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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:47:32 UTC

Update Date

2023-02-21 17:21:34 UTC

HMDB ID

HMDB0032061

Secondary Accession Numbers

HMDB32061

Metabolite Identification

Common Name

3-Butylidene-1(3H)-isobenzofuranone

Description

3-Butylidene-1(3H)-isobenzofuranone, also known as 3-butylidenephthalide, 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. 3-Butylidene-1(3H)-isobenzofuranone is a celery, herbal, and lovage tasting compound. 3-Butylidene-1(3H)-isobenzofuranone is found, on average, in the highest concentration within lovages (Levisticum officinale). 3-Butylidene-1(3H)-isobenzofuranone has also been detected, but not quantified in, celery stalks (Apium graveolens var. dulce) and wild celeries (Apium graveolens). This could make 3-butylidene-1(3H)-isobenzofuranone a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 3-Butylidene-1(3H)-isobenzofuranone.

Structure

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


  Mrv0541 05061306202D          

 14 15  0  0  0  0            999 V2000
    1.7329   -1.9399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1809   -1.3268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -0.5422    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  3  1  0  0  0  0
  9  6  2  0  0  0  0
 10  7  2  0  0  0  0
 10  9  1  0  0  0  0
 11  8  2  0  0  0  0
 11  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13 12  2  0  0  0  0
 14 11  1  0  0  0  0
 14 12  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032061

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C12H12O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h4-8H,2-3H2,1H3/b11-8+

> <INCHI_KEY>
WMBOCUXXNSOQHM-DHZHZOJOSA-N

> <FORMULA>
C12H12O2

> <MOLECULAR_WEIGHT>
188.2225

> <EXACT_MASS>
188.083729628

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
20.373240159443654

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.38

> <JCHEM_LOGP>
3.023928228

> <ALOGPS_LOGS>
-3.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.059364804113812

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
56.27610000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.45e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
butylidenephthalide

> <JCHEM_VEBER_RULE>
1

$$$$

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       3.235  -3.621   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.204  -2.477   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.680  -1.012   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.650   0.132   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.650   5.553   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       1.220   2.843   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    8                                                       
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4    9                                                       
CONECT    7    5   10                                                       
CONECT    8    3   11                                                       
CONECT    9    6   10   11                                                  
CONECT   10    7    9   12                                                  
CONECT   11    8    9   14                                                  
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   11   12                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   30    0
END

COMPND    HMDB0032061
HETATM    1  C1  UNL     1       2.385   0.619   1.175  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.014  -0.251   0.114  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.920  -0.860  -0.792  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.186   0.202  -1.422  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.053   0.582  -1.252  1.00  0.00           C  
HETATM    6  O1  UNL     1      -0.694   1.642  -1.927  1.00  0.00           O  
HETATM    7  C6  UNL     1      -1.988   1.749  -1.492  1.00  0.00           C  
HETATM    8  O2  UNL     1      -2.888   2.554  -1.837  1.00  0.00           O  
HETATM    9  C7  UNL     1      -2.206   0.705  -0.477  1.00  0.00           C  
HETATM   10  C8  UNL     1      -3.312   0.379   0.278  1.00  0.00           C  
HETATM   11  C9  UNL     1      -3.200  -0.660   1.169  1.00  0.00           C  
HETATM   12  C10 UNL     1      -2.033  -1.366   1.320  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.899  -1.035   0.550  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.010   0.002  -0.343  1.00  0.00           C  
HETATM   15  H1  UNL     1       1.543   0.102   1.642  1.00  0.00           H  
HETATM   16  H2  UNL     1       3.157   0.769   1.963  1.00  0.00           H  
HETATM   17  H3  UNL     1       2.108   1.578   0.700  1.00  0.00           H  
HETATM   18  H4  UNL     1       3.748   0.309  -0.479  1.00  0.00           H  
HETATM   19  H5  UNL     1       3.529  -1.099   0.609  1.00  0.00           H  
HETATM   20  H6  UNL     1       2.631  -1.248  -1.659  1.00  0.00           H  
HETATM   21  H7  UNL     1       1.521  -1.702  -0.320  1.00  0.00           H  
HETATM   22  H8  UNL     1       1.721   0.833  -2.184  1.00  0.00           H  
HETATM   23  H9  UNL     1      -4.222   0.939   0.152  1.00  0.00           H  
HETATM   24  H10 UNL     1      -4.028  -0.981   1.802  1.00  0.00           H  
HETATM   25  H11 UNL     1      -1.913  -2.180   2.005  1.00  0.00           H  
HETATM   26  H12 UNL     1      -0.017  -1.582   0.703  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3   18   19
CONECT    3    4   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
3-Butylidenephthalide	MeSH
Butylidenephthalide	MeSH
N-Butylidenephthalide	MeSH
(Z)-3-Butylidenephthalide	ChEMBL, HMDB
(e)-3-Butylidenephthalide	HMDB
3-Butylidene-phthalide	HMDB
3-Butylidenephthalide, 8ci	HMDB
FEMA 3333	HMDB
Ligusticum lactone	HMDB
3-Butylidene-1(3H)-isobenzofuranone	MeSH

Chemical Formula

C₁₂H₁₂O₂

Average Molecular Weight

188.2225

Monoisotopic Molecular Weight

188.083729628

IUPAC Name

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

Traditional Name

butylidenephthalide

CAS Registry Number

551-08-6

SMILES

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

InChI Identifier

InChI=1S/C12H12O2/c1-2-3-8-11-9-6-4-5-7-10(9)12(13)14-11/h4-8H,2-3H2,1H3/b11-8+

InChI Key

WMBOCUXXNSOQHM-DHZHZOJOSA-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

Cell membrane (FooDB: )
Membrane (FooDB: )

Route of exposure

Enteral

Ingestion (FooDB: )

Source

Endogenous

Endogenous (FooDB: )

Plant

Plant (FooDB: )

Exogenous

Food

Food (FooDB: )

Herb and spice

Spice

Wild celery (FooDB: FOOD00015)

Vegetable

Stalk vegetable

Celery stalks (FooDB: FOOD00215)

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	319.00 to 321.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0	The Good Scents Company Information System
LogP	3.388 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	3.38	ALOGPS
logP	3.02	ChemAxon
logS	-3.1	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	2	ChemAxon
Refractivity	56.28 m³·mol⁻¹	ChemAxon
Polarizability	20.37 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]+	145.641	31661259
DarkChem	[M-H]-	144.072	31661259
DeepCCS	[M-2H]-	177.301	30932474
DeepCCS	[M+Na]+	152.897	30932474
AllCCS	[M+H]+	141.4	32859911
AllCCS	[M+H-H2O]+	137.1	32859911
AllCCS	[M+NH4]+	145.5	32859911
AllCCS	[M+Na]+	146.7	32859911
AllCCS	[M-H]-	145.2	32859911
AllCCS	[M+Na-2H]-	145.5	32859911
AllCCS	[M+HCOO]-	145.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Butylidene-1(3H)-isobenzofuranone	CCC\C=C1\OC(=O)C2=CC=CC=C12	2616.7	Standard polar	33892256
3-Butylidene-1(3H)-isobenzofuranone	CCC\C=C1\OC(=O)C2=CC=CC=C12	1668.0	Standard non polar	33892256
3-Butylidene-1(3H)-isobenzofuranone	CCC\C=C1\OC(=O)C2=CC=CC=C12	1705.9	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 - 3-Butylidene-1(3H)-isobenzofuranone GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-6900000000-732e96716c41a04fb3fa	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Butylidene-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 - 3-Butylidene-1(3H)-isobenzofuranone 10V, Positive-QTOF	splash10-000i-2900000000-8ae9e1a01eaa6fecf1b4	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Butylidene-1(3H)-isobenzofuranone 20V, Positive-QTOF	splash10-000i-5900000000-f3bbe4d26792fe9d6533	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Butylidene-1(3H)-isobenzofuranone 40V, Positive-QTOF	splash10-0pbc-9100000000-3c7f96234901b9d9e933	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Butylidene-1(3H)-isobenzofuranone 10V, Negative-QTOF	splash10-000i-0900000000-95d702d187abea157d2e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Butylidene-1(3H)-isobenzofuranone 20V, Negative-QTOF	splash10-000f-0900000000-551a78bdb3bd751e3988	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Butylidene-1(3H)-isobenzofuranone 40V, Negative-QTOF	splash10-0006-3900000000-f234896ae771c1f4eb20	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Butylidene-1(3H)-isobenzofuranone 10V, Negative-QTOF	splash10-000i-0900000000-0efd5563391c35d6cf2a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Butylidene-1(3H)-isobenzofuranone 20V, Negative-QTOF	splash10-000i-0900000000-03cc6cd126f49f632654	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Butylidene-1(3H)-isobenzofuranone 40V, Negative-QTOF	splash10-0a4i-2900000000-fe566d20babcbcbca0ce	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Butylidene-1(3H)-isobenzofuranone 10V, Positive-QTOF	splash10-000i-0900000000-18975ec6e59c754be61e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Butylidene-1(3H)-isobenzofuranone 20V, Positive-QTOF	splash10-000b-0900000000-6eebf85402bef8698a16	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Butylidene-1(3H)-isobenzofuranone 40V, Positive-QTOF	splash10-0ar9-9600000000-82c62a98392b22d4237c	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5352899

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1027291

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 3-Butylidene-1(3H)-isobenzofuranone (HMDB0032061)

MOL for HMDB0032061 (3-Butylidene-1(3H)-isobenzofuranone)

3D MOL for HMDB0032061 (3-Butylidene-1(3H)-isobenzofuranone)

3D SDF for HMDB0032061 (3-Butylidene-1(3H)-isobenzofuranone)

3D-SDF for HMDB0032061 (3-Butylidene-1(3H)-isobenzofuranone)

PDB for HMDB0032061 (3-Butylidene-1(3H)-isobenzofuranone)

3D PDB for HMDB0032061 (3-Butylidene-1(3H)-isobenzofuranone)

SMILES for HMDB0032061 (3-Butylidene-1(3H)-isobenzofuranone)

INCHI for HMDB0032061 (3-Butylidene-1(3H)-isobenzofuranone)

Structure for HMDB0032061 (3-Butylidene-1(3H)-isobenzofuranone)

3D Structure for HMDB0032061 (3-Butylidene-1(3H)-isobenzofuranone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra