Jump To Section:

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

Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-10 21:32:21 UTC

Update Date

2021-09-26 22:52:04 UTC

HMDB ID

HMDB0244375

Secondary Accession Numbers

None

Metabolite Identification

Common Name

2,5,9-Trimethyl-11-oxotricyclo[6.3.0.01,5]undec-3-ene-3-carboxylic acid

Description

2,5,9-Trimethyl-11-oxotricyclo[6.3.0.01,5]undec-3-ene-3-carboxylic acid, also known as suberogorgin, belongs to the class of organic compounds known as angular triquinanes. These are triquinane with a structure based on a [6.3.0.0^1,5] undecane carbon skeleton. Based on a literature review a significant number of articles have been published on 2,5,9-Trimethyl-11-oxotricyclo[6.3.0.01,5]undec-3-ene-3-carboxylic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). 2,5,9-trimethyl-11-oxotricyclo[6.3.0.01,5]undec-3-ene-3-carboxylic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 2,5,9-Trimethyl-11-oxotricyclo[6.3.0.01,5]undec-3-ene-3-carboxylic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

HMDB0258529
     RDKit          3D
Sodium suberogorgin
 38 40  0  0  0  0  0  0  0  0999 V2000
   -3.0322    1.7359    0.5912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6514    1.5742   -0.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7392    1.0146   -1.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9731   -0.2838   -1.3501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1644   -1.2122   -2.1296 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0562   -0.1350   -0.2238 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2038    0.6082   -0.5308 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6737    0.2799   -1.9130 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1156    0.0764    0.5298 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3699    0.7486    0.8562 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0943    0.2613    1.7514 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7735    1.8915    0.2135 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6266   -1.0277    1.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3288   -1.3828    0.4697 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5535   -2.5641   -0.4332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7436   -1.6440    1.4998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7845   -0.5640    1.2836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8999    0.5849    0.8069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9689    1.6583    1.6860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5355    2.6565    0.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6324    0.8718    0.2258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1304    2.5508    0.0165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2059    1.7060   -2.1285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7654    0.8009   -1.7272 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0424    1.7032   -0.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5642   -0.3916   -1.8289 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9735    1.2078   -2.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9098   -0.2082   -2.5299 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6097    1.9831   -0.3392 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1716   -1.5400    1.8732 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1449   -2.2510   -1.2927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3845   -3.0643   -0.7363 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1315   -3.3181    0.1513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3598   -1.5617    2.5367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1707   -2.6651    1.3815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3168   -0.3127    2.2190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4624   -0.8116    0.4455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3101    1.0241    1.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  9 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18  2  1  0
 14  6  1  0
 18  6  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  0
M  END

  Mrv1533004241513192D          

 18 20  0  0  0  0            999 V2000
    0.0343   -0.7267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8190   -0.4718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0739    0.3128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8989    0.3128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3838    0.9803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1538   -0.4718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4088    0.3128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6637    1.0974    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2338    0.3128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4887   -0.4718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8213   -0.9567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4887   -1.4416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5663   -1.7413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7413   -1.7413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4864   -0.9567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7187    0.9803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3832    1.7339    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5392    0.8940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  2 15  1  0  0  0  0
  6 15  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0244375

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CC(=O)C23C(C)C(=CC2(C)CCC13)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O3/c1-8-6-12(16)15-9(2)10(13(17)18)7-14(15,3)5-4-11(8)15/h7-9,11H,4-6H2,1-3H3,(H,17,18)

> <INCHI_KEY>
LFKSRWRSZVCLFJ-UHFFFAOYSA-N

> <FORMULA>
C15H20O3

> <MOLECULAR_WEIGHT>
