Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:55:07 UTC

Update Date

2022-03-07 02:54:18 UTC

HMDB ID

HMDB0034983

Secondary Accession Numbers

HMDB34983

Metabolite Identification

Common Name

Cynaratriol

Description

Cynaratriol belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. Based on a literature review a small amount of articles have been published on Cynaratriol.

Structure

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

HMDB0034983
     RDKit          3D
Cynaratriol
 42 44  0  0  0  0  0  0  0  0999 V2000
    1.3228    3.1079    0.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6809    2.0025    0.3932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7825    2.1024    0.5991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6230    1.5607   -0.5118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4062    0.1376   -0.8360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4648   -0.5880    0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7523   -1.9393   -0.2075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0383   -2.0753   -0.6871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6468   -3.1127   -1.0803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6418   -0.7133   -0.6683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5620   -0.5370   -1.6823 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2995   -0.5391    0.6772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3212   -1.5075    0.7827 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9139   -0.2783   -0.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4902    0.7817    0.5787 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8864    0.8588    0.0058 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2430   -0.6228   -0.2047 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7733   -0.7232   -1.4811 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9161   -1.3715   -0.2037 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7441   -2.1847    1.0529 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7159    4.0220   -0.1150 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3868    3.1590   -0.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0196    3.1871    0.7017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0133    1.6400    1.5814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6799    1.7764   -0.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4113    2.1741   -1.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0303    0.0098   -1.8497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6507   -0.3411    1.1677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7526    0.4412   -1.7301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6247   -0.6950    1.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8186    0.4359    0.7752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0247   -2.2922    1.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9715    0.1311   -1.3660 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4965    0.4458    1.6361 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5747    1.3516    0.6806 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8457    1.3863   -0.9521 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9223   -0.9873    0.5831 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7494   -0.8945   -1.4678 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8381   -2.0328   -1.0911 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9145   -1.8089    1.6919 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4865   -3.2367    0.8101 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6919   -2.2304    1.6522 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  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
 10 12  1  0
 12 13  1  0
  6 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 15  2  1  0
 10  5  1  0
 19 14  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  6 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
 20 41  1  0
 20 42  1  0
M  END


  Mrv0541 05061308102D          

 20 22  0  0  0  0            999 V2000
    4.6417    1.7897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8305   -1.6349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2534    1.6333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5101    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9527    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7384    0.0582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9967    1.2753    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1204   -0.8625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1803    0.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3265    0.4710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9157   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6659   -0.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8409   -0.1740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5912   -0.6430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5541    0.1811    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2240    0.7032    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5607   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9461   -1.1574    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3466    0.9796    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3864   -0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  7  1  2  0  0  0  0
  7  3  1  0  0  0  0
  8  2  1  0  0  0  0
  9  5  1  0  0  0  0
  9  7  1  0  0  0  0
 10  4  1  0  0  0  0
 11  5  1  0  0  0  0
 11  8  1  0  0  0  0
 12  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13 10  1  0  0  0  0
 13 12  1  0  0  0  0
 15  6  1  0  0  0  0
 15 10  1  0  0  0  0
 15 14  1  0  0  0  0
 16  6  1  0  0  0  0
 17 11  1  0  0  0  0
 18 14  2  0  0  0  0
 19 15  1  0  0  0  0
 20 13  1  0  0  0  0
 20 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034983

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1C(O)CC2C1C1OC(=O)C(O)(CO)C1CCC2=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O5/c1-7-3-4-10-13(20-14(18)15(10,19)6-16)12-8(2)11(17)5-9(7)12/h8-13,16-17,19H,1,3-6H2,2H3

> <INCHI_KEY>
OHBHGGYGWZIWCX-UHFFFAOYSA-N

> <FORMULA>
C15H22O5

> <MOLECULAR_WEIGHT>
282.3322

> <EXACT_MASS>
282.146723814

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.54307389395067

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,8-dihydroxy-3-(hydroxymethyl)-9-methyl-6-methylidene-dodecahydroazuleno[4,5-b]furan-2-one

> <ALOGPS_LOGP>
0.24

> <JCHEM_LOGP>
-0.01415802566666749

> <ALOGPS_LOGS>
-1.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.644242028020482

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.361840983359809

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8316259821793404

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
71.0589

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.71e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,8-dihydroxy-3-(hydroxymethyl)-9-methyl-6-methylidene-octahydro-3aH-azuleno[4,5-b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0034983
     RDKit          3D
Cynaratriol
 42 44  0  0  0  0  0  0  0  0999 V2000
    1.3228    3.1079    0.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6809    2.0025    0.3932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7825    2.1024    0.5991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6230    1.5607   -0.5118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4062    0.1376   -0.8360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4648   -0.5880    0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7523   -1.9393   -0.2075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0383   -2.0753   -0.6871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6468   -3.1127   -1.0803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6418   -0.7133   -0.6683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5620   -0.5370   -1.6823 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2995   -0.5391    0.6772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3212   -1.5075    0.7827 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9139   -0.2783   -0.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4902    0.7817    0.5787 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8864    0.8588    0.0058 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2430   -0.6228   -0.2047 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7733   -0.7232   -1.4811 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9161   -1.3715   -0.2037 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7441   -2.1847    1.0529 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7159    4.0220   -0.1150 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3868    3.1590   -0.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0196    3.1871    0.7017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0133    1.6400    1.5814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6799    1.7764   -0.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4113    2.1741   -1.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0303    0.0098   -1.8497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6507   -0.3411    1.1677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7526    0.4412   -1.7301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6247   -0.6950    1.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8186    0.4359    0.7752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0247   -2.2922    1.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9715    0.1311   -1.3660 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4965    0.4458    1.6361 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5747    1.3516    0.6806 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8457    1.3863   -0.9521 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9223   -0.9873    0.5831 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7494   -0.8945   -1.4678 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8381   -2.0328   -1.0911 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9145   -1.8089    1.6919 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4865   -3.2367    0.8101 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6919   -2.2304    1.6522 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  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
 10 12  1  0
 12 13  1  0
  6 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 15  2  1  0
 10  5  1  0
 19 14  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  6 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
 20 41  1  0
 20 42  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       8.665   3.341   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.150  -3.052   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.073   3.049   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.686   2.381   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.245   0.338   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.378   0.109   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.461   2.381   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.691  -1.610   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.803   0.879   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.343   0.879   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.176  -1.200   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.843  -0.325   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.303  -0.325   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.970  -1.200   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.901   0.338   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.418   1.313   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      10.380  -2.160   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.766  -2.160   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.514   1.829   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       4.455  -1.610   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    8                                                            
CONECT    3    4    7                                                       
CONECT    4    3   10                                                       
CONECT    5    9   11                                                       
CONECT    6   15   16                                                       
CONECT    7    1    3    9                                                  
CONECT    8    2   11   12                                                  
CONECT    9    5    7   12                                                  
CONECT   10    4   13   15                                                  
CONECT   11    5    8   17                                                  
CONECT   12    8    9   13                                                  
CONECT   13   10   12   20                                                  
CONECT   14   15   18   20                                                  
CONECT   15    6   10   14   19                                             
CONECT   16    6                                                            
CONECT   17   11                                                            
CONECT   18   14                                                            
CONECT   19   15                                                            
CONECT   20   13   14                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

COMPND    HMDB0034983
HETATM    1  C1  UNL     1       1.323   3.108   0.017  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.681   2.002   0.393  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.782   2.102   0.599  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.623   1.561  -0.512  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.406   0.138  -0.836  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.465  -0.588   0.101  1.00  0.00           C  
HETATM    7  O1  UNL     1      -0.752  -1.939  -0.208  1.00  0.00           O  
HETATM    8  C7  UNL     1      -2.038  -2.075  -0.687  1.00  0.00           C  
HETATM    9  O2  UNL     1      -2.647  -3.113  -1.080  1.00  0.00           O  
HETATM   10  C8  UNL     1      -2.642  -0.713  -0.668  1.00  0.00           C  
HETATM   11  O3  UNL     1      -3.562  -0.537  -1.682  1.00  0.00           O  
HETATM   12  C9  UNL     1      -3.299  -0.539   0.677  1.00  0.00           C  
HETATM   13  O4  UNL     1      -4.321  -1.508   0.783  1.00  0.00           O  
HETATM   14  C10 UNL     1       0.914  -0.278  -0.341  1.00  0.00           C  
HETATM   15  C11 UNL     1       1.490   0.782   0.579  1.00  0.00           C  
HETATM   16  C12 UNL     1       2.886   0.859   0.006  1.00  0.00           C  
HETATM   17  C13 UNL     1       3.243  -0.623  -0.205  1.00  0.00           C  
HETATM   18  O5  UNL     1       3.773  -0.723  -1.481  1.00  0.00           O  
HETATM   19  C14 UNL     1       1.916  -1.372  -0.204  1.00  0.00           C  
HETATM   20  C15 UNL     1       1.744  -2.185   1.053  1.00  0.00           C  
HETATM   21  H1  UNL     1       0.716   4.022  -0.115  1.00  0.00           H  
HETATM   22  H2  UNL     1       2.387   3.159  -0.158  1.00  0.00           H  
HETATM   23  H3  UNL     1      -1.020   3.187   0.702  1.00  0.00           H  
HETATM   24  H4  UNL     1      -1.013   1.640   1.581  1.00  0.00           H  
HETATM   25  H5  UNL     1      -2.680   1.776  -0.251  1.00  0.00           H  
HETATM   26  H6  UNL     1      -1.411   2.174  -1.415  1.00  0.00           H  
HETATM   27  H7  UNL     1      -1.030   0.010  -1.850  1.00  0.00           H  
HETATM   28  H8  UNL     1      -0.651  -0.341   1.168  1.00  0.00           H  
HETATM   29  H9  UNL     1      -3.753   0.441  -1.730  1.00  0.00           H  
HETATM   30  H10 UNL     1      -2.625  -0.695   1.517  1.00  0.00           H  
HETATM   31  H11 UNL     1      -3.819   0.436   0.775  1.00  0.00           H  
HETATM   32  H12 UNL     1      -4.025  -2.292   1.296  1.00  0.00           H  
HETATM   33  H13 UNL     1       0.972   0.131  -1.366  1.00  0.00           H  
HETATM   34  H14 UNL     1       1.496   0.446   1.636  1.00  0.00           H  
HETATM   35  H15 UNL     1       3.575   1.352   0.681  1.00  0.00           H  
HETATM   36  H16 UNL     1       2.846   1.386  -0.952  1.00  0.00           H  
HETATM   37  H17 UNL     1       3.922  -0.987   0.583  1.00  0.00           H  
HETATM   38  H18 UNL     1       4.749  -0.895  -1.468  1.00  0.00           H  
HETATM   39  H19 UNL     1       1.838  -2.033  -1.091  1.00  0.00           H  
HETATM   40  H20 UNL     1       0.914  -1.809   1.692  1.00  0.00           H  
HETATM   41  H21 UNL     1       1.486  -3.237   0.810  1.00  0.00           H  
HETATM   42  H22 UNL     1       2.692  -2.230   1.652  1.00  0.00           H  
CONECT    1    2    2   21   22
CONECT    2    3   15
CONECT    3    4   23   24
CONECT    4    5   25   26
CONECT    5    6   10   27
CONECT    6    7   14   28
CONECT    7    8
CONECT    8    9    9   10
CONECT   10   11   12
CONECT   11   29
CONECT   12   13   30   31
CONECT   13   32
CONECT   14   15   19   33
CONECT   15   16   34
CONECT   16   17   35   36
CONECT   17   18   19   37
CONECT   18   38
CONECT   19   20   39
CONECT   20   40   41   42
END

HMDB0034983
     RDKit          3D
Cynaratriol
 42 44  0  0  0  0  0  0  0  0999 V2000
    1.3228    3.1079    0.0172 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6809    2.0025    0.3932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7825    2.1024    0.5991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6230    1.5607   -0.5118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4062    0.1376   -0.8360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4648   -0.5880    0.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7523   -1.9393   -0.2075 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0383   -2.0753   -0.6871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6468   -3.1127   -1.0803 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6418   -0.7133   -0.6683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5620   -0.5370   -1.6823 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2995   -0.5391    0.6772 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3212   -1.5075    0.7827 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9139   -0.2783   -0.3414 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4902    0.7817    0.5787 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8864    0.8588    0.0058 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2430   -0.6228   -0.2047 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7733   -0.7232   -1.4811 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9161   -1.3715   -0.2037 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7441   -2.1847    1.0529 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7159    4.0220   -0.1150 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3868    3.1590   -0.1581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0196    3.1871    0.7017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0133    1.6400    1.5814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6799    1.7764   -0.2510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4113    2.1741   -1.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0303    0.0098   -1.8497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6507   -0.3411    1.1677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7526    0.4412   -1.7301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6247   -0.6950    1.5167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8186    0.4359    0.7752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0247   -2.2922    1.2963 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9715    0.1311   -1.3660 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4965    0.4458    1.6361 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5747    1.3516    0.6806 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8457    1.3863   -0.9521 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9223   -0.9873    0.5831 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7494   -0.8945   -1.4678 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8381   -2.0328   -1.0911 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9145   -1.8089    1.6919 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4865   -3.2367    0.8101 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6919   -2.2304    1.6522 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  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
 10 12  1  0
 12 13  1  0
  6 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 15  2  1  0
 10  5  1  0
 19 14  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  4 26  1  0
  5 27  1  0
  6 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
 17 37  1  0
 18 38  1  0
 19 39  1  0
 20 40  1  0
 20 41  1  0
 20 42  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
3,11,13-Trihydroxy-10(14)-guaien-12,6-olide	HMDB
Tipropidil	HMDB

Chemical Formula

C₁₅H₂₂O₅

Average Molecular Weight

282.3322

Monoisotopic Molecular Weight

282.146723814

IUPAC Name

3,8-dihydroxy-3-(hydroxymethyl)-9-methyl-6-methylidene-dodecahydroazuleno[4,5-b]furan-2-one

Traditional Name

3,8-dihydroxy-3-(hydroxymethyl)-9-methyl-6-methylidene-octahydro-3aH-azuleno[4,5-b]furan-2-one

CAS Registry Number

70894-20-1

SMILES

CC1C(O)CC2C1C1OC(=O)C(O)(CO)C1CCC2=C

InChI Identifier

InChI=1S/C15H22O5/c1-7-3-4-10-13(20-14(18)15(10,19)6-16)12-8(2)11(17)5-9(7)12/h8-13,16-17,19H,1,3-6H2,2H3

InChI Key

OHBHGGYGWZIWCX-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Substituents

Guaianolide-skeleton
Guaiane sesquiterpenoid
Sesquiterpenoid
Gamma butyrolactone
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Primary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034983)

Source

Endogenous

Endogenous (HMDB: HMDB0034983)

Plant

Plant (HMDB: HMDB0034983)

Animal

Animal (HMDB: HMDB0034983)

Exogenous

Food

Food (HMDB: HMDB0034983)

Vegetable

Shoot vegetable

Globe artichoke (FooDB: FOOD00071)
Cardoon (FooDB: FOOD00319)

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0034983)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0034983)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0034983)

Lipid metabolism pathway (HMDB: HMDB0034983)

Cellular process

Cell signaling (HMDB: HMDB0034983)

Biochemical process

Lipid transport (HMDB: HMDB0034983)

Role

Biological role

Energy source (HMDB: HMDB0034983)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0034983)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	178 - 179 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	6738 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	17.1 g/L	ALOGPS
logP	0.24	ALOGPS
logP	-0.014	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	11.36	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	71.06 m³·mol⁻¹	ChemAxon
Polarizability	29.54 Å³	ChemAxon
Number of Rings	3	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]+	165.442	31661259
DarkChem	[M-H]-	160.878	31661259
DeepCCS	[M+H]+	163.384	30932474
DeepCCS	[M-H]-	161.026	30932474
DeepCCS	[M-2H]-	193.912	30932474
DeepCCS	[M+Na]+	169.477	30932474
AllCCS	[M+H]+	166.4	32859911
AllCCS	[M+H-H2O]+	163.0	32859911
AllCCS	[M+NH4]+	169.5	32859911
AllCCS	[M+Na]+	170.4	32859911
AllCCS	[M-H]-	168.8	32859911
AllCCS	[M+Na-2H]-	168.7	32859911
AllCCS	[M+HCOO]-	168.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.36 minutes	32390414
Predicted by Siyang on May 30, 2022	10.0712 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.9 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1567.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	199.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	112.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	161.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	80.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	321.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	441.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	160.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	677.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	299.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1072.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	222.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	246.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	356.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	193.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	201.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cynaratriol	CC1C(O)CC2C1C1OC(=O)C(O)(CO)C1CCC2=C	3335.7	Standard polar	33892256
Cynaratriol	CC1C(O)CC2C1C1OC(=O)C(O)(CO)C1CCC2=C	2504.1	Standard non polar	33892256
Cynaratriol	CC1C(O)CC2C1C1OC(=O)C(O)(CO)C1CCC2=C	2501.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cynaratriol,1TMS,isomer #1	C=C1CCC2C(OC(=O)C2(O)CO)C2C1CC(O[Si](C)(C)C)C2C	2306.1	Semi standard non polar	33892256
Cynaratriol,1TMS,isomer #2	C=C1CCC2C(OC(=O)C2(CO)O[Si](C)(C)C)C2C1CC(O)C2C	2364.4	Semi standard non polar	33892256
Cynaratriol,1TMS,isomer #3	C=C1CCC2C(OC(=O)C2(O)CO[Si](C)(C)C)C2C1CC(O)C2C	2329.6	Semi standard non polar	33892256
Cynaratriol,2TMS,isomer #1	C=C1CCC2C(OC(=O)C2(CO)O[Si](C)(C)C)C2C1CC(O[Si](C)(C)C)C2C	2415.2	Semi standard non polar	33892256
Cynaratriol,2TMS,isomer #2	C=C1CCC2C(OC(=O)C2(O)CO[Si](C)(C)C)C2C1CC(O[Si](C)(C)C)C2C	2367.6	Semi standard non polar	33892256
Cynaratriol,2TMS,isomer #3	C=C1CCC2C(OC(=O)C2(CO[Si](C)(C)C)O[Si](C)(C)C)C2C1CC(O)C2C	2412.9	Semi standard non polar	33892256
Cynaratriol,3TMS,isomer #1	C=C1CCC2C(OC(=O)C2(CO[Si](C)(C)C)O[Si](C)(C)C)C2C1CC(O[Si](C)(C)C)C2C	2447.1	Semi standard non polar	33892256
Cynaratriol,1TBDMS,isomer #1	C=C1CCC2C(OC(=O)C2(O)CO)C2C1CC(O[Si](C)(C)C(C)(C)C)C2C	2559.2	Semi standard non polar	33892256
Cynaratriol,1TBDMS,isomer #2	C=C1CCC2C(OC(=O)C2(CO)O[Si](C)(C)C(C)(C)C)C2C1CC(O)C2C	2608.8	Semi standard non polar	33892256
Cynaratriol,1TBDMS,isomer #3	C=C1CCC2C(OC(=O)C2(O)CO[Si](C)(C)C(C)(C)C)C2C1CC(O)C2C	2573.6	Semi standard non polar	33892256
Cynaratriol,2TBDMS,isomer #1	C=C1CCC2C(OC(=O)C2(CO)O[Si](C)(C)C(C)(C)C)C2C1CC(O[Si](C)(C)C(C)(C)C)C2C	2881.6	Semi standard non polar	33892256
Cynaratriol,2TBDMS,isomer #2	C=C1CCC2C(OC(=O)C2(O)CO[Si](C)(C)C(C)(C)C)C2C1CC(O[Si](C)(C)C(C)(C)C)C2C	2845.3	Semi standard non polar	33892256
Cynaratriol,2TBDMS,isomer #3	C=C1CCC2C(OC(=O)C2(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C2C1CC(O)C2C	2882.7	Semi standard non polar	33892256
Cynaratriol,3TBDMS,isomer #1	C=C1CCC2C(OC(=O)C2(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C2C1CC(O[Si](C)(C)C(C)(C)C)C2C	3123.2	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Cytoplasm
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

FDB013584

KNApSAcK ID

C00020855

Chemspider ID

26503332

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14138149

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1846781

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Cynaratriol (HMDB0034983)

MOL for HMDB0034983 (Cynaratriol)

3D MOL for HMDB0034983 (Cynaratriol)

3D SDF for HMDB0034983 (Cynaratriol)

3D-SDF for HMDB0034983 (Cynaratriol)

PDB for HMDB0034983 (Cynaratriol)

3D PDB for HMDB0034983 (Cynaratriol)

SMILES for HMDB0034983 (Cynaratriol)

INCHI for HMDB0034983 (Cynaratriol)

Structure for HMDB0034983 (Cynaratriol)

3D Structure for HMDB0034983 (Cynaratriol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized