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Showing metabocard for Parasorbic acid (HMDB0301801)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-09-22 21:12:30 UTC
Update Date2021-09-22 21:12:30 UTC
HMDB IDHMDB0301801
Secondary Accession NumbersNone
Metabolite Identification
Common NameParasorbic acid
DescriptionParasorbic acid, also known as parasorbate, is a member of the class of compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond. Parasorbic acid is soluble (in water) and an extremely weak acidic compound (based on its pKa). Parasorbic acid can be found in american cranberry and rowanberry, which makes parasorbic acid a potential biomarker for the consumption of these food products. Parasorbic acid is the cyclic lactone of sorbic acid. Thermal treatment or hydrolysis converts the lactone to sorbic acid .
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0301801 (Parasorbic acid)


  Mrv0541 02241221062D          

  8  8  0  0  0  0            999 V2000
    0.7145    2.0625    0.0000 O   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
    1.4289    0.8250    0.0000 O   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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  2  8  1  0  0  0  0
M  END
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3D MOL for HMDB0301801 (Parasorbic acid)

HMDB0301801
     RDKit          3D
Parasorbic acid
 16 16  0  0  0  0  0  0  0  0999 V2000
   -2.1238    0.3656   -0.1853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6536    0.3105    0.1782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1159   -1.0656   -0.1280 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3163   -1.0703    0.2403 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0274    0.0367    0.1996 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4582    1.3304   -0.2057 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1286    2.3926   -0.2500 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0905    1.2816   -0.5432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5745   -0.5835    0.1827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2368    0.5084   -1.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6124    1.1791    0.4011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5502    0.4712    1.2657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7120   -1.7767    0.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2596   -1.3336   -1.2041 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7495   -2.0233    0.5435 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0685   -0.0229    0.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  2  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  3 13  1  0
  3 14  1  0
  4 15  1  0
  5 16  1  0
M  END
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3D SDF for HMDB0301801 (Parasorbic acid)


  Mrv0541 02241221062D          

  8  8  0  0  0  0            999 V2000
    0.7145    2.0625    0.0000 O   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
    1.4289    0.8250    0.0000 O   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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  2  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0301801

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CC=CC(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C6H8O2/c1-5-3-2-4-6(7)8-5/h2,4-5H,3H2,1H3

> <INCHI_KEY>
DYNKRGCMLGUEMN-UHFFFAOYSA-N

> <FORMULA>
C6H8O2

> <MOLECULAR_WEIGHT>
112.1265

> <EXACT_MASS>
112.0524295

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
11.385721858132527

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-methyl-5,6-dihydro-2H-pyran-2-one

> <ALOGPS_LOGP>
0.74

> <JCHEM_LOGP>
1.2418518183333331

> <ALOGPS_LOGS>
-0.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.46278277665503

> <JCHEM_PKA_STRONGEST_BASIC>
-6.799839660398484

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
30.421200000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.66e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
parasorbic acid

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0301801 (Parasorbic acid)

HMDB0301801
     RDKit          3D
Parasorbic acid
 16 16  0  0  0  0  0  0  0  0999 V2000
   -2.1238    0.3656   -0.1853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6536    0.3105    0.1782 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1159   -1.0656   -0.1280 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3163   -1.0703    0.2403 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0274    0.0367    0.1996 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4582    1.3304   -0.2057 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1286    2.3926   -0.2500 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0905    1.2816   -0.5432 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5745   -0.5835    0.1827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2368    0.5084   -1.2722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6124    1.1791    0.4011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5502    0.4712    1.2657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7120   -1.7767    0.4873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2596   -1.3336   -1.2041 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7495   -2.0233    0.5435 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0685   -0.0229    0.4775 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  2  1  0
  1  9  1  0
  1 10  1  0
  1 11  1  0
  2 12  1  0
  3 13  1  0
  3 14  1  0
  4 15  1  0
  5 16  1  0
M  END
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PDB for HMDB0301801 (Parasorbic acid)

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       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    2                                                       
MASTER        0    0    0    0    0    0    0    0    8    0   16    0
END
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3D PDB for HMDB0301801 (Parasorbic acid)

