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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2019-10-08 18:13:29 UTC

Update Date

2022-03-07 03:18:17 UTC

HMDB ID

HMDB0240472

Secondary Accession Numbers

None

Metabolite Identification

Common Name

5-(3',4'-Dihydroxyphenyl)-γ-valerolactone

Description

5-(3',4'-Dihydroxyphenyl)-gamma-valerolactone belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. Based on a literature review very few articles have been published on 5-(3',4'-Dihydroxyphenyl)-gamma-valerolactone.

Structure

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


  Mrv1652310081920132D          

 15 16  0  0  0  0            999 V2000
   -1.7613    0.1080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020    2.1965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4257   -0.6457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0470    2.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6119    1.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4559    0.6892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2763    0.7754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    2.1965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6052   -0.7319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1203   -0.0645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.4661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2697   -1.4856    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7002   -0.1507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.2911    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3819    2.9812    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  2  0  0  0  0
  4  2  1  0  0  0  0
  7  1  1  0  0  0  0
  7  5  1  0  0  0  0
  7  6  2  0  0  0  0
  8  2  1  0  0  0  0
  8  5  1  0  0  0  0
  9  3  1  0  0  0  0
 10  6  1  0  0  0  0
 10  9  2  0  0  0  0
 11  4  1  0  0  0  0
 12  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14 11  2  0  0  0  0
 15  8  1  0  0  0  0
 15 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0240472

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1=C(O)C=C(CC2CCC(=O)O2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2

> <INCHI_KEY>
ZNXXWTPQHVLMQT-UHFFFAOYSA-N

> <FORMULA>
C11H12O4

> <MOLECULAR_WEIGHT>
208.2106

> <EXACT_MASS>
208.073558872

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
27

> <JCHEM_AVERAGE_POLARIZABILITY>
20.715639916565465

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-[(3,4-dihydroxyphenyl)methyl]oxolan-2-one

> <ALOGPS_LOGP>
1.47

> <JCHEM_LOGP>
1.6153220546666665

> <ALOGPS_LOGS>
-2.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.73403802973936

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.284113130939318

> <JCHEM_PKA_STRONGEST_BASIC>
-6.289147264805462

> <JCHEM_POLAR_SURFACE_AREA>
66.75999999999999

> <JCHEM_REFRACTIVITY>
53.307700000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.38e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-[(3,4-dihydroxyphenyl)methyl]oxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-OCT-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-OCT-19         0                                  
HETATM    1  C   UNK     0      -3.288   0.202   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.564   4.100   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.661  -1.205   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.088   5.565   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.009   2.854   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.851   1.286   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.382   1.447   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.104   4.100   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.130  -1.366   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.225  -0.120   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334   6.470   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.503  -2.773   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.307  -0.281   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -1.334   8.010   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -2.580   5.565   0.000  0.00  0.00           O+0
CONECT    1    3    7                                                       
CONECT    2    4    8                                                       
CONECT    3    1    9                                                       
CONECT    4    2   11                                                       
CONECT    5    7    8                                                       
CONECT    6    7   10                                                       
CONECT    7    1    5    6                                                  
CONECT    8    2    5   15                                                  
CONECT    9    3   10   12                                                  
CONECT   10    6    9   13                                                  
CONECT   11    4   14   15                                                  
CONECT   12    9                                                            
CONECT   13   10                                                            
CONECT   14   11                                                            
CONECT   15    8   11                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0240472
HETATM    1  O1  UNL     1       3.269  -0.126  -2.928  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.853   0.014  -1.748  1.00  0.00           C  
HETATM    3  C2  UNL     1       3.534   0.656  -0.590  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.064  -0.238   0.552  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.654  -0.587   0.121  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.715   0.342   0.847  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.705   0.098   0.506  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.502  -0.778   1.197  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.808  -0.939   0.809  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.380  -0.264  -0.250  1.00  0.00           C  
HETATM   11  O2  UNL     1      -4.715  -0.467  -0.601  1.00  0.00           O  
HETATM   12  C10 UNL     1      -2.569   0.616  -0.938  1.00  0.00           C  
HETATM   13  O3  UNL     1      -3.116   1.310  -2.009  1.00  0.00           O  
HETATM   14  C11 UNL     1      -1.246   0.789  -0.557  1.00  0.00           C  
HETATM   15  O4  UNL     1       1.632  -0.417  -1.271  1.00  0.00           O  
HETATM   16  H1  UNL     1       3.106   1.679  -0.419  1.00  0.00           H  
HETATM   17  H2  UNL     1       4.627   0.663  -0.688  1.00  0.00           H  
HETATM   18  H3  UNL     1       3.693  -1.150   0.569  1.00  0.00           H  
HETATM   19  H4  UNL     1       3.089   0.326   1.506  1.00  0.00           H  
HETATM   20  H5  UNL     1       1.481  -1.645   0.347  1.00  0.00           H  
HETATM   21  H6  UNL     1       0.827   0.136   1.932  1.00  0.00           H  
HETATM   22  H7  UNL     1       1.034   1.372   0.673  1.00  0.00           H  
HETATM   23  H8  UNL     1      -1.068  -1.318   2.033  1.00  0.00           H  
HETATM   24  H9  UNL     1      -3.446  -1.634   1.353  1.00  0.00           H  
HETATM   25  H10 UNL     1      -5.272  -1.122  -0.068  1.00  0.00           H  
HETATM   26  H11 UNL     1      -4.079   1.182  -2.283  1.00  0.00           H  
HETATM   27  H12 UNL     1      -0.671   1.503  -1.152  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   15
CONECT    3    4   16   17
CONECT    4    5   18   19
CONECT    5    6   15   20
CONECT    6    7   21   22
CONECT    7    8    8   14
CONECT    8    9   23
CONECT    9   10   10   24
CONECT   10   11   12
CONECT   11   25
CONECT   12   13   14   14
CONECT   13   26
CONECT   14   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5-(3',4'-Dihydroxyphenyl)-g-valerolactone	Generator
5-(3',4'-Dihydroxyphenyl)-γ-valerolactone	Generator
5-(3,4-Dihydroxybenzyl)dihydrofuran-2(3H)-one	HMDB
5-(3',4'-Dihydroxyphenyl)-gamma-valerolactone	HMDB
5-(3,4-Dihydroxyphenyl)-gamma-valerolactone	HMDB
5-[(3,4-Dihydroxyphenyl)methyl]oxolan-2-one	HMDB

Chemical Formula

C₁₁H₁₂O₄

Average Molecular Weight

208.2106

Monoisotopic Molecular Weight

208.073558872

IUPAC Name

5-[(3,4-dihydroxyphenyl)methyl]oxolan-2-one

Traditional Name

5-[(3,4-dihydroxyphenyl)methyl]oxolan-2-one

CAS Registry Number

Not Available

SMILES

OC1=C(O)C=C(CC2CCC(=O)O2)C=C1

InChI Identifier

InChI=1S/C11H12O4/c12-9-3-1-7(6-10(9)13)5-8-2-4-11(14)15-8/h1,3,6,8,12-13H,2,4-5H2

InChI Key

ZNXXWTPQHVLMQT-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Lactone
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Organic oxygen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0240472)

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
logP	1.47	ALOGPS
logP	1.62	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	9.28	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	53.31 m³·mol⁻¹	ChemAxon
Polarizability	20.72 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]+	149.069	31661259
DarkChem	[M-H]-	147.77	31661259
DeepCCS	[M+H]+	146.928	30932474
DeepCCS	[M-H]-	144.537	30932474
DeepCCS	[M-2H]-	178.687	30932474
DeepCCS	[M+Na]+	153.305	30932474
AllCCS	[M+H]+	147.4	32859911
AllCCS	[M+H-H2O]+	143.1	32859911
AllCCS	[M+NH4]+	151.4	32859911
AllCCS	[M+Na]+	152.5	32859911
AllCCS	[M-H]-	147.8	32859911
AllCCS	[M+Na-2H]-	147.9	32859911
AllCCS	[M+HCOO]-	148.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
5-(3',4'-Dihydroxyphenyl)-??-valerolactone	OC1=C(O)C=C(CC2CCC(=O)O2)C=C1	3525.8	Standard polar	33892256
5-(3',4'-Dihydroxyphenyl)-??-valerolactone	OC1=C(O)C=C(CC2CCC(=O)O2)C=C1	2096.5	Standard non polar	33892256
5-(3',4'-Dihydroxyphenyl)-??-valerolactone	OC1=C(O)C=C(CC2CCC(=O)O2)C=C1	2236.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-(3',4'-Dihydroxyphenyl)-??-valerolactone,1TMS,isomer #1	C[Si](C)(C)OC1=CC=C(CC2CCC(=O)O2)C=C1O	2089.4	Semi standard non polar	33892256
5-(3',4'-Dihydroxyphenyl)-??-valerolactone,1TMS,isomer #2	C[Si](C)(C)OC1=CC(CC2CCC(=O)O2)=CC=C1O	2064.7	Semi standard non polar	33892256
5-(3',4'-Dihydroxyphenyl)-??-valerolactone,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(CC2CCC(=O)O2)C=C1O[Si](C)(C)C	2144.8	Semi standard non polar	33892256
5-(3',4'-Dihydroxyphenyl)-??-valerolactone,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(CC2CCC(=O)O2)C=C1O	2376.1	Semi standard non polar	33892256
5-(3',4'-Dihydroxyphenyl)-??-valerolactone,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC(CC2CCC(=O)O2)=CC=C1O	2344.4	Semi standard non polar	33892256
5-(3',4'-Dihydroxyphenyl)-??-valerolactone,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(CC2CCC(=O)O2)C=C1O[Si](C)(C)C(C)(C)C	2624.8	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 - 5-(3',4'-Dihydroxyphenyl)-γ-valerolactone GC-MS (Non-derivatized) - 70eV, Positive	splash10-05br-5900000000-cd9fe9ddbcf0bef4e451	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-(3',4'-Dihydroxyphenyl)-γ-valerolactone GC-MS (2 TMS) - 70eV, Positive	splash10-0103-5092000000-84e3c67e2ffe9333da13	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-(3',4'-Dihydroxyphenyl)-γ-valerolactone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 5-(3',4'-Dihydroxyphenyl)-γ-valerolactone 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 - 5-(3',4'-Dihydroxyphenyl)-γ-valerolactone 10V, Positive-QTOF	splash10-0a4i-0790000000-3af2f37c7cfb610de061	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(3',4'-Dihydroxyphenyl)-γ-valerolactone 20V, Positive-QTOF	splash10-0a4s-2910000000-8e053379868a8ba75061	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(3',4'-Dihydroxyphenyl)-γ-valerolactone 40V, Positive-QTOF	splash10-0kfx-9500000000-2ed8d68fa04acd159576	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(3',4'-Dihydroxyphenyl)-γ-valerolactone 10V, Negative-QTOF	splash10-0a4i-0390000000-11295d73a4b837461a85	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(3',4'-Dihydroxyphenyl)-γ-valerolactone 20V, Negative-QTOF	splash10-0bt9-4960000000-03bd02aa692ae2a3cdf0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(3',4'-Dihydroxyphenyl)-γ-valerolactone 40V, Negative-QTOF	splash10-0006-9400000000-139dc860dea66d5b322a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(3',4'-Dihydroxyphenyl)-γ-valerolactone 10V, Negative-QTOF	splash10-0a4i-1490000000-ec828d89aebc8ed026a4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(3',4'-Dihydroxyphenyl)-γ-valerolactone 20V, Negative-QTOF	splash10-0019-9500000000-a59c0f26c2f4508f2c4e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(3',4'-Dihydroxyphenyl)-γ-valerolactone 40V, Negative-QTOF	splash10-0076-6900000000-6b3eed581075ea184a37	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(3',4'-Dihydroxyphenyl)-γ-valerolactone 10V, Positive-QTOF	splash10-0a4i-5690000000-426cef4dbeb10dafeeae	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(3',4'-Dihydroxyphenyl)-γ-valerolactone 20V, Positive-QTOF	splash10-05fs-7900000000-608cd683d3b6dda831d1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-(3',4'-Dihydroxyphenyl)-γ-valerolactone 40V, Positive-QTOF	splash10-066v-9600000000-33bdad61d6a30e899f6f	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB029853

KNApSAcK ID

Not Available

Chemspider ID

134347

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

152432

PDB ID

Not Available

ChEBI ID

89285

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

Not Available

Showing metabocard for 5-(3',4'-Dihydroxyphenyl)-γ-valerolactone (HMDB0240472)

MOL for HMDB0240472 (5-(3',4'-Dihydroxyphenyl)-γ-valerolactone)

3D MOL for HMDB0240472 (5-(3',4'-Dihydroxyphenyl)-γ-valerolactone)

3D SDF for HMDB0240472 (5-(3',4'-Dihydroxyphenyl)-γ-valerolactone)

3D-SDF for HMDB0240472 (5-(3',4'-Dihydroxyphenyl)-γ-valerolactone)

PDB for HMDB0240472 (5-(3',4'-Dihydroxyphenyl)-γ-valerolactone)

3D PDB for HMDB0240472 (5-(3',4'-Dihydroxyphenyl)-γ-valerolactone)

SMILES for HMDB0240472 (5-(3',4'-Dihydroxyphenyl)-γ-valerolactone)

INCHI for HMDB0240472 (5-(3',4'-Dihydroxyphenyl)-γ-valerolactone)

Structure for HMDB0240472 (5-(3',4'-Dihydroxyphenyl)-γ-valerolactone)

3D Structure for HMDB0240472 (5-(3',4'-Dihydroxyphenyl)-γ-valerolactone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra