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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:42:14 UTC

Update Date

2022-03-07 02:54:14 UTC

HMDB ID

HMDB0034780

Secondary Accession Numbers

HMDB34780

Metabolite Identification

Common Name

Capsiate

Description

Capsiate, also known as capsiic acid, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Capsiate has been detected, but not quantified in, several different foods, such as orange bell peppers (Capsicum annuum), red bell peppers (Capsicum annuum), yellow bell peppers (Capsicum annuum), italian sweet red peppers (Capsicum annuum), and green bell peppers (Capsicum annuum). This could make capsiate a potential biomarker for the consumption of these foods. Capsiate 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 a significant number of articles have been published on Capsiate.

Structure

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

HMDB0034780
     RDKit          3D
Capsiate
 48 48  0  0  0  0  0  0  0  0999 V2000
   -8.0199   -1.1275   -0.8560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5829    0.0596   -0.2246 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2073    0.3055   -0.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3131   -0.5898   -0.7066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9639   -0.2940   -0.6168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9522   -1.2044   -1.1794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6339   -0.9266   -0.7670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1962   -0.9448    0.5338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0113   -1.2284    1.4496 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2126   -0.6440    0.9429 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9660   -0.3414   -0.3309 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4148   -0.0121   -0.0918 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1145   -1.1684    0.5735 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5420   -0.9051    0.8319 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1703    0.2173    0.5238 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6138    0.4534    0.7978 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7548    1.7059    1.6307 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2825    0.7132   -0.5340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5421    0.8660    0.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4576    1.7418    0.5337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7875    1.4832    0.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7553    2.3556    0.9978 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6893   -2.0334   -0.2896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5817   -1.2170   -1.8858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1220   -1.1039   -0.9064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6349   -1.5104   -1.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2726   -2.2449   -0.9219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9641   -1.1522   -2.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6165   -1.5624    1.4168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2911    0.2259    1.5943 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8274   -1.1554   -1.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4971    0.5985   -0.7456 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8962    0.1469   -1.0762 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4641    0.9150    0.4712 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0210   -2.0797   -0.0506 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6357   -1.3990    1.5597 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1193   -1.6882    1.3091 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6167    1.0113    0.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0786   -0.3933    1.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8152    1.7636    1.9999 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1095    1.6866    2.5293 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5832    2.6134    1.0111 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5470    0.8000   -1.3687 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8814   -0.2089   -0.7734 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9466    1.6052   -0.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4842    1.0900    0.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1078    2.6366    1.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7379    2.1404    0.9325 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
  5 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21  3  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  6 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  0
 18 44  1  0
 18 45  1  0
 19 46  1  0
 20 47  1  0
 22 48  1  0
M  END


  Mrv0541 05061308042D          

 22 22  0  0  0  0            999 V2000
   -7.8592    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    0.8250    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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    0.8250    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
    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
   -2.1434    1.2375    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    2.0625    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
   -1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  2  0  0  0  0
  9  7  1  0  0  0  0
 11 10  2  0  0  0  0
 14  1  1  0  0  0  0
 14  2  1  0  0  0  0
 14  8  1  0  0  0  0
 15 10  1  0  0  0  0
 15 12  2  0  0  0  0
 15 13  1  0  0  0  0
 16 11  1  0  0  0  0
 17 12  1  0  0  0  0
 17 16  2  0  0  0  0
 18  9  1  0  0  0  0
 19 16  1  0  0  0  0
 20 18  2  0  0  0  0
 21  3  1  0  0  0  0
 21 17  1  0  0  0  0
 22 13  1  0  0  0  0
 22 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034780

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C=CC(COC(=O)CCCC\C=C\C(C)C)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C18H26O4/c1-14(2)8-6-4-5-7-9-18(20)22-13-15-10-11-16(19)17(12-15)21-3/h6,8,10-12,14,19H,4-5,7,9,13H2,1-3H3/b8-6+

> <INCHI_KEY>
ZICNYIDDNJYKCP-SOFGYWHQSA-N

> <FORMULA>
C18H26O4

> <MOLECULAR_WEIGHT>
306.3966

> <EXACT_MASS>
306.18310932

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
35.58777719049335

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4-hydroxy-3-methoxyphenyl)methyl (6E)-8-methylnon-6-enoate

> <ALOGPS_LOGP>
4.50

> <JCHEM_LOGP>
4.4788301483333335

> <ALOGPS_LOGS>
-4.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.914333183815874

> <JCHEM_PKA_STRONGEST_BASIC>
-4.890495158700626

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
88.36759999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.08e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4-hydroxy-3-methoxyphenyl)methyl (6E)-8-methylnon-6-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034780
     RDKit          3D
Capsiate
 48 48  0  0  0  0  0  0  0  0999 V2000
   -8.0199   -1.1275   -0.8560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5829    0.0596   -0.2246 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2073    0.3055   -0.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3131   -0.5898   -0.7066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9639   -0.2940   -0.6168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9522   -1.2044   -1.1794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6339   -0.9266   -0.7670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1962   -0.9448    0.5338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0113   -1.2284    1.4496 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2126   -0.6440    0.9429 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9660   -0.3414   -0.3309 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4148   -0.0121   -0.0918 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1145   -1.1684    0.5735 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5420   -0.9051    0.8319 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1703    0.2173    0.5238 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6138    0.4534    0.7978 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7548    1.7059    1.6307 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2825    0.7132   -0.5340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5421    0.8660    0.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4576    1.7418    0.5337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7875    1.4832    0.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7553    2.3556    0.9978 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6893   -2.0334   -0.2896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5817   -1.2170   -1.8858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1220   -1.1039   -0.9064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6349   -1.5104   -1.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2726   -2.2449   -0.9219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9641   -1.1522   -2.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6165   -1.5624    1.4168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2911    0.2259    1.5943 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8274   -1.1554   -1.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4971    0.5985   -0.7456 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8962    0.1469   -1.0762 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4641    0.9150    0.4712 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0210   -2.0797   -0.0506 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6357   -1.3990    1.5597 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1193   -1.6882    1.3091 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6167    1.0113    0.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0786   -0.3933    1.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8152    1.7636    1.9999 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1095    1.6866    2.5293 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5832    2.6134    1.0111 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5470    0.8000   -1.3687 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8814   -0.2089   -0.7734 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9466    1.6052   -0.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4842    1.0900    0.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1078    2.6366    1.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7379    2.1404    0.9325 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
  5 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21  3  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  6 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  0
 18 44  1  0
 18 45  1  0
 19 46  1  0
 20 47  1  0
 22 48  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     -14.671   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -13.337   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.336   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -8.002   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -10.669   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.668   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -12.003   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -13.337   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -4.001   3.850   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      -2.667   1.540   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2   14                                                            
CONECT    3   21                                                            
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   14                                                       
CONECT    9    7   18                                                       
CONECT   10   11   15                                                       
CONECT   11   10   16                                                       
CONECT   12   15   17                                                       
CONECT   13   15   22                                                       
CONECT   14    1    2    8                                                  
CONECT   15   10   12   13                                                  
CONECT   16   11   17   19                                                  
CONECT   17   12   16   21                                                  
CONECT   18    9   20   22                                                  
CONECT   19   16                                                            
CONECT   20   18                                                            
CONECT   21    3   17                                                       
CONECT   22   13   18                                                       
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

COMPND    HMDB0034780
HETATM    1  C1  UNL     1      -8.020  -1.127  -0.856  1.00  0.00           C  
HETATM    2  O1  UNL     1      -7.583   0.060  -0.225  1.00  0.00           O  
HETATM    3  C2  UNL     1      -6.207   0.306  -0.164  1.00  0.00           C  
HETATM    4  C3  UNL     1      -5.313  -0.590  -0.707  1.00  0.00           C  
HETATM    5  C4  UNL     1      -3.964  -0.294  -0.617  1.00  0.00           C  
HETATM    6  C5  UNL     1      -2.952  -1.204  -1.179  1.00  0.00           C  
HETATM    7  O2  UNL     1      -1.634  -0.927  -0.767  1.00  0.00           O  
HETATM    8  C6  UNL     1      -1.196  -0.945   0.534  1.00  0.00           C  
HETATM    9  O3  UNL     1      -2.011  -1.228   1.450  1.00  0.00           O  
HETATM   10  C7  UNL     1       0.213  -0.644   0.943  1.00  0.00           C  
HETATM   11  C8  UNL     1       0.966  -0.341  -0.331  1.00  0.00           C  
HETATM   12  C9  UNL     1       2.415  -0.012  -0.092  1.00  0.00           C  
HETATM   13  C10 UNL     1       3.114  -1.168   0.573  1.00  0.00           C  
HETATM   14  C11 UNL     1       4.542  -0.905   0.832  1.00  0.00           C  
HETATM   15  C12 UNL     1       5.170   0.217   0.524  1.00  0.00           C  
HETATM   16  C13 UNL     1       6.614   0.453   0.798  1.00  0.00           C  
HETATM   17  C14 UNL     1       6.755   1.706   1.631  1.00  0.00           C  
HETATM   18  C15 UNL     1       7.282   0.713  -0.534  1.00  0.00           C  
HETATM   19  C16 UNL     1      -3.542   0.866   0.000  1.00  0.00           C  
HETATM   20  C17 UNL     1      -4.458   1.742   0.534  1.00  0.00           C  
HETATM   21  C18 UNL     1      -5.788   1.483   0.464  1.00  0.00           C  
HETATM   22  O4  UNL     1      -6.755   2.356   0.998  1.00  0.00           O  
HETATM   23  H1  UNL     1      -7.689  -2.033  -0.290  1.00  0.00           H  
HETATM   24  H2  UNL     1      -7.582  -1.217  -1.886  1.00  0.00           H  
HETATM   25  H3  UNL     1      -9.122  -1.104  -0.906  1.00  0.00           H  
HETATM   26  H4  UNL     1      -5.635  -1.510  -1.197  1.00  0.00           H  
HETATM   27  H5  UNL     1      -3.273  -2.245  -0.922  1.00  0.00           H  
HETATM   28  H6  UNL     1      -2.964  -1.152  -2.287  1.00  0.00           H  
HETATM   29  H7  UNL     1       0.617  -1.562   1.417  1.00  0.00           H  
HETATM   30  H8  UNL     1       0.291   0.226   1.594  1.00  0.00           H  
HETATM   31  H9  UNL     1       0.827  -1.155  -1.069  1.00  0.00           H  
HETATM   32  H10 UNL     1       0.497   0.599  -0.746  1.00  0.00           H  
HETATM   33  H11 UNL     1       2.896   0.147  -1.076  1.00  0.00           H  
HETATM   34  H12 UNL     1       2.464   0.915   0.471  1.00  0.00           H  
HETATM   35  H13 UNL     1       3.021  -2.080  -0.051  1.00  0.00           H  
HETATM   36  H14 UNL     1       2.636  -1.399   1.560  1.00  0.00           H  
HETATM   37  H15 UNL     1       5.119  -1.688   1.309  1.00  0.00           H  
HETATM   38  H16 UNL     1       4.617   1.011   0.048  1.00  0.00           H  
HETATM   39  H17 UNL     1       7.079  -0.393   1.341  1.00  0.00           H  
HETATM   40  H18 UNL     1       7.815   1.764   2.000  1.00  0.00           H  
HETATM   41  H19 UNL     1       6.110   1.687   2.529  1.00  0.00           H  
HETATM   42  H20 UNL     1       6.583   2.613   1.011  1.00  0.00           H  
HETATM   43  H21 UNL     1       6.547   0.800  -1.369  1.00  0.00           H  
HETATM   44  H22 UNL     1       7.881  -0.209  -0.773  1.00  0.00           H  
HETATM   45  H23 UNL     1       7.947   1.605  -0.497  1.00  0.00           H  
HETATM   46  H24 UNL     1      -2.484   1.090   0.063  1.00  0.00           H  
HETATM   47  H25 UNL     1      -4.108   2.637   1.009  1.00  0.00           H  
HETATM   48  H26 UNL     1      -7.738   2.140   0.933  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3
CONECT    3    4    4   21
CONECT    4    5   26
CONECT    5    6   19   19
CONECT    6    7   27   28
CONECT    7    8
CONECT    8    9    9   10
CONECT   10   11   29   30
CONECT   11   12   31   32
CONECT   12   13   33   34
CONECT   13   14   35   36
CONECT   14   15   15   37
CONECT   15   16   38
CONECT   16   17   18   39
CONECT   17   40   41   42
CONECT   18   43   44   45
CONECT   19   20   46
CONECT   20   21   21   47
CONECT   21   22
CONECT   22   48
END

HMDB0034780
     RDKit          3D
Capsiate
 48 48  0  0  0  0  0  0  0  0999 V2000
   -8.0199   -1.1275   -0.8560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5829    0.0596   -0.2246 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2073    0.3055   -0.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3131   -0.5898   -0.7066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9639   -0.2940   -0.6168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9522   -1.2044   -1.1794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6339   -0.9266   -0.7670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1962   -0.9448    0.5338 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0113   -1.2284    1.4496 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2126   -0.6440    0.9429 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9660   -0.3414   -0.3309 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4148   -0.0121   -0.0918 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1145   -1.1684    0.5735 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5420   -0.9051    0.8319 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1703    0.2173    0.5238 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6138    0.4534    0.7978 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7548    1.7059    1.6307 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2825    0.7132   -0.5340 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5421    0.8660    0.0004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4576    1.7418    0.5337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7875    1.4832    0.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7553    2.3556    0.9978 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6893   -2.0334   -0.2896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5817   -1.2170   -1.8858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1220   -1.1039   -0.9064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6349   -1.5104   -1.1972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2726   -2.2449   -0.9219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9641   -1.1522   -2.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6165   -1.5624    1.4168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2911    0.2259    1.5943 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8274   -1.1554   -1.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4971    0.5985   -0.7456 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8962    0.1469   -1.0762 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4641    0.9150    0.4712 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0210   -2.0797   -0.0506 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6357   -1.3990    1.5597 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1193   -1.6882    1.3091 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6167    1.0113    0.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0786   -0.3933    1.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8152    1.7636    1.9999 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1095    1.6866    2.5293 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5832    2.6134    1.0111 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5470    0.8000   -1.3687 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8814   -0.2089   -0.7734 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9466    1.6052   -0.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4842    1.0900    0.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1078    2.6366    1.0086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7379    2.1404    0.9325 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
  5 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21  3  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  4 26  1  0
  6 27  1  0
  6 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  1  0
 17 42  1  0
 18 43  1  0
 18 44  1  0
 18 45  1  0
 19 46  1  0
 20 47  1  0
 22 48  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Vanillyl (6E)-8-methylnon-6-enoate	ChEBI
Vanillyl (6E)-8-methylnon-6-enoic acid	Generator
Capsiic acid	Generator
4-Hydroxy-3-methoxybenzyl 8-methyl-6-nonenoate	HMDB
Dihydrocapsiate	MeSH, HMDB
Nonanoic acid, 8-methyl-, (4-hydroxy-3-methoxyphenyl)methyl ester	MeSH

Chemical Formula

C₁₈H₂₆O₄

Average Molecular Weight

306.3966

Monoisotopic Molecular Weight

306.18310932

IUPAC Name

(4-hydroxy-3-methoxyphenyl)methyl (6E)-8-methylnon-6-enoate

Traditional Name

(4-hydroxy-3-methoxyphenyl)methyl (6E)-8-methylnon-6-enoate

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=CC(COC(=O)CCCC\C=C\C(C)C)=C1

InChI Identifier

InChI=1S/C18H26O4/c1-14(2)8-6-4-5-7-9-18(20)22-13-15-10-11-16(19)17(12-15)21-3/h6,8,10-12,14,19H,4-5,7,9,13H2,1-3H3/b8-6+

InChI Key

ZICNYIDDNJYKCP-SOFGYWHQSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Benzyloxycarbonyl
Methoxyphenol
Anisole
Phenoxy compound
Phenol ether
Methoxybenzene
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Alkyl aryl ether
Fatty acyl
Monocyclic benzene moiety
Carboxylic acid ester
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organooxygen compound
Carbonyl group
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

Cell membrane (HMDB: HMDB0034780)

Cellular substructure

Membrane (HMDB: HMDB0034780)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034780)

Source

Exogenous

Food

Food (HMDB: HMDB0034780)

Vegetable

Fruit vegetable

Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Orange bell pepper (FooDB: FOOD00879)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Fruit

Fruits (FooDB: FOOD00871)

Endogenous

Plant

Plant (HMDB: HMDB0034780)

Not Available

Nutrient (HMDB: HMDB0034780)

Pro-oxidant (HMDB: HMDB0034780)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	421.27 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.53 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	4.515 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.011 g/L	ALOGPS
logP	4.5	ALOGPS
logP	4.48	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	9.91	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	88.37 m³·mol⁻¹	ChemAxon
Polarizability	35.59 Å³	ChemAxon
Number of Rings	1	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
DarkChem	[M+H]+	175.898	31661259
DarkChem	[M-H]-	173.576	31661259
DeepCCS	[M+H]+	192.788	30932474
DeepCCS	[M-H]-	190.43	30932474
DeepCCS	[M-2H]-	223.317	30932474
DeepCCS	[M+Na]+	198.881	30932474
AllCCS	[M+H]+	176.8	32859911
AllCCS	[M+H-H2O]+	173.8	32859911
AllCCS	[M+NH4]+	179.6	32859911
AllCCS	[M+Na]+	180.4	32859911
AllCCS	[M-H]-	178.5	32859911
AllCCS	[M+Na-2H]-	179.2	32859911
AllCCS	[M+HCOO]-	180.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Capsiate	COC1=C(O)C=CC(COC(=O)CCCC\C=C\C(C)C)=C1	3690.2	Standard polar	33892256
Capsiate	COC1=C(O)C=CC(COC(=O)CCCC\C=C\C(C)C)=C1	2283.3	Standard non polar	33892256
Capsiate	COC1=C(O)C=CC(COC(=O)CCCC\C=C\C(C)C)=C1	2301.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Capsiate,1TMS,isomer #1	COC1=CC(COC(=O)CCCC/C=C/C(C)C)=CC=C1O[Si](C)(C)C	2422.4	Semi standard non polar	33892256
Capsiate,1TBDMS,isomer #1	COC1=CC(COC(=O)CCCC/C=C/C(C)C)=CC=C1O[Si](C)(C)C(C)(C)C	2658.2	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 - Capsiate GC-MS (Non-derivatized) - 70eV, Positive	splash10-055u-5920000000-60d000d43b1f9096c192	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Capsiate GC-MS (1 TMS) - 70eV, Positive	splash10-01t9-7965000000-9061c1d933cf836a3a4c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Capsiate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Capsiate 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 - Capsiate 10V, Positive-QTOF	splash10-0a4r-0915000000-d19997b754042e7519cd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capsiate 20V, Positive-QTOF	splash10-000i-2900000000-f589d122afe9d7c95df2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capsiate 40V, Positive-QTOF	splash10-052r-8900000000-45c9e4b9e1a49bb886d2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capsiate 10V, Negative-QTOF	splash10-0pb9-0908000000-d0650030a37b0e1edd5f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capsiate 20V, Negative-QTOF	splash10-0uxr-0901000000-41bf8df5d7f9f5c0de1d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capsiate 40V, Negative-QTOF	splash10-0k9f-3900000000-ea96ed7aae0cb04b6649	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capsiate 10V, Negative-QTOF	splash10-014i-0900000000-3af65de2869b973825d6	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capsiate 20V, Negative-QTOF	splash10-0v6r-1900000000-973956f425d4207c3559	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capsiate 40V, Negative-QTOF	splash10-0udi-3912000000-fa5e9b2552f99de0f277	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capsiate 10V, Positive-QTOF	splash10-052r-0900000000-7fa0654d4ef4c85920a2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capsiate 20V, Positive-QTOF	splash10-0a4r-1900000000-f6058625f5a778bf7299	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capsiate 40V, Positive-QTOF	splash10-052r-3900000000-97d9169adb4f26f974b8	2021-09-22	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9839519

PDB ID

Not Available

ChEBI ID

134190

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1679241

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Macho A, Sancho R, Minassi A, Appendino G, Lawen A, Munoz E: Involvement of reactive oxygen species in capsaicinoid-induced apoptosis in transformed cells. Free Radic Res. 2003 Jun;37(6):611-9. [PubMed:12868488 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Capsiate (HMDB0034780)

MOL for HMDB0034780 (Capsiate)

3D MOL for HMDB0034780 (Capsiate)

3D SDF for HMDB0034780 (Capsiate)

3D-SDF for HMDB0034780 (Capsiate)

PDB for HMDB0034780 (Capsiate)

3D PDB for HMDB0034780 (Capsiate)

SMILES for HMDB0034780 (Capsiate)

INCHI for HMDB0034780 (Capsiate)

Structure for HMDB0034780 (Capsiate)

3D Structure for HMDB0034780 (Capsiate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra