Showing metabocard for Caffeic acid (MMDBc0000577)

Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:50:20 UTC
Update Date2024-04-30 19:33:05 UTC
Metabolite IDMMDBc0000577
Metabolite Identification
Common NameCaffeic acid
DescriptionCaffeic acid (CAS: 331-39-5) is a polyphenol present in normal human urine positively correlated to coffee consumption and influenced by the dietary intake of diverse types of food (PMID:16870009 ). Caffeic acid has been found to be a microbial metabolite of Escherichia (PMID: 28396925 ).
Structure
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for #<Metabolite:0x00007fa4b2d7c9f0>


  Mrv1652309272007472D          

 13 13  0  0  0  0            999 V2000
   -0.8703    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5847    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2993    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2993   -0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5848   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8703   -0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1558    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5586    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2730    0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2730    1.6499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9876    0.4124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0137    0.8248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0137   -0.8248    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  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  3 12  1  0  0  0  0
  4 13  1  0  0  0  0
M  END
Download

3D MOL for #<Metabolite:0x00007fa4b2d7c9f0>

HMDB0001964
     RDKit          3D
Caffeic acid
 21 21  0  0  0  0  0  0  0  0999 V2000
    4.0991    1.0388   -0.6387 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8145   -0.1557   -0.5224 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7862   -1.1276   -0.5853 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3912   -0.5006   -0.3133 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4625    0.4188   -0.2526 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0379    0.1452   -0.0480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4823   -1.1161    0.1034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8505   -1.3363    0.2971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7279   -0.2846    0.3425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0836   -0.4964    0.5340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2265    0.9903    0.1927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1463    2.0338    0.2442 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8793    1.1945    0.0028 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8671   -1.8202    0.1510 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1149   -1.5487   -0.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8217    1.4544   -0.3681 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1876   -1.9766    0.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1762   -2.3683    0.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7360    0.2746    0.5685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7828    2.9671    0.1349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4912    2.2137   -0.1154 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  2  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
  5 16  1  0
  7 17  1  0
  8 18  1  0
 10 19  1  0
 12 20  1  0
 13 21  1  0
M  END
Download

3D SDF for #<Metabolite:0x00007fa4b2d7c9f0>


  Mrv1652309272007472D          

 13 13  0  0  0  0            999 V2000
   -0.8703    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5847    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2993    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2993   -0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5848   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8703   -0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1558    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5586    0.4124    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2730    0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2730    1.6499    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9876    0.4124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0137    0.8248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0137   -0.8248    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  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  3 12  1  0  0  0  0
  4 13  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000577

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+

> <INCHI_KEY>
QAIPRVGONGVQAS-DUXPYHPUSA-N

> <FORMULA>
C9H8O4

> <MOLECULAR_WEIGHT>
180.1574

> <EXACT_MASS>
180.042258744

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
17.335364136589572

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid

> <ALOGPS_LOGP>
1.67

> <JCHEM_LOGP>
1.5289556166666665

> <ALOGPS_LOGS>
-2.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.276437669500657

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6438401388538604

> <JCHEM_PKA_STRONGEST_BASIC>
-6.283746523508147

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
47.021699999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.61e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
caffeic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for #<Metabolite:0x00007fa4b2d7c9f0>

HMDB0001964
     RDKit          3D
Caffeic acid
 21 21  0  0  0  0  0  0  0  0999 V2000
    4.0991    1.0388   -0.6387 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8145   -0.1557   -0.5224 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7862   -1.1276   -0.5853 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3912   -0.5006   -0.3133 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4625    0.4188   -0.2526 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0379    0.1452   -0.0480 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4823   -1.1161    0.1034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8505   -1.3363    0.2971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7279   -0.2846    0.3425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0836   -0.4964    0.5340 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2265    0.9903    0.1927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1463    2.0338    0.2442 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8793    1.1945    0.0028 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8671   -1.8202    0.1510 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1149   -1.5487   -0.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8217    1.4544   -0.3681 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1876   -1.9766    0.0726 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1762   -2.3683    0.4079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7360    0.2746    0.5685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7828    2.9671    0.1349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4912    2.2137   -0.1154 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  2  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
  5 16  1  0
  7 17  1  0
  8 18  1  0
 10 19  1  0
 12 20  1  0
 13 21  1  0
M  END
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PDB for #<Metabolite:0x00007fa4b2d7c9f0>

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0      -1.625   0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.958   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.292   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.292  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.958  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.625  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.291   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.043   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.376   1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.376   3.080   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       3.710   0.770   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -5.626   1.540   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -5.626  -1.540   0.000  0.00  0.00           O+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   12                                                  
CONECT    4    3    5   13                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    1    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    3                                                            
CONECT   13    4                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END
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3D PDB for #<Metabolite:0x00007fa4b2d7c9f0>

COMPND    HMDB0001964
HETATM    1  O1  UNL     1       4.099   1.039  -0.639  1.00  0.00           O  
HETATM    2  C1  UNL     1       3.814  -0.156  -0.522  1.00  0.00           C  
HETATM    3  O2  UNL     1       4.786  -1.128  -0.585  1.00  0.00           O  
HETATM    4  C2  UNL     1       2.391  -0.501  -0.313  1.00  0.00           C  
HETATM    5  C3  UNL     1       1.462   0.419  -0.253  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.038   0.145  -0.048  1.00  0.00           C  
HETATM    7  C5  UNL     1      -0.482  -1.116   0.103  1.00  0.00           C  
HETATM    8  C6  UNL     1      -1.851  -1.336   0.297  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.728  -0.285   0.343  1.00  0.00           C  
HETATM   10  O3  UNL     1      -4.084  -0.496   0.534  1.00  0.00           O  
HETATM   11  C8  UNL     1      -2.227   0.990   0.193  1.00  0.00           C  
HETATM   12  O4  UNL     1      -3.146   2.034   0.244  1.00  0.00           O  
HETATM   13  C9  UNL     1      -0.879   1.194   0.003  1.00  0.00           C  
HETATM   14  H1  UNL     1       4.867  -1.820   0.151  1.00  0.00           H  
HETATM   15  H2  UNL     1       2.115  -1.549  -0.208  1.00  0.00           H  
HETATM   16  H3  UNL     1       1.822   1.454  -0.368  1.00  0.00           H  
HETATM   17  H4  UNL     1       0.188  -1.977   0.073  1.00  0.00           H  
HETATM   18  H5  UNL     1      -2.176  -2.368   0.408  1.00  0.00           H  
HETATM   19  H6  UNL     1      -4.736   0.275   0.569  1.00  0.00           H  
HETATM   20  H7  UNL     1      -2.783   2.967   0.135  1.00  0.00           H  
HETATM   21  H8  UNL     1      -0.491   2.214  -0.115  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   14
CONECT    4    5    5   15
CONECT    5    6   16
CONECT    6    7    7   13
CONECT    7    8   17
CONECT    8    9    9   18
CONECT    9   10   11
CONECT   10   19
CONECT   11   12   13   13
CONECT   12   20
CONECT   13   21
END
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SMILES for #<Metabolite:0x00007fa4b2d7c9f0>

OC(=O)\C=C\C1=CC(O)=C(O)C=C1
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INCHI for #<Metabolite:0x00007fa4b2d7c9f0>

InChI=1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+
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Synonyms
ValueSource
3,4-Dihydroxy-trans-cinnamateChEBI
3,4-Dihydroxycinnamic acidChEBI
trans-CaffeateChEBI
3,4-Dihydroxy-trans-cinnamic acidGenerator
3,4-DihydroxycinnamateGenerator
CaffeateGenerator
Caffeic acid, monosodium saltHMDB
Caffeic acid, (e)-isomerHMDB
Sodium caffeateHMDB
(2E)-(3,4-Dihydroxyphenyl)-2-propenoic acidHMDB
(2E)-3-(3,4-Dihydroxyphenyl)-2-propenoic acidHMDB
(e)-3,4-Dihydroxycinnamic acidHMDB
(e)-3-(3,4-Dihydroxyphenyl)-2-propenoic acidHMDB
(e)-3-(3,4-Dihydroxyphenyl)acrylic acidHMDB
(e)-Caffeic acidHMDB
3,4-Dihydroxybenzeneacrylic acidHMDB
3-(3,4-Dihydroxyphenyl)-2-propenoic acidHMDB
3-(3,4-Dihydroxyphenyl)propenoic acidHMDB
4-(2'-Carboxyvinyl)-1,2-dihydroxybenzeneHMDB
4-(2-Carboxyethenyl)-1,2-dihydroxybenzeneHMDB
4-(2’-carboxyvinyl)-1,2-dihydroxybenzeneHMDB
DHCAHMDB
trans-3,4-Dihydroxycinnamic acidHMDB
Caffeic acidHMDB
3',4'-Dihydroxycinnamic acidHMDB
(2E)-3-(3,4-Dihydroxyphenyl)prop-2-enoic acid;HMDB
Molecular FormulaC9H8O4
Average Mass180.1574
Monoisotopic Mass180.042258744
IUPAC Name(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid
Traditional Namecaffeic acid
CAS Registry NumberNot Available
SMILES
OC(=O)\C=C\C1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C9H8O4/c10-7-3-1-6(5-8(7)11)2-4-9(12)13/h1-5,10-11H,(H,12,13)/b4-2+
InChI KeyQAIPRVGONGVQAS-DUXPYHPUSA-N