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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:39:45 UTC

Update Date

2022-03-07 02:52:44 UTC

HMDB ID

HMDB0030903

Secondary Accession Numbers

HMDB30903

Metabolite Identification

Common Name

3-(4-Methylphenyl)oxiranecarboxylic acid

Description

3-(4-Methylphenyl)oxiranecarboxylic acid belongs to the class of organic compounds known as toluenes. Toluenes are compounds containing a benzene ring which bears a methane group. Based on a literature review very few articles have been published on 3-(4-Methylphenyl)oxiranecarboxylic acid.

Structure

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

  Mrv0541 05061305352D          

 13 14  0  0  0  0            999 V2000
    5.8263   -2.5388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118   -1.3013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974   -2.5388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974   -0.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -2.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118   -2.1263    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -1.3013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684   -0.8888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559   -0.1743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5559    0.6507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414    1.0632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2704    1.0632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.8888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  6  1  1  0  0  0  0
  6  2  2  0  0  0  0
  6  3  1  0  0  0  0
  7  4  2  0  0  0  0
  7  5  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  2  0  0  0  0
 12 10  1  0  0  0  0
 13  8  1  0  0  0  0
 13  9  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0030903

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CC=C(C=C1)C1OC1C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H10O3/c1-6-2-4-7(5-3-6)8-9(13-8)10(11)12/h2-5,8-9H,1H3,(H,11,12)

> <INCHI_KEY>
KYFKCKUXXZSOTF-UHFFFAOYSA-N

> <FORMULA>
C10H10O3

> <MOLECULAR_WEIGHT>
178.1846

> <EXACT_MASS>
178.062994186

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
18.26162423350822

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(4-methylphenyl)oxirane-2-carboxylic acid

> <ALOGPS_LOGP>
1.13

> <JCHEM_LOGP>
1.940625664333333

> <ALOGPS_LOGS>
-1.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
19.670633840811135

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8534535209300262

> <JCHEM_PKA_STRONGEST_BASIC>
-4.311685428748706

> <JCHEM_POLAR_SURFACE_AREA>
49.83

> <JCHEM_REFRACTIVITY>
46.197400000000016

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.57e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(4-methylphenyl)oxirane-2-carboxylic 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      10.876  -4.739   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.542  -2.429   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.208  -4.739   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.208  -1.659   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.875  -3.969   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.542  -3.969   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.875  -2.429   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.541  -1.659   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.771  -0.325   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.771   1.215   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.437   1.985   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       6.105   1.985   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       4.001  -1.659   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    4    6                                                       
CONECT    3    5    6                                                       
CONECT    4    2    7                                                       
CONECT    5    3    7                                                       
CONECT    6    1    2    3                                                  
CONECT    7    4    5    8                                                  
CONECT    8    7    9   13                                                  
CONECT    9    8   10   13                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    8    9                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   28    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3-(4-Methylphenyl)oxiranecarboxylate	Generator
3-(4-Methylphenyl)oxirane-2-carboxylate	HMDB

Chemical Formula

C₁₀H₁₀O₃

Average Molecular Weight

178.1846

Monoisotopic Molecular Weight

178.062994186

IUPAC Name

3-(4-methylphenyl)oxirane-2-carboxylic acid

Traditional Name

3-(4-methylphenyl)oxirane-2-carboxylic acid

CAS Registry Number

81476-88-2

SMILES

CC1=CC=C(C=C1)C1OC1C(O)=O

InChI Identifier

InChI=1S/C10H10O3/c1-6-2-4-7(5-3-6)8-9(13-8)10(11)12/h2-5,8-9H,1H3,(H,11,12)

InChI Key

KYFKCKUXXZSOTF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as toluenes. Toluenes are compounds containing a benzene ring which bears a methane group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Toluenes

Direct Parent

Toluenes

Alternative Parents

Substituents

Toluene
Oxirane carboxylic acid
Oxirane carboxylic acid or derivatives
Carboxylic acid derivative
Carboxylic acid
Dialkyl ether
Oxirane
Ether
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0030903)
Cytoplasm (HMDB: HMDB0030903)

Source

Endogenous

Endogenous (HMDB: HMDB0030903)

Exogenous

Food

Food (HMDB: HMDB0030903)

Exogenous (HMDB: HMDB0030903)

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	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.57 g/L	ALOGPS
logP	1.13	ALOGPS
logP	1.94	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	3.85	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	49.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	46.2 m³·mol⁻¹	ChemAxon
Polarizability	18.26 Å³	ChemAxon
Number of Rings	2	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]+	139.273	31661259
DarkChem	[M-H]-	135.038	31661259
DeepCCS	[M+H]+	138.662	30932474
DeepCCS	[M-H]-	134.835	30932474
DeepCCS	[M-2H]-	172.32	30932474
DeepCCS	[M+Na]+	147.858	30932474
AllCCS	[M+H]+	139.0	32859911
AllCCS	[M+H-H2O]+	134.5	32859911
AllCCS	[M+NH4]+	143.1	32859911
AllCCS	[M+Na]+	144.3	32859911
AllCCS	[M-H]-	139.2	32859911
AllCCS	[M+Na-2H]-	139.6	32859911
AllCCS	[M+HCOO]-	140.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-(4-Methylphenyl)oxiranecarboxylic acid	CC1=CC=C(C=C1)C1OC1C(O)=O	2861.7	Standard polar	33892256
3-(4-Methylphenyl)oxiranecarboxylic acid	CC1=CC=C(C=C1)C1OC1C(O)=O	1444.9	Standard non polar	33892256
3-(4-Methylphenyl)oxiranecarboxylic acid	CC1=CC=C(C=C1)C1OC1C(O)=O	1689.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-(4-Methylphenyl)oxiranecarboxylic acid,1TMS,isomer #1	CC1=CC=C(C2OC2C(=O)O[Si](C)(C)C)C=C1	1641.9	Semi standard non polar	33892256
3-(4-Methylphenyl)oxiranecarboxylic acid,1TBDMS,isomer #1	CC1=CC=C(C2OC2C(=O)O[Si](C)(C)C(C)(C)C)C=C1	1857.7	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-(4-Methylphenyl)oxiranecarboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udi-1900000000-fba20ed8b7b4e803ab22	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(4-Methylphenyl)oxiranecarboxylic acid GC-MS (1 TMS) - 70eV, Positive	splash10-0uki-9700000000-a20b482a4951288a2975	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(4-Methylphenyl)oxiranecarboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(4-Methylphenyl)oxiranecarboxylic 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 - 3-(4-Methylphenyl)oxiranecarboxylic acid 10V, Positive-QTOF	splash10-01t9-0900000000-0edf4361af712154516e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Methylphenyl)oxiranecarboxylic acid 20V, Positive-QTOF	splash10-03fr-1900000000-7ec7640c234e33815d9c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Methylphenyl)oxiranecarboxylic acid 40V, Positive-QTOF	splash10-014i-8900000000-e9308c01d47d78725662	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Methylphenyl)oxiranecarboxylic acid 10V, Negative-QTOF	splash10-004i-0900000000-5b0a9fbe92e04222b714	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Methylphenyl)oxiranecarboxylic acid 20V, Negative-QTOF	splash10-001i-1900000000-f35e3e72b72bdca40e07	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Methylphenyl)oxiranecarboxylic acid 40V, Negative-QTOF	splash10-001l-6900000000-54d352efb6908edfe0f7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Methylphenyl)oxiranecarboxylic acid 10V, Positive-QTOF	splash10-0006-6900000000-a178d73e062567988864	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Methylphenyl)oxiranecarboxylic acid 20V, Positive-QTOF	splash10-000x-6900000000-576ebc58e8e21024f20b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Methylphenyl)oxiranecarboxylic acid 40V, Positive-QTOF	splash10-05mo-9600000000-88f3e291fb304be7297b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Methylphenyl)oxiranecarboxylic acid 10V, Negative-QTOF	splash10-053r-1900000000-bd09797ff2111548a881	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Methylphenyl)oxiranecarboxylic acid 20V, Negative-QTOF	splash10-001i-5900000000-ef381071dab7fab28128	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(4-Methylphenyl)oxiranecarboxylic acid 40V, Negative-QTOF	splash10-00l6-6900000000-730d5d5134ef604c116e	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-30	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

FDB002868

KNApSAcK ID

Not Available

Chemspider ID

13630303

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15225103

PDB ID

Not Available

ChEBI ID

Not Available

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 3-(4-Methylphenyl)oxiranecarboxylic acid (HMDB0030903)

MOL for HMDB0030903 (3-(4-Methylphenyl)oxiranecarboxylic acid)

3D MOL for HMDB0030903 (3-(4-Methylphenyl)oxiranecarboxylic acid)

3D SDF for HMDB0030903 (3-(4-Methylphenyl)oxiranecarboxylic acid)

3D-SDF for HMDB0030903 (3-(4-Methylphenyl)oxiranecarboxylic acid)

PDB for HMDB0030903 (3-(4-Methylphenyl)oxiranecarboxylic acid)

3D PDB for HMDB0030903 (3-(4-Methylphenyl)oxiranecarboxylic acid)

SMILES for HMDB0030903 (3-(4-Methylphenyl)oxiranecarboxylic acid)

INCHI for HMDB0030903 (3-(4-Methylphenyl)oxiranecarboxylic acid)

Structure for HMDB0030903 (3-(4-Methylphenyl)oxiranecarboxylic acid)

3D Structure for HMDB0030903 (3-(4-Methylphenyl)oxiranecarboxylic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra