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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:30:30 UTC

Update Date

2022-03-07 02:56:05 UTC

HMDB ID

HMDB0039141

Secondary Accession Numbers

HMDB39141

Metabolite Identification

Common Name

Wyeronic acid

Description

Wyeronic acid, also known as wyeronate, belongs to the class of organic compounds known as furanoid fatty acids. These are fatty acids containing a 5-alkylfuran-2-alkanoic acid. Based on a literature review a significant number of articles have been published on Wyeronic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 05061310522D          

 17 17  0  0  0  0            999 V2000
    4.1401    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4256    2.7643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7112    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9967    2.7643    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2822    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3297   -0.8227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0059   -1.5764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8264   -1.6626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3113   -0.9952    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1619   -2.4163    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  2  0  0  0  0
  4  3  1  0  0  0  0
  5  4  3  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 10  6  2  0  0  0  0
 10  7  1  0  0  0  0
 11  5  1  0  0  0  0
 12  8  2  0  0  0  0
 12 11  1  0  0  0  0
 13  9  1  0  0  0  0
 14 11  2  0  0  0  0
 15 13  2  0  0  0  0
 16 13  1  0  0  0  0
 17 10  1  0  0  0  0
 17 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0039141

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C=C\C#CC(=O)C1=CC=C(O1)\C=C/C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H10O4/c1-2-3-4-5-11(14)12-8-6-10(17-12)7-9-13(15)16/h2-3,6-9H,1H3,(H,15,16)/b3-2+,9-7-

> <INCHI_KEY>
DMVOIMZYBMLJHN-XKURDXHJSA-N

> <FORMULA>
C13H10O4

> <MOLECULAR_WEIGHT>
230.2161

> <EXACT_MASS>
230.057908808

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
23.43708867250446

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-3-{5-[(4E)-hex-4-en-2-ynoyl]furan-2-yl}prop-2-enoic acid

> <ALOGPS_LOGP>
2.58

> <JCHEM_LOGP>
2.4429427603333327

> <ALOGPS_LOGS>
-3.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.198642622020252

> <JCHEM_PKA_STRONGEST_BASIC>
-4.361006261705594

> <JCHEM_POLAR_SURFACE_AREA>
67.51

> <JCHEM_REFRACTIVITY>
64.6908

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.49e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-3-{5-[(4E)-hex-4-en-2-ynoyl]furan-2-yl}prop-2-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       7.728   5.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.394   5.160   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.061   5.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.727   5.160   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.393   4.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.830  -0.290   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.615  -1.536   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.011  -2.943   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.543  -3.104   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -0.274   4.390   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.448  -1.858   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.169  -4.510   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -0.186   1.175   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4   11                                                       
CONECT    6    8   10                                                       
CONECT    7    9   10                                                       
CONECT    8    6   12                                                       
CONECT    9    7   13                                                       
CONECT   10    6    7   17                                                  
CONECT   11    5   12   14                                                  
CONECT   12    8   11   17                                                  
CONECT   13    9   15   16                                                  
CONECT   14   11                                                            
CONECT   15   13                                                            
CONECT   16   13                                                            
CONECT   17   10   12                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0039141
HETATM    1  C1  UNL     1       6.108  -0.786   0.467  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.673  -0.494   0.206  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.162   0.727   0.247  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.754   0.967  -0.016  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.580   1.147  -0.239  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.183   1.335  -0.507  1.00  0.00           C  
HETATM    7  O1  UNL     1      -0.210   2.379  -1.084  1.00  0.00           O  
HETATM    8  C7  UNL     1      -0.825   0.351  -0.134  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.548  -0.854   0.509  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.749  -1.496   0.686  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.734  -0.643   0.134  1.00  0.00           C  
HETATM   12  C11 UNL     1      -4.127  -0.959   0.121  1.00  0.00           C  
HETATM   13  C12 UNL     1      -5.086  -0.229  -0.366  1.00  0.00           C  
HETATM   14  C13 UNL     1      -4.911   1.036  -0.984  1.00  0.00           C  
HETATM   15  O2  UNL     1      -5.998   1.602  -1.405  1.00  0.00           O  
HETATM   16  O3  UNL     1      -3.733   1.685  -1.167  1.00  0.00           O  
HETATM   17  O4  UNL     1      -2.102   0.393  -0.313  1.00  0.00           O  
HETATM   18  H1  UNL     1       6.656  -1.039  -0.461  1.00  0.00           H  
HETATM   19  H2  UNL     1       6.118  -1.696   1.126  1.00  0.00           H  
HETATM   20  H3  UNL     1       6.611   0.016   1.038  1.00  0.00           H  
HETATM   21  H4  UNL     1       4.012  -1.316  -0.030  1.00  0.00           H  
HETATM   22  H5  UNL     1       4.848   1.529   0.485  1.00  0.00           H  
HETATM   23  H6  UNL     1       0.399  -1.244   0.823  1.00  0.00           H  
HETATM   24  H7  UNL     1      -1.888  -2.448   1.150  1.00  0.00           H  
HETATM   25  H8  UNL     1      -4.419  -1.942   0.583  1.00  0.00           H  
HETATM   26  H9  UNL     1      -6.128  -0.669  -0.272  1.00  0.00           H  
HETATM   27  H10 UNL     1      -3.644   2.647  -0.838  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    3   21
CONECT    3    4   22
CONECT    4    5    5    5
CONECT    5    6
CONECT    6    7    7    8
CONECT    8    9    9   17
CONECT    9   10   23
CONECT   10   11   11   24
CONECT   11   12   17
CONECT   12   13   13   25
CONECT   13   14   26
CONECT   14   15   15   16
CONECT   16   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Wyeronate	Generator
3-[5-(1-oxo-4-Hexen-2-ynyl)-2-furanyl]-2-propenoic acid, 9ci	HMDB
(2Z)-3-{5-[(4E)-hex-4-en-2-ynoyl]furan-2-yl}prop-2-enoate	Generator

Chemical Formula

C₁₃H₁₀O₄

Average Molecular Weight

230.2161

Monoisotopic Molecular Weight

230.057908808

IUPAC Name

(2Z)-3-{5-[(4E)-hex-4-en-2-ynoyl]furan-2-yl}prop-2-enoic acid

Traditional Name

(2Z)-3-{5-[(4E)-hex-4-en-2-ynoyl]furan-2-yl}prop-2-enoic acid

CAS Registry Number

117783-52-5

SMILES

C\C=C\C#CC(=O)C1=CC=C(O1)\C=C/C(O)=O

InChI Identifier

InChI=1S/C13H10O4/c1-2-3-4-5-11(14)12-8-6-10(17-12)7-9-13(15)16/h2-3,6-9H,1H3,(H,15,16)/b3-2+,9-7-

InChI Key

DMVOIMZYBMLJHN-XKURDXHJSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furanoid fatty acids. These are fatty acids containing a 5-alkylfuran-2-alkanoic acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Furanoid fatty acids

Alternative Parents

Substituents

Furanoid fatty acid
Aryl ketone
Furan
Heteroaromatic compound
Alpha,beta-unsaturated ketone
Ketone
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Urine (HMDB: HMDB0039141)

Cellular substructure

Extracellular (HMDB: HMDB0039141)
Membrane (HMDB: HMDB0039141)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039141)

Source

Endogenous

Endogenous (HMDB: HMDB0039141)

Plant

Fabaceae (HMDB: HMDB0039141)

Animal

Animal (HMDB: HMDB0039141)

Exogenous

Food

Food (HMDB: HMDB0039141)

Pulse

Pulses (FooDB: FOOD00867)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0039141)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0039141)

Cellular process

Cell signaling (HMDB: HMDB0039141)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0039141)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0039141)

Nutrient

Nutrient (HMDB: HMDB0039141)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0039141)

Emulsifier (HMDB: HMDB0039141)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	1771 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.035 g/L	ALOGPS
logP	2.58	ALOGPS
logP	2.44	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	2.2	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	67.51 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	64.69 m³·mol⁻¹	ChemAxon
Polarizability	23.44 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	150.858	30932474
DeepCCS	[M-H]-	148.462	30932474
DeepCCS	[M-2H]-	181.346	30932474
DeepCCS	[M+Na]+	156.818	30932474
AllCCS	[M+H]+	151.8	32859911
AllCCS	[M+H-H2O]+	147.8	32859911
AllCCS	[M+NH4]+	155.5	32859911
AllCCS	[M+Na]+	156.6	32859911
AllCCS	[M-H]-	148.9	32859911
AllCCS	[M+Na-2H]-	148.9	32859911
AllCCS	[M+HCOO]-	149.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Wyeronic acid	C\C=C\C#CC(=O)C1=CC=C(O1)\C=C/C(O)=O	3654.5	Standard polar	33892256
Wyeronic acid	C\C=C\C#CC(=O)C1=CC=C(O1)\C=C/C(O)=O	1972.5	Standard non polar	33892256
Wyeronic acid	C\C=C\C#CC(=O)C1=CC=C(O1)\C=C/C(O)=O	2128.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Wyeronic acid,1TMS,isomer #1	C/C=C/C#CC(=O)C1=CC=C(/C=C\C(=O)O[Si](C)(C)C)O1	2230.0	Semi standard non polar	33892256
Wyeronic acid,1TBDMS,isomer #1	C/C=C/C#CC(=O)C1=CC=C(/C=C\C(=O)O[Si](C)(C)C(C)(C)C)O1	2465.9	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Wyeronic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0cdi-4930000000-91e0b7fbef41f56a2d19	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Wyeronic acid GC-MS (1 TMS) - 70eV, Positive	splash10-0080-9760000000-5c58086800980ec92a36	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Wyeronic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wyeronic acid 10V, Positive-QTOF	splash10-01q9-1390000000-8add7c35bc6339f5a9c9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wyeronic acid 20V, Positive-QTOF	splash10-00y0-5910000000-2c3bc6d8d0fbf235ecae	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wyeronic acid 40V, Positive-QTOF	splash10-0fr6-9300000000-6481beb9505bb2e2e78f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wyeronic acid 10V, Negative-QTOF	splash10-004i-2390000000-7530a2825ffd6a7dafaf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wyeronic acid 20V, Negative-QTOF	splash10-02du-6940000000-cdee835c97e9d259ee14	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wyeronic acid 40V, Negative-QTOF	splash10-00kf-9500000000-3e4a2393a8db3049f809	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wyeronic acid 10V, Positive-QTOF	splash10-001i-3090000000-53b0dd3711f936e299ba	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wyeronic acid 20V, Positive-QTOF	splash10-00fu-9740000000-f9a4c8dfe306965d845d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wyeronic acid 40V, Positive-QTOF	splash10-02bk-9400000000-162a679a4073c9b91fcb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wyeronic acid 10V, Negative-QTOF	splash10-004r-1590000000-9f913f554c1f2afb14c8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wyeronic acid 20V, Negative-QTOF	splash10-000f-9410000000-a961bc59fefe3237736d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Wyeronic acid 40V, Negative-QTOF	splash10-014l-9200000000-cecd40c2d2e63ede2874	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB018661

KNApSAcK ID

C00056901

Chemspider ID

30777329

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752560

PDB ID

Not Available

ChEBI ID

168520

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1874621

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
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 ]
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 ]
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 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Wyeronic acid (HMDB0039141)

MOL for HMDB0039141 (Wyeronic acid)

3D MOL for HMDB0039141 (Wyeronic acid)

3D SDF for HMDB0039141 (Wyeronic acid)

3D-SDF for HMDB0039141 (Wyeronic acid)

PDB for HMDB0039141 (Wyeronic acid)

3D PDB for HMDB0039141 (Wyeronic acid)

SMILES for HMDB0039141 (Wyeronic acid)

INCHI for HMDB0039141 (Wyeronic acid)

Structure for HMDB0039141 (Wyeronic acid)

3D Structure for HMDB0039141 (Wyeronic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra