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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:03:41 UTC

Update Date

2022-03-07 02:55:31 UTC

HMDB ID

HMDB0037801

Secondary Accession Numbers

HMDB37801

Metabolite Identification

Common Name

Annuolide A

Description

Annuolide A 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 A.

Structure

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

HMDB0037801
     RDKit          3D
Annuolide A
 36 38  0  0  0  0  0  0  0  0999 V2000
    3.8755   -1.5725   -0.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5829   -1.3745   -0.3345 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6710   -2.0473   -1.2538 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0123   -2.9498   -2.0643 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3769   -1.5165   -1.0724 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3921   -0.9779    0.2318 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7574   -0.4003    0.4331 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9859    0.9400   -0.1615 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3188    2.0866    0.5237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0508    2.2024   -0.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5698    3.3897   -0.2967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9454    1.0645   -0.3598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4099    1.3957   -0.0279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9661   -0.0038    0.0249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0105   -0.8544    0.3601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2122   -2.3440    0.5070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5160   -2.6791    0.2447 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7462   -0.0994    0.5647 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4198   -0.9914    0.5351 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4479   -2.2813   -0.7606 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3272   -1.8734    0.9205 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9995   -0.3907    1.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6657    0.9341   -1.2391 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0826    1.1256   -0.1858 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8884    3.0359    0.4691 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1831    1.8665    1.6184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0045    4.3144   -0.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5568    3.5003   -0.7035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8420    0.7130   -1.3963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4333    1.8657    0.9614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8833    1.9633   -0.8347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9925   -0.2372   -0.1851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9447   -2.6423    1.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5544   -2.9071   -0.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7079   -2.4617   -0.7017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6407    0.2068    1.6261 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  3
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
  7  2  1  0
 18 12  1  0
 18  6  1  0
  1 19  1  0
  1 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  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  2  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>
HMDB0037801

> <DATABASE_NAME>
hmdb

> <SMILES>
OCC1=CCC2C1C1OC(=O)C(=C)C1CCC2=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O3/c1-8-3-5-12-9(2)15(17)18-14(12)13-10(7-16)4-6-11(8)13/h4,11-14,16H,1-3,5-7H2

> <INCHI_KEY>
XIKLPPAERLRBPO-UHFFFAOYSA-N

> <FORMULA>
C15H18O3

> <MOLECULAR_WEIGHT>
246.3016

> <EXACT_MASS>
246.125594442

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
26.692382835184127

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.93

> <JCHEM_LOGP>
1.7365503903333332

> <ALOGPS_LOGS>
-2.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.148442063332695

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7338714414982794

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
68.8186

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.96e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037801
     RDKit          3D
Annuolide A
 36 38  0  0  0  0  0  0  0  0999 V2000
    3.8755   -1.5725   -0.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5829   -1.3745   -0.3345 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6710   -2.0473   -1.2538 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0123   -2.9498   -2.0643 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3769   -1.5165   -1.0724 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3921   -0.9779    0.2318 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7574   -0.4003    0.4331 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9859    0.9400   -0.1615 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3188    2.0866    0.5237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0508    2.2024   -0.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5698    3.3897   -0.2967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9454    1.0645   -0.3598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4099    1.3957   -0.0279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9661   -0.0038    0.0249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0105   -0.8544    0.3601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2122   -2.3440    0.5070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5160   -2.6791    0.2447 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7462   -0.0994    0.5647 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4198   -0.9914    0.5351 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4479   -2.2813   -0.7606 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3272   -1.8734    0.9205 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9995   -0.3907    1.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6657    0.9341   -1.2391 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0826    1.1256   -0.1858 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8884    3.0359    0.4691 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1831    1.8665    1.6184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0045    4.3144   -0.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5568    3.5003   -0.7035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8420    0.7130   -1.3963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4333    1.8657    0.9614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8833    1.9633   -0.8347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9925   -0.2372   -0.1851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9447   -2.6423    1.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5544   -2.9071   -0.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7079   -2.4617   -0.7017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6407    0.2068    1.6261 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  3
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
  7  2  1  0
 18 12  1  0
 18  6  1  0
  1 19  1  0
  1 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  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    HMDB0037801
HETATM    1  C1  UNL     1       3.876  -1.573  -0.195  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.583  -1.374  -0.334  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.671  -2.047  -1.254  1.00  0.00           C  
HETATM    4  O1  UNL     1       2.012  -2.950  -2.064  1.00  0.00           O  
HETATM    5  O2  UNL     1       0.377  -1.516  -1.072  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.392  -0.978   0.232  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.757  -0.400   0.433  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.986   0.940  -0.162  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.319   2.087   0.524  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.051   2.202  -0.039  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.570   3.390  -0.297  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.945   1.065  -0.360  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.410   1.396  -0.028  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.966  -0.004   0.025  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.010  -0.854   0.360  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.212  -2.344   0.507  1.00  0.00           C  
HETATM   17  O3  UNL     1      -3.516  -2.679   0.245  1.00  0.00           O  
HETATM   18  C15 UNL     1      -0.746  -0.099   0.565  1.00  0.00           C  
HETATM   19  H1  UNL     1       4.420  -0.991   0.535  1.00  0.00           H  
HETATM   20  H2  UNL     1       4.448  -2.281  -0.761  1.00  0.00           H  
HETATM   21  H3  UNL     1       0.327  -1.873   0.921  1.00  0.00           H  
HETATM   22  H4  UNL     1       1.999  -0.391   1.503  1.00  0.00           H  
HETATM   23  H5  UNL     1       1.666   0.934  -1.239  1.00  0.00           H  
HETATM   24  H6  UNL     1       3.083   1.126  -0.186  1.00  0.00           H  
HETATM   25  H7  UNL     1       1.888   3.036   0.469  1.00  0.00           H  
HETATM   26  H8  UNL     1       1.183   1.866   1.618  1.00  0.00           H  
HETATM   27  H9  UNL     1      -0.004   4.314  -0.102  1.00  0.00           H  
HETATM   28  H10 UNL     1      -1.557   3.500  -0.703  1.00  0.00           H  
HETATM   29  H11 UNL     1      -0.842   0.713  -1.396  1.00  0.00           H  
HETATM   30  H12 UNL     1      -2.433   1.866   0.961  1.00  0.00           H  
HETATM   31  H13 UNL     1      -2.883   1.963  -0.835  1.00  0.00           H  
HETATM   32  H14 UNL     1      -3.993  -0.237  -0.185  1.00  0.00           H  
HETATM   33  H15 UNL     1      -1.945  -2.642   1.553  1.00  0.00           H  
HETATM   34  H16 UNL     1      -1.554  -2.907  -0.163  1.00  0.00           H  
HETATM   35  H17 UNL     1      -3.708  -2.462  -0.702  1.00  0.00           H  
HETATM   36  H18 UNL     1      -0.641   0.207   1.626  1.00  0.00           H  
CONECT    1    2    2   19   20
CONECT    2    3    7
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   18   21
CONECT    7    8   22
CONECT    8    9   23   24
CONECT    9   10   25   26
CONECT   10   11   11   12
CONECT   11   27   28
CONECT   12   13   18   29
CONECT   13   14   30   31
CONECT   14   15   15   32
CONECT   15   16   18
CONECT   16   17   33   34
CONECT   17   35
CONECT   18   36
END

HMDB0037801
     RDKit          3D
Annuolide A
 36 38  0  0  0  0  0  0  0  0999 V2000
    3.8755   -1.5725   -0.1950 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5829   -1.3745   -0.3345 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6710   -2.0473   -1.2538 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0123   -2.9498   -2.0643 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3769   -1.5165   -1.0724 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3921   -0.9779    0.2318 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7574   -0.4003    0.4331 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9859    0.9400   -0.1615 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3188    2.0866    0.5237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0508    2.2024   -0.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5698    3.3897   -0.2967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9454    1.0645   -0.3598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4099    1.3957   -0.0279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9661   -0.0038    0.0249 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0105   -0.8544    0.3601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2122   -2.3440    0.5070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5160   -2.6791    0.2447 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7462   -0.0994    0.5647 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4198   -0.9914    0.5351 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4479   -2.2813   -0.7606 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3272   -1.8734    0.9205 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9995   -0.3907    1.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6657    0.9341   -1.2391 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0826    1.1256   -0.1858 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8884    3.0359    0.4691 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1831    1.8665    1.6184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0045    4.3144   -0.1022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5568    3.5003   -0.7035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8420    0.7130   -1.3963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4333    1.8657    0.9614 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8833    1.9633   -0.8347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9925   -0.2372   -0.1851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9447   -2.6423    1.5535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5544   -2.9071   -0.1633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7079   -2.4617   -0.7017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6407    0.2068    1.6261 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  3
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 15 18  1  0
  7  2  1  0
 18 12  1  0
 18  6  1  0
  1 19  1  0
  1 20  1  0
  6 21  1  0
  7 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
 18 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
15-Hydroxy-3,10(14),11(13)-guaiatrien-12,6-olide	HMDB

Chemical Formula

C₁₅H₁₈O₃

Average Molecular Weight

246.3016

Monoisotopic Molecular Weight

246.125594442

IUPAC Name

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

Traditional Name

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

CAS Registry Number

152442-48-3

SMILES

OCC1=CCC2C1C1OC(=O)C(=C)C1CCC2=C

InChI Identifier

InChI=1S/C15H18O3/c1-8-3-5-12-9(2)15(17)18-14(12)13-10(7-16)4-6-11(8)13/h4,11-14,16H,1-3,5-7H2

InChI Key

XIKLPPAERLRBPO-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
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Alcohol
Primary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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: HMDB0037801)

Source

Endogenous

Endogenous (HMDB: HMDB0037801)

Animal

Animal (HMDB: HMDB0037801)

Exogenous

Food

Food (HMDB: HMDB0037801)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Exogenous (HMDB: HMDB0037801)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0037801)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0037801)

Lipid metabolism pathway (HMDB: HMDB0037801)

Cellular process

Cell signaling (HMDB: HMDB0037801)

Biochemical process

Lipid transport (HMDB: HMDB0037801)

Role

Biological role

Energy source (HMDB: HMDB0037801)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0037801)

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	2485 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	0.9 g/L	ALOGPS
logP	1.93	ALOGPS
logP	1.74	ChemAxon
logS	-2.4	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	68.82 m³·mol⁻¹	ChemAxon
Polarizability	26.69 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]+	159.474	31661259
DarkChem	[M-H]-	154.686	31661259
DeepCCS	[M+H]+	157.541	30932474
DeepCCS	[M-H]-	155.183	30932474
DeepCCS	[M-2H]-	188.19	30932474
DeepCCS	[M+Na]+	163.634	30932474
AllCCS	[M+H]+	157.7	32859911
AllCCS	[M+H-H2O]+	154.0	32859911
AllCCS	[M+NH4]+	161.2	32859911
AllCCS	[M+Na]+	162.2	32859911
AllCCS	[M-H]-	161.0	32859911
AllCCS	[M+Na-2H]-	160.8	32859911
AllCCS	[M+HCOO]-	160.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Annuolide A	OCC1=CCC2C1C1OC(=O)C(=C)C1CCC2=C	3114.8	Standard polar	33892256
Annuolide A	OCC1=CCC2C1C1OC(=O)C(=C)C1CCC2=C	2099.7	Standard non polar	33892256
Annuolide A	OCC1=CCC2C1C1OC(=O)C(=C)C1CCC2=C	2307.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Annuolide A,1TMS,isomer #1	C=C1C(=O)OC2C1CCC(=C)C1CC=C(CO[Si](C)(C)C)C12	2185.4	Semi standard non polar	33892256
Annuolide A,1TBDMS,isomer #1	C=C1C(=O)OC2C1CCC(=C)C1CC=C(CO[Si](C)(C)C(C)(C)C)C12	2404.7	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 A GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f6t-4940000000-6599e925fe9f46797b54	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annuolide A GC-MS (1 TMS) - 70eV, Positive	splash10-0ukc-3690000000-26fe5fb7227930160080	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Annuolide A 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 A 10V, Positive-QTOF	splash10-004j-0290000000-4264be28ad163a20a252	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annuolide A 20V, Positive-QTOF	splash10-056r-0950000000-2a062bd9c045f7e5f35b	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annuolide A 40V, Positive-QTOF	splash10-0pb9-6910000000-fa02815e794a71d760db	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annuolide A 10V, Negative-QTOF	splash10-0002-0090000000-ccab6068ec3a6d300b2a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annuolide A 20V, Negative-QTOF	splash10-0ftb-0290000000-ad38987e4f12417f9144	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annuolide A 40V, Negative-QTOF	splash10-0uka-6910000000-76695d46dc80b81b371a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annuolide A 10V, Negative-QTOF	splash10-014j-0090000000-41f91938a2388dec7713	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annuolide A 20V, Negative-QTOF	splash10-0002-0090000000-99ef8bcde447b8bb37ef	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annuolide A 40V, Negative-QTOF	splash10-00y0-0930000000-426d080f825b0133c8bd	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annuolide A 10V, Positive-QTOF	splash10-0002-0090000000-a3cf7eee8166bfde606a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annuolide A 20V, Positive-QTOF	splash10-002b-0390000000-c9b58398ff95ab25afb3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Annuolide A 40V, Positive-QTOF	splash10-06fv-1910000000-c87a76a61e64df7b585d	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

FDB016945

KNApSAcK ID

C00054894

Chemspider ID

35014475

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

75051793

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1863701

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 A (HMDB0037801)

MOL for HMDB0037801 (Annuolide A)

3D MOL for HMDB0037801 (Annuolide A)

3D SDF for HMDB0037801 (Annuolide A)

3D-SDF for HMDB0037801 (Annuolide A)

PDB for HMDB0037801 (Annuolide A)

3D PDB for HMDB0037801 (Annuolide A)

SMILES for HMDB0037801 (Annuolide A)

INCHI for HMDB0037801 (Annuolide A)

Structure for HMDB0037801 (Annuolide A)

3D Structure for HMDB0037801 (Annuolide A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra