MiMeDB: Showing metabocard for 5-O-Caffeoylshikimic acid (MMDBc0052278)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-05-16 20:50:42 UTC

Update Date

2024-04-30 20:43:22 UTC

Metabolite ID

MMDBc0052278

Metabolite Identification

Common Name

5-O-Caffeoylshikimic acid

Description

Dattelic acid, also known as dattelate or dactylifric acid, belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. Dattelic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review very few articles have been published on Dattelic acid.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0033999
     RDKit          3D
Dattelic acid
 40 41  0  0  0  0  0  0  0  0999 V2000
    0.5529   -1.0791   -2.3671 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0441   -0.5965   -1.3283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4079   -0.7340   -1.1693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0430   -0.2633   -0.1164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4966   -0.3728    0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3437   -0.9747   -0.7786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7035   -1.0271   -0.4883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2517   -0.4927    0.6577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6236   -0.5677    0.9098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3806    0.1139    1.5333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8851    0.6671    2.7017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0358    0.1730    1.2597 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8279    0.0362   -0.3794 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2085    0.1328   -0.5937 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9696   -0.4776    0.5548 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3601   -0.0225    0.6706 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1917   -0.6169    1.7293 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3998   -0.2661    1.8807 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6585   -1.5705    2.5749 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9233    0.8985   -0.1242 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1037    1.5081   -1.1953 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1051    0.6113   -2.2849 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6724    1.5698   -0.7053 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8985    2.3234   -1.5603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9868   -1.2308   -1.9247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4133    0.2331    0.6239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9669   -1.4112   -1.6946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3204   -1.5217   -1.2288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9602   -0.1597    1.7616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3007    1.1243    3.3823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3577    0.6623    1.9728 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4858   -0.3473   -1.5621 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8913   -1.5807    0.4431 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3989   -0.2302    1.4966 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9402   -2.5562    2.5138 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9710    1.1696    0.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4839    2.5029   -1.5059 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6621   -0.1773   -2.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7123    2.0570    0.3079 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0159    2.4930   -1.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  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  1  0
 10 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 16 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 12  5  1  0
 23 14  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
  9 29  1  0
 11 30  1  0
 12 31  1  0
 14 32  1  6
 15 33  1  0
 15 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  6
 22 38  1  0
 23 39  1  1
 24 40  1  0
M  END


  Mrv1652309272007262D          

 24 25  0  0  0  0            999 V2000
 9998.9178 9999.5882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6327 9999.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3472 9999.5882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.0634 9999.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.4936 9997.5233    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.9218 9998.3489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.632710000.8255    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.485910002.0638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.200810002.4766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.771010002.4766    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4859 9998.7627    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.0581 9999.5882    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.487310001.2379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.772810000.8254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.772810000.0003    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9997.4873 9999.5879    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9998.201810000.0003    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.201810000.8254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.2074 9999.5877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.493010000.0001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.7784 9999.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.7784 9998.7626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.4929 9998.3501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.2074 9998.7626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  7  2  0  0  0  0
  3  4  2  0  0  0  0
  8  9  1  0  0  0  0
  8 10  2  0  0  0  0
 13 14  2  0  0  0  0
 13 18  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 11  1  6  0  0  0
 15 12  1  6  0  0  0
 13  8  1  0  0  0  0
 17  1  1  1  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 19  1  0  0  0  0
 24  6  1  0  0  0  0
 23  5  1  0  0  0  0
  4 21  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0052278

> <DATABASE_NAME>
MIME

> <SMILES>
O[C@@H]1C=C(C[C@@H](OC(=O)\C=C\C2=CC(O)=C(O)C=C2)[C@@H]1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C16H16O8/c17-10-3-1-8(5-11(10)18)2-4-14(20)24-13-7-9(16(22)23)6-12(19)15(13)21/h1-6,12-13,15,17-19,21H,7H2,(H,22,23)/b4-2+/t12-,13-,15-/m1/s1

> <INCHI_KEY>
QMPHZIPNNJOWQI-GDDAOPKQSA-N

> <FORMULA>
C16H16O8

> <MOLECULAR_WEIGHT>
336.296

> <EXACT_MASS>
336.084517475

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
32.32737808241103

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,4R,5R)-5-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid

> <ALOGPS_LOGP>
1.17

> <JCHEM_LOGP>
0.7866859976666667

> <ALOGPS_LOGS>
-2.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.208550231347209

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.937063432609867

> <JCHEM_PKA_STRONGEST_BASIC>
-3.378175780771425

> <JCHEM_POLAR_SURFACE_AREA>
144.52

> <JCHEM_REFRACTIVITY>
82.4898

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.01e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-O-caffeoylshikimic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033999
     RDKit          3D
Dattelic acid
 40 41  0  0  0  0  0  0  0  0999 V2000
    0.5529   -1.0791   -2.3671 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0441   -0.5965   -1.3283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4079   -0.7340   -1.1693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0430   -0.2633   -0.1164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4966   -0.3728    0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3437   -0.9747   -0.7786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7035   -1.0271   -0.4883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2517   -0.4927    0.6577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6236   -0.5677    0.9098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3806    0.1139    1.5333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8851    0.6671    2.7017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0358    0.1730    1.2597 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8279    0.0362   -0.3794 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2085    0.1328   -0.5937 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9696   -0.4776    0.5548 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3601   -0.0225    0.6706 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1917   -0.6169    1.7293 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3998   -0.2661    1.8807 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6585   -1.5705    2.5749 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9233    0.8985   -0.1242 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1037    1.5081   -1.1953 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1051    0.6113   -2.2849 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6724    1.5698   -0.7053 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8985    2.3234   -1.5603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9868   -1.2308   -1.9247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4133    0.2331    0.6239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9669   -1.4112   -1.6946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3204   -1.5217   -1.2288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9602   -0.1597    1.7616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3007    1.1243    3.3823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3577    0.6623    1.9728 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4858   -0.3473   -1.5621 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8913   -1.5807    0.4431 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3989   -0.2302    1.4966 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9402   -2.5562    2.5138 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9710    1.1696    0.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4839    2.5029   -1.5059 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6621   -0.1773   -2.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7123    2.0570    0.3079 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0159    2.4930   -1.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  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  1  0
 10 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 16 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 12  5  1  0
 23 14  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
  9 29  1  0
 11 30  1  0
 12 31  1  0
 14 32  1  6
 15 33  1  0
 15 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  6
 22 38  1  0
 23 39  1  1
 24 40  1  0
M  END

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  O   UNK     0    8664.6478665.898   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0    8665.9818666.666   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8667.3158665.898   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8668.6528666.666   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0    8671.3218662.043   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8673.9878663.585   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0    8665.9818668.208   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0    8661.9748670.519   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0    8663.3088671.290   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0    8660.6398671.290   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8661.9748664.357   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    8659.3088665.898   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0    8661.9768668.977   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8660.6438668.207   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8660.6438666.667   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8661.9768665.897   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8663.3108666.667   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8663.3108668.207   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8672.6548665.897   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8671.3208666.667   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8669.9868665.897   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8669.9868664.357   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0    8671.3208663.587   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0    8672.6548664.357   0.000  0.00  0.00           C+0
CONECT    1    2   17                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3   21                                                       
CONECT    5   23                                                            
CONECT    6   24                                                            
CONECT    7    2                                                            
CONECT    8    9   10   13                                                  
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11   16                                                            
CONECT   12   15                                                            
CONECT   13   14   18    8                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   12                                                  
CONECT   16   15   17   11                                                  
CONECT   17   16   18    1                                                  
CONECT   18   13   17                                                       
CONECT   19   20   24                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22    4                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24    5                                                  
CONECT   24   23   19    6                                                  
MASTER        0    0    0    0    0    0    0    0   24    0   50    0
END

COMPND    HMDB0033999
HETATM    1  O1  UNL     1       0.553  -1.079  -2.367  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.044  -0.597  -1.328  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.408  -0.734  -1.169  1.00  0.00           C  
HETATM    4  C3  UNL     1      -2.043  -0.263  -0.116  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.497  -0.373   0.095  1.00  0.00           C  
HETATM    6  C5  UNL     1      -4.344  -0.975  -0.779  1.00  0.00           C  
HETATM    7  C6  UNL     1      -5.703  -1.027  -0.488  1.00  0.00           C  
HETATM    8  C7  UNL     1      -6.252  -0.493   0.658  1.00  0.00           C  
HETATM    9  O2  UNL     1      -7.624  -0.568   0.910  1.00  0.00           O  
HETATM   10  C8  UNL     1      -5.381   0.114   1.533  1.00  0.00           C  
HETATM   11  O3  UNL     1      -5.885   0.667   2.702  1.00  0.00           O  
HETATM   12  C9  UNL     1      -4.036   0.173   1.260  1.00  0.00           C  
HETATM   13  O4  UNL     1       0.828   0.036  -0.379  1.00  0.00           O  
HETATM   14  C10 UNL     1       2.209   0.133  -0.594  1.00  0.00           C  
HETATM   15  C11 UNL     1       2.970  -0.478   0.555  1.00  0.00           C  
HETATM   16  C12 UNL     1       4.360  -0.023   0.671  1.00  0.00           C  
HETATM   17  C13 UNL     1       5.192  -0.617   1.729  1.00  0.00           C  
HETATM   18  O5  UNL     1       6.400  -0.266   1.881  1.00  0.00           O  
HETATM   19  O6  UNL     1       4.658  -1.570   2.575  1.00  0.00           O  
HETATM   20  C14 UNL     1       4.923   0.899  -0.124  1.00  0.00           C  
HETATM   21  C15 UNL     1       4.104   1.508  -1.195  1.00  0.00           C  
HETATM   22  O7  UNL     1       4.105   0.611  -2.285  1.00  0.00           O  
HETATM   23  C16 UNL     1       2.672   1.570  -0.705  1.00  0.00           C  
HETATM   24  O8  UNL     1       1.899   2.323  -1.560  1.00  0.00           O  
HETATM   25  H1  UNL     1      -1.987  -1.231  -1.925  1.00  0.00           H  
HETATM   26  H2  UNL     1      -1.413   0.233   0.624  1.00  0.00           H  
HETATM   27  H3  UNL     1      -3.967  -1.411  -1.695  1.00  0.00           H  
HETATM   28  H4  UNL     1      -6.320  -1.522  -1.229  1.00  0.00           H  
HETATM   29  H5  UNL     1      -7.960  -0.160   1.762  1.00  0.00           H  
HETATM   30  H6  UNL     1      -5.301   1.124   3.382  1.00  0.00           H  
HETATM   31  H7  UNL     1      -3.358   0.662   1.973  1.00  0.00           H  
HETATM   32  H8  UNL     1       2.486  -0.347  -1.562  1.00  0.00           H  
HETATM   33  H9  UNL     1       2.891  -1.581   0.443  1.00  0.00           H  
HETATM   34  H10 UNL     1       2.399  -0.230   1.497  1.00  0.00           H  
HETATM   35  H11 UNL     1       4.940  -2.556   2.514  1.00  0.00           H  
HETATM   36  H12 UNL     1       5.971   1.170   0.045  1.00  0.00           H  
HETATM   37  H13 UNL     1       4.484   2.503  -1.506  1.00  0.00           H  
HETATM   38  H14 UNL     1       4.662  -0.177  -2.114  1.00  0.00           H  
HETATM   39  H15 UNL     1       2.712   2.057   0.308  1.00  0.00           H  
HETATM   40  H16 UNL     1       1.016   2.493  -1.127  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   13
CONECT    3    4    4   25
CONECT    4    5   26
CONECT    5    6    6   12
CONECT    6    7   27
CONECT    7    8    8   28
CONECT    8    9   10
CONECT    9   29
CONECT   10   11   12   12
CONECT   11   30
CONECT   12   31
CONECT   13   14
CONECT   14   15   23   32
CONECT   15   16   33   34
CONECT   16   17   20   20
CONECT   17   18   18   19
CONECT   19   35
CONECT   20   21   36
CONECT   21   22   23   37
CONECT   22   38
CONECT   23   24   39
CONECT   24   40
END

HMDB0033999
     RDKit          3D
Dattelic acid
 40 41  0  0  0  0  0  0  0  0999 V2000
    0.5529   -1.0791   -2.3671 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0441   -0.5965   -1.3283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4079   -0.7340   -1.1693 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0430   -0.2633   -0.1164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4966   -0.3728    0.0950 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3437   -0.9747   -0.7786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7035   -1.0271   -0.4883 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2517   -0.4927    0.6577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6236   -0.5677    0.9098 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3806    0.1139    1.5333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8851    0.6671    2.7017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0358    0.1730    1.2597 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8279    0.0362   -0.3794 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2085    0.1328   -0.5937 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9696   -0.4776    0.5548 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3601   -0.0225    0.6706 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1917   -0.6169    1.7293 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3998   -0.2661    1.8807 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6585   -1.5705    2.5749 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9233    0.8985   -0.1242 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1037    1.5081   -1.1953 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1051    0.6113   -2.2849 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6724    1.5698   -0.7053 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8985    2.3234   -1.5603 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9868   -1.2308   -1.9247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4133    0.2331    0.6239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9669   -1.4112   -1.6946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3204   -1.5217   -1.2288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9602   -0.1597    1.7616 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3007    1.1243    3.3823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3577    0.6623    1.9728 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4858   -0.3473   -1.5621 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8913   -1.5807    0.4431 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3989   -0.2302    1.4966 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9402   -2.5562    2.5138 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9710    1.1696    0.0452 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4839    2.5029   -1.5059 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6621   -0.1773   -2.1137 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7123    2.0570    0.3079 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0159    2.4930   -1.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  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  1  0
 10 12  2  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 16 20  2  0
 20 21  1  0
 21 22  1  0
 21 23  1  0
 23 24  1  0
 12  5  1  0
 23 14  1  0
  3 25  1  0
  4 26  1  0
  6 27  1  0
  7 28  1  0
  9 29  1  0
 11 30  1  0
 12 31  1  0
 14 32  1  6
 15 33  1  0
 15 34  1  0
 19 35  1  0
 20 36  1  0
 21 37  1  6
 22 38  1  0
 23 39  1  1
 24 40  1  0
M  END

Synonyms

Value	Source
5-Caffeoylshikimic acid	ChEBI
5-Caffeoylshikimate	Generator
Dattelate	Generator
Dactylifric acid	HMDB
5-O-Caffeoylshikimate	HMDB
5-O-Caffeoylshikimic acid	HMDB
Caffeoylshikimate	HMDB
Caffeoylshikimic acid	HMDB
trans-5-O-Caffeoylshikimic acid	HMDB
trans-Caffeic acid 5-O-shikimate	HMDB
5-[(e)-Caffeoyl]shikimate	HMDB
Dattelic acid	HMDB

Molecular Formula

C₁₆H₁₆O₈

Average Mass

336.296

Monoisotopic Mass

336.084517475

IUPAC Name

(3R,4R,5R)-5-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4-dihydroxycyclohex-1-ene-1-carboxylic acid

Traditional Name

5-O-caffeoylshikimic acid

CAS Registry Number

Not Available

SMILES

O[C@@H]1C=C(C[C@@H](OC(=O)\C=C\C2=CC(O)=C(O)C=C2)[C@@H]1O)C(O)=O

InChI Identifier

InChI=1S/C16H16O8/c17-10-3-1-8(5-11(10)18)2-4-14(20)24-13-7-9(16(22)23)6-12(19)15(13)21/h1-6,12-13,15,17-19,21H,7H2,(H,22,23)/b4-2+/t12-,13-,15-/m1/s1

InChI Key

QMPHZIPNNJOWQI-GDDAOPKQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Coumaric acid or derivatives
Cinnamic acid ester
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Cyclitol or derivatives
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Dicarboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
1,2-diol
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Carboxylic acid
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

hydroxycinnamic acid (CHEBI:2106 )
Caffeate derivatives (C10434 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	1.01 g/L	ALOGPS
logP	1.17	ALOGPS
logP	0.79	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	3.94	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	144.52 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	82.49 m³·mol⁻¹	ChemAxon
Polarizability	32.33 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - NA , positive	splash10-03dr-0900000000-027d1582ffcfcbcc8a66	2020-07-21	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - NA , positive	splash10-03di-0900000000-7d436c53d76aac008735	2020-07-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014r-0359000000-a6e04662b2dd608e99a3	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-002r-0921000000-d01231ac2163cb94472a	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000i-1910000000-84945d7f7dc8798c6fa2	2021-09-23	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-03y0-0907000000-95d3be88a395a4fa7c31	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03dr-0933000000-09eaf74af70551c0fd06	2021-09-24	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03dr-0900000000-6fa17ca3359a11a2eb39	2021-09-24	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Basidiomycota	8	Human feces
Eukaryota/Fungi	Ascomycota	2

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

HMDB0033999

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281762

PDB ID

Not Available

ChEBI ID

2106

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]
Yannai, Shmuel (2004). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. Boca Raton: Chapman & Hall/CRC..

Showing metabocard for 5-O-Caffeoylshikimic acid (MMDBc0052278)

MOL for #<Metabolite:0x00007fdb254a1e80>

3D MOL for #<Metabolite:0x00007fdb254a1e80>

3D SDF for #<Metabolite:0x00007fdb254a1e80>

3D-SDF for #<Metabolite:0x00007fdb254a1e80>

PDB for #<Metabolite:0x00007fdb254a1e80>

3D PDB for #<Metabolite:0x00007fdb254a1e80>

SMILES for #<Metabolite:0x00007fdb254a1e80>

INCHI for #<Metabolite:0x00007fdb254a1e80>

Structure for #<Metabolite:0x00007fdb254a1e80>

3D Structure for #<Metabolite:0x00007fdb254a1e80>