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Showing metabocard for 6-hydroxy-2-cyclohexen-one-carboxylate (HMDB0304226)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-09-24 08:10:19 UTC
Update Date2021-09-24 08:10:20 UTC
HMDB IDHMDB0304226
Secondary Accession NumbersNone
Metabolite Identification
Common Name6-hydroxy-2-cyclohexen-one-carboxylate
Description6-hydroxy-2-cyclohexen-one-carboxylate, also known as hcc, is a member of the class of compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond. 6-hydroxy-2-cyclohexen-one-carboxylate is soluble (in water) and a weakly acidic compound (based on its pKa). 6-hydroxy-2-cyclohexen-one-carboxylate can be found in a number of food items such as avocado, bitter gourd, endive, and pepper (c. frutescens), which makes 6-hydroxy-2-cyclohexen-one-carboxylate a potential biomarker for the consumption of these food products.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0304226 (6-hydroxy-2-cyclohexen-one-carboxylate)


  Mrv1533005141521412D          

 11 11  0  0  0  0            999 V2000
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0572    1.7262    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
    0.1842    1.8695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   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
    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
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626    2.6447    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  3  9  1  0  0  0  0
  1 11  1  0  0  0  0
M  CHG  1  11  -1
M  END
Download

3D MOL for HMDB0304226 (6-hydroxy-2-cyclohexen-one-carboxylate)

HMDB0304226
     RDKit          3D
6-hydroxy-2-cyclohexen-one-carboxylate
 18 18  0  0  0  0  0  0  0  0999 V2000
    1.7822   -1.6164   -1.5913 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0814   -0.8261   -0.6758 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4005   -0.6374   -0.3455 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.0477   -0.0869    0.0629 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6545    0.7137    1.0177 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2309   -1.0961    0.8018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0654   -0.9733    0.8839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9105    0.0850    0.3186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1938    1.0655   -0.5384 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2131    0.7751   -0.7918 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7458    1.2696   -1.7685 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9516    1.5819    0.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7968   -1.9130    1.2499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5959   -1.7617    1.4478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7356   -0.4041   -0.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4167    0.6005    1.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7180    1.1383   -1.5367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2686    2.0855   -0.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10  4  1  0
  5 12  1  0
  6 13  1  0
  7 14  1  0
  8 15  1  0
  8 16  1  0
  9 17  1  0
  9 18  1  0
M  CHG  1   3  -1
M  END
Download

3D SDF for HMDB0304226 (6-hydroxy-2-cyclohexen-one-carboxylate)


  Mrv1533005141521412D          

 11 11  0  0  0  0            999 V2000
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0572    1.7262    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
    0.1842    1.8695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   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
    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
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9626    2.6447    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  3  9  1  0  0  0  0
  1 11  1  0  0  0  0
M  CHG  1  11  -1
M  END
> <DATABASE_ID>
HMDB0304226

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1(C=CCCC1=O)C([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C7H8O4/c8-5-3-1-2-4-7(5,11)6(9)10/h2,4,11H,1,3H2,(H,9,10)/p-1

> <INCHI_KEY>
WEZWWZKUBQCMBL-UHFFFAOYSA-M

> <FORMULA>
C7H7O4

> <MOLECULAR_WEIGHT>
155.13

> <EXACT_MASS>
155.034982285

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
13.688118379911424

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-hydroxy-6-oxocyclohex-2-ene-1-carboxylate

> <ALOGPS_LOGP>
-0.20

> <JCHEM_LOGP>
0.26943382233333335

> <ALOGPS_LOGS>
-0.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.83579193965954

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3716768564590383

> <JCHEM_PKA_STRONGEST_BASIC>
-4.839461018484294

> <JCHEM_POLAR_SURFACE_AREA>
77.42999999999999

> <JCHEM_REFRACTIVITY>
47.7388

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.11e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-hydroxy-6-oxocyclohex-2-ene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0304226 (6-hydroxy-2-cyclohexen-one-carboxylate)

