Showing metabocard for mandelate (MMDBc0054555)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2022-06-05 23:17:38 UTC
Update Date2022-08-12 20:09:01 UTC
Metabolite IDMMDBc0054555
Metabolite Identification
Common Namemandelate
Descriptionmandelate, also known as mandelic acid ion, belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. The drugs cyclandelate and homatropine are esters of mandelic acid. Isolation, synthesis, occurrence Mandelic acid was discovered in 1831 by the German pharmacist Ferdinand Ludwig Winckler (1801–1868) while heating amygdalin, an extract of bitter almonds, with diluted hydrochloric acid. mandelate is an extremely weak basic (essentially neutral) compound (based on its pKa). It is a white crystalline solid that is soluble in water and polar organic solvents. Derivatives of mandelic acid are formed as a result of metabolism of adrenaline and noradrenaline by monoamine oxidase and catechol-O-methyl transferase. It also arises by heating phenylglyoxal with alkalis. It is a useful precursor to various drugs. Mandelonitrile can also be prepared by reacting benzaldehyde with sodium bisulfite to give the corresponding adduct, forming mandelonitrile with sodium cyanide, which is hydrolyzed:Alternatively, it can be prepared by base hydrolysis of phenylchloroacetic acid and dibromacetophenone.
Structure
MOLSDFPDBSMILESInChI

MOL for #<Metabolite:0x00007fecfd3d1250>


  Mrv1652310101719412D          

 11 11  0  0  0  0            999 V2000
    0.7145   -0.4125    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
   -0.0000    0.0000    0.0000 C   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
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  2  0  0  0  0
 11  8  1  0  0  0  0
M  CHG  1  11  -1
M  END
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3D MOL for #<Metabolite:0x00007fecfd3d1250>

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3D SDF for #<Metabolite:0x00007fecfd3d1250>

  Mrv1652310101719412D          

 11 11  0  0  0  0            999 V2000
    0.7145   -0.4125    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
   -0.0000    0.0000    0.0000 C   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
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  7  1  0  0  0  0
 10  8  2  0  0  0  0
 11  8  1  0  0  0  0
M  CHG  1  11  -1
M  END
> <DATABASE_ID>
MMDBc0054555

> <DATABASE_NAME>
MIME

> <SMILES>
OC(C([O-])=O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)/p-1

> <INCHI_KEY>
IWYDHOAUDWTVEP-UHFFFAOYSA-M

> <FORMULA>
C8H7O3

> <MOLECULAR_WEIGHT>
151.142

> <EXACT_MASS>
151.040067665

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
14.222215549273766

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
-1

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxy-2-phenylacetate

> <ALOGPS_LOGP>
0.67

> <JCHEM_LOGP>
0.8958356446666668

> <ALOGPS_LOGS>
-0.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.568490699995834

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.751233575646761

> <JCHEM_PKA_STRONGEST_BASIC>
-4.110158859648652

> <JCHEM_POLAR_SURFACE_AREA>
60.36

> <JCHEM_REFRACTIVITY>
49.5409

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.78e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hydroxy(phenyl)acetate

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for #<Metabolite:0x00007fecfd3d1250>
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PDB for #<Metabolite:0x00007fecfd3d1250>
HEADER    PROTEIN                                 10-OCT-17   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-OCT-17         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O-1
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    6                                                       
CONECT    6    4    5    7                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7   10   11                                                  
CONECT    9    7                                                            
CONECT   10    8                                                            
CONECT   11    8                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for #<Metabolite:0x00007fecfd3d1250>
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SMILES for #<Metabolite:0x00007fecfd3d1250>
OC(C([O-])=O)C1=CC=CC=C1
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INCHI for #<Metabolite:0x00007fecfd3d1250>
InChI=1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)/p-1
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Synonyms
ValueSource
2-Hydroxy-2-(4-hydroxyphenyl)acetateChEBI
alpha-HydroxybenzeneacetateChEBI
alpha-Hydroxybenzeneacetic acid, ion(1-)ChEBI
Mandelate ionChEBI
2-Hydroxy-2-(4-hydroxyphenyl)acetic acidGenerator
a-HydroxybenzeneacetateGenerator
a-Hydroxybenzeneacetic acidGenerator
alpha-Hydroxybenzeneacetic acidGenerator
Α-hydroxybenzeneacetateGenerator
Α-hydroxybenzeneacetic acidGenerator
a-Hydroxybenzeneacetate, ion(1-)Generator
a-Hydroxybenzeneacetic acid, ion(1-)Generator
alpha-Hydroxybenzeneacetate, ion(1-)Generator
Α-hydroxybenzeneacetate, ion(1-)Generator
Α-hydroxybenzeneacetic acid, ion(1-)Generator
Mandelic acid ionGenerator
Mandelic acidGenerator
Molecular FormulaC8H7O3
Average Mass151.142
Monoisotopic Mass151.040067665
IUPAC Name2-hydroxy-2-phenylacetate
Traditional Namehydroxy(phenyl)acetate
CAS Registry NumberNot Available
SMILES
OC(C([O-])=O)C1=CC=CC=C1
InChI Identifier
InChI=1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)/p-1
InChI KeyIWYDHOAUDWTVEP-UHFFFAOYSA-M