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Showing metabocard for alpha-Cyano-4-hydroxycinnamate (HMDB0248196)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 01:22:16 UTC
Update Date2021-09-26 22:58:21 UTC
HMDB IDHMDB0248196
Secondary Accession NumbersNone
Metabolite Identification
Common Namealpha-Cyano-4-hydroxycinnamate
Descriptionalpha-Cyano-4-hydroxycinnamate, also known as 4-CIN or 4-hydroxy-alpha-cyanocinnamate, belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. Based on a literature review a significant number of articles have been published on alpha-Cyano-4-hydroxycinnamate. This compound has been identified in human blood as reported by (PMID: 31557052 ). Alpha-cyano-4-hydroxycinnamate is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically alpha-Cyano-4-hydroxycinnamate is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0248196 (alpha-Cyano-4-hydroxycinnamate)

  Mrv1652309112103222D          

 14 14  0  0  0  0            999 V2000
    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 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
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  7  6  1  4  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  3  0  0  0  0
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  3 14  1  0  0  0  0
M  END
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3D MOL for HMDB0248196 (alpha-Cyano-4-hydroxycinnamate)

HMDB0248196
     RDKit          3D
alpha-Cyano-4-hydroxycinnamate
 21 21  0  0  0  0  0  0  0  0999 V2000
   -4.1797   -2.7867    0.0637 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3208   -2.0095    0.0874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2545   -1.0152    0.1055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0296   -1.4202    0.0143 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1885   -0.6160    0.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5040    0.2721    1.0140 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6571    1.0470    0.9693 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5426    0.9585   -0.0828 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6997    1.7366   -0.1278 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2385    0.0706   -1.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0955   -0.6998   -1.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6338    0.3672    0.1558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8715    0.6919    0.2678 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7693    1.4286    0.0900 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9069   -2.5337   -0.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1716    0.3510    1.8823 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9001    1.7451    1.7574 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5868    1.4330    0.2657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9343   -0.0073   -1.9258 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8490   -1.4006   -1.8359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0585    2.3874   -0.0377 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  2  3
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  3 12  1  0
 12 13  2  0
 12 14  1  0
 11  5  1  0
  4 15  1  0
  6 16  1  0
  7 17  1  0
  9 18  1  0
 10 19  1  0
 11 20  1  0
 14 21  1  0
M  END
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3D SDF for HMDB0248196 (alpha-Cyano-4-hydroxycinnamate)

  Mrv1652309112103222D          

 14 14  0  0  0  0            999 V2000
    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 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
    1.4289    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    4.1250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   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
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  7  6  1  4  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  3  0  0  0  0
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  3 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0248196

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)C(=CC1=CC=C(O)C=C1)C#N

> <INCHI_IDENTIFIER>
InChI=1S/C10H7NO3/c11-6-8(10(13)14)5-7-1-3-9(12)4-2-7/h1-5,12H,(H,13,14)

> <INCHI_KEY>
AFVLVVWMAFSXCK-UHFFFAOYSA-N

> <FORMULA>
C10H7NO3

> <MOLECULAR_WEIGHT>
189.17

> <EXACT_MASS>
189.042593089

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
18.194274544394595

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-cyano-3-(4-hydroxyphenyl)prop-2-enoic acid

> <ALOGPS_LOGP>
1.89

> <JCHEM_LOGP>
1.6443795600000004

> <ALOGPS_LOGS>
-2.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.507715794233725

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.3885844698197722

> <JCHEM_PKA_STRONGEST_BASIC>
-6.815824011694624

> <JCHEM_POLAR_SURFACE_AREA>
81.32000000000001

> <JCHEM_REFRACTIVITY>
50.09440000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.29e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-cyano-4-hydroxycinnamic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0248196 (alpha-Cyano-4-hydroxycinnamate)

HMDB0248196
     RDKit          3D
alpha-Cyano-4-hydroxycinnamate
 21 21  0  0  0  0  0  0  0  0999 V2000
   -4.1797   -2.7867    0.0637 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3208   -2.0095    0.0874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2545   -1.0152    0.1055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0296   -1.4202    0.0143 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1885   -0.6160    0.0177 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5040    0.2721    1.0140 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6571    1.0470    0.9693 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5426    0.9585   -0.0828 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6997    1.7366   -0.1278 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2385    0.0706   -1.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0955   -0.6998   -1.0482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6338    0.3672    0.1558 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8715    0.6919    0.2678 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7693    1.4286    0.0900 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9069   -2.5337   -0.0793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1716    0.3510    1.8823 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9001    1.7451    1.7574 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5868    1.4330    0.2657 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9343   -0.0073   -1.9258 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8490   -1.4006   -1.8359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0585    2.3874   -0.0377 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  3  0
  2  3  1  0
  3  4  2  3
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
  3 12  1  0
 12 13  2  0
 12 14  1  0
 11  5  1  0
  4 15  1  0
  6 16  1  0
  7 17  1  0
  9 18  1  0
 10 19  1  0
 11 20  1  0
 14 21  1  0
M  END
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PDB for HMDB0248196 (alpha-Cyano-4-hydroxycinnamate)

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         0                                  
HETATM    1  C   UNK     0       2.667   1.540   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       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000  -0.000   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  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       2.667   7.700   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.335   4.620   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    3                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END
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3D PDB for HMDB0248196 (alpha-Cyano-4-hydroxycinnamate)

COMPND    HMDB0248197
HETATM    1  N1  UNL     1      -1.674  -1.904  -1.893  1.00  0.00           N  
HETATM    2  C1  UNL     1      -1.883  -1.099  -1.058  1.00  0.00           C  
HETATM    3  C2  UNL     1      -2.166  -0.103  -0.048  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.165   0.532   0.518  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.247   0.335   0.233  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.115   1.430   0.146  1.00  0.00           C  
HETATM    7  C6  UNL     1       2.456   1.264  -0.112  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.013   0.013  -0.300  1.00  0.00           C  
HETATM    9  O1  UNL     1       4.363  -0.114  -0.558  1.00  0.00           O  
HETATM   10  C8  UNL     1       2.184  -1.078  -0.220  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.827  -0.902   0.043  1.00  0.00           C  
HETATM   12  C10 UNL     1      -3.540   0.177   0.319  1.00  0.00           C  
HETATM   13  O2  UNL     1      -3.784   1.034   1.185  1.00  0.00           O  
HETATM   14  O3  UNL     1      -4.566  -0.500  -0.287  1.00  0.00           O  
HETATM   15  H1  UNL     1      -1.397   1.289   1.286  1.00  0.00           H  
HETATM   16  H2  UNL     1       0.724   2.425   0.286  1.00  0.00           H  
HETATM   17  H3  UNL     1       3.094   2.135  -0.172  1.00  0.00           H  
HETATM   18  H4  UNL     1       4.808  -0.996  -0.699  1.00  0.00           H  
HETATM   19  H5  UNL     1       2.614  -2.052  -0.365  1.00  0.00           H  
HETATM   20  H6  UNL     1       0.225  -1.782   0.102  1.00  0.00           H  
HETATM   21  H7  UNL     1      -5.496  -0.103  -0.320  1.00  0.00           H  
CONECT    1    2    2    2
CONECT    2    3
CONECT    3    4    4   12
CONECT    4    5   15
CONECT    5    6    6   11
CONECT    6    7   16
CONECT    7    8    8   17
CONECT    8    9   10
CONECT    9   18
CONECT   10   11   11   19
CONECT   11   20
CONECT   12   13   13   14
CONECT   14   21
END
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SMILES for HMDB0248196 (alpha-Cyano-4-hydroxycinnamate)

OC(=O)C(=CC1=CC=C(O)C=C1)C#N
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INCHI for HMDB0248196 (alpha-Cyano-4-hydroxycinnamate)

InChI=1S/C10H7NO3/c11-6-8(10(13)14)5-7-1-3-9(12)4-2-7/h1-5,12H,(H,13,14)
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View in JSmolView Stereo Labels
Synonyms
ValueSource
a-Cyano-4-hydroxycinnamateGenerator
a-Cyano-4-hydroxycinnamic acidGenerator
alpha-Cyano-4-hydroxycinnamic acidGenerator
Α-cyano-4-hydroxycinnamateGenerator
Α-cyano-4-hydroxycinnamic acidGenerator
2-Cyano-3-(4-hydroxyphenyl)prop-2-enoateHMDB
2-Cyano-4-hydroxycinnamateHMDB
4-CINHMDB
4-Hydroxy-alpha-cyanocinnamateHMDB
Chemical FormulaC10H7NO3
Average Molecular Weight189.17
Monoisotopic Molecular Weight189.042593089
IUPAC Name2-cyano-3-(4-hydroxyphenyl)prop-2-enoic acid
Traditional Nameα-cyano-4-hydroxycinnamic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C(=CC1=CC=C(O)C=C1)C#N
InChI Identifier
InChI=1S/C10H7NO3/c11-6-8(10(13)14)5-7-1-3-9(12)4-2-7/h1-5,12H,(H,13,14)
InChI KeyAFVLVVWMAFSXCK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCinnamic acids and derivatives
Sub ClassHydroxycinnamic acids and derivatives
Direct ParentHydroxycinnamic acids
Alternative Parents
Substituents
  • Cinnamic acid
  • Coumaric acid
  • Coumaric acid or derivatives
  • Hydroxycinnamic acid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Carbonitrile
  • Nitrile
  • Carbonyl group
  • Organic oxide
  • Cyanide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
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
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2018
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkΑ-Cyano-4-hydroxycinnamic acid
METLIN IDNot Available
PubChem Compound2102
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 References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]