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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:31:11 UTC

Update Date

2022-03-07 02:52:12 UTC

HMDB ID

HMDB0029566

Secondary Accession Numbers

HMDB29566

Metabolite Identification

Common Name

Isopulegone caffeate

Description

Isopulegone caffeate 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. Based on a literature review very few articles have been published on Isopulegone caffeate.

Structure

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

HMDB0029566
     RDKit          3D
Isopulegone caffeate
 47 48  0  0  0  0  0  0  0  0999 V2000
    6.0412    1.9565   -0.0311 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5146    1.1530   -0.9453 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8493    1.3517   -2.3804 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5966    0.0542   -0.5881 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3198    0.1814   -1.3586 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1687    0.2342   -0.3672 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1782   -0.9770    0.5399 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0201   -0.8103    1.5142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1972   -0.7348    0.7746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4254   -0.5813    1.3947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4614   -0.5072    2.6433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6671   -0.5039    0.6466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7952   -0.3589    1.2875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1055   -0.2684    0.6528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2379   -0.1157    1.4225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5185   -0.0235    0.8687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6823   -0.0851   -0.4976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9524    0.0055   -1.0601 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5647   -0.2377   -1.2887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7562   -0.2969   -2.6622 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3014   -0.3267   -0.7094 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4808   -1.1812    1.2437 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3749    0.0065    0.9055 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7883    1.8013    1.0201 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7047    2.7426   -0.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6649    2.1225   -2.4732 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9605    1.6518   -2.9684 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2405    0.3686   -2.7464 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0736   -0.9248   -0.8637 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1701   -0.6311   -2.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2911    1.1443   -1.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2868    1.1768    0.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1976    0.2092   -0.9121 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9972   -1.8705   -0.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9371   -1.6961    2.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1826    0.0689    2.1446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6759   -0.5642   -0.4339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7649   -0.2994    2.3894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1099   -0.0670    2.4994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3577    0.0956    1.5437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7538    0.1171   -0.4545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9270   -0.4092   -3.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4602   -0.4443   -1.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3372   -1.1727    2.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9937   -2.1204    0.9536 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3749   -0.1637    1.3768 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9697    0.9303    1.3247 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  2  0
  7 22  1  0
 22 23  1  0
 23  4  1  0
 21 14  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
 12 37  1  0
 13 38  1  0
 15 39  1  0
 16 40  1  0
 18 41  1  0
 20 42  1  0
 21 43  1  0
 22 44  1  0
 22 45  1  0
 23 46  1  0
 23 47  1  0
M  END

  Mrv0541 05061304492D          

 23 24  0  0  0  0            999 V2000
   -2.8579    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    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
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    5.7750    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
   -0.7145    2.0625    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
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    7.0125    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
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    6.1875    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
    1.4289    0.8250    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
    2.1434   -0.4125    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
   -2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  2  0  0  0  0
 10  6  2  0  0  0  0
 13  1  2  0  0  0  0
 13  2  1  0  0  0  0
 14  5  1  0  0  0  0
 14  6  1  0  0  0  0
 14 11  2  0  0  0  0
 15  3  1  0  0  0  0
 15  4  1  0  0  0  0
 15 12  1  0  0  0  0
 16  7  1  0  0  0  0
 16  8  1  0  0  0  0
 16 13  1  0  0  0  0
 17  9  1  0  0  0  0
 18 11  1  0  0  0  0
 18 17  2  0  0  0  0
 19 10  1  0  0  0  0
 20 17  1  0  0  0  0
 21 18  1  0  0  0  0
 22 19  2  0  0  0  0
 23 12  1  0  0  0  0
 23 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0029566

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=C)C1CCC(COC(=O)\C=C\C2=CC(O)=C(O)C=C2)CC1

> <INCHI_IDENTIFIER>
InChI=1S/C19H24O4/c1-13(2)16-7-3-15(4-8-16)12-23-19(22)10-6-14-5-9-17(20)18(21)11-14/h5-6,9-11,15-16,20-21H,1,3-4,7-8,12H2,2H3/b10-6+

> <INCHI_KEY>
SSVXLIRLGPMWSL-UXBLZVDNSA-N

> <FORMULA>
C19H24O4

> <MOLECULAR_WEIGHT>
316.3915

> <EXACT_MASS>
316.167459256

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
35.929907751202215

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[4-(prop-1-en-2-yl)cyclohexyl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
4.21

> <JCHEM_LOGP>
4.6934273210000015

> <ALOGPS_LOGS>
-4.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.612490857934215

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.208643055675978

> <JCHEM_PKA_STRONGEST_BASIC>
-6.283759956276708

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
91.01149999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.72e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[4-(prop-1-en-2-yl)cyclohexyl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0029566
     RDKit          3D
Isopulegone caffeate
 47 48  0  0  0  0  0  0  0  0999 V2000
    6.0412    1.9565   -0.0311 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5146    1.1530   -0.9453 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8493    1.3517   -2.3804 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5966    0.0542   -0.5881 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3198    0.1814   -1.3586 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1687    0.2342   -0.3672 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1782   -0.9770    0.5399 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0201   -0.8103    1.5142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1972   -0.7348    0.7746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4254   -0.5813    1.3947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4614   -0.5072    2.6433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6671   -0.5039    0.6466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7952   -0.3589    1.2875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1055   -0.2684    0.6528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2379   -0.1157    1.4225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5185   -0.0235    0.8687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6823   -0.0851   -0.4976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9524    0.0055   -1.0601 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5647   -0.2377   -1.2887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7562   -0.2969   -2.6622 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3014   -0.3267   -0.7094 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4808   -1.1812    1.2437 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3749    0.0065    0.9055 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7883    1.8013    1.0201 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7047    2.7426   -0.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6649    2.1225   -2.4732 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9605    1.6518   -2.9684 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2405    0.3686   -2.7464 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0736   -0.9248   -0.8637 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1701   -0.6311   -2.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2911    1.1443   -1.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2868    1.1768    0.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1976    0.2092   -0.9121 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9972   -1.8705   -0.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9371   -1.6961    2.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1826    0.0689    2.1446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6759   -0.5642   -0.4339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7649   -0.2994    2.3894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1099   -0.0670    2.4994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3577    0.0956    1.5437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7538    0.1171   -0.4545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9270   -0.4092   -3.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4602   -0.4443   -1.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3372   -1.1727    2.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9937   -2.1204    0.9536 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3749   -0.1637    1.3768 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9697    0.9303    1.3247 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  2  0
  7 22  1  0
 22 23  1  0
 23  4  1  0
 21 14  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
 12 37  1  0
 13 38  1  0
 15 39  1  0
 16 40  1  0
 18 41  1  0
 20 42  1  0
 21 43  1  0
 22 44  1  0
 22 45  1  0
 23 46  1  0
 23 47  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -5.335  13.860   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  13.860   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   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      -2.667  10.780   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.335  10.780   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.001  13.090   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.001  11.550   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -4.001   3.850   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2   13                                                            
CONECT    3    7   15                                                       
CONECT    4    8   15                                                       
CONECT    5    9   14                                                       
CONECT    6   10   14                                                       
CONECT    7    3   16                                                       
CONECT    8    4   16                                                       
CONECT    9    5   17                                                       
CONECT   10    6   19                                                       
CONECT   11   14   18                                                       
CONECT   12   15   23                                                       
CONECT   13    1    2   16                                                  
CONECT   14    5    6   11                                                  
CONECT   15    3    4   12                                                  
CONECT   16    7    8   13                                                  
CONECT   17    9   18   20                                                  
CONECT   18   11   17   21                                                  
CONECT   19   10   22   23                                                  
CONECT   20   17                                                            
CONECT   21   18                                                            
CONECT   22   19                                                            
CONECT   23   12   19                                                       
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

COMPND    HMDB0029566
HETATM    1  C1  UNL     1       6.041   1.957  -0.031  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.515   1.153  -0.945  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.849   1.352  -2.380  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.597   0.054  -0.588  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.320   0.181  -1.359  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.169   0.234  -0.367  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.178  -0.977   0.540  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.020  -0.810   1.514  1.00  0.00           C  
HETATM    9  O1  UNL     1      -0.197  -0.735   0.775  1.00  0.00           O  
HETATM   10  C9  UNL     1      -1.425  -0.581   1.395  1.00  0.00           C  
HETATM   11  O2  UNL     1      -1.461  -0.507   2.643  1.00  0.00           O  
HETATM   12  C10 UNL     1      -2.667  -0.504   0.647  1.00  0.00           C  
HETATM   13  C11 UNL     1      -3.795  -0.359   1.288  1.00  0.00           C  
HETATM   14  C12 UNL     1      -5.106  -0.268   0.653  1.00  0.00           C  
HETATM   15  C13 UNL     1      -6.238  -0.116   1.422  1.00  0.00           C  
HETATM   16  C14 UNL     1      -7.518  -0.024   0.869  1.00  0.00           C  
HETATM   17  C15 UNL     1      -7.682  -0.085  -0.498  1.00  0.00           C  
HETATM   18  O3  UNL     1      -8.952   0.006  -1.060  1.00  0.00           O  
HETATM   19  C16 UNL     1      -6.565  -0.238  -1.289  1.00  0.00           C  
HETATM   20  O4  UNL     1      -6.756  -0.297  -2.662  1.00  0.00           O  
HETATM   21  C17 UNL     1      -5.301  -0.327  -0.709  1.00  0.00           C  
HETATM   22  C18 UNL     1       3.481  -1.181   1.244  1.00  0.00           C  
HETATM   23  C19 UNL     1       4.375   0.006   0.905  1.00  0.00           C  
HETATM   24  H1  UNL     1       5.788   1.801   1.020  1.00  0.00           H  
HETATM   25  H2  UNL     1       6.705   2.743  -0.342  1.00  0.00           H  
HETATM   26  H3  UNL     1       6.665   2.123  -2.473  1.00  0.00           H  
HETATM   27  H4  UNL     1       4.960   1.652  -2.968  1.00  0.00           H  
HETATM   28  H5  UNL     1       6.241   0.369  -2.746  1.00  0.00           H  
HETATM   29  H6  UNL     1       5.074  -0.925  -0.864  1.00  0.00           H  
HETATM   30  H7  UNL     1       3.170  -0.631  -2.103  1.00  0.00           H  
HETATM   31  H8  UNL     1       3.291   1.144  -1.912  1.00  0.00           H  
HETATM   32  H9  UNL     1       2.287   1.177   0.199  1.00  0.00           H  
HETATM   33  H10 UNL     1       1.198   0.209  -0.912  1.00  0.00           H  
HETATM   34  H11 UNL     1       1.997  -1.871  -0.098  1.00  0.00           H  
HETATM   35  H12 UNL     1       0.937  -1.696   2.177  1.00  0.00           H  
HETATM   36  H13 UNL     1       1.183   0.069   2.145  1.00  0.00           H  
HETATM   37  H14 UNL     1      -2.676  -0.564  -0.434  1.00  0.00           H  
HETATM   38  H15 UNL     1      -3.765  -0.299   2.389  1.00  0.00           H  
HETATM   39  H16 UNL     1      -6.110  -0.067   2.499  1.00  0.00           H  
HETATM   40  H17 UNL     1      -8.358   0.096   1.544  1.00  0.00           H  
HETATM   41  H18 UNL     1      -9.754   0.117  -0.454  1.00  0.00           H  
HETATM   42  H19 UNL     1      -5.927  -0.409  -3.231  1.00  0.00           H  
HETATM   43  H20 UNL     1      -4.460  -0.444  -1.355  1.00  0.00           H  
HETATM   44  H21 UNL     1       3.337  -1.173   2.353  1.00  0.00           H  
HETATM   45  H22 UNL     1       3.994  -2.120   0.954  1.00  0.00           H  
HETATM   46  H23 UNL     1       5.375  -0.164   1.377  1.00  0.00           H  
HETATM   47  H24 UNL     1       3.970   0.930   1.325  1.00  0.00           H  
CONECT    1    2    2   24   25
CONECT    2    3    4
CONECT    3   26   27   28
CONECT    4    5   23   29
CONECT    5    6   30   31
CONECT    6    7   32   33
CONECT    7    8   22   34
CONECT    8    9   35   36
CONECT    9   10
CONECT   10   11   11   12
CONECT   12   13   13   37
CONECT   13   14   38
CONECT   14   15   15   21
CONECT   15   16   39
CONECT   16   17   17   40
CONECT   17   18   19
CONECT   18   41
CONECT   19   20   21   21
CONECT   20   42
CONECT   21   43
CONECT   22   23   44   45
CONECT   23   46   47
END

HMDB0029566
     RDKit          3D
Isopulegone caffeate
 47 48  0  0  0  0  0  0  0  0999 V2000
    6.0412    1.9565   -0.0311 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5146    1.1530   -0.9453 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8493    1.3517   -2.3804 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5966    0.0542   -0.5881 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3198    0.1814   -1.3586 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1687    0.2342   -0.3672 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1782   -0.9770    0.5399 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0201   -0.8103    1.5142 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1972   -0.7348    0.7746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4254   -0.5813    1.3947 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4614   -0.5072    2.6433 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6671   -0.5039    0.6466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7952   -0.3589    1.2875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1055   -0.2684    0.6528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2379   -0.1157    1.4225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5185   -0.0235    0.8687 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6823   -0.0851   -0.4976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9524    0.0055   -1.0601 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5647   -0.2377   -1.2887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7562   -0.2969   -2.6622 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3014   -0.3267   -0.7094 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4808   -1.1812    1.2437 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3749    0.0065    0.9055 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7883    1.8013    1.0201 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7047    2.7426   -0.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6649    2.1225   -2.4732 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9605    1.6518   -2.9684 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2405    0.3686   -2.7464 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0736   -0.9248   -0.8637 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1701   -0.6311   -2.1025 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2911    1.1443   -1.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2868    1.1768    0.1985 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1976    0.2092   -0.9121 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9972   -1.8705   -0.0979 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9371   -1.6961    2.1771 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1826    0.0689    2.1446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6759   -0.5642   -0.4339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7649   -0.2994    2.3894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1099   -0.0670    2.4994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3577    0.0956    1.5437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7538    0.1171   -0.4545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9270   -0.4092   -3.2313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4602   -0.4443   -1.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3372   -1.1727    2.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9937   -2.1204    0.9536 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3749   -0.1637    1.3768 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9697    0.9303    1.3247 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 19 21  2  0
  7 22  1  0
 22 23  1  0
 23  4  1  0
 21 14  1  0
  1 24  1  0
  1 25  1  0
  3 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
 12 37  1  0
 13 38  1  0
 15 39  1  0
 16 40  1  0
 18 41  1  0
 20 42  1  0
 21 43  1  0
 22 44  1  0
 22 45  1  0
 23 46  1  0
 23 47  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Isopulegone caffeic acid	Generator
p-Menth-8-en-7-yl caffeate	HMDB
[4-(Prop-1-en-2-yl)cyclohexyl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid	HMDB

Chemical Formula

C₁₉H₂₄O₄

Average Molecular Weight

316.3915

Monoisotopic Molecular Weight

316.167459256

IUPAC Name

[4-(prop-1-en-2-yl)cyclohexyl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

Traditional Name

[4-(prop-1-en-2-yl)cyclohexyl]methyl (2E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

CAS Registry Number

179694-78-1

SMILES

CC(=C)C1CCC(COC(=O)\C=C\C2=CC(O)=C(O)C=C2)CC1

InChI Identifier

InChI=1S/C19H24O4/c1-13(2)16-7-3-15(4-8-16)12-23-19(22)10-6-14-5-9-17(20)18(21)11-14/h5-6,9-11,15-16,20-21H,1,3-4,7-8,12H2,2H3/b10-6+

InChI Key

SSVXLIRLGPMWSL-UXBLZVDNSA-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
Aromatic monoterpenoid
Monocyclic monoterpenoid
Monoterpenoid
P-menthane monoterpenoid
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Phenol
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0029566)
Cell membrane (HMDB: HMDB0029566)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0029566)

Source

Endogenous

Endogenous (HMDB: HMDB0029566)

Plant

Plant (HMDB: HMDB0029566)

Exogenous

Food

Food (HMDB: HMDB0029566)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Exogenous (HMDB: HMDB0029566)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	155 - 156 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.027 g/L	ALOGPS
logP	4.21	ALOGPS
logP	4.69	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	9.21	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	91.01 m³·mol⁻¹	ChemAxon
Polarizability	35.93 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	180.688	30932474
DeepCCS	[M-H]-	178.07	30932474
DeepCCS	[M-2H]-	212.795	30932474
DeepCCS	[M+Na]+	189.086	30932474
AllCCS	[M+H]+	178.6	32859911
AllCCS	[M+H-H2O]+	175.4	32859911
AllCCS	[M+NH4]+	181.5	32859911
AllCCS	[M+Na]+	182.3	32859911
AllCCS	[M-H]-	180.6	32859911
AllCCS	[M+Na-2H]-	180.6	32859911
AllCCS	[M+HCOO]-	180.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isopulegone caffeate	CC(=C)C1CCC(COC(=O)\C=C\C2=CC(O)=C(O)C=C2)CC1	4098.2	Standard polar	33892256
Isopulegone caffeate	CC(=C)C1CCC(COC(=O)\C=C\C2=CC(O)=C(O)C=C2)CC1	2668.5	Standard non polar	33892256
Isopulegone caffeate	CC(=C)C1CCC(COC(=O)\C=C\C2=CC(O)=C(O)C=C2)CC1	2895.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isopulegone caffeate,1TMS,isomer #1	C=C(C)C1CCC(COC(=O)/C=C/C2=CC=C(O)C(O[Si](C)(C)C)=C2)CC1	2800.2	Semi standard non polar	33892256
Isopulegone caffeate,1TMS,isomer #2	C=C(C)C1CCC(COC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C(O)=C2)CC1	2804.2	Semi standard non polar	33892256
Isopulegone caffeate,2TMS,isomer #1	C=C(C)C1CCC(COC(=O)/C=C/C2=CC=C(O[Si](C)(C)C)C(O[Si](C)(C)C)=C2)CC1	2877.0	Semi standard non polar	33892256
Isopulegone caffeate,1TBDMS,isomer #1	C=C(C)C1CCC(COC(=O)/C=C/C2=CC=C(O)C(O[Si](C)(C)C(C)(C)C)=C2)CC1	3063.4	Semi standard non polar	33892256
Isopulegone caffeate,1TBDMS,isomer #2	C=C(C)C1CCC(COC(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O)=C2)CC1	3067.5	Semi standard non polar	33892256
Isopulegone caffeate,2TBDMS,isomer #1	C=C(C)C1CCC(COC(=O)/C=C/C2=CC=C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)=C2)CC1	3360.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Isopulegone caffeate GC-MS (Non-derivatized) - 70eV, Positive	splash10-03l9-4910000000-eb8170d86cb25e60cf5c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isopulegone caffeate GC-MS (2 TMS) - 70eV, Positive	splash10-006t-9634800000-0fdbaecd56e145bd99a5	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isopulegone caffeate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopulegone caffeate 10V, Positive-QTOF	splash10-014r-1914000000-c813e507dad590a8d476	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopulegone caffeate 20V, Positive-QTOF	splash10-000i-2900000000-dbea2b095d9297bcff02	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopulegone caffeate 40V, Positive-QTOF	splash10-015i-8900000000-ceeecd2c144b807769c4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopulegone caffeate 10V, Negative-QTOF	splash10-02t9-0906000000-8516959bfbb1d9fee729	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopulegone caffeate 20V, Negative-QTOF	splash10-03mi-0900000000-93e68dafe30a48f5dafa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopulegone caffeate 40V, Negative-QTOF	splash10-03k9-0900000000-9523ff63a5a2796cad75	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopulegone caffeate 10V, Negative-QTOF	splash10-014i-0109000000-993cee15d153b222cf58	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopulegone caffeate 20V, Negative-QTOF	splash10-00kr-0903000000-f7d12aa913dff83a6ad7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopulegone caffeate 40V, Negative-QTOF	splash10-0019-1910000000-f21ab0ea3af20b5601d9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopulegone caffeate 10V, Positive-QTOF	splash10-014i-0119000000-06c34e9496cebd576cc9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopulegone caffeate 20V, Positive-QTOF	splash10-014s-5975000000-ae76243a34ed2b0f9c66	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isopulegone caffeate 40V, Positive-QTOF	splash10-001d-5900000000-a840c398276dfc78e1ae	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB000721

KNApSAcK ID

Not Available

Chemspider ID

13385963

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

18406287

PDB ID

Not Available

ChEBI ID

172548

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Isopulegone caffeate (HMDB0029566)

MOL for HMDB0029566 (Isopulegone caffeate)

3D MOL for HMDB0029566 (Isopulegone caffeate)

3D SDF for HMDB0029566 (Isopulegone caffeate)

3D-SDF for HMDB0029566 (Isopulegone caffeate)

PDB for HMDB0029566 (Isopulegone caffeate)

3D PDB for HMDB0029566 (Isopulegone caffeate)

SMILES for HMDB0029566 (Isopulegone caffeate)

INCHI for HMDB0029566 (Isopulegone caffeate)

Structure for HMDB0029566 (Isopulegone caffeate)

3D Structure for HMDB0029566 (Isopulegone caffeate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra