Bovine Metabolome Database: Showing metabocard for Eicosenoic acid (BMDB0002231)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:52:58 UTC

Update Date

2020-06-04 21:52:01 UTC

BMDB ID

BMDB0002231

Secondary Accession Numbers

BMDB02231

Metabolite Identification

Common Name

Eicosenoic acid

Description

11Z-Eicosenoic acid, also known as 11-eicosenoate or cis-gondoic acid, 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 11Z-Eicosenoic acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(11Z)-Eicosenoic acid	ChEBI
(11Z)-Icosenoic acid	ChEBI
(Z)-Eicos-11-enoic acid	ChEBI
(Z)-Icos-11-enoic acid	ChEBI
(Z)-Icosa-11-enoic acid	ChEBI
11-Eicosenoic acid	ChEBI
11-Icosenoic acid	ChEBI
20:1	ChEBI
cis-11-Eicosenoic acid	ChEBI
cis-Delta(11)-Eicosenoic acid	ChEBI
cis-Gondoic acid	ChEBI
Eicosenoic acid	ChEBI
Gondoic acid	ChEBI
Z-Delta(11)-Eicosensaeure	ChEBI
(11Z)-Eicosenoate	Generator
(11Z)-Icosenoate	Generator
(Z)-Eicos-11-enoate	Generator
(Z)-Icos-11-enoate	Generator
(Z)-Icosa-11-enoate	Generator
11-Eicosenoate	Generator
11-Icosenoate	Generator
cis-11-Eicosenoate	Generator
cis-delta(11)-Eicosenoate	Generator
cis-Δ(11)-eicosenoate	Generator
cis-Δ(11)-eicosenoic acid	Generator
cis-Gondoate	Generator
Eicosenoate	Generator
Gondoate	Generator
Z-Δ(11)-eicosensaeure	Generator
11Z-Eicosenoate	Generator
(11Z)-Icos-11-enoate	HMDB
(11Z)-Icos-11-enoic acid	HMDB
11(Z)-Eicosenoate	HMDB
11(Z)-Eicosenoic acid	HMDB
11-cis-Eicosenoate	HMDB
11-cis-Eicosenoic acid	HMDB
11Z-Eicosenoic acid	HMDB
20:1(N-9)	HMDB
20:1n9	HMDB
cis-11-Icosenoate	HMDB
cis-11-Icosenoic acid	HMDB
FA(20:1(11Z))	HMDB
FA(20:1n9)	HMDB
(11Z)-11-Eicosenoic acid	PhytoBank
(Z)-11-Eicosenoic acid	PhytoBank
cis-delta11-Eicosenoic acid	PhytoBank
cis-Δ11-Eicosenoic acid	PhytoBank

Chemical Formula

C₂₀H₃₈O₂

Average Molecular Weight

310.5145

Monoisotopic Molecular Weight

310.28718046

IUPAC Name

(11Z)-icos-11-enoic acid

Traditional Name

cis-11-eicosenoic acid

CAS Registry Number

26764-41-0

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 Key

BITHHVVYSMSWAG-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.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-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 Framework

Aliphatic acyclic compounds

External Descriptors

icosenoic acid (CHEBI:32425 )
Unsaturated fatty acids (C16526 )
Monounsaturated fatty acids (C16526 )
Unsaturated fatty acids (LMFA01030085 )

Ontology

Status

Detected and Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Adiposome
Cell membrane
Cytoplasm
Membrane

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	8.4	ALOGPS
logP	7.67	ChemAxon
logS	-6.8	ALOGPS
pKa (Strongest Acidic)	4.95	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	96.6 m³·mol⁻¹	ChemAxon
Polarizability	41.32 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00mk-3900000000-c719ddc966597d00d2c5	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-00mk-3900000000-c719ddc966597d00d2c5	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9450000000-350fb3d4ba5a967ba8b5	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-0g70-9551000000-c82b71c168fb5563f7d4	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	View in JSpectraViewer
LC-MS/MS	LC-MS/MS Spectrum - n/a 21V, negative	splash10-0006-0090000000-1756232c26bf8fc138c5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 21V, positive	splash10-0006-0290000000-fa5d9f6e60781ae83e2e	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 10V, positive	splash10-0006-5490000000-0cbb37e5b7ecad5adaaa	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 12V, positive	splash10-000y-9650000000-ba5e2b939e8a556b6d1f	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 14V, positive	splash10-00l2-9410000000-9496a07390108fe35cab	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 16V, positive	splash10-05nb-9300000000-b3b200aebba967262b9b	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 17V, positive	splash10-067j-9200000000-91f2ccafad22a2bb8069	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 21V, positive	splash10-067j-9100000000-dbb0d513ad4f77e24d3c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 26V, positive	splash10-067i-9000000000-1b21d5d4d80742618d4c	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 32V, positive	splash10-067i-9000000000-d00f7dd8a36d506bf1b5	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 39V, positive	splash10-0aor-9000000000-de7f5670d39d685918e0	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Orbitrap 47V, positive	splash10-0ar0-9000000000-509d8fad571b85568099	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 21V, positive	splash10-004i-2890000000-dcdc3d85495da91cc6db	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - n/a 21V, positive	splash10-070e-1920000000-1c2aeaf08cc4ea4f0540	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0029000000-c49b53bb3e3caf9cb042	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-1079000000-9504027ae4d5b071c4a0	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4l-9240000000-7e3a558d23fc622e0aa2	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0019000000-0d96115f81e42756fc2f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-1059000000-4c31464e6f8ead1139f3	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9020000000-90362612fe130589b56d	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dl-0197000000-fa25affc2bb6f0cd695b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0i03-4691000000-b79f41c0508982a46111	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0007-9850000000-3d2cfec12ab1aec5686b	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03dl-5397000000-d942974f980afe9a14c5	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0btc-9561000000-bf355ad19adfba5af8df	View in MoNA
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Adiposome
Cell membrane
Cytoplasm
Membrane

Biospecimen Locations

Adipose Tissue
Erythrocyte
Liver
Mammary Gland
Milk
Oocyte
Placenta

Pathways

Not Available

Name	SMPDB/Pathwhiz	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Adipose Tissue	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 25093808	details
Adipose Tissue	Detected and Quantified	254.67 nmol/g of tissue	Not Specified	Not Specified	Normal	C. Mapiye, T.D.Tu...	details
Adipose Tissue	Detected and Quantified	282.37 nmol/g of tissue	Not Specified	Not Specified	Normal	C. Mapiye, T.D.Tu...	details
Adipose Tissue	Detected and Quantified	2743.93 nmol/g of tissue	Not Specified	Not Specified	Normal	C. Mapiye, T.D.Tu...	details
Adipose Tissue	Detected and Quantified	3234.66 nmol/g of tissue	Not Specified	Not Specified	Normal	C. Mapiye, T.D.Tu...	details
Adipose Tissue	Detected and Quantified	4849.0167 nmol/g of tissue	Not Specified	Not Specified	Normal	C. Mapiye, T.D.Tu...	details
Adipose Tissue	Detected and Quantified	5011.97 nmol/g of tissue	Not Specified	Not Specified	Normal	C. Mapiye, T.D.Tu...	details
Adipose Tissue	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 25093808	details
Adipose Tissue	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 25093808	details
Adipose Tissue	Detected and Quantified	9274.93 nmol/g of tissue	Not Specified	Not Specified	Normal	PMID: 24188642	details
Adipose Tissue	Detected and Quantified	7825.72 nmol/g of tissue	Not Specified	Not Specified	Normal	PMID: 24188642	details
Adipose Tissue	Detected and Quantified	9184.76 nmol/g of tissue	Not Specified	Not Specified	Normal	PMID: 24188642	details
Adipose Tissue	Detected and Quantified	7787.076 nmol/g of tissue	Not Specified	Not Specified	Normal	PMID: 24188642	details
Adipose Tissue	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 25093808	details
Erythrocyte	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31867104	details
Liver	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Mammary Gland	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 31873721	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 11913692	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 28219465	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 1779072	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 29570652	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Kurt J. Boudonck,...	details
Milk	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Kurt J. Boudonck,...	details
Oocyte	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	PMID: 10793638	details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0002231

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Eicosenoic acid

METLIN ID

6563

PubChem Compound

5282768

PDB ID

Not Available

ChEBI ID

32425

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
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 ]
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 ]
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.
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.

Showing metabocard for Eicosenoic acid (BMDB0002231)

Structure for BMDB0002231 (Eicosenoic acid)