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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:47:21 UTC

Update Date

2023-02-21 17:21:30 UTC

HMDB ID

HMDB0032028

Secondary Accession Numbers

HMDB32028

Metabolite Identification

Common Name

(E)-3-(2-Methylpropylidene)-1(3H)-isobenzofuranone

Description

(E)-3-(2-Methylpropylidene)-1(3H)-isobenzofuranone belongs to the class of organic compounds known as isobenzofuranones. Isobenzofuranones are compounds containing a 2-benzofuran moiety that carries an oxo group at the 1 position (E)-3-(2-Methylpropylidene)-1(3H)-isobenzofuranone has been detected, but not quantified in, celery stalks (Apium graveolens var. dulce) and wild celeries (Apium graveolens). This could make (e)-3-(2-methylpropylidene)-1(3H)-isobenzofuranone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on (E)-3-(2-Methylpropylidene)-1(3H)-isobenzofuranone.

Structure

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


  Mrv0541 02241215552D          

 14 15  0  0  0  0            999 V2000
   -0.5772    0.8249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5772    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2469   -0.2481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5772   -0.9900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4020   -1.0721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8974   -0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4849    0.3295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7423    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2469    1.0721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4950    1.8148    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2369   -0.4946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1547   -1.3195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4950   -1.8148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8974   -1.7319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  9  1  0  0  0  0
  2  3  1  0  0  0  0
  2 11  2  0  0  0  0
  3  4  2  0  0  0  0
  3  8  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032028

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)\C=C1\OC(=O)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C12H12O2/c1-8(2)7-11-9-5-3-4-6-10(9)12(13)14-11/h3-8H,1-2H3/b11-7+

> <INCHI_KEY>
LYSNVWBBICAAMS-YRNVUSSQSA-N

> <FORMULA>
C12H12O2

> <MOLECULAR_WEIGHT>
188.2225

> <EXACT_MASS>
188.083729628

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
20.478997397697192

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3E)-3-(2-methylpropylidene)-1,3-dihydro-2-benzofuran-1-one

> <ALOGPS_LOGP>
2.98

> <JCHEM_LOGP>
2.866378659333333

> <ALOGPS_LOGS>
-2.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.059439725631429

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
56.2237

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.94e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3E)-3-(2-methylpropylidene)-2-benzofuran-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -1.077   1.540   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.077   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.461  -0.463   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.077  -1.848   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.617  -2.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.542  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.772   0.615   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.386   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.461   2.001   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.924   3.388   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.309  -0.923   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.155  -2.463   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.924  -3.388   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.542  -3.233   0.000  0.00  0.00           C+0
CONECT    1    2    9                                                       
CONECT    2    1    3   11                                                  
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    3    7    9                                                  
CONECT    9    1    8   10                                                  
CONECT   10    9                                                            
CONECT   11    2   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

COMPND    HMDB0032028
HETATM    1  C1  UNL     1      -2.955  -1.129  -0.729  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.871  -0.024  -0.530  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.793   1.235  -0.305  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.292  -0.268   0.753  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.046  -0.284   1.117  1.00  0.00           C  
HETATM    6  O1  UNL     1       0.417  -0.537   2.419  1.00  0.00           O  
HETATM    7  C6  UNL     1       1.789  -0.477   2.455  1.00  0.00           C  
HETATM    8  O2  UNL     1       2.557  -0.652   3.460  1.00  0.00           O  
HETATM    9  C7  UNL     1       2.217  -0.168   1.095  1.00  0.00           C  
HETATM   10  C8  UNL     1       3.475   0.009   0.549  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.612   0.297  -0.781  1.00  0.00           C  
HETATM   12  C10 UNL     1       2.506   0.412  -1.576  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.218   0.238  -1.054  1.00  0.00           C  
HETATM   14  C12 UNL     1       1.103  -0.050   0.283  1.00  0.00           C  
HETATM   15  H1  UNL     1      -2.467  -2.124  -0.765  1.00  0.00           H  
HETATM   16  H2  UNL     1      -3.635  -1.149   0.147  1.00  0.00           H  
HETATM   17  H3  UNL     1      -3.539  -0.923  -1.645  1.00  0.00           H  
HETATM   18  H4  UNL     1      -1.393   0.198  -1.422  1.00  0.00           H  
HETATM   19  H5  UNL     1      -3.379   1.091   0.613  1.00  0.00           H  
HETATM   20  H6  UNL     1      -3.368   1.352  -1.222  1.00  0.00           H  
HETATM   21  H7  UNL     1      -2.134   2.118  -0.168  1.00  0.00           H  
HETATM   22  H8  UNL     1      -2.035  -0.477   1.575  1.00  0.00           H  
HETATM   23  H9  UNL     1       4.314  -0.094   1.231  1.00  0.00           H  
HETATM   24  H10 UNL     1       4.620   0.422  -1.137  1.00  0.00           H  
HETATM   25  H11 UNL     1       2.649   0.637  -2.606  1.00  0.00           H  
HETATM   26  H12 UNL     1       0.431   0.348  -1.755  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3    4   18
CONECT    3   19   20   21
CONECT    4    5    5   22
CONECT    5    6   14
CONECT    6    7
CONECT    7    8    8    9
CONECT    9   10   10   14
CONECT   10   11   23
CONECT   11   12   12   24
CONECT   12   13   25
CONECT   13   14   14   26
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(e)-3-Isobutylidenephthalide	HMDB
2-Methylpropylidenephthalide (e)	HMDB
3-(2-Methylpropylidene)-(3E)-1(3H)-isobenzofuranone	HMDB

Chemical Formula

C₁₂H₁₂O₂

Average Molecular Weight

188.2225

Monoisotopic Molecular Weight

188.083729628

IUPAC Name

(3E)-3-(2-methylpropylidene)-1,3-dihydro-2-benzofuran-1-one

Traditional Name

(3E)-3-(2-methylpropylidene)-2-benzofuran-1-one

CAS Registry Number

56014-69-8

SMILES

CC(C)\C=C1\OC(=O)C2=CC=CC=C12

InChI Identifier

InChI=1S/C12H12O2/c1-8(2)7-11-9-5-3-4-6-10(9)12(13)14-11/h3-8H,1-2H3/b11-7+

InChI Key

LYSNVWBBICAAMS-YRNVUSSQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isobenzofuranones. Isobenzofuranones are compounds containing a 2-benzofuran moiety that carries an oxo group at the 1 position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isocoumarans

Sub Class

Isobenzofuranones

Direct Parent

Isobenzofuranones

Alternative Parents

Substituents

Isobenzofuranone
Benzenoid
Enol ester
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0032028)

Green vegetables (FooDB: FOOD00872)

Process

Not Available

Role

Not Available

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	408.5 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	0.19 g/L	ALOGPS
logP	2.98	ALOGPS
logP	2.87	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	56.22 m³·mol⁻¹	ChemAxon
Polarizability	20.48 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	146.303	31661259
DarkChem	[M-H]-	143.825	31661259
DeepCCS	[M-2H]-	177.477	30932474
DeepCCS	[M+Na]+	153.051	30932474
AllCCS	[M+H]+	139.6	32859911
AllCCS	[M+H-H2O]+	135.2	32859911
AllCCS	[M+NH4]+	143.7	32859911
AllCCS	[M+Na]+	144.9	32859911
AllCCS	[M-H]-	143.8	32859911
AllCCS	[M+Na-2H]-	144.1	32859911
AllCCS	[M+HCOO]-	144.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(E)-3-(2-Methylpropylidene)-1(3H)-isobenzofuranone	CC(C)\C=C1\OC(=O)C2=CC=CC=C12	2552.4	Standard polar	33892256
(E)-3-(2-Methylpropylidene)-1(3H)-isobenzofuranone	CC(C)\C=C1\OC(=O)C2=CC=CC=C12	1566.0	Standard non polar	33892256
(E)-3-(2-Methylpropylidene)-1(3H)-isobenzofuranone	CC(C)\C=C1\OC(=O)C2=CC=CC=C12	1626.4	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 - (E)-3-(2-Methylpropylidene)-1(3H)-isobenzofuranone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-7900000000-23e4d3be256c369f3b1a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (E)-3-(2-Methylpropylidene)-1(3H)-isobenzofuranone 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 - (E)-3-(2-Methylpropylidene)-1(3H)-isobenzofuranone 10V, Positive-QTOF	splash10-000i-0900000000-f43e59a15f3eaabe898d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-3-(2-Methylpropylidene)-1(3H)-isobenzofuranone 20V, Positive-QTOF	splash10-000i-2900000000-7f136c69283d4a3e0981	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-3-(2-Methylpropylidene)-1(3H)-isobenzofuranone 40V, Positive-QTOF	splash10-004i-9600000000-450b112390c6316e8581	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-3-(2-Methylpropylidene)-1(3H)-isobenzofuranone 10V, Negative-QTOF	splash10-000i-0900000000-2ee851bde589aaef5231	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-3-(2-Methylpropylidene)-1(3H)-isobenzofuranone 20V, Negative-QTOF	splash10-000f-0900000000-53ea0e27f96c4dcee904	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-3-(2-Methylpropylidene)-1(3H)-isobenzofuranone 40V, Negative-QTOF	splash10-0006-1900000000-301b9f3e9d1b9ef6269d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-3-(2-Methylpropylidene)-1(3H)-isobenzofuranone 10V, Negative-QTOF	splash10-000i-0900000000-1d70bfb42d3bcf886a1e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-3-(2-Methylpropylidene)-1(3H)-isobenzofuranone 20V, Negative-QTOF	splash10-000i-0900000000-bbb58d58420f74be0f58	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-3-(2-Methylpropylidene)-1(3H)-isobenzofuranone 40V, Negative-QTOF	splash10-004i-9500000000-b3ce1957fd27d29d2e92	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-3-(2-Methylpropylidene)-1(3H)-isobenzofuranone 10V, Positive-QTOF	splash10-000i-0900000000-66d51d25e2d4f36d77dd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-3-(2-Methylpropylidene)-1(3H)-isobenzofuranone 20V, Positive-QTOF	splash10-000b-0900000000-d81b1225eeaa15b18967	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-3-(2-Methylpropylidene)-1(3H)-isobenzofuranone 40V, Positive-QTOF	splash10-0zi0-6900000000-e16225805c0ab7e90e0a	2021-09-24	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB008727

KNApSAcK ID

Not Available

Chemspider ID

4941245

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6436620

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1829441

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 (E)-3-(2-Methylpropylidene)-1(3H)-isobenzofuranone (HMDB0032028)

MOL for HMDB0032028 ((E)-3-(2-Methylpropylidene)-1(3H)-isobenzofuranone)

3D MOL for HMDB0032028 ((E)-3-(2-Methylpropylidene)-1(3H)-isobenzofuranone)

3D SDF for HMDB0032028 ((E)-3-(2-Methylpropylidene)-1(3H)-isobenzofuranone)

3D-SDF for HMDB0032028 ((E)-3-(2-Methylpropylidene)-1(3H)-isobenzofuranone)

PDB for HMDB0032028 ((E)-3-(2-Methylpropylidene)-1(3H)-isobenzofuranone)

3D PDB for HMDB0032028 ((E)-3-(2-Methylpropylidene)-1(3H)-isobenzofuranone)

SMILES for HMDB0032028 ((E)-3-(2-Methylpropylidene)-1(3H)-isobenzofuranone)

INCHI for HMDB0032028 ((E)-3-(2-Methylpropylidene)-1(3H)-isobenzofuranone)

Structure for HMDB0032028 ((E)-3-(2-Methylpropylidene)-1(3H)-isobenzofuranone)

3D Structure for HMDB0032028 ((E)-3-(2-Methylpropylidene)-1(3H)-isobenzofuranone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra