Showing metabocard for Eicosenoic acid (BMDB0002231)

IdentificationTaxonomyPhysical propertiesSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-09-30 22:52:58 UTC
Update Date2020-06-04 21:52:01 UTC
MCDB ID BMDB0002231
Secondary Accession Numbers
  • BMDB02231
Metabolite Identification
Common NameEicosenoic acid
Description11Z-Eicosenoic acid, also known as 11-eicosenoate or 20:1, 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. 11Z-Eicosenoic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(11Z)-Eicosenoic acidChEBI
(11Z)-Icosenoic acidChEBI
(Z)-Eicos-11-enoic acidChEBI
(Z)-Icos-11-enoic acidChEBI
(Z)-Icosa-11-enoic acidChEBI
11-Eicosenoic acidChEBI
11-Icosenoic acidChEBI
20:1ChEBI
cis-11-Eicosenoic acidChEBI
cis-Delta(11)-Eicosenoic acidChEBI
cis-Gondoic acidChEBI
Eicosenoic acidChEBI
Gondoic acidChEBI
Z-Delta(11)-EicosensaeureChEBI
(11Z)-EicosenoateGenerator
(11Z)-IcosenoateGenerator
(Z)-Eicos-11-enoateGenerator
(Z)-Icos-11-enoateGenerator
(Z)-Icosa-11-enoateGenerator
11-EicosenoateGenerator
11-IcosenoateGenerator
cis-11-EicosenoateGenerator
cis-delta(11)-EicosenoateGenerator
cis-Δ(11)-eicosenoateGenerator
cis-Δ(11)-eicosenoic acidGenerator
cis-GondoateGenerator
EicosenoateGenerator
GondoateGenerator
Z-Δ(11)-eicosensaeureGenerator
11Z-EicosenoateGenerator
(11Z)-Icos-11-enoateHMDB
(11Z)-Icos-11-enoic acidHMDB
11(Z)-EicosenoateHMDB
11(Z)-Eicosenoic acidHMDB
11-cis-EicosenoateHMDB
11-cis-Eicosenoic acidHMDB
11Z-Eicosenoic acidHMDB
20:1(N-9)HMDB
20:1n9HMDB
cis-11-IcosenoateHMDB
cis-11-Icosenoic acidHMDB
FA(20:1(11Z))HMDB
FA(20:1n9)HMDB
(11Z)-11-Eicosenoic acidPhytoBank
(Z)-11-Eicosenoic acidPhytoBank
cis-delta11-Eicosenoic acidPhytoBank
cis-Δ11-Eicosenoic acidPhytoBank
Chemical FormulaC20H38O2
Average Molecular Weight310.5145
Monoisotopic Molecular Weight310.28718046
IUPAC Name(11Z)-icos-11-enoic acid
Traditional Namecis-11-eicosenoic acid
CAS Registry Number26764-41-0
SMILES
CCCCCCCC\C=C/CCCCCCCCCC(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/h9-10H,2-8,11-19H2,1H3,(H,21,22)/b10-9-
InChI KeyBITHHVVYSMSWAG-KTKRTIGZSA-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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP8.4ALOGPS
logP7.67ChemAxon
logS-6.8ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00mk-3900000000-c719ddc966597d00d2c52017-09-12View Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00mk-3900000000-c719ddc966597d00d2c52018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9450000000-350fb3d4ba5a967ba8b52017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0g70-9551000000-c82b71c168fb5563f7d42017-10-06View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, negativesplash10-0006-0090000000-1756232c26bf8fc138c52020-07-21View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-0006-0290000000-fa5d9f6e60781ae83e2e2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 10V, positivesplash10-0006-5490000000-0cbb37e5b7ecad5adaaa2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 12V, positivesplash10-000y-9650000000-ba5e2b939e8a556b6d1f2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 14V, positivesplash10-00l2-9410000000-9496a07390108fe35cab2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 16V, positivesplash10-05nb-9300000000-b3b200aebba967262b9b2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 17V, positivesplash10-067j-9200000000-91f2ccafad22a2bb80692020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 21V, positivesplash10-067j-9100000000-dbb0d513ad4f77e24d3c2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 26V, positivesplash10-067i-9000000000-1b21d5d4d80742618d4c2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 32V, positivesplash10-067i-9000000000-d00f7dd8a36d506bf1b52020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 39V, positivesplash10-0aor-9000000000-de7f5670d39d685918e02020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 47V, positivesplash10-0ar0-9000000000-509d8fad571b855680992020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-004i-2890000000-dcdc3d85495da91cc6db2020-07-22View Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-070e-1920000000-1c2aeaf08cc4ea4f05402020-07-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0029000000-c49b53bb3e3caf9cb0422016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1079000000-9504027ae4d5b071c4a02016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9240000000-7e3a558d23fc622e0aa22016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0019000000-0d96115f81e42756fc2f2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1059000000-4c31464e6f8ead1139f32021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9020000000-90362612fe130589b56d2021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-0197000000-fa25affc2bb6f0cd695b2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0i03-4691000000-b79f41c0508982a461112016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0007-9850000000-3d2cfec12ab1aec5686b2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dl-5397000000-d942974f980afe9a14c52021-09-22View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0btc-9561000000-bf355ad19adfba5af8df2021-09-22View Spectrum
1D NMR13C NMR Spectrum (1D, 100 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Not Available2022-08-22View Spectrum
Concentrations
StatusValueReferenceDetails
Detected but not QuantifiedNot Applicable
  • Kurt J. Boudonck,...
 details
Detected but not QuantifiedNot Applicable details
Detected but not QuantifiedNot Applicable
  • Kurt J. Boudonck,...
 details
Detected but not QuantifiedNot Applicable details
Detected but not QuantifiedNot Applicable details
Detected but not QuantifiedNot Applicable details
HMDB IDHMDB0002231
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB012569
KNApSAcK IDC00035628
Chemspider ID4445895
KEGG Compound IDC16526
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkEicosenoic acid
METLIN ID6563
PubChem Compound5282768
PDB IDNot Available
ChEBI ID32425
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3. [PubMed:1779072 ]
  2. Trimigno A, Munger L, Picone G, Freiburghaus C, Pimentel G, Vionnet N, Pralong F, Capozzi F, Badertscher R, Vergeres G: GC-MS Based Metabolomics and NMR Spectroscopy Investigation of Food Intake Biomarkers for Milk and Cheese in Serum of Healthy Humans. Metabolites. 2018 Mar 23;8(2). pii: metabo8020026. doi: 10.3390/metabo8020026. [PubMed:29570652 ]
  3. van Gastelen S, Antunes-Fernandes EC, Hettinga KA, Dijkstra J: Relationships between methane emission of Holstein Friesian dairy cows and fatty acids, volatile metabolites and non-volatile metabolites in milk. Animal. 2017 Sep;11(9):1539-1548. doi: 10.1017/S1751731117000295. Epub 2017 Feb 21. [PubMed:28219465 ]
  4. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386. Metabolomics.
  5. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals (2009). Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff, John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375-386 doi: 10.1007/s11306-009-0160-8. Metabolomics.