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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:03:38 UTC

Update Date

2022-03-07 02:55:31 UTC

HMDB ID

HMDB0037800

Secondary Accession Numbers

HMDB37800

Metabolite Identification

Common Name

Annuolide B

Description

Annuolide B 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 Annuolide B.

Structure

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

HMDB0037800
     RDKit          3D
Annuolide B
 38 40  0  0  0  0  0  0  0  0999 V2000
   -1.8106   -3.0880    0.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0695   -2.0992   -0.1671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2578   -2.5125   -0.6936 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2732   -1.6651    0.0530 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5088   -0.3669   -0.6598 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8323    0.1898   -0.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5839    0.9043   -1.2475 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3242    1.2533    0.7866 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8393    1.6164    1.8817 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1753    1.7268    0.1659 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4807    0.6636   -0.4630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6650    0.2921    0.4126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6021    1.4343    0.5388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2435    2.8828    0.3968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3704    3.6767    0.5769 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8076    0.9481    0.7980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7428   -0.5632    0.8594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5820   -0.7427   -0.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4532   -4.0973    0.2930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8074   -2.9337    0.7223 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3478   -2.2097   -1.7773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4511   -3.5903   -0.5818 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2368   -2.2370    0.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9828   -1.5294    1.1102 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6650   -0.6000   -1.7384 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4319   -0.5659    0.3749 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2963    1.6335   -0.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8490    1.4946   -1.8325 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1026    0.1756   -1.9029 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0745    1.0434   -1.4209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3602    0.0104    1.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8213    3.1099   -0.6044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4490    3.1036    1.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1419    3.3329    0.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7003    1.5593    0.9425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4241   -0.8094    1.8710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6587   -1.0282    0.5079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0036   -0.4126   -1.1237 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
  6  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  2  0
 16 17  1  0
 17 18  1  0
 18  2  1  0
 11  5  1  0
 18 12  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
 11 30  1  0
 12 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  0
M  END


  Mrv0541 05061310012D          

 18 20  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
    0.8656    0.6356    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
    4.9157   -0.6430    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
    3.8305   -1.6349    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
    1.5541    0.1811    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
    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
    3.0167   -1.7701    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
    2.3864   -0.8625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  8  1  2  0  0  0  0
  8  3  1  0  0  0  0
  9  2  1  0  0  0  0
 10  4  2  0  0  0  0
 10  7  1  0  0  0  0
 11  6  1  0  0  0  0
 11  8  1  0  0  0  0
 12  5  1  0  0  0  0
 12  9  1  0  0  0  0
 13 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15  9  1  0  0  0  0
 16  7  1  0  0  0  0
 17 15  2  0  0  0  0
 18 14  1  0  0  0  0
 18 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037800

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1C2CCC(=C)C3CC=C(CO)C3C2OC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O3/c1-8-3-5-12-9(2)15(17)18-14(12)13-10(7-16)4-6-11(8)13/h4,9,11-14,16H,1,3,5-7H2,2H3

> <INCHI_KEY>
PTSCCEBQBSUFRX-UHFFFAOYSA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.3175

> <EXACT_MASS>
248.141244506

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.446344283687267

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9-(hydroxymethyl)-3-methyl-6-methylidene-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-2-one

> <ALOGPS_LOGP>
2.13

> <JCHEM_LOGP>
1.5948956860000003

> <ALOGPS_LOGS>
-2.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.148454105254718

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7338661743615855

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
69.01520000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.44e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
9-(hydroxymethyl)-3-methyl-6-methylidene-3H,3aH,4H,5H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037800
     RDKit          3D
Annuolide B
 38 40  0  0  0  0  0  0  0  0999 V2000
   -1.8106   -3.0880    0.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0695   -2.0992   -0.1671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2578   -2.5125   -0.6936 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2732   -1.6651    0.0530 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5088   -0.3669   -0.6598 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8323    0.1898   -0.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5839    0.9043   -1.2475 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3242    1.2533    0.7866 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8393    1.6164    1.8817 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1753    1.7268    0.1659 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4807    0.6636   -0.4630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6650    0.2921    0.4126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6021    1.4343    0.5388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2435    2.8828    0.3968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3704    3.6767    0.5769 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8076    0.9481    0.7980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7428   -0.5632    0.8594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5820   -0.7427   -0.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4532   -4.0973    0.2930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8074   -2.9337    0.7223 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3478   -2.2097   -1.7773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4511   -3.5903   -0.5818 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2368   -2.2370    0.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9828   -1.5294    1.1102 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6650   -0.6000   -1.7384 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4319   -0.5659    0.3749 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2963    1.6335   -0.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8490    1.4946   -1.8325 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1026    0.1756   -1.9029 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0745    1.0434   -1.4209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3602    0.0104    1.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8213    3.1099   -0.6044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4490    3.1036    1.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1419    3.3329    0.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7003    1.5593    0.9425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4241   -0.8094    1.8710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6587   -1.0282    0.5079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0036   -0.4126   -1.1237 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
  6  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  2  0
 16 17  1  0
 17 18  1  0
 18  2  1  0
 11  5  1  0
 18 12  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
 11 30  1  0
 12 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  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       1.616   1.186   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       9.176  -1.200   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.686   2.381   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.245   0.338   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.150  -3.052   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.461   2.381   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.901   0.338   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.691  -1.610   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.803   0.879   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.343   0.879   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.843  -0.325   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.303  -0.325   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.970  -1.200   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       5.631  -3.304   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.766  -2.160   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.455  -1.610   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3    5    8                                                       
CONECT    4    6   10                                                       
CONECT    5    3   12                                                       
CONECT    6    4   11                                                       
CONECT    7   10   16                                                       
CONECT    8    1    3   11                                                  
CONECT    9    2   12   15                                                  
CONECT   10    4    7   13                                                  
CONECT   11    6    8   13                                                  
CONECT   12    5    9   14                                                  
CONECT   13   10   11   14                                                  
CONECT   14   12   13   18                                                  
CONECT   15    9   17   18                                                  
CONECT   16    7                                                            
CONECT   17   15                                                            
CONECT   18   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0037800
HETATM    1  C1  UNL     1      -1.811  -3.088   0.304  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.069  -2.099  -0.167  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.258  -2.513  -0.694  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.273  -1.665   0.053  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.509  -0.367  -0.660  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.832   0.190  -0.152  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.584   0.904  -1.247  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.324   1.253   0.787  1.00  0.00           C  
HETATM    9  O1  UNL     1       2.839   1.616   1.882  1.00  0.00           O  
HETATM   10  O2  UNL     1       1.175   1.727   0.166  1.00  0.00           O  
HETATM   11  C9  UNL     1       0.481   0.664  -0.463  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.665   0.292   0.413  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.602   1.434   0.539  1.00  0.00           C  
HETATM   14  C12 UNL     1      -1.243   2.883   0.397  1.00  0.00           C  
HETATM   15  O3  UNL     1      -2.370   3.677   0.577  1.00  0.00           O  
HETATM   16  C13 UNL     1      -2.808   0.948   0.798  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.743  -0.563   0.859  1.00  0.00           C  
HETATM   18  C15 UNL     1      -1.582  -0.743  -0.138  1.00  0.00           C  
HETATM   19  H1  UNL     1      -1.453  -4.097   0.293  1.00  0.00           H  
HETATM   20  H2  UNL     1      -2.807  -2.934   0.722  1.00  0.00           H  
HETATM   21  H3  UNL     1       0.348  -2.210  -1.777  1.00  0.00           H  
HETATM   22  H4  UNL     1       0.451  -3.590  -0.582  1.00  0.00           H  
HETATM   23  H5  UNL     1       2.237  -2.237   0.026  1.00  0.00           H  
HETATM   24  H6  UNL     1       0.983  -1.529   1.110  1.00  0.00           H  
HETATM   25  H7  UNL     1       1.665  -0.600  -1.738  1.00  0.00           H  
HETATM   26  H8  UNL     1       3.432  -0.566   0.375  1.00  0.00           H  
HETATM   27  H9  UNL     1       4.296   1.634  -0.791  1.00  0.00           H  
HETATM   28  H10 UNL     1       2.849   1.495  -1.832  1.00  0.00           H  
HETATM   29  H11 UNL     1       4.103   0.176  -1.903  1.00  0.00           H  
HETATM   30  H12 UNL     1       0.074   1.043  -1.421  1.00  0.00           H  
HETATM   31  H13 UNL     1      -0.360   0.010   1.439  1.00  0.00           H  
HETATM   32  H14 UNL     1      -0.821   3.110  -0.604  1.00  0.00           H  
HETATM   33  H15 UNL     1      -0.449   3.104   1.127  1.00  0.00           H  
HETATM   34  H16 UNL     1      -3.142   3.333   0.105  1.00  0.00           H  
HETATM   35  H17 UNL     1      -3.700   1.559   0.943  1.00  0.00           H  
HETATM   36  H18 UNL     1      -2.424  -0.809   1.871  1.00  0.00           H  
HETATM   37  H19 UNL     1      -3.659  -1.028   0.508  1.00  0.00           H  
HETATM   38  H20 UNL     1      -2.004  -0.413  -1.124  1.00  0.00           H  
CONECT    1    2    2   19   20
CONECT    2    3   18
CONECT    3    4   21   22
CONECT    4    5   23   24
CONECT    5    6   11   25
CONECT    6    7    8   26
CONECT    7   27   28   29
CONECT    8    9    9   10
CONECT   10   11
CONECT   11   12   30
CONECT   12   13   18   31
CONECT   13   14   16   16
CONECT   14   15   32   33
CONECT   15   34
CONECT   16   17   35
CONECT   17   18   36   37
CONECT   18   38
END

HMDB0037800
     RDKit          3D
Annuolide B
 38 40  0  0  0  0  0  0  0  0999 V2000
   -1.8106   -3.0880    0.3042 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0695   -2.0992   -0.1671 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2578   -2.5125   -0.6936 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2732   -1.6651    0.0530 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5088   -0.3669   -0.6598 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8323    0.1898   -0.1518 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5839    0.9043   -1.2475 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3242    1.2533    0.7866 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8393    1.6164    1.8817 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1753    1.7268    0.1659 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4807    0.6636   -0.4630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6650    0.2921    0.4126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6021    1.4343    0.5388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2435    2.8828    0.3968 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3704    3.6767    0.5769 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8076    0.9481    0.7980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7428   -0.5632    0.8594 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5820   -0.7427   -0.1378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4532   -4.0973    0.2930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8074   -2.9337    0.7223 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3478   -2.2097   -1.7773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4511   -3.5903   -0.5818 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2368   -2.2370    0.0260 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9828   -1.5294    1.1102 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6650   -0.6000   -1.7384 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4319   -0.5659    0.3749 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2963    1.6335   -0.7910 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8490    1.4946   -1.8325 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1026    0.1756   -1.9029 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0745    1.0434   -1.4209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3602    0.0104    1.4391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8213    3.1099   -0.6044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4490    3.1036    1.1272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1419    3.3329    0.1054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7003    1.5593    0.9425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4241   -0.8094    1.8710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6587   -1.0282    0.5079 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0036   -0.4126   -1.1237 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
  6  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  2  0
 16 17  1  0
 17 18  1  0
 18  2  1  0
 11  5  1  0
 18 12  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
 11 30  1  0
 12 31  1  0
 14 32  1  0
 14 33  1  0
 15 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O₃

Average Molecular Weight

248.3175

Monoisotopic Molecular Weight

248.141244506

IUPAC Name

9-(hydroxymethyl)-3-methyl-6-methylidene-2H,3H,3aH,4H,5H,6H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-2-one

Traditional Name

9-(hydroxymethyl)-3-methyl-6-methylidene-3H,3aH,4H,5H,6aH,7H,9aH,9bH-azuleno[4,5-b]furan-2-one

CAS Registry Number

152442-50-7

SMILES

CC1C2CCC(=C)C3CC=C(CO)C3C2OC1=O

InChI Identifier

InChI=1S/C15H20O3/c1-8-3-5-12-9(2)15(17)18-14(12)13-10(7-16)4-6-11(8)13/h4,9,11-14,16H,1,3,5-7H2,2H3

InChI Key

PTSCCEBQBSUFRX-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
Tetrahydrofuran
Carboxylic acid ester
Lactone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
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

Cell membrane (HMDB: HMDB0037800)

Cellular substructure

Extracellular (HMDB: HMDB0037800)
Cytoplasm (HMDB: HMDB0037800)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037800)

Source

Endogenous

Endogenous (HMDB: HMDB0037800)

Animal

Animal (HMDB: HMDB0037800)

Exogenous

Food

Food (HMDB: HMDB0037800)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0037800)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0037800)

Cellular process

Cell signaling (HMDB: HMDB0037800)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0037800)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0037800)

Nutrient

Nutrient (HMDB: HMDB0037800)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0037800)

Emulsifier (HMDB: HMDB0037800)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	2390 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	0.84 g/L	ALOGPS
logP	2.13	ALOGPS
logP	1.59	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	15.15	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	69.02 m³·mol⁻¹	ChemAxon
Polarizability	27.45 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]+	158.459	31661259
DarkChem	[M-H]-	155.437	31661259
DeepCCS	[M+H]+	157.665	30932474
DeepCCS	[M-H]-	155.307	30932474
DeepCCS	[M-2H]-	189.815	30932474
DeepCCS	[M+Na]+	165.068	30932474
AllCCS	[M+H]+	158.5	32859911
AllCCS	[M+H-H2O]+	154.8	32859911
AllCCS	[M+NH4]+	162.0	32859911
AllCCS	[M+Na]+	163.0	32859911
AllCCS	[M-H]-	162.7	32859911
AllCCS	[M+Na-2H]-	162.6	32859911
AllCCS	[M+HCOO]-	162.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Annuolide B	CC1C2CCC(=C)C3CC=C(CO)C3C2OC1=O	3119.1	Standard polar	33892256
Annuolide B	CC1C2CCC(=C)C3CC=C(CO)C3C2OC1=O	2164.7	Standard non polar	33892256
Annuolide B	CC1C2CCC(=C)C3CC=C(CO)C3C2OC1=O	2239.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Annuolide B,1TMS,isomer #1	C=C1CCC2C(C)C(=O)OC2C2C(CO[Si](C)(C)C)=CCC12	2126.7	Semi standard non polar	33892256
Annuolide B,1TBDMS,isomer #1	C=C1CCC2C(C)C(=O)OC2C2C(CO[Si](C)(C)C(C)(C)C)=CCC12	2362.2	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Annuolide B GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fi0-4940000000-3486fb53f5f05cc3b35d	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annuolide B GC-MS (1 TMS) - 70eV, Positive	splash10-0c00-2390000000-e086fbbf8b870ffbb7eb	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annuolide B GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annuolide B 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 - Annuolide B 10V, Positive-QTOF	splash10-000t-0290000000-b171c02b5d5b79fe45fc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annuolide B 20V, Positive-QTOF	splash10-053r-0950000000-d0346f6519713a6a83fa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annuolide B 40V, Positive-QTOF	splash10-0pb9-5910000000-6edf2b70fd31a9fcd0e8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annuolide B 10V, Negative-QTOF	splash10-0002-0190000000-3be64209b08390596a85	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annuolide B 20V, Negative-QTOF	splash10-0ftb-0290000000-df42236a307a1cbf1a70	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annuolide B 40V, Negative-QTOF	splash10-0udi-5910000000-d36c552c0647248e59bb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annuolide B 10V, Negative-QTOF	splash10-0002-0090000000-7b3a58b796a0e4263959	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annuolide B 20V, Negative-QTOF	splash10-0002-0090000000-c1c969788f7ea66e674a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annuolide B 40V, Negative-QTOF	splash10-066s-5940000000-0fd0704b5a1d3b133bd1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annuolide B 10V, Positive-QTOF	splash10-0002-0090000000-d075ce931df6d8d6bcbb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annuolide B 20V, Positive-QTOF	splash10-0002-0490000000-fdb3cd9d49cac2fdb675	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annuolide B 40V, Positive-QTOF	splash10-002g-3920000000-607fbc8b18a580ca8560	2021-09-22	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

FDB016944

KNApSAcK ID

Not Available

Chemspider ID

35014474

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752239

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1863691

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 Annuolide B (HMDB0037800)

MOL for HMDB0037800 (Annuolide B)

3D MOL for HMDB0037800 (Annuolide B)

3D SDF for HMDB0037800 (Annuolide B)

3D-SDF for HMDB0037800 (Annuolide B)

PDB for HMDB0037800 (Annuolide B)

3D PDB for HMDB0037800 (Annuolide B)

SMILES for HMDB0037800 (Annuolide B)

INCHI for HMDB0037800 (Annuolide B)

Structure for HMDB0037800 (Annuolide B)

3D Structure for HMDB0037800 (Annuolide B)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra