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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 02:40:30 UTC

Update Date

2022-03-07 02:56:51 UTC

HMDB ID

HMDB0041037

Secondary Accession Numbers

HMDB41037

Metabolite Identification

Common Name

8-Deoxy-11-hydroxy-13-chlorogrosheimin

Description

8-Deoxy-11-hydroxy-13-chlorogrosheimin 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 8-Deoxy-11-hydroxy-13-chlorogrosheimin.

Structure

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

HMDB0041037
     RDKit          3D
8-Deoxy-11-hydroxy-13-chlorogrosheimin
 39 41  0  0  0  0  0  0  0  0999 V2000
    1.9496   -2.9328    0.3483 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0743   -1.9370    0.1799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2104   -2.3021   -0.4764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3884   -1.5540    0.1643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3943   -0.1742   -0.3757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4674    0.6997    0.4577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9508    1.9954    0.1707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3035    1.9549   -0.1519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1406    2.8935   -0.2166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6729    0.5289   -0.4380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2437    0.5314   -1.7216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7323    0.1276    0.5268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3139    0.3089    2.2162 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.9416    0.5025   -0.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8303    1.6795    0.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7803    2.7369   -0.8168 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1794    1.0599    0.2743 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2086    1.6746    0.1593 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0345   -0.4282    0.4730 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5718   -0.6354    0.6941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9158   -2.7911    0.8122 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7294   -3.9562    0.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1763   -1.9775   -1.5238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3999   -3.3854   -0.3795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1435   -1.5966    1.2674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2962   -2.1423   -0.0748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9339   -0.1880   -1.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5697    0.5286    1.5293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3346   -0.3729   -2.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6300    0.7589    0.3242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0677   -0.9209    0.2775 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8721    0.2500   -1.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5316    2.1134    1.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7453    3.0761   -1.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3229    3.6265   -0.4280 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2291    2.4117   -1.7599 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6491   -0.6820    1.3593 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4271   -0.8915   -0.4490 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3770   -0.5908    1.7835 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
 15 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20  2  1  0
 10  5  1  0
 20 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
 14 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 19 37  1  0
 19 38  1  0
 20 39  1  0
M  END


  Mrv0541 05061312212D          

 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 Cl  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  2  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>
HMDB0041037

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1C2C(CC1=O)C(=C)CCC1C2OC(=O)C1(O)CCl

> <INCHI_IDENTIFIER>
InChI=1S/C15H19ClO4/c1-7-3-4-10-13(20-14(18)15(10,19)6-16)12-8(2)11(17)5-9(7)12/h8-10,12-13,19H,1,3-6H2,2H3

> <INCHI_KEY>
RXUIKPFKVDKIDO-UHFFFAOYSA-N

> <FORMULA>
C15H19ClO4

> <MOLECULAR_WEIGHT>
298.762

> <EXACT_MASS>
298.097186803

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
29.51274584046039

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(chloromethyl)-3-hydroxy-9-methyl-6-methylidene-dodecahydroazuleno[4,5-b]furan-2,8-dione

> <ALOGPS_LOGP>
0.92

> <JCHEM_LOGP>
1.7259480839999999

> <ALOGPS_LOGS>
-2.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.68864162914848

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.3942830028798

> <JCHEM_PKA_STRONGEST_BASIC>
-4.375940603927099

> <JCHEM_POLAR_SURFACE_AREA>
63.60000000000001

> <JCHEM_REFRACTIVITY>
73.18469999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.24e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(chloromethyl)-3-hydroxy-9-methyl-6-methylidene-octahydroazuleno[4,5-b]furan-2,8-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0041037
     RDKit          3D
8-Deoxy-11-hydroxy-13-chlorogrosheimin
 39 41  0  0  0  0  0  0  0  0999 V2000
    1.9496   -2.9328    0.3483 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0743   -1.9370    0.1799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2104   -2.3021   -0.4764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3884   -1.5540    0.1643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3943   -0.1742   -0.3757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4674    0.6997    0.4577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9508    1.9954    0.1707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3035    1.9549   -0.1519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1406    2.8935   -0.2166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6729    0.5289   -0.4380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2437    0.5314   -1.7216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7323    0.1276    0.5268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3139    0.3089    2.2162 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.9416    0.5025   -0.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8303    1.6795    0.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7803    2.7369   -0.8168 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1794    1.0599    0.2743 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2086    1.6746    0.1593 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0345   -0.4282    0.4730 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5718   -0.6354    0.6941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9158   -2.7911    0.8122 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7294   -3.9562    0.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1763   -1.9775   -1.5238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3999   -3.3854   -0.3795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1435   -1.5966    1.2674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2962   -2.1423   -0.0748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9339   -0.1880   -1.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5697    0.5286    1.5293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3346   -0.3729   -2.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6300    0.7589    0.3242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0677   -0.9209    0.2775 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8721    0.2500   -1.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5316    2.1134    1.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7453    3.0761   -1.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3229    3.6265   -0.4280 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2291    2.4117   -1.7599 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6491   -0.6820    1.3593 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4271   -0.8915   -0.4490 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3770   -0.5908    1.7835 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
 15 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20  2  1  0
 10  5  1  0
 20 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
 14 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 19 37  1  0
 19 38  1  0
 20 39  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 Cl   UNK     0       0.418   1.313   0.000  0.00  0.00          Cl+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    HMDB0041037
HETATM    1  C1  UNL     1       1.950  -2.933   0.348  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.074  -1.937   0.180  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.210  -2.302  -0.476  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.388  -1.554   0.164  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.394  -0.174  -0.376  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.467   0.700   0.458  1.00  0.00           C  
HETATM    7  O1  UNL     1      -0.951   1.995   0.171  1.00  0.00           O  
HETATM    8  C7  UNL     1      -2.304   1.955  -0.152  1.00  0.00           C  
HETATM    9  O2  UNL     1      -3.141   2.894  -0.217  1.00  0.00           O  
HETATM   10  C8  UNL     1      -2.673   0.529  -0.438  1.00  0.00           C  
HETATM   11  O3  UNL     1      -3.244   0.531  -1.722  1.00  0.00           O  
HETATM   12  C9  UNL     1      -3.732   0.128   0.527  1.00  0.00           C  
HETATM   13 CL1  UNL     1      -3.314   0.309   2.216  1.00  0.00          CL  
HETATM   14  C10 UNL     1       0.942   0.503  -0.043  1.00  0.00           C  
HETATM   15  C11 UNL     1       1.830   1.680   0.239  1.00  0.00           C  
HETATM   16  C12 UNL     1       1.780   2.737  -0.817  1.00  0.00           C  
HETATM   17  C13 UNL     1       3.179   1.060   0.274  1.00  0.00           C  
HETATM   18  O4  UNL     1       4.209   1.675   0.159  1.00  0.00           O  
HETATM   19  C14 UNL     1       3.034  -0.428   0.473  1.00  0.00           C  
HETATM   20  C15 UNL     1       1.572  -0.635   0.694  1.00  0.00           C  
HETATM   21  H1  UNL     1       2.916  -2.791   0.812  1.00  0.00           H  
HETATM   22  H2  UNL     1       1.729  -3.956   0.021  1.00  0.00           H  
HETATM   23  H3  UNL     1      -0.176  -1.978  -1.524  1.00  0.00           H  
HETATM   24  H4  UNL     1      -0.400  -3.385  -0.380  1.00  0.00           H  
HETATM   25  H5  UNL     1      -1.143  -1.597   1.267  1.00  0.00           H  
HETATM   26  H6  UNL     1      -2.296  -2.142  -0.075  1.00  0.00           H  
HETATM   27  H7  UNL     1      -0.934  -0.188  -1.408  1.00  0.00           H  
HETATM   28  H8  UNL     1      -0.570   0.529   1.529  1.00  0.00           H  
HETATM   29  H9  UNL     1      -3.335  -0.373  -2.087  1.00  0.00           H  
HETATM   30  H10 UNL     1      -4.630   0.759   0.324  1.00  0.00           H  
HETATM   31  H11 UNL     1      -4.068  -0.921   0.277  1.00  0.00           H  
HETATM   32  H12 UNL     1       0.872   0.250  -1.118  1.00  0.00           H  
HETATM   33  H13 UNL     1       1.532   2.113   1.212  1.00  0.00           H  
HETATM   34  H14 UNL     1       0.745   3.076  -1.022  1.00  0.00           H  
HETATM   35  H15 UNL     1       2.323   3.626  -0.428  1.00  0.00           H  
HETATM   36  H16 UNL     1       2.229   2.412  -1.760  1.00  0.00           H  
HETATM   37  H17 UNL     1       3.649  -0.682   1.359  1.00  0.00           H  
HETATM   38  H18 UNL     1       3.427  -0.891  -0.449  1.00  0.00           H  
HETATM   39  H19 UNL     1       1.377  -0.591   1.784  1.00  0.00           H  
CONECT    1    2    2   21   22
CONECT    2    3   20
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   14   15   20   32
CONECT   15   16   17   33
CONECT   16   34   35   36
CONECT   17   18   18   19
CONECT   19   20   37   38
CONECT   20   39
END

HMDB0041037
     RDKit          3D
8-Deoxy-11-hydroxy-13-chlorogrosheimin
 39 41  0  0  0  0  0  0  0  0999 V2000
    1.9496   -2.9328    0.3483 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0743   -1.9370    0.1799 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2104   -2.3021   -0.4764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3884   -1.5540    0.1643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3943   -0.1742   -0.3757 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4674    0.6997    0.4577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9508    1.9954    0.1707 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3035    1.9549   -0.1519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1406    2.8935   -0.2166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6729    0.5289   -0.4380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2437    0.5314   -1.7216 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7323    0.1276    0.5268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3139    0.3089    2.2162 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.9416    0.5025   -0.0429 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8303    1.6795    0.2393 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7803    2.7369   -0.8168 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1794    1.0599    0.2743 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2086    1.6746    0.1593 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0345   -0.4282    0.4730 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5718   -0.6354    0.6941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9158   -2.7911    0.8122 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7294   -3.9562    0.0205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1763   -1.9775   -1.5238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3999   -3.3854   -0.3795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1435   -1.5966    1.2674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2962   -2.1423   -0.0748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9339   -0.1880   -1.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5697    0.5286    1.5293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3346   -0.3729   -2.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6300    0.7589    0.3242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0677   -0.9209    0.2775 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8721    0.2500   -1.1179 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5316    2.1134    1.2118 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7453    3.0761   -1.0215 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3229    3.6265   -0.4280 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2291    2.4117   -1.7599 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6491   -0.6820    1.3593 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4271   -0.8915   -0.4490 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3770   -0.5908    1.7835 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
 15 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20  2  1  0
 10  5  1  0
 20 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
 14 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 16 36  1  0
 19 37  1  0
 19 38  1  0
 20 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₁₉ClO₄

Average Molecular Weight

298.762

Monoisotopic Molecular Weight

298.097186803

IUPAC Name

3-(chloromethyl)-3-hydroxy-9-methyl-6-methylidene-dodecahydroazuleno[4,5-b]furan-2,8-dione

Traditional Name

3-(chloromethyl)-3-hydroxy-9-methyl-6-methylidene-octahydroazuleno[4,5-b]furan-2,8-dione

CAS Registry Number

83551-02-4

SMILES

CC1C2C(CC1=O)C(=C)CCC1C2OC(=O)C1(O)CCl

InChI Identifier

InChI=1S/C15H19ClO4/c1-7-3-4-10-13(20-14(18)15(10,19)6-16)12-8(2)11(17)5-9(7)12/h8-10,12-13,19H,1,3-6H2,2H3

InChI Key

RXUIKPFKVDKIDO-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
Tertiary alcohol
Tetrahydrofuran
Carboxylic acid ester
Chlorohydrin
Halohydrin
Ketone
Lactone
Cyclic ketone
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carbonyl group
Alkyl halide
Alkyl chloride
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Organohalogen compound
Organochloride
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0041037)

Cellular substructure

Extracellular (HMDB: HMDB0041037)
Cytoplasm (HMDB: HMDB0041037)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0041037)

Source

Endogenous

Endogenous (HMDB: HMDB0041037)

Plant

Plant (HMDB: HMDB0041037)

Animal

Animal (HMDB: HMDB0041037)

Exogenous

Food

Food (HMDB: HMDB0041037)

Vegetable

Leaf vegetable

Green vegetables (FooDB: FOOD00872)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0041037)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0041037)

Cellular process

Cell signaling (HMDB: HMDB0041037)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0041037)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0041037)

Nutrient

Nutrient (HMDB: HMDB0041037)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0041037)

Emulsifier (HMDB: HMDB0041037)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	228 - 230 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.24 g/L	ALOGPS
logP	0.92	ALOGPS
logP	1.73	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	11.39	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	73.18 m³·mol⁻¹	ChemAxon
Polarizability	29.51 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
DeepCCS	[M+H]+	171.596	30932474
DeepCCS	[M-H]-	169.238	30932474
DeepCCS	[M-2H]-	202.124	30932474
DeepCCS	[M+Na]+	177.689	30932474
AllCCS	[M+H]+	167.0	32859911
AllCCS	[M+H-H2O]+	163.7	32859911
AllCCS	[M+NH4]+	170.0	32859911
AllCCS	[M+Na]+	170.9	32859911
AllCCS	[M-H]-	169.7	32859911
AllCCS	[M+Na-2H]-	169.7	32859911
AllCCS	[M+HCOO]-	169.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
8-Deoxy-11-hydroxy-13-chlorogrosheimin	CC1C2C(CC1=O)C(=C)CCC1C2OC(=O)C1(O)CCl	3172.2	Standard polar	33892256
8-Deoxy-11-hydroxy-13-chlorogrosheimin	CC1C2C(CC1=O)C(=C)CCC1C2OC(=O)C1(O)CCl	2384.1	Standard non polar	33892256
8-Deoxy-11-hydroxy-13-chlorogrosheimin	CC1C2C(CC1=O)C(=C)CCC1C2OC(=O)C1(O)CCl	2425.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
8-Deoxy-11-hydroxy-13-chlorogrosheimin,1TMS,isomer #1	C=C1CCC2C(OC(=O)C2(CCl)O[Si](C)(C)C)C2C(C)C(=O)CC12	2345.8	Semi standard non polar	33892256
8-Deoxy-11-hydroxy-13-chlorogrosheimin,1TMS,isomer #2	C=C1CCC2C(OC(=O)C2(O)CCl)C2C(C)=C(O[Si](C)(C)C)CC12	2344.3	Semi standard non polar	33892256
8-Deoxy-11-hydroxy-13-chlorogrosheimin,1TMS,isomer #3	C=C1CCC2C(OC(=O)C2(O)CCl)C2C(C)C(O[Si](C)(C)C)=CC12	2266.7	Semi standard non polar	33892256
8-Deoxy-11-hydroxy-13-chlorogrosheimin,2TMS,isomer #1	C=C1CCC2C(OC(=O)C2(CCl)O[Si](C)(C)C)C2C(C)=C(O[Si](C)(C)C)CC12	2439.4	Semi standard non polar	33892256
8-Deoxy-11-hydroxy-13-chlorogrosheimin,2TMS,isomer #1	C=C1CCC2C(OC(=O)C2(CCl)O[Si](C)(C)C)C2C(C)=C(O[Si](C)(C)C)CC12	2317.4	Standard non polar	33892256
8-Deoxy-11-hydroxy-13-chlorogrosheimin,2TMS,isomer #2	C=C1CCC2C(OC(=O)C2(CCl)O[Si](C)(C)C)C2C(C)C(O[Si](C)(C)C)=CC12	2353.2	Semi standard non polar	33892256
8-Deoxy-11-hydroxy-13-chlorogrosheimin,2TMS,isomer #2	C=C1CCC2C(OC(=O)C2(CCl)O[Si](C)(C)C)C2C(C)C(O[Si](C)(C)C)=CC12	2275.2	Standard non polar	33892256
8-Deoxy-11-hydroxy-13-chlorogrosheimin,1TBDMS,isomer #1	C=C1CCC2C(OC(=O)C2(CCl)O[Si](C)(C)C(C)(C)C)C2C(C)C(=O)CC12	2582.0	Semi standard non polar	33892256
8-Deoxy-11-hydroxy-13-chlorogrosheimin,1TBDMS,isomer #2	C=C1CCC2C(OC(=O)C2(O)CCl)C2C(C)=C(O[Si](C)(C)C(C)(C)C)CC12	2560.3	Semi standard non polar	33892256
8-Deoxy-11-hydroxy-13-chlorogrosheimin,1TBDMS,isomer #3	C=C1CCC2C(OC(=O)C2(O)CCl)C2C(C)C(O[Si](C)(C)C(C)(C)C)=CC12	2494.6	Semi standard non polar	33892256
8-Deoxy-11-hydroxy-13-chlorogrosheimin,2TBDMS,isomer #1	C=C1CCC2C(OC(=O)C2(CCl)O[Si](C)(C)C(C)(C)C)C2C(C)=C(O[Si](C)(C)C(C)(C)C)CC12	2891.9	Semi standard non polar	33892256
8-Deoxy-11-hydroxy-13-chlorogrosheimin,2TBDMS,isomer #1	C=C1CCC2C(OC(=O)C2(CCl)O[Si](C)(C)C(C)(C)C)C2C(C)=C(O[Si](C)(C)C(C)(C)C)CC12	2771.8	Standard non polar	33892256
8-Deoxy-11-hydroxy-13-chlorogrosheimin,2TBDMS,isomer #2	C=C1CCC2C(OC(=O)C2(CCl)O[Si](C)(C)C(C)(C)C)C2C(C)C(O[Si](C)(C)C(C)(C)C)=CC12	2815.1	Semi standard non polar	33892256
8-Deoxy-11-hydroxy-13-chlorogrosheimin,2TBDMS,isomer #2	C=C1CCC2C(OC(=O)C2(CCl)O[Si](C)(C)C(C)(C)C)C2C(C)C(O[Si](C)(C)C(C)(C)C)=CC12	2633.9	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Deoxy-11-hydroxy-13-chlorogrosheimin GC-MS (Non-derivatized) - 70eV, Positive	splash10-008c-2920000000-44ae0b69be8d75a2a187	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Deoxy-11-hydroxy-13-chlorogrosheimin GC-MS (1 TMS) - 70eV, Positive	splash10-004i-4902000000-50f17b549f2e6e7f90b4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 8-Deoxy-11-hydroxy-13-chlorogrosheimin 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 - 8-Deoxy-11-hydroxy-13-chlorogrosheimin 10V, Positive-QTOF	splash10-002b-0890000000-40f6f688c2acce1d1184	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Deoxy-11-hydroxy-13-chlorogrosheimin 20V, Positive-QTOF	splash10-009t-0390000000-08991e47ab6812ec5ab4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Deoxy-11-hydroxy-13-chlorogrosheimin 40V, Positive-QTOF	splash10-014i-5900000000-8b89b2cc6d7b62e09711	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Deoxy-11-hydroxy-13-chlorogrosheimin 10V, Negative-QTOF	splash10-0002-0090000000-47a20af26bd64262e0c1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Deoxy-11-hydroxy-13-chlorogrosheimin 20V, Negative-QTOF	splash10-0002-0090000000-e826cd39455497d2dccd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Deoxy-11-hydroxy-13-chlorogrosheimin 40V, Negative-QTOF	splash10-03xr-3900000000-7666c2778dae979efc5c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Deoxy-11-hydroxy-13-chlorogrosheimin 10V, Positive-QTOF	splash10-0002-0090000000-714a78dc20d5d6ba33e8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Deoxy-11-hydroxy-13-chlorogrosheimin 20V, Positive-QTOF	splash10-000t-0090000000-570bd856dcf23ec3ece3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Deoxy-11-hydroxy-13-chlorogrosheimin 40V, Positive-QTOF	splash10-05di-2930000000-92a37ea277bcf8d701f9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Deoxy-11-hydroxy-13-chlorogrosheimin 10V, Negative-QTOF	splash10-0002-0090000000-86aef986368eb478dde3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Deoxy-11-hydroxy-13-chlorogrosheimin 20V, Negative-QTOF	splash10-0002-1090000000-c3e577c87e0a2ce70497	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 8-Deoxy-11-hydroxy-13-chlorogrosheimin 40V, Negative-QTOF	splash10-001l-4290000000-d45be43cfe8adaedd5c9	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB020909

KNApSAcK ID

C00054168

Chemspider ID

35015082

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131753015

PDB ID

Not Available

ChEBI ID

Not Available

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

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 8-Deoxy-11-hydroxy-13-chlorogrosheimin (HMDB0041037)

MOL for HMDB0041037 (8-Deoxy-11-hydroxy-13-chlorogrosheimin)

3D MOL for HMDB0041037 (8-Deoxy-11-hydroxy-13-chlorogrosheimin)

3D SDF for HMDB0041037 (8-Deoxy-11-hydroxy-13-chlorogrosheimin)

3D-SDF for HMDB0041037 (8-Deoxy-11-hydroxy-13-chlorogrosheimin)

PDB for HMDB0041037 (8-Deoxy-11-hydroxy-13-chlorogrosheimin)

3D PDB for HMDB0041037 (8-Deoxy-11-hydroxy-13-chlorogrosheimin)

SMILES for HMDB0041037 (8-Deoxy-11-hydroxy-13-chlorogrosheimin)

INCHI for HMDB0041037 (8-Deoxy-11-hydroxy-13-chlorogrosheimin)

Structure for HMDB0041037 (8-Deoxy-11-hydroxy-13-chlorogrosheimin)

3D Structure for HMDB0041037 (8-Deoxy-11-hydroxy-13-chlorogrosheimin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra