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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:34:12 UTC

Update Date

2022-03-07 02:52:23 UTC

HMDB ID

HMDB0030018

Secondary Accession Numbers

HMDB30018

Metabolite Identification

Common Name

Elenolide

Description

Elenolide belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond. Based on a literature review very few articles have been published on Elenolide.

Structure

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


  Mrv0541 05061304582D          

 16 16  0  0  0  0            999 V2000
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  0  0  0  0
  7  3  2  0  0  0  0
  7  5  1  0  0  0  0
  8  4  1  0  0  0  0
  8  7  1  0  0  0  0
  9  6  2  0  0  0  0
  9  8  1  0  0  0  0
 10  4  1  0  0  0  0
 11  9  1  0  0  0  0
 12  5  2  0  0  0  0
 13 10  2  0  0  0  0
 14 11  2  0  0  0  0
 15  2  1  0  0  0  0
 15 11  1  0  0  0  0
 16  6  1  0  0  0  0
 16 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030018

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(=O)C1=COC(=O)CC1\C(=C\C)C=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H12O5/c1-3-7(5-12)8-4-10(13)16-6-9(8)11(14)15-2/h3,5-6,8H,4H2,1-2H3/b7-3+

> <INCHI_KEY>
TXTINTVPMBCGKO-XVNBXDOJSA-N

> <FORMULA>
C11H12O5

> <MOLECULAR_WEIGHT>
224.21

> <EXACT_MASS>
224.068473494

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
21.403815485021568

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2-oxo-4-[(2Z)-1-oxobut-2-en-2-yl]-3,4-dihydro-2H-pyran-5-carboxylate

> <ALOGPS_LOGP>
0.98

> <JCHEM_LOGP>
0.5110526636666667

> <ALOGPS_LOGS>
-2.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
-10.421377839901005

> <JCHEM_PKA_STRONGEST_BASIC>
0.8333914388881678

> <JCHEM_POLAR_SURFACE_AREA>
69.67

> <JCHEM_REFRACTIVITY>
55.711500000000015

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.61e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 6-oxo-4-[(2Z)-1-oxobut-2-en-2-yl]-4,5-dihydropyran-3-carboxylate

> <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       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2   15                                                            
CONECT    3    1    7                                                       
CONECT    4    8   10                                                       
CONECT    5    7   12                                                       
CONECT    6    9   16                                                       
CONECT    7    3    5    8                                                  
CONECT    8    4    7    9                                                  
CONECT    9    6    8   11                                                  
CONECT   10    4   13   16                                                  
CONECT   11    9   14   15                                                  
CONECT   12    5                                                            
CONECT   13   10                                                            
CONECT   14   11                                                            
CONECT   15    2   11                                                       
CONECT   16    6   10                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0030018
HETATM    1  C1  UNL     1      -3.563   0.965  -0.144  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.522  -0.108  -0.096  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.271   0.151  -0.520  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.037   1.501  -1.009  1.00  0.00           C  
HETATM    5  O1  UNL     1       0.027   1.950  -1.433  1.00  0.00           O  
HETATM    6  C5  UNL     1      -0.231  -0.913  -0.389  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.787  -2.019   0.548  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.981  -1.451   1.907  1.00  0.00           C  
HETATM    9  O2  UNL     1      -2.041  -1.432   2.571  1.00  0.00           O  
HETATM   10  O3  UNL     1       0.207  -0.899   2.436  1.00  0.00           O  
HETATM   11  C8  UNL     1       1.138  -0.404   1.574  1.00  0.00           C  
HETATM   12  C9  UNL     1       0.991  -0.398   0.275  1.00  0.00           C  
HETATM   13  C10 UNL     1       2.125   0.050  -0.581  1.00  0.00           C  
HETATM   14  O4  UNL     1       2.004   0.006  -1.812  1.00  0.00           O  
HETATM   15  O5  UNL     1       3.272   0.499   0.023  1.00  0.00           O  
HETATM   16  C11 UNL     1       4.382   0.937  -0.712  1.00  0.00           C  
HETATM   17  H1  UNL     1      -3.681   1.317  -1.207  1.00  0.00           H  
HETATM   18  H2  UNL     1      -3.308   1.797   0.522  1.00  0.00           H  
HETATM   19  H3  UNL     1      -4.540   0.564   0.185  1.00  0.00           H  
HETATM   20  H4  UNL     1      -2.824  -1.054   0.236  1.00  0.00           H  
HETATM   21  H5  UNL     1      -1.871   2.238  -1.022  1.00  0.00           H  
HETATM   22  H6  UNL     1       0.030  -1.312  -1.374  1.00  0.00           H  
HETATM   23  H7  UNL     1      -1.644  -2.486   0.107  1.00  0.00           H  
HETATM   24  H8  UNL     1       0.060  -2.772   0.610  1.00  0.00           H  
HETATM   25  H9  UNL     1       2.097   0.030   1.974  1.00  0.00           H  
HETATM   26  H10 UNL     1       4.708   1.905  -0.264  1.00  0.00           H  
HETATM   27  H11 UNL     1       4.063   1.146  -1.752  1.00  0.00           H  
HETATM   28  H12 UNL     1       5.197   0.191  -0.656  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    3   20
CONECT    3    4    6
CONECT    4    5    5   21
CONECT    6    7   12   22
CONECT    7    8   23   24
CONECT    8    9    9   10
CONECT   10   11
CONECT   11   12   12   25
CONECT   12   13
CONECT   13   14   14   15
CONECT   15   16
CONECT   16   26   27   28
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Michelenolide	HMDB
Methyl 2-oxo-4-[(2Z)-1-oxobut-2-en-2-yl]-3,4-dihydro-2H-pyran-5-carboxylic acid	Generator

Chemical Formula

C₁₁H₁₂O₅

Average Molecular Weight

224.21

Monoisotopic Molecular Weight

224.068473494

IUPAC Name

methyl 2-oxo-4-[(2Z)-1-oxobut-2-en-2-yl]-3,4-dihydro-2H-pyran-5-carboxylate

Traditional Name

methyl 6-oxo-4-[(2Z)-1-oxobut-2-en-2-yl]-4,5-dihydropyran-3-carboxylate

CAS Registry Number

24582-91-0

SMILES

COC(=O)C1=COC(=O)CC1\C(=C\C)C=O

InChI Identifier

InChI=1S/C11H12O5/c1-3-7(5-12)8-4-10(13)16-6-9(8)11(14)15-2/h3,5-6,8H,4H2,1-2H3/b7-3+

InChI Key

TXTINTVPMBCGKO-XVNBXDOJSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Pyranones and derivatives

Direct Parent

Dihydropyranones

Alternative Parents

Substituents

Dihydropyranone
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated aldehyde
Enal
Enol ester
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Carboxylic acid derivative
Oxacycle
Aldehyde
Organic oxide
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0030018)
Cytoplasm (HMDB: HMDB0030018)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0030018)

Source

Endogenous

Endogenous (HMDB: HMDB0030018)

Plant

Plant (HMDB: HMDB0030018)

Exogenous

Food

Food (HMDB: HMDB0030018)

Vegetable

Fruit vegetable

Olive (FooDB: FOOD00121)

Fruit

Pome

Pomes (FooDB: FOOD00856)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Process

Not Available

Role

Biological role

hypotensive (HMDB: HMDB0030018)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	155 - 156 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	47530 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	1.61 g/L	ALOGPS
logP	0.98	ALOGPS
logP	0.51	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	-10	ChemAxon
pKa (Strongest Basic)	0.83	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	69.67 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	55.71 m³·mol⁻¹	ChemAxon
Polarizability	21.4 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
DarkChem	[M+H]+	153.401	31661259
DarkChem	[M-H]-	151.884	31661259
DeepCCS	[M+H]+	152.388	30932474
DeepCCS	[M-H]-	150.03	30932474
DeepCCS	[M-2H]-	183.214	30932474
DeepCCS	[M+Na]+	158.481	30932474
AllCCS	[M+H]+	149.7	32859911
AllCCS	[M+H-H2O]+	145.8	32859911
AllCCS	[M+NH4]+	153.3	32859911
AllCCS	[M+Na]+	154.4	32859911
AllCCS	[M-H]-	148.8	32859911
AllCCS	[M+Na-2H]-	149.2	32859911
AllCCS	[M+HCOO]-	149.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Elenolide	COC(=O)C1=COC(=O)CC1\C(=C\C)C=O	2822.2	Standard polar	33892256
Elenolide	COC(=O)C1=COC(=O)CC1\C(=C\C)C=O	1793.3	Standard non polar	33892256
Elenolide	COC(=O)C1=COC(=O)CC1\C(=C\C)C=O	1854.1	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 - Elenolide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0295-4910000000-1d7def926e07350bec0b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Elenolide 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 - Elenolide 10V, Positive-QTOF	splash10-004i-1970000000-0bdf920eccfda4447209	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Elenolide 20V, Positive-QTOF	splash10-056r-2930000000-25f5aec57895a51d770c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Elenolide 40V, Positive-QTOF	splash10-0044-9600000000-1f15347333b42f915b2d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Elenolide 10V, Negative-QTOF	splash10-00fr-2890000000-f3d7d7a46dfda42039a1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Elenolide 20V, Negative-QTOF	splash10-00fu-6960000000-926e0c9bb82afc6e1394	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Elenolide 40V, Negative-QTOF	splash10-053u-9600000000-f6068b6afab8efea267a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Elenolide 10V, Negative-QTOF	splash10-00di-1890000000-151b2572b166805c8345	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Elenolide 20V, Negative-QTOF	splash10-000i-1910000000-d6e9510165532d98ada8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Elenolide 40V, Negative-QTOF	splash10-000j-7900000000-5e8cf1ca3b69eff02412	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Elenolide 10V, Positive-QTOF	splash10-004i-0590000000-c5f1a56bc5c0041dd2e6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Elenolide 20V, Positive-QTOF	splash10-004i-2930000000-d34e33114bd965a0ba4e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Elenolide 40V, Positive-QTOF	splash10-0002-9600000000-b5c7c31373e8d90f11dd	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

Not Available

KNApSAcK ID

C00003327

Chemspider ID

16735791

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

20054903

PDB ID

Not Available

ChEBI ID

172461

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Elenolide (HMDB0030018)

MOL for HMDB0030018 (Elenolide)

3D MOL for HMDB0030018 (Elenolide)

3D SDF for HMDB0030018 (Elenolide)

3D-SDF for HMDB0030018 (Elenolide)

PDB for HMDB0030018 (Elenolide)

3D PDB for HMDB0030018 (Elenolide)

SMILES for HMDB0030018 (Elenolide)

INCHI for HMDB0030018 (Elenolide)

Structure for HMDB0030018 (Elenolide)

3D Structure for HMDB0030018 (Elenolide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra