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Showing NP-Card for 3,4-Dihydroxyhydrocinnamic acid (NP0000157)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2022-06-09 21:11:57 UTC
NP-MRD IDNP0000157
Secondary Accession NumbersNone
Natural Product Identification
Common Name3,4-Dihydroxyhydrocinnamic acid
Description3,4-Dihydroxyhydrocinnamic acid (or Dihydrocaffeic acid, DHCA) is a metabolite product of the hydrogenation of caffeoylquinic acids, occurring in normal human biofluids, with potent antioxidant properties. DHCA has been detected in human plasma following coffee ingestion (PMID 15607645 ), and is increased with some dietary sources, such as after ingestion of phenolic constituents of artichoke leaf extract. (PMID 15693705 ) Polyphenol-rich foods such as vegetables and fruits have been shown to significantly improve platelet function in ex vivo studies in humans. (PMID 16038718 ) Its antioxidant activity has been tested to reduce ferric iron in the ferric reducing antioxidant power (FRAP) assay, and it has been suggested that its catechol structure convey the antioxidant effect in plasma and in erythrocytes. (PMID 11768243 ).
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000157 (3,4-Dihydroxyhydrocinnamic acid)


  Mrv1652306131921432D          

 13 13  0  0  0  0            999 V2000
   -1.6292   -0.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3436   -0.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0582   -0.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0582   -1.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3438   -1.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6292   -1.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7727   -0.0902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7727   -1.7401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9148   -0.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2003   -0.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5141   -0.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5141    0.7349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2286   -0.5025    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
  6  1  1  0  0  0  0
  1  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
M  END
Download

3D MOL for NP0000157 (3,4-Dihydroxyhydrocinnamic acid)

HMDB0000423
     RDKit          3D
3,4-Dihydroxyhydrocinnamic acid
 23 23  0  0  0  0  0  0  0  0999 V2000
   -3.7667   -0.2806   -1.9303 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5150   -0.3761   -0.7084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5635   -0.6023    0.1713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1562   -0.2628   -0.1263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1141   -0.0169   -1.2017 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1956    0.0792   -0.5154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6073    1.3205   -0.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8222    1.4285    0.5514 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6139    0.3055    0.7604 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8413    0.3984    1.4041 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1966   -0.9374    0.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0064   -2.0440    0.5514 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9894   -1.0262   -0.3023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6355   -0.1110    1.0713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1244    0.6039    0.5623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8905   -1.2223    0.3619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2776    0.9426   -1.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1315   -0.8772   -1.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0099    2.2132   -0.2484 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1787    2.3975    0.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1856    1.3034    1.7379 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8796   -1.9636    1.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6686   -2.0024   -0.6365 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
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  2  0
 13  6  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  5 17  1  0
  5 18  1  0
  7 19  1  0
  8 20  1  0
 10 21  1  0
 12 22  1  0
 13 23  1  0
M  END
Download

3D SDF for NP0000157 (3,4-Dihydroxyhydrocinnamic acid)


  Mrv1652306131921432D          

 13 13  0  0  0  0            999 V2000
   -1.6292   -0.5026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3436   -0.0901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0582   -0.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0582   -1.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3438   -1.7401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6292   -1.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7727   -0.0902    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7727   -1.7401    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9148   -0.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2003   -0.5025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5141   -0.0900    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5141    0.7349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2286   -0.5025    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
  6  1  1  0  0  0  0
  1  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
  3  7  1  0  0  0  0
  4  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000157

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)CCC1=CC(O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1,3,5,10-11H,2,4H2,(H,12,13)

> <INCHI_KEY>
DZAUWHJDUNRCTF-UHFFFAOYSA-N

> <FORMULA>
C9H10O4

> <MOLECULAR_WEIGHT>
182.1733

> <EXACT_MASS>
182.057908808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
17.848789876051534

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(3,4-dihydroxyphenyl)propanoic acid

> <ALOGPS_LOGP>
1.04

> <JCHEM_LOGP>
1.448432127

> <ALOGPS_LOGS>
-1.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.290319681157882

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.8379150142223004

> <JCHEM_PKA_STRONGEST_BASIC>
-6.28908665826041

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
45.9284

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.62e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dihydrocaffeic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000157 (3,4-Dihydroxyhydrocinnamic acid)

HMDB0000423
     RDKit          3D
3,4-Dihydroxyhydrocinnamic acid
 23 23  0  0  0  0  0  0  0  0999 V2000
   -3.7667   -0.2806   -1.9303 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5150   -0.3761   -0.7084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5635   -0.6023    0.1713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1562   -0.2628   -0.1263 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1141   -0.0169   -1.2017 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1956    0.0792   -0.5154 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6073    1.3205   -0.0885 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8222    1.4285    0.5514 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6139    0.3055    0.7604 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8413    0.3984    1.4041 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1966   -0.9374    0.3304 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0064   -2.0440    0.5514 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9894   -1.0262   -0.3023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6355   -0.1110    1.0713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1244    0.6039    0.5623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8905   -1.2223    0.3619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2776    0.9426   -1.7325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1315   -0.8772   -1.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0099    2.2132   -0.2484 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1787    2.3975    0.9026 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1856    1.3034    1.7379 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8796   -1.9636    1.0119 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6686   -2.0024   -0.6365 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
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 11 13  2  0
 13  6  1  0
  3 14  1  0
  4 15  1  0
  4 16  1  0
  5 17  1  0
  5 18  1  0
  7 19  1  0
  8 20  1  0
 10 21  1  0
 12 22  1  0
 13 23  1  0
M  END
Download

PDB for NP0000157 (3,4-Dihydroxyhydrocinnamic acid)

HEADER    PROTEIN                                 13-JUN-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-JUN-19         0                                  
HETATM    1  C   UNK     0      -3.041  -0.938   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.375  -0.168   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.709  -0.938   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.709  -2.478   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.375  -3.248   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.041  -2.478   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -7.042  -0.168   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -7.042  -3.248   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.708  -0.168   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.374  -0.938   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.960  -0.168   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.960   1.372   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       2.293  -0.938   0.000  0.00  0.00           O+0
CONECT    1    2    6    9                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4    7                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    3                                                            
CONECT    8    4                                                            
CONECT    9    1   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END
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3D PDB for NP0000157 (3,4-Dihydroxyhydrocinnamic acid)

COMPND    HMDB0000423
HETATM    1  O1  UNL     1      -3.767  -0.281  -1.930  1.00  0.00           O  
HETATM    2  C1  UNL     1      -3.515  -0.376  -0.708  1.00  0.00           C  
HETATM    3  O2  UNL     1      -4.564  -0.602   0.171  1.00  0.00           O  
HETATM    4  C2  UNL     1      -2.156  -0.263  -0.126  1.00  0.00           C  
HETATM    5  C3  UNL     1      -1.114  -0.017  -1.202  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.196   0.079  -0.515  1.00  0.00           C  
HETATM    7  C5  UNL     1       0.607   1.320  -0.089  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.822   1.428   0.551  1.00  0.00           C  
HETATM    9  C7  UNL     1       2.614   0.305   0.760  1.00  0.00           C  
HETATM   10  O3  UNL     1       3.841   0.398   1.404  1.00  0.00           O  
HETATM   11  C8  UNL     1       2.197  -0.937   0.330  1.00  0.00           C  
HETATM   12  O4  UNL     1       3.006  -2.044   0.551  1.00  0.00           O  
HETATM   13  C9  UNL     1       0.989  -1.026  -0.302  1.00  0.00           C  
HETATM   14  H1  UNL     1      -4.636  -0.111   1.071  1.00  0.00           H  
HETATM   15  H2  UNL     1      -2.124   0.604   0.562  1.00  0.00           H  
HETATM   16  H3  UNL     1      -1.891  -1.222   0.362  1.00  0.00           H  
HETATM   17  H4  UNL     1      -1.278   0.943  -1.732  1.00  0.00           H  
HETATM   18  H5  UNL     1      -1.131  -0.877  -1.927  1.00  0.00           H  
HETATM   19  H6  UNL     1      -0.010   2.213  -0.248  1.00  0.00           H  
HETATM   20  H7  UNL     1       2.179   2.397   0.903  1.00  0.00           H  
HETATM   21  H8  UNL     1       4.186   1.303   1.738  1.00  0.00           H  
HETATM   22  H9  UNL     1       3.880  -1.964   1.012  1.00  0.00           H  
HETATM   23  H10 UNL     1       0.669  -2.002  -0.636  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   14
CONECT    4    5   15   16
CONECT    5    6   17   18
CONECT    6    7    7   13
CONECT    7    8   19
CONECT    8    9    9   20
CONECT    9   10   11
CONECT   10   21
CONECT   11   12   13   13
CONECT   12   22
CONECT   13   23
END
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SMILES for NP0000157 (3,4-Dihydroxyhydrocinnamic acid)

OC(=O)CCC1=CC(O)=C(O)C=C1
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INCHI for NP0000157 (3,4-Dihydroxyhydrocinnamic acid)

InChI=1S/C9H10O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1,3,5,10-11H,2,4H2,(H,12,13)
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View in JSmol
Synonyms
ValueSource
3,4-Dihydroxy-beta-phenylpropionic acidChEBI
3,4-Dihydroxybenzenepropanoic acidChEBI
3,4-Dihydroxybenzenepropionic acidChEBI
3,4-Dihydroxydihydrocinnamic acidChEBI
3,4-Dihydroxyphenylpropionic acidChEBI
3-(3,4-Dihydroxyphenyl)propionic acidChEBI
Dihydrocaffeic acidChEBI
Hydrocaffeic acidChEBI
3-(3,4-Dihydroxyphenyl)propanoateKegg
3,4-Dihydroxy-b-phenylpropionateGenerator
3,4-Dihydroxy-b-phenylpropionic acidGenerator
3,4-Dihydroxy-beta-phenylpropionateGenerator
3,4-Dihydroxy-β-phenylpropionateGenerator
3,4-Dihydroxy-β-phenylpropionic acidGenerator
3,4-DihydroxybenzenepropanoateGenerator
3,4-DihydroxybenzenepropionateGenerator
3,4-DihydroxydihydrocinnamateGenerator
3,4-DihydroxyphenylpropionateGenerator
3-(3,4-Dihydroxyphenyl)propionateGenerator
DihydrocaffeateGenerator
HydrocaffeateGenerator
3-(3,4-Dihydroxyphenyl)propanoic acidGenerator
3,4-DihydroxyhydrocinnamateGenerator
3,4-Dihydroxy-(6ci,7ci,8ci)hydrocinnamateHMDB
3,4-Dihydroxy-(6ci,7ci,8ci)hydrocinnamic acidHMDB
3,4-Dihydroxyphenylpropionic acid, potassium saltHMDB
DHCHMDB
3-(3',4'-Dihydroxyphenyl)propanoic acidHMDB
3,4-Dihydroxyhydrocinnamic acidHMDB
3,4-Dihydroxy-dihydrocinnamic acid
Chemical FormulaC9H10O4
Average Mass182.1733 Da
Monoisotopic Mass182.05791 Da
IUPAC Name3-(3,4-dihydroxyphenyl)propanoic acid
Traditional Namedihydrocaffeic acid
CAS Registry Number1078-61-1
SMILES
[H]OC(=O)C([H])([H])C([H])([H])C1=C([H])C(O[H])=C(O[H])C([H])=C1[H]
InChI Identifier
InChI=1S/C9H10O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1,3,5,10-11H,2,4H2,(H,12,13)
InChI KeyDZAUWHJDUNRCTF-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-06-09View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, experimental)Ahselim2022-06-09View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)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
Beta vulgarisFooDB
Brassica oleracea var. italicaFooDB
Citrus aurantiifoliaFooDB
Citrus limonFooDB
Coffea arabica L.FooDB
Coffea canephoraFooDB
Homo sapiens (Urine)Animalia
Isatis tinctoriaLOTUS Database
Lactuca sativaFooDB
Lindera glaucaLOTUS Database
Lycopodium clavatumLOTUS Database
Olea europaeaFooDB
Polyscias murrayiLOTUS Database
Pyrrosia petiolosaLOTUS Database
Spinacia oleraceaFooDB
Triticum aestivumFooDB
VitisFooDB
Zea mays L.FooDB
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassPhenylpropanoic acids
Sub ClassNot Available
Direct ParentPhenylpropanoic acids
Alternative Parents
Substituents
  • 3-phenylpropanoic-acid
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Monocyclic benzene moiety
  • Benzenoid
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organic oxide
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Hydrocarbon derivative
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point136 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility428 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.62 g/LALOGPS
logP1.04ALOGPS
logP1.45ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)3.84ChemAxon
pKa (Strongest Basic)-6.3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area77.76 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.93 m³·mol⁻¹ChemAxon
Polarizability17.85 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000423
DrugBank IDNot Available
Phenol Explorer Compound ID579
FoodDB IDFDB008857
KNApSAcK IDC00002735
Chemspider ID308986
KEGG Compound IDC10447
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5412
PubChem Compound348154
PDB IDNot Available
ChEBI ID48400
Good Scents IDrw1183441
References
General References
  1. Vickers S, Stuart EK, Hucker HB: Further studies on the metabolism of carbidopa, (minus)-L-alpha-hydrazino-3,4-dihydroxy-alpha-methylbenzenepropanoic acid monohydrate, in the human, Rhesus monkey, dog, and rat. J Med Chem. 1975 Feb;18(2):134-8. [PubMed:804550 ]
  2. Wittemer SM, Ploch M, Windeck T, Muller SC, Drewelow B, Derendorf H, Veit M: Bioavailability and pharmacokinetics of caffeoylquinic acids and flavonoids after oral administration of Artichoke leaf extracts in humans. Phytomedicine. 2005 Jan;12(1-2):28-38. [PubMed:15693705 ]
  3. Huang J, de Paulis T, May JM: Antioxidant effects of dihydrocaffeic acid in human EA.hy926 endothelial cells. J Nutr Biochem. 2004 Dec;15(12):722-9. [PubMed:15607645 ]
  4. Rechner AR, Kroner C: Anthocyanins and colonic metabolites of dietary polyphenols inhibit platelet function. Thromb Res. 2005;116(4):327-34. Epub 2005 Feb 8. [PubMed:16038718 ]
  5. Lekse JM, Xia L, Stark J, Morrow JD, May JM: Plant catechols prevent lipid peroxidation in human plasma and erythrocytes. Mol Cell Biochem. 2001 Oct;226(1-2):89-95. [PubMed:11768243 ]
  6. Yang Z, Feddern V, Glasius M, Guo Z, Xu X: Improved enzymatic production of phenolated acylglycerols through alkyl phenolate intermediates. Biotechnol Lett. 2011 Apr;33(4):673-9. doi: 10.1007/s10529-010-0486-3. Epub 2010 Dec 1. [PubMed:21120584 ]