HMDB0304226
     RDKit          3D
6-hydroxy-2-cyclohexen-one-carboxylate
 18 18  0  0  0  0  0  0  0  0999 V2000
    1.7822   -1.6164   -1.5913 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0814   -0.8261   -0.6758 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4005   -0.6374   -0.3455 O   0  0  0  0  0  1  0  0  0  0  0  0
    1.0477   -0.0869    0.0629 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6545    0.7137    1.0177 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2309   -1.0961    0.8018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0654   -0.9733    0.8839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9105    0.0850    0.3186 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1938    1.0655   -0.5384 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2131    0.7751   -0.7918 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7458    1.2696   -1.7685 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9516    1.5819    0.6256 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7968   -1.9130    1.2499 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5959   -1.7617    1.4478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7356   -0.4041   -0.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4167    0.6005    1.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7180    1.1383   -1.5367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2686    2.0855   -0.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10  4  1  0
  5 12  1  0
  6 13  1  0
  7 14  1  0
  8 15  1  0
  8 16  1  0
  9 17  1  0
  9 18  1  0
M  CHG  1   3  -1
M  END
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PDB for HMDB0304226 (6-hydroxy-2-cyclohexen-one-carboxylate)

HEADER    PROTEIN                                 14-MAY-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-MAY-15         0                                  
HETATM    1  C   UNK     0       2.324   3.490   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.840   3.222   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.344   3.490   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.797   4.937   0.000  0.00  0.00           O-1
CONECT    1    2    3   11                                                  
CONECT    2    1                                                            
CONECT    3    1    4    5    9                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10    3                                                  
CONECT   10    9                                                            
CONECT   11    1                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for HMDB0304226 (6-hydroxy-2-cyclohexen-one-carboxylate)

COMPND    HMDB0304226
HETATM    1  O1  UNL     1       1.782  -1.616  -1.591  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.081  -0.826  -0.676  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.401  -0.637  -0.345  1.00  0.00           O1-
HETATM    4  C2  UNL     1       1.048  -0.087   0.063  1.00  0.00           C  
HETATM    5  O3  UNL     1       1.654   0.714   1.018  1.00  0.00           O  
HETATM    6  C3  UNL     1       0.231  -1.096   0.802  1.00  0.00           C  
HETATM    7  C4  UNL     1      -1.065  -0.973   0.884  1.00  0.00           C  
HETATM    8  C5  UNL     1      -1.911   0.085   0.319  1.00  0.00           C  
HETATM    9  C6  UNL     1      -1.194   1.066  -0.538  1.00  0.00           C  
HETATM   10  C7  UNL     1       0.213   0.775  -0.792  1.00  0.00           C  
HETATM   11  O4  UNL     1       0.746   1.270  -1.768  1.00  0.00           O  
HETATM   12  H1  UNL     1       1.952   1.582   0.626  1.00  0.00           H  
HETATM   13  H2  UNL     1       0.797  -1.913   1.250  1.00  0.00           H  
HETATM   14  H3  UNL     1      -1.596  -1.762   1.448  1.00  0.00           H  
HETATM   15  H4  UNL     1      -2.736  -0.404  -0.241  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.417   0.601   1.183  1.00  0.00           H  
HETATM   17  H6  UNL     1      -1.718   1.138  -1.537  1.00  0.00           H  
HETATM   18  H7  UNL     1      -1.269   2.085  -0.102  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    4    5    6   10
CONECT    5   12
CONECT    6    7    7   13
CONECT    7    8   14
CONECT    8    9   15   16
CONECT    9   10   17   18
CONECT   10   11   11
END
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SMILES for HMDB0304226 (6-hydroxy-2-cyclohexen-one-carboxylate)

OC1(C=CCCC1=O)C([O-])=O
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INCHI for HMDB0304226 (6-hydroxy-2-cyclohexen-one-carboxylate)

InChI=1S/C7H8O4/c8-5-3-1-2-4-7(5,11)6(9)10/h2,4,11H,1,3H2,(H,9,10)/p-1
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View in JSmolView Stereo Labels
Synonyms
ValueSource
1-Hydroxy-6-oxocyclohex-2-ene-1-carboxylic acidGenerator
6-Hydroxy-2-cyclohexen-one-carboxylic acidMetaCyc, Generator
HCCMetaCyc
Chemical FormulaC7H7O4
Average Molecular Weight155.13
Monoisotopic Molecular Weight155.034982285
IUPAC Name1-hydroxy-6-oxocyclohex-2-ene-1-carboxylate
Traditional Name1-hydroxy-6-oxocyclohex-2-ene-1-carboxylate
CAS Registry NumberNot Available
SMILES
OC1(C=CCCC1=O)C([O-])=O
InChI Identifier
InChI=1S/C7H8O4/c8-5-3-1-2-4-7(5,11)6(9)10/h2,4,11H,1,3H2,(H,9,10)/p-1
InChI KeyWEZWWZKUBQCMBL-UHFFFAOYSA-M
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentCyclohexenones
Alternative Parents
Substituents
  • Cyclohexenone
  • Acyloin
  • Tertiary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Hydrocarbon derivative
  • Alcohol
  • Organic anion
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Source
ProcessNot Available
RoleNot Available
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
logP-0.2ALOGPS
logP0.27ChemAxon
logS-0.28ALOGPS
pKa (Strongest Acidic)3.37ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area77.43 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity47.74 m³·mol⁻¹ChemAxon
Polarizability13.69 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+133.64832859911
AllCCS[M+H-H2O]+129.16932859911
AllCCS[M+Na]+139.0332859911
AllCCS[M+NH4]+137.82532859911
AllCCS[M-H]-125.9432859911
AllCCS[M+Na-2H]-127.19932859911
AllCCS[M+HCOO]-128.63832859911
DeepCCS[M+H]+141.6430932474
DeepCCS[M-H]-138.02830932474
DeepCCS[M-2H]-175.25330932474
DeepCCS[M+Na]+150.45530932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
6-hydroxy-2-cyclohexen-one-carboxylate,2TMS,isomer #1C[Si](C)(C)OC1=CCC=CC1(O[Si](C)(C)C)C(=O)[O-]1495.3Semi standard non polar33892256
6-hydroxy-2-cyclohexen-one-carboxylate,2TMS,isomer #1C[Si](C)(C)OC1=CCC=CC1(O[Si](C)(C)C)C(=O)[O-]1498.2Standard non polar33892256
6-hydroxy-2-cyclohexen-one-carboxylate,2TMS,isomer #1C[Si](C)(C)OC1=CCC=CC1(O[Si](C)(C)C)C(=O)[O-]1839.6Standard polar33892256
6-hydroxy-2-cyclohexen-one-carboxylate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CCC=CC1(O[Si](C)(C)C(C)(C)C)C(=O)[O-]1966.5Semi standard non polar33892256
6-hydroxy-2-cyclohexen-one-carboxylate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CCC=CC1(O[Si](C)(C)C(C)(C)C)C(=O)[O-]1812.5Standard non polar33892256
6-hydroxy-2-cyclohexen-one-carboxylate,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC1=CCC=CC1(O[Si](C)(C)C(C)(C)C)C(=O)[O-]2055.7Standard polar33892256
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-hydroxy-2-cyclohexen-one-carboxylate 10V, Negative-QTOFsplash10-0bt9-0900000000-4322cfaca6695de6087f2019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-hydroxy-2-cyclohexen-one-carboxylate 20V, Negative-QTOFsplash10-08fr-0900000000-a030413135574169cd062019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 6-hydroxy-2-cyclohexen-one-carboxylate 40V, Negative-QTOFsplash10-114l-9500000000-a13ce6bb6b381b543e362019-02-23Wishart 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 IDFDB030596
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound52940166
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