Showing metabocard for Benzaldehyde-cyanohydrin (MMDBc0033597)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 04:55:09 UTC
Update Date2024-04-30 20:13:31 UTC
Metabolite IDMMDBc0033597
Metabolite Identification
Common NameBenzaldehyde-cyanohydrin
Description(±)-2-Hydroxy-2-phenylacetonitrile, also known as mandelonitrile, alpha-hydroxybenzeneacetonitrile or benzal dehyde cyanohydrin, 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. Mandelonitrile is a chemical compound of the cyanohydrin class. Hydroxy-2-phenylacetonitrile is a potentially toxic compound. The primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. (±)-2-Hydroxy-2-phenylacetonitrile has been detected, but not quantified, in fruits. This could make (±)-2-hydroxy-2-phenylacetonitrile a potential biomarker for the consumption of these foods. (±)-2- Oxygen therapy can also be administered.
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x0000559d02fc7278>


  Mrv1652305261923492D          

 10 10  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
    0.0000    2.4750    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
   -0.7145    2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  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
  7  4  2  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  6  3  0  0  0  0
 10  8  1  0  0  0  0
M  END
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3D MOL for #<Metabolite:0x0000559d02fc7278>

HMDB0034666
     RDKit          3D
(±)-2-Hydroxy-2-phenylacetonitrile
 17 17  0  0  0  0  0  0  0  0999 V2000
   -3.0322    1.8423   -0.6218 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4980    0.8783   -0.2657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8115   -0.3609    0.1674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1919   -1.3909   -0.6940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3431   -0.1265    0.1036 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1406    1.1630    0.0268 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5028    1.4024   -0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4252    0.3746   -0.0193 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9440   -0.9182    0.0577 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5809   -1.1458    0.1173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1277   -0.5682    1.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2825   -2.2255   -0.1518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5694    1.9731    0.0150 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8854    2.4311   -0.0946 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4980    0.5639   -0.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6694   -1.7420    0.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2101   -2.1506    0.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  3 11  1  0
  4 12  1  0
  6 13  1  0
  7 14  1  0
  8 15  1  0
  9 16  1  0
 10 17  1  0
M  END
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3D SDF for #<Metabolite:0x0000559d02fc7278>


  Mrv1652305261923492D          

 10 10  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
    0.0000    2.4750    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
   -0.7145    2.8875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  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
  7  4  2  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  6  3  0  0  0  0
 10  8  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033597

> <DATABASE_NAME>
MIME

> <SMILES>
OC(C#N)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C8H7NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8,10H

> <INCHI_KEY>
NNICRUQPODTGRU-UHFFFAOYSA-N

> <FORMULA>
C8H7NO

> <MOLECULAR_WEIGHT>
133.1473

> <EXACT_MASS>
133.052763851

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
13.551942157589872

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxy-2-phenylacetonitrile

> <ALOGPS_LOGP>
0.68

> <JCHEM_LOGP>
0.9537845113333332

> <ALOGPS_LOGS>
-1.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.666910761057423

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.795695242182852

> <JCHEM_PKA_STRONGEST_BASIC>
-4.200129584931049

> <JCHEM_POLAR_SURFACE_AREA>
44.019999999999996

> <JCHEM_REFRACTIVITY>
37.6831

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.89e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
mandelonitrile

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x0000559d02fc7278>

HMDB0034666
     RDKit          3D
(±)-2-Hydroxy-2-phenylacetonitrile
 17 17  0  0  0  0  0  0  0  0999 V2000
   -3.0322    1.8423   -0.6218 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4980    0.8783   -0.2657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8115   -0.3609    0.1674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1919   -1.3909   -0.6940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3431   -0.1265    0.1036 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1406    1.1630    0.0268 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5028    1.4024   -0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4252    0.3746   -0.0193 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9440   -0.9182    0.0577 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5809   -1.1458    0.1173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1277   -0.5682    1.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2825   -2.2255   -0.1518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5694    1.9731    0.0150 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8854    2.4311   -0.0946 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4980    0.5639   -0.0667 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6694   -1.7420    0.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2101   -2.1506    0.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10  5  1  0
  3 11  1  0
  4 12  1  0
  6 13  1  0
  7 14  1  0
  8 15  1  0
  9 16  1  0
 10 17  1  0
M  END
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PDB for #<Metabolite:0x0000559d02fc7278>

HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         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       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -1.334   5.390   0.000  0.00  0.00           N+0
HETATM   10  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    7                                                       
CONECT    5    3    7                                                       
CONECT    6    8    9                                                       
CONECT    7    4    5    8                                                  
CONECT    8    6    7   10                                                  
CONECT    9    6                                                            
CONECT   10    8                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   20    0
END
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3D PDB for #<Metabolite:0x0000559d02fc7278>

COMPND    HMDB0034666
HETATM    1  N1  UNL     1      -3.032   1.842  -0.622  1.00  0.00           N  
HETATM    2  C1  UNL     1      -2.498   0.878  -0.266  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.811  -0.361   0.167  1.00  0.00           C  
HETATM    4  O1  UNL     1      -2.192  -1.391  -0.694  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.343  -0.126   0.104  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.141   1.163   0.027  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.503   1.402  -0.033  1.00  0.00           C  
HETATM    8  C6  UNL     1       2.425   0.375  -0.019  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.944  -0.918   0.058  1.00  0.00           C  
HETATM   10  C8  UNL     1       0.581  -1.146   0.117  1.00  0.00           C  
HETATM   11  H1  UNL     1      -2.128  -0.568   1.213  1.00  0.00           H  
HETATM   12  H2  UNL     1      -2.282  -2.226  -0.152  1.00  0.00           H  
HETATM   13  H3  UNL     1      -0.569   1.973   0.015  1.00  0.00           H  
HETATM   14  H4  UNL     1       1.885   2.431  -0.095  1.00  0.00           H  
HETATM   15  H5  UNL     1       3.498   0.564  -0.067  1.00  0.00           H  
HETATM   16  H6  UNL     1       2.669  -1.742   0.069  1.00  0.00           H  
HETATM   17  H7  UNL     1       0.210  -2.151   0.177  1.00  0.00           H  
CONECT    1    2    2    2
CONECT    2    3
CONECT    3    4    5   11
CONECT    4   12
CONECT    5    6    6   10
CONECT    6    7   13
CONECT    7    8    8   14
CONECT    8    9   15
CONECT    9   10   10   16
CONECT   10   17
END
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SMILES for #<Metabolite:0x0000559d02fc7278>

OC(C#N)C1=CC=CC=C1
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INCHI for #<Metabolite:0x0000559d02fc7278>

InChI=1S/C8H7NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8,10H
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Synonyms
ValueSource
alpha-HydroxybenzeneacetonitrileChEBI
Benzaldehyde cyanohydrinChEBI
Mandelic acid nitrileChEBI
PhenylglycolonitrileChEBI
a-HydroxybenzeneacetonitrileGenerator
Α-hydroxybenzeneacetonitrileGenerator
Mandelate nitrileGenerator
Mandelonitrile, (+-)-isomerHMDB
Molecular FormulaC8H7NO
Average Mass133.1473
Monoisotopic Mass133.052763851
IUPAC Name2-hydroxy-2-phenylacetonitrile
Traditional Namemandelonitrile
CAS Registry Number532-28-5
SMILES
OC(C#N)C1=CC=CC=C1
InChI Identifier
InChI=1S/C8H7NO/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8,10H
InChI KeyNNICRUQPODTGRU-UHFFFAOYSA-N