COMPND    HMDB0301801
HETATM    1  C1  UNL     1      -2.124   0.366  -0.185  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.654   0.310   0.178  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.116  -1.066  -0.128  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.316  -1.070   0.240  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.027   0.037   0.200  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.458   1.330  -0.206  1.00  0.00           C  
HETATM    7  O1  UNL     1       2.129   2.393  -0.250  1.00  0.00           O  
HETATM    8  O2  UNL     1       0.090   1.282  -0.543  1.00  0.00           O  
HETATM    9  H1  UNL     1      -2.574  -0.583   0.183  1.00  0.00           H  
HETATM   10  H2  UNL     1      -2.237   0.508  -1.272  1.00  0.00           H  
HETATM   11  H3  UNL     1      -2.612   1.179   0.401  1.00  0.00           H  
HETATM   12  H4  UNL     1      -0.550   0.471   1.266  1.00  0.00           H  
HETATM   13  H5  UNL     1      -0.712  -1.777   0.487  1.00  0.00           H  
HETATM   14  H6  UNL     1      -0.260  -1.334  -1.204  1.00  0.00           H  
HETATM   15  H7  UNL     1       1.749  -2.023   0.544  1.00  0.00           H  
HETATM   16  H8  UNL     1       3.068  -0.023   0.477  1.00  0.00           H  
CONECT    1    2    9   10   11
CONECT    2    3    8   12
CONECT    3    4   13   14
CONECT    4    5    5   15
CONECT    5    6   16
CONECT    6    7    7    8
END
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SMILES for HMDB0301801 (Parasorbic acid)

CC1CC=CC(=O)O1
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INCHI for HMDB0301801 (Parasorbic acid)

InChI=1S/C6H8O2/c1-5-3-2-4-6(7)8-5/h2,4-5H,3H2,1H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
ParasorbateGenerator
Chemical FormulaC6H8O2
Average Molecular Weight112.1265
Monoisotopic Molecular Weight112.0524295
IUPAC Name6-methyl-5,6-dihydro-2H-pyran-2-one
Traditional Nameparasorbic acid
CAS Registry Number10048-32-5
SMILES
CC1CC=CC(=O)O1
InChI Identifier
InChI=1S/C6H8O2/c1-5-3-2-4-6(7)8-5/h2,4-5H,3H2,1H3
InChI KeyDYNKRGCMLGUEMN-UHFFFAOYSA-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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyrans
Sub ClassPyranones and derivatives
Direct ParentDihydropyranones
Alternative Parents
Substituents
  • Dihydropyranone
  • Alpha,beta-unsaturated carboxylic ester
  • Enoate ester
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Source
ProcessNot Available
Role
Biological roleIndustrial application
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP0.74ALOGPS
logP1.24ChemAxon
logS-0.62ALOGPS
pKa (Strongest Acidic)17.46ChemAxon
pKa (Strongest Basic)-6.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area26.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity30.42 m³·mol⁻¹ChemAxon
Polarizability11.39 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+122.09232859911
AllCCS[M+H-H2O]+117.05832859911
AllCCS[M+Na]+128.15432859911
AllCCS[M+NH4]+126.79532859911
AllCCS[M-H]-121.60432859911
AllCCS[M+Na-2H]-124.12332859911
AllCCS[M+HCOO]-126.9332859911
DeepCCS[M+H]+125.88730932474
DeepCCS[M-H]-123.86730932474
DeepCCS[M-2H]-159.78530932474
DeepCCS[M+Na]+134.24330932474

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Predicted by Siyang on May 30, 202213.0908 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.84 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1634.7 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid448.2 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid160.7 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid319.6 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid152.1 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid453.1 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid533.9 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)207.5 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1051.7 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid376.6 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1199.2 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid338.7 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid368.4 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate576.0 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA444.8 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water91.3 seconds40023050

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Parasorbic acid 10V, Positive-QTOFsplash10-0ik9-9800000000-2654e16fe8b6498672552019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Parasorbic acid 20V, Positive-QTOFsplash10-0uxr-9100000000-f643f6f08f0a4dd398bb2019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Parasorbic acid 40V, Positive-QTOFsplash10-0frf-9000000000-e5d42971940f043c7ca62019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Parasorbic acid 10V, Negative-QTOFsplash10-03xr-5900000000-57a7c033a841203fd4972019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Parasorbic acid 20V, Negative-QTOFsplash10-03xr-9700000000-b301d4427e34091afe1f2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Parasorbic acid 40V, Negative-QTOFsplash10-00kf-9000000000-eb85b900f31cc7648a852019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Parasorbic acid 10V, Positive-QTOFsplash10-03di-9800000000-3c1b9625251f8393d8fe2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Parasorbic acid 20V, Positive-QTOFsplash10-00kf-9000000000-b5bd408aea7f088224052021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Parasorbic acid 40V, Positive-QTOFsplash10-000f-9000000000-ba8e6f76f6b6a22f5db32021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Parasorbic acid 10V, Negative-QTOFsplash10-03di-4900000000-9dad5fad6a11a60d2e742021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Parasorbic acid 20V, Negative-QTOFsplash10-0cdl-9300000000-7ad22dfef27898aac15c2021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Parasorbic acid 40V, Negative-QTOFsplash10-0a4i-9000000000-f6073b6fc3d28308959f2021-10-21Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB001425
KNApSAcK IDNot Available
Chemspider ID23250
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound24869
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available