3b1d592fd190c22016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9Z-Eicosenoic acid 20V, Negative-QTOFsplash10-0a4i-1079000000-323c653227521538a43c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9Z-Eicosenoic acid 40V, Negative-QTOFsplash10-0a4l-9230000000-33c06ae5cc68dad152912016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9Z-Eicosenoic acid 10V, Positive-QTOFsplash10-03dl-4297000000-a679e8ed0942db48f6722021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9Z-Eicosenoic acid 20V, Positive-QTOFsplash10-06r6-9572000000-31bd41e72217aeb759982021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9Z-Eicosenoic acid 40V, Positive-QTOFsplash10-0a4l-9100000000-e4e0ee937a9dc02d22a02021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9Z-Eicosenoic acid 10V, Negative-QTOFsplash10-0a4i-0019000000-0d96115f81e42756fc2f2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9Z-Eicosenoic acid 20V, Negative-QTOFsplash10-0a4i-1069000000-e54a7d130deccefa86bb2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 9Z-Eicosenoic acid 40V, Negative-QTOFsplash10-0006-9020000000-c097ab1d18e1ea28f2f12021-09-22Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified11.722 +/- 5.378 uMAdult (>18 years old)FemaleNormal details
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
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 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB003771
KNApSAcK IDC00053190
Chemspider ID4445894
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkGadoleic acid
METLIN IDNot Available
PubChem Compound5282767
PDB IDNot Available
ChEBI ID32419
Food Biomarker OntologyNot Available
VMH IDM01235
MarkerDB IDNot Available
Good Scents IDrw1110411
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. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.