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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-05-22 14:17:49 UTC

Update Date

2022-03-07 02:49:15 UTC

HMDB ID

HMDB0002352

Secondary Accession Numbers

HMDB02352

Metabolite Identification

Common Name

Capsidiol

Description

Capsidiol is a phytoalexin, a natural fungicide present in pepper. (PMID: 10335386 ). Capsidiol shows bacteriostatic properties in vitro against Helicobacter pylori with a minimum inhibitory concentration (MIC) of 200 microg/mL. (PMID: 17002415 ). Capsidiol is a bicyclic, dihydroxylated sesquiterpene produced by several solanaceous species in response to a variety of environmental stimuli. It is the primary antimicrobial compound produced by Nicotiana tabacum in response to fungal elicitation, and it is formed via the isoprenoid pathway from 5-epi-aristolochene. (PMID: 11556809 ).

Structure

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

HMDB0002352
     RDKit          3D
Capsidiol
 41 42  0  0  0  0  0  0  0  0999 V2000
    3.9331    0.6623   -0.2253 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0794   -0.3493   -0.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5599   -1.5834    0.5976 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7086   -0.3218   -0.7225 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5048    0.9280   -1.5249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0645    0.9273   -1.9279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8787    0.6813   -1.0343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2856    0.6956   -1.5007 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6817    2.0347   -1.5589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2189   -0.1019   -0.6599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5729   -0.9185    0.4059 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9976   -2.0673   -0.1191 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5752   -0.1078    1.2167 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0860   -0.9979    2.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4492    0.4162    0.3593 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0459    1.7725    0.9547 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7073   -0.5199    0.3599 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9074    0.5709    0.2217 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7313    1.6036   -0.7225 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5793   -1.7743    0.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5194   -1.4381    1.6816 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9184   -2.4291    0.2972 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6831   -1.1743   -1.4639 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1797    0.8808   -2.4010 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7627    1.8651   -0.9825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1786    1.1310   -2.9567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3078    0.3257   -2.5497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2636    2.1831   -2.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9570    0.5982   -0.1796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8170   -0.8026   -1.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3592   -1.2432    1.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6646   -2.8026   -0.1588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1641    0.7072    1.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8495   -2.0241    1.9855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9281   -1.0969    3.0525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2462   -0.5475    2.8988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6350    2.0195    1.8612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2112    2.6036    0.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0203    1.7271    1.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1964   -0.4726    1.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3179   -1.5606    0.2871 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  2  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  1
 15 17  1  0
 17  4  1  0
 15  7  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  6
  5 24  1  0
  5 25  1  0
  6 26  1  0
  8 27  1  6
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  1
 12 32  1  0
 13 33  1  1
 14 34  1  0
 14 35  1  0
 14 36  1  0
 16 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  1  0
M  END

Capsidiol
  Mrv1572001071617112D          

 17 18  0  0  1  0            999 V2000
   -0.2101   -0.1213    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2101    0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5043   -0.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9246   -0.5338    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2101   -0.9463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9246    1.1162    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5043    1.1162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2188   -0.1213    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6391   -0.1213    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9246   -1.3588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6391    0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9246    1.9412    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2188    0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9333   -0.5338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3536   -0.5338    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6477   -0.1213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9333   -1.3588    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  1  5  1  1  0  0  0
  2  6  1  0  0  0  0
  2  7  2  0  0  0  0
  3  8  1  0  0  0  0
  4  9  1  0  0  0  0
  4 10  1  6  0  0  0
  6 11  1  0  0  0  0
  6 12  1  1  0  0  0
  7 13  1  0  0  0  0
  8 14  1  1  0  0  0
  9 15  1  6  0  0  0
 14 16  2  0  0  0  0
 14 17  1  0  0  0  0
  8 13  1  0  0  0  0
  9 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002352

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@@H]1[C@H](O)C[C@@H](O)C2=CC[C@H](C[C@]12C)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O2/c1-9(2)11-5-6-12-14(17)7-13(16)10(3)15(12,4)8-11/h6,10-11,13-14,16-17H,1,5,7-8H2,2-4H3/t10-,11-,13-,14-,15-/m1/s1

> <INCHI_KEY>
BXXSHQYDJWZXPB-OKNSCYNVSA-N

> <FORMULA>
C15H24O2

> <MOLECULAR_WEIGHT>
236.355

> <EXACT_MASS>
236.177630013

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
41

> <JCHEM_AVERAGE_POLARIZABILITY>
27.63993652611021

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3R,4S,4aR,6R)-4,4a-dimethyl-6-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalene-1,3-diol

> <ALOGPS_LOGP>
2.70

> <JCHEM_LOGP>
1.9069395216666671

> <ALOGPS_LOGS>
-2.45

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.109427768957616

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.349248791835812

> <JCHEM_PKA_STRONGEST_BASIC>
-2.870269296051214

> <JCHEM_POLAR_SURFACE_AREA>
40.46

> <JCHEM_REFRACTIVITY>
70.51679999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.47e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
capsidiol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002352
     RDKit          3D
Capsidiol
 41 42  0  0  0  0  0  0  0  0999 V2000
    3.9331    0.6623   -0.2253 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0794   -0.3493   -0.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5599   -1.5834    0.5976 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7086   -0.3218   -0.7225 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5048    0.9280   -1.5249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0645    0.9273   -1.9279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8787    0.6813   -1.0343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2856    0.6956   -1.5007 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6817    2.0347   -1.5589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2189   -0.1019   -0.6599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5729   -0.9185    0.4059 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9976   -2.0673   -0.1191 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5752   -0.1078    1.2167 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0860   -0.9979    2.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4492    0.4162    0.3593 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0459    1.7725    0.9547 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7073   -0.5199    0.3599 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9074    0.5709    0.2217 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7313    1.6036   -0.7225 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5793   -1.7743    0.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5194   -1.4381    1.6816 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9184   -2.4291    0.2972 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6831   -1.1743   -1.4639 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1797    0.8808   -2.4010 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7627    1.8651   -0.9825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1786    1.1310   -2.9567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3078    0.3257   -2.5497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2636    2.1831   -2.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9570    0.5982   -0.1796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8170   -0.8026   -1.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3592   -1.2432    1.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6646   -2.8026   -0.1588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1641    0.7072    1.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8495   -2.0241    1.9855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9281   -1.0969    3.0525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2462   -0.5475    2.8988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6350    2.0195    1.8612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2112    2.6036    0.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0203    1.7271    1.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1964   -0.4726    1.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3179   -1.5606    0.2871 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  2  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  1
 15 17  1  0
 17  4  1  0
 15  7  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  6
  5 24  1  0
  5 25  1  0
  6 26  1  0
  8 27  1  6
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  1
 12 32  1  0
 13 33  1  1
 14 34  1  0
 14 35  1  0
 14 36  1  0
 16 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  1  0
M  END

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Capsidiol                                         
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  C   UNK     0      -0.392  -0.226   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.392   1.314   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.941  -0.996   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.726  -0.996   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.392  -1.766   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.726   2.084   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.941   2.084   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.275  -0.226   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.060  -0.226   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.726  -2.536   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.060   1.314   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.726   3.624   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.275   1.314   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.609  -0.996   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.393  -0.996   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       4.942  -0.226   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.609  -2.536   0.000  0.00  0.00           C+0
CONECT    1    2    3    4    5                                             
CONECT    2    1    6    7                                                  
CONECT    3    1    8                                                       
CONECT    4    1    9   10                                                  
CONECT    5    1                                                            
CONECT    6    2   11   12                                                  
CONECT    7    2   13                                                       
CONECT    8    3   14   13                                                  
CONECT    9    4   15   11                                                  
CONECT   10    4                                                            
CONECT   11    6    9                                                       
CONECT   12    6                                                            
CONECT   13    7    8                                                       
CONECT   14    8   16   17                                                  
CONECT   15    9                                                            
CONECT   16   14                                                            
CONECT   17   14                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0002352
HETATM    1  C1  UNL     1       3.933   0.662  -0.225  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.079  -0.349  -0.141  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.560  -1.583   0.598  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.709  -0.322  -0.723  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.505   0.928  -1.525  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.064   0.927  -1.928  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.879   0.681  -1.034  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.286   0.696  -1.501  1.00  0.00           C  
HETATM    9  O1  UNL     1      -2.682   2.035  -1.559  1.00  0.00           O  
HETATM   10  C9  UNL     1      -3.219  -0.102  -0.660  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.573  -0.918   0.406  1.00  0.00           C  
HETATM   12  O2  UNL     1      -1.998  -2.067  -0.119  1.00  0.00           O  
HETATM   13  C11 UNL     1      -1.575  -0.108   1.217  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.086  -0.998   2.336  1.00  0.00           C  
HETATM   15  C13 UNL     1      -0.449   0.416   0.359  1.00  0.00           C  
HETATM   16  C14 UNL     1      -0.046   1.772   0.955  1.00  0.00           C  
HETATM   17  C15 UNL     1       0.707  -0.520   0.360  1.00  0.00           C  
HETATM   18  H1  UNL     1       4.907   0.571   0.222  1.00  0.00           H  
HETATM   19  H2  UNL     1       3.731   1.604  -0.722  1.00  0.00           H  
HETATM   20  H3  UNL     1       4.579  -1.774   0.229  1.00  0.00           H  
HETATM   21  H4  UNL     1       3.519  -1.438   1.682  1.00  0.00           H  
HETATM   22  H5  UNL     1       2.918  -2.429   0.297  1.00  0.00           H  
HETATM   23  H6  UNL     1       1.683  -1.174  -1.464  1.00  0.00           H  
HETATM   24  H7  UNL     1       2.180   0.881  -2.401  1.00  0.00           H  
HETATM   25  H8  UNL     1       1.763   1.865  -0.982  1.00  0.00           H  
HETATM   26  H9  UNL     1      -0.179   1.131  -2.957  1.00  0.00           H  
HETATM   27  H10 UNL     1      -2.308   0.326  -2.550  1.00  0.00           H  
HETATM   28  H11 UNL     1      -3.264   2.183  -2.344  1.00  0.00           H  
HETATM   29  H12 UNL     1      -3.957   0.598  -0.180  1.00  0.00           H  
HETATM   30  H13 UNL     1      -3.817  -0.803  -1.299  1.00  0.00           H  
HETATM   31  H14 UNL     1      -3.359  -1.243   1.119  1.00  0.00           H  
HETATM   32  H15 UNL     1      -2.665  -2.803  -0.159  1.00  0.00           H  
HETATM   33  H16 UNL     1      -2.164   0.707   1.696  1.00  0.00           H  
HETATM   34  H17 UNL     1      -0.850  -2.024   1.985  1.00  0.00           H  
HETATM   35  H18 UNL     1      -1.928  -1.097   3.052  1.00  0.00           H  
HETATM   36  H19 UNL     1      -0.246  -0.548   2.899  1.00  0.00           H  
HETATM   37  H20 UNL     1      -0.635   2.019   1.861  1.00  0.00           H  
HETATM   38  H21 UNL     1      -0.211   2.604   0.243  1.00  0.00           H  
HETATM   39  H22 UNL     1       1.020   1.727   1.296  1.00  0.00           H  
HETATM   40  H23 UNL     1       1.196  -0.473   1.375  1.00  0.00           H  
HETATM   41  H24 UNL     1       0.318  -1.561   0.287  1.00  0.00           H  
CONECT    1    2    2   18   19
CONECT    2    3    4
CONECT    3   20   21   22
CONECT    4    5   17   23
CONECT    5    6   24   25
CONECT    6    7    7   26
CONECT    7    8   15
CONECT    8    9   10   27
CONECT    9   28
CONECT   10   11   29   30
CONECT   11   12   13   31
CONECT   12   32
CONECT   13   14   15   33
CONECT   14   34   35   36
CONECT   15   16   17
CONECT   16   37   38   39
CONECT   17   40   41
END

HMDB0002352
     RDKit          3D
Capsidiol
 41 42  0  0  0  0  0  0  0  0999 V2000
    3.9331    0.6623   -0.2253 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0794   -0.3493   -0.1409 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5599   -1.5834    0.5976 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7086   -0.3218   -0.7225 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.5048    0.9280   -1.5249 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0645    0.9273   -1.9279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8787    0.6813   -1.0343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2856    0.6956   -1.5007 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6817    2.0347   -1.5589 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2189   -0.1019   -0.6599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5729   -0.9185    0.4059 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9976   -2.0673   -0.1191 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5752   -0.1078    1.2167 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0860   -0.9979    2.3357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4492    0.4162    0.3593 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0459    1.7725    0.9547 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7073   -0.5199    0.3599 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9074    0.5709    0.2217 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7313    1.6036   -0.7225 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5793   -1.7743    0.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5194   -1.4381    1.6816 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9184   -2.4291    0.2972 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6831   -1.1743   -1.4639 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1797    0.8808   -2.4010 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7627    1.8651   -0.9825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1786    1.1310   -2.9567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3078    0.3257   -2.5497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2636    2.1831   -2.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9570    0.5982   -0.1796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8170   -0.8026   -1.2989 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3592   -1.2432    1.1192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6646   -2.8026   -0.1588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1641    0.7072    1.6956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8495   -2.0241    1.9855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9281   -1.0969    3.0525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2462   -0.5475    2.8988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6350    2.0195    1.8612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2112    2.6036    0.2429 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0203    1.7271    1.2955 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1964   -0.4726    1.3748 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3179   -1.5606    0.2871 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  2  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  1
 15 17  1  0
 17  4  1  0
 15  7  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  6
  5 24  1  0
  5 25  1  0
  6 26  1  0
  8 27  1  6
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  1
 12 32  1  0
 13 33  1  1
 14 34  1  0
 14 35  1  0
 14 36  1  0
 16 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(1R,3R,4S,4AR,6R)-6-isopropenyl-4,4a-dimethyl-1,2,3,4,4a,5,6,7-octahydronaphthalene-1,3-diol	ChEBI
(1R,3R,4S,4AR,6R)-4,4a-dimethyl-6-prop-1-en-2-yl-2,3,4,5,6,7-hexahydro-1H-naphthalene-1,3-diol	HMDB

Chemical Formula

C₁₅H₂₄O₂

Average Molecular Weight

236.355

Monoisotopic Molecular Weight

236.177630013

IUPAC Name

(1R,3R,4S,4aR,6R)-4,4a-dimethyl-6-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalene-1,3-diol

Traditional Name

capsidiol

CAS Registry Number

37208-05-2

SMILES

C[C@@H]1[C@H](O)C[C@@H](O)C2=CC[C@H](C[C@]12C)C(C)=C

InChI Identifier

InChI=1S/C15H24O2/c1-9(2)11-5-6-12-14(17)7-13(16)10(3)15(12,4)8-11/h6,10-11,13-14,16-17H,1,5,7-8H2,2-4H3/t10-,11-,13-,14-,15-/m1/s1

InChI Key

BXXSHQYDJWZXPB-OKNSCYNVSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

Alternative Parents

Substituents

Eremophilane sesquiterpenoid
Cyclic alcohol
Secondary alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

eremophilane sesquiterpenoid (CHEBI:28283 )
Eremophilane sesquiterpenoids (C09627 )
Germacrenes (C09627 )
Eremophilane sesquiterpenoids (LMPR0103250002 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0002352)
Membrane (HMDB: HMDB0002352)

Source

Exogenous

Exogenous (HMDB: HMDB0002352)

Food

Vegetable

Fruit vegetable

Pepper (FooDB: FOOD00040)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Italian sweet red pepper (FooDB: FOOD00881)
Pepper (C. frutescens) (FooDB: FOOD00428)
Orange bell pepper (FooDB: FOOD00879)

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Process

Not Available

Role

Industrial application

Agriculture

Pesticide

Fungicide (HMDB: HMDB0002352)

Pesticide (HMDB: HMDB0002352)

Biological role

Phytoalexin (HMDB: HMDB0002352)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	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	0.85 g/L	ALOGPS
logP	2.7	ALOGPS
logP	1.91	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	14.35	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	40.46 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	70.52 m³·mol⁻¹	ChemAxon
Polarizability	27.64 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
DarkChem	[M+H]+	159.163	31661259
DarkChem	[M-H]-	154.332	31661259
DeepCCS	[M-2H]-	196.577	30932474
DeepCCS	[M+Na]+	171.518	30932474
AllCCS	[M+H]+	157.4	32859911
AllCCS	[M+H-H2O]+	153.7	32859911
AllCCS	[M+NH4]+	160.8	32859911
AllCCS	[M+Na]+	161.8	32859911
AllCCS	[M-H]-	162.5	32859911
AllCCS	[M+Na-2H]-	163.0	32859911
AllCCS	[M+HCOO]-	163.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Capsidiol	C[C@@H]1[C@H](O)C[C@@H](O)C2=CC[C@H](C[C@]12C)C(C)=C	2801.0	Standard polar	33892256
Capsidiol	C[C@@H]1[C@H](O)C[C@@H](O)C2=CC[C@H](C[C@]12C)C(C)=C	1847.8	Standard non polar	33892256
Capsidiol	C[C@@H]1[C@H](O)C[C@@H](O)C2=CC[C@H](C[C@]12C)C(C)=C	1909.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Capsidiol,1TMS,isomer #1	C=C(C)[C@@H]1CC=C2[C@H](O)C[C@@H](O[Si](C)(C)C)[C@@H](C)[C@@]2(C)C1	1925.7	Semi standard non polar	33892256
Capsidiol,1TMS,isomer #2	C=C(C)[C@@H]1CC=C2[C@H](O[Si](C)(C)C)C[C@@H](O)[C@@H](C)[C@@]2(C)C1	1936.6	Semi standard non polar	33892256
Capsidiol,2TMS,isomer #1	C=C(C)[C@@H]1CC=C2[C@H](O[Si](C)(C)C)C[C@@H](O[Si](C)(C)C)[C@@H](C)[C@@]2(C)C1	1937.1	Semi standard non polar	33892256
Capsidiol,1TBDMS,isomer #1	C=C(C)[C@@H]1CC=C2[C@H](O)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](C)[C@@]2(C)C1	2207.6	Semi standard non polar	33892256
Capsidiol,1TBDMS,isomer #2	C=C(C)[C@@H]1CC=C2[C@H](O[Si](C)(C)C(C)(C)C)C[C@@H](O)[C@@H](C)[C@@]2(C)C1	2206.2	Semi standard non polar	33892256
Capsidiol,2TBDMS,isomer #1	C=C(C)[C@@H]1CC=C2[C@H](O[Si](C)(C)C(C)(C)C)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H](C)[C@@]2(C)C1	2413.3	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 - Capsidiol GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-2930000000-c6a7a1a3b2cd45b78729	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Capsidiol GC-MS (2 TMS) - 70eV, Positive	splash10-016u-6197000000-8f3e3a1289174fe1cd87	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Capsidiol 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 - Capsidiol 10V, Positive-QTOF	splash10-014r-0190000000-4f408854a045f002ce8c	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capsidiol 20V, Positive-QTOF	splash10-0gbi-2690000000-f2e94dce44ae9b9ac2df	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capsidiol 40V, Positive-QTOF	splash10-0uxr-9710000000-4e4ebb2003b289f81d11	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capsidiol 10V, Negative-QTOF	splash10-000i-0090000000-e1fa0089980b18e8a422	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capsidiol 20V, Negative-QTOF	splash10-00kr-0190000000-5cc78cd709d6e3a58815	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capsidiol 40V, Negative-QTOF	splash10-0i09-2960000000-4d5021b41dbcabf76b87	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capsidiol 10V, Negative-QTOF	splash10-000i-0090000000-c0031dc201eac6b6350a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capsidiol 20V, Negative-QTOF	splash10-000i-0190000000-c5d1ce0d6817df353cab	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capsidiol 40V, Negative-QTOF	splash10-001i-0940000000-b0c4585c354b5421c7d1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capsidiol 10V, Positive-QTOF	splash10-002r-0970000000-ddcf71bbc9544a614675	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capsidiol 20V, Positive-QTOF	splash10-00n0-3940000000-fdbebf5ba44e69f05505	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Capsidiol 40V, Positive-QTOF	splash10-015c-9310000000-1b969f3a620273af3ea8	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
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

Capsidiol

METLIN ID

Not Available

PubChem Compound

161937

PDB ID

Not Available

ChEBI ID

28283

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

De Marino S, Borbone N, Gala F, Zollo F, Fico G, Pagiotti R, Iorizzi M: New constituents of sweet Capsicum annuum L. fruits and evaluation of their biological activity. J Agric Food Chem. 2006 Oct 4;54(20):7508-16. [PubMed:17002415 ]
Lozoya-Gloria E: Biochemical and molecular tools for the production of useful terpene products from pepper (Capsicum annuum). Adv Exp Med Biol. 1999;464:63-76. [PubMed:10335386 ]
Ralston L, Kwon ST, Schoenbeck M, Ralston J, Schenk DJ, Coates RM, Chappell J: Cloning, heterologous expression, and functional characterization of 5-epi-aristolochene-1,3-dihydroxylase from tobacco (Nicotiana tabacum). Arch Biochem Biophys. 2001 Sep 15;393(2):222-35. [PubMed:11556809 ]

Showing metabocard for Capsidiol (HMDB0002352)

MOL for HMDB0002352 (Capsidiol)

3D MOL for HMDB0002352 (Capsidiol)

3D SDF for HMDB0002352 (Capsidiol)

3D-SDF for HMDB0002352 (Capsidiol)

PDB for HMDB0002352 (Capsidiol)

3D PDB for HMDB0002352 (Capsidiol)

SMILES for HMDB0002352 (Capsidiol)

INCHI for HMDB0002352 (Capsidiol)

Structure for HMDB0002352 (Capsidiol)

3D Structure for HMDB0002352 (Capsidiol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra