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Showing NP-Card for Mandelic acid (NP0000882)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2024-04-19 10:04:19 UTC
NP-MRD IDNP0000882
Secondary Accession NumbersNone
Natural Product Identification
Common NameMandelic acid
DescriptionIt is an isomer of cresotinic acid (2-hydroxy-3-methylbenzoic acid) and oxymethylbenzoic acid (2-methoxybenzoic acid). Derivatives of mandelic acid are formed as a result of metabolism of adrenaline and noradrenaline by monoamine oxidase and catechol-o-methyl transferase. It is also present in certain skin care products, is an intermediate molecule in the production of other biochemicals, may be used as an analytical reagent and is a precursor in the manufacture of dyes. Mandelic acid is an aromatic alpha hydroxy acid with the molecular formula C8H8O3. It is a white crystalline solid that is soluble in water and most common organic solvents. Mandelic acid is found to be associated with phenylketonuria, which is an inborn error of metabolism.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000882 (Mandelic acid)


  Mrv1652305271900202D          

 11 11  0  0  1  0            999 V2000
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -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 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
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  2  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
M  END
Download

3D MOL for NP0000882 (Mandelic acid)

HMDB0000703
     RDKit          3D
Mandelic acid
 19 19  0  0  0  0  0  0  0  0999 V2000
    1.7443    1.5659    1.3954 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0770    0.5290    0.8001 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1165   -0.2578    1.2762 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3841    0.0975   -0.4273 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9162   -1.0882   -0.9291 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0821    0.0091   -0.2504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9085    1.0441   -0.6665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2859    0.9897   -0.5140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8783   -0.1082    0.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0703   -1.1598    0.4879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7015   -1.0805    0.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0757   -0.1424    0.9149 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5813    0.8752   -1.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8934   -0.8971   -1.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4445    1.9241   -1.1274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8838    1.8351   -0.8609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9479   -0.1821    0.1958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5202   -2.0449    0.9500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0655   -1.9087    0.6596 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  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  3 12  1  0
  4 13  1  6
  5 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
 10 18  1  0
 11 19  1  0
M  END
Download

3D SDF for NP0000882 (Mandelic acid)


  Mrv1652305271900202D          

 11 11  0  0  1  0            999 V2000
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -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 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
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  2  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  6 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000882

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H](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)/t7-/m0/s1

> <INCHI_KEY>
IWYDHOAUDWTVEP-ZETCQYMHSA-N

> <FORMULA>
C8H8O3

> <MOLECULAR_WEIGHT>
152.1473

> <EXACT_MASS>
152.047344122

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
14.656944642404099

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-2-hydroxy-2-phenylacetic acid

> <ALOGPS_LOGP>
0.66

> <JCHEM_LOGP>
0.8958356446666668

> <ALOGPS_LOGS>
-0.96

> <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>
57.53

> <JCHEM_REFRACTIVITY>
38.7038

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.68e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(S)-mandelic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000882 (Mandelic acid)

HMDB0000703
     RDKit          3D
Mandelic acid
 19 19  0  0  0  0  0  0  0  0999 V2000
    1.7443    1.5659    1.3954 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0770    0.5290    0.8001 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1165   -0.2578    1.2762 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3841    0.0975   -0.4273 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9162   -1.0882   -0.9291 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0821    0.0091   -0.2504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9085    1.0441   -0.6665 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2859    0.9897   -0.5140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8783   -0.1082    0.0624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0703   -1.1598    0.4879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7015   -1.0805    0.3244 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0757   -0.1424    0.9149 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5813    0.8752   -1.2044 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8934   -0.8971   -1.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4445    1.9241   -1.1274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8838    1.8351   -0.8609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9479   -0.1821    0.1958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5202   -2.0449    0.9500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0655   -1.9087    0.6596 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  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  3 12  1  0
  4 13  1  6
  5 14  1  0
  7 15  1  0
  8 16  1  0
  9 17  1  0
 10 18  1  0
 11 19  1  0
M  END
Download

PDB for NP0000882 (Mandelic acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.000   6.160   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    2    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    6                                                       
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for NP0000882 (Mandelic acid)

COMPND    HMDB0000703
HETATM    1  O1  UNL     1       1.744   1.566   1.395  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.077   0.529   0.800  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.116  -0.258   1.276  1.00  0.00           O  
HETATM    4  C2  UNL     1       1.384   0.097  -0.427  1.00  0.00           C  
HETATM    5  O3  UNL     1       1.916  -1.088  -0.929  1.00  0.00           O  
HETATM    6  C3  UNL     1      -0.082   0.009  -0.250  1.00  0.00           C  
HETATM    7  C4  UNL     1      -0.909   1.044  -0.666  1.00  0.00           C  
HETATM    8  C5  UNL     1      -2.286   0.990  -0.514  1.00  0.00           C  
HETATM    9  C6  UNL     1      -2.878  -0.108   0.062  1.00  0.00           C  
HETATM   10  C7  UNL     1      -2.070  -1.160   0.488  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.701  -1.081   0.324  1.00  0.00           C  
HETATM   12  H1  UNL     1       4.076  -0.142   0.915  1.00  0.00           H  
HETATM   13  H2  UNL     1       1.581   0.875  -1.204  1.00  0.00           H  
HETATM   14  H3  UNL     1       2.893  -0.897  -1.087  1.00  0.00           H  
HETATM   15  H4  UNL     1      -0.445   1.924  -1.127  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.884   1.835  -0.861  1.00  0.00           H  
HETATM   17  H6  UNL     1      -3.948  -0.182   0.196  1.00  0.00           H  
HETATM   18  H7  UNL     1      -2.520  -2.045   0.950  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.065  -1.909   0.660  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   12
CONECT    4    5    6   13
CONECT    5   14
CONECT    6    7    7   11
CONECT    7    8   15
CONECT    8    9    9   16
CONECT    9   10   17
CONECT   10   11   11   18
CONECT   11   19
END
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SMILES for NP0000882 (Mandelic acid)

O[C@H](C(O)=O)C1=CC=CC=C1
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INCHI for NP0000882 (Mandelic acid)

InChI=1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)/t7-/m0/s1
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View in JSmol
Synonyms
ValueSource
(S)-2-Hydroxy-2-phenylacetic acidChEBI
(S)-alpha-Hydroxybenzeneacetic acidChEBI
(S)-MandelsaeureChEBI
L-Mandelic acidChEBI
(S)-2-Hydroxy-2-phenylacetateKegg
(S)-Mandelic acidKegg
(S)-a-HydroxybenzeneacetateGenerator
(S)-a-Hydroxybenzeneacetic acidGenerator
(S)-alpha-HydroxybenzeneacetateGenerator
(S)-Α-hydroxybenzeneacetateGenerator
(S)-Α-hydroxybenzeneacetic acidGenerator
L-MandelateGenerator
(S)-MandelateGenerator
MandelateGenerator
(RS)-MandelateHMDB
(RS)-Mandelic acidHMDB
2-Hydroxy-2-phenylacetateHMDB
2-Hydroxy-2-phenylacetic acidHMDB
2-Hydroxy-2-phenylethanoateHMDB
2-Hydroxy-2-phenylethanoic acidHMDB
2-Phenyl-2-hydroxyacetateHMDB
2-Phenyl-2-hydroxyacetic acidHMDB
2-PhenylglycolateHMDB
2-Phenylglycolic acidHMDB
a-Hydroxy-a-toluateHMDB
a-Hydroxy-a-toluic acidHMDB
a-HydroxybenzeneacetateHMDB
a-Hydroxybenzeneacetic acidHMDB
a-HydroxyphenylacetateHMDB
a-Hydroxyphenylacetic acidHMDB
Almond acidHMDB
alpha-Hydroxy-alpha-toluateHMDB
alpha-Hydroxy-alpha-toluic acidHMDB
alpha-HydroxybenzeneacetateHMDB
alpha-Hydroxybenzeneacetic acidHMDB
alpha-HydroxyphenylacetateHMDB
alpha-Hydroxyphenylacetic acidHMDB
AmygdalateHMDB
Amygdalic acidHMDB
DL-AmygdalateHMDB
DL-Amygdalic acidHMDB
DL-Hydroxy(phenyl)acetateHMDB
DL-Hydroxy(phenyl)acetic acidHMDB
DL-MandelateHMDB
DL-Mandelic acidHMDB
ParamandelateHMDB
Paramandelic acidHMDB
PhenylglycolateHMDB
Phenylglycolic acidHMDB
PhenylhydroxyacetateHMDB
Phenylhydroxyacetic acidHMDB
UromalineHMDB
Chemical FormulaC8H8O3
Average Mass152.1473 Da
Monoisotopic Mass152.04734 Da
IUPAC Name(2S)-2-hydroxy-2-phenylacetic acid
Traditional Name(S)-mandelic acid
CAS Registry Number90-64-2
SMILES
O[C@H](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)/t7-/m0/s1
InChI KeyIWYDHOAUDWTVEP-ZETCQYMHSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Not AvailableSumner lab, University of MissouriZach Tretter2024-01-11View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Not AvailableSumner lab, University of MissouriZach Tretter2024-01-11View Spectrum
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Not AvailableSumner lab, University of MissouriZach Tretter2024-01-11View Spectrum
1D NMR[1H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Not AvailableSumner lab, University of MissouriZach Tretter2024-01-11View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600.133705802 MHz, CD3OD, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Achillea millefoliumLOTUS Database
Aloe africanaLOTUS Database
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Pisolithus arhizusLOTUS Database
Pogostemon cablinLOTUS Database
Prunus maximowicziiLOTUS Database
Prunus persicaLOTUS Database
Prunus zippelianaLOTUS Database
Sambucus nigraPlant
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Species Where Detected
Species NameSourceReference
Homo sapiens (Urine)KNApSAcK Database
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
Substituents
  • Hydroxy acid
  • Monocyclic benzene moiety
  • Alpha-hydroxy acid
  • Secondary alcohol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point120 - 122 °CNot Available
Boiling Point321.83 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility181 mg/mLNot Available
LogP0.62Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility16.8 g/LALOGPS
logP0.66ALOGPS
logP0.9ChemAxon
logS-0.96ALOGPS
pKa (Strongest Acidic)3.75ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity38.7 m³·mol⁻¹ChemAxon
Polarizability14.66 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000703
DrugBank IDDB03357
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022191
KNApSAcK IDC00037426
Chemspider ID388690
KEGG Compound IDC01984
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMandelic acid
METLIN ID5671
PubChem Compound439616
PDB IDNot Available
ChEBI ID32800
Good Scents IDrw1136021
References
General References
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  8. Suarez A, Rico F, Clavero-Nunez JA, Garcia-Barreno P: Amniotic fluid catecholamine metabolites in maternal smoking. Gynecol Obstet Invest. 1990;30(3):143-6. [PubMed:2265798 ]
  9. Kolstad HA, Bonde JP, Spano M, Giwercman A, Zschiesche W, Kaae D, Larsen SB, Roeleveld N: Change in semen quality and sperm chromatin structure following occupational styrene exposure. ASCLEPIOS. Int Arch Occup Environ Health. 1999 May;72(3):135-41. [PubMed:10392560 ]
  10. Corona GL, Cucchi ML, Frattini P, Santagostino G, Schinelli S, Romani A, Pola A, Zerbi F, Savoldi F: Clinical and biochemical responses to therapy in Alzheimer's disease and multi-infarct dementia. Eur Arch Psychiatry Neurol Sci. 1989;239(2):79-86. [PubMed:2478368 ]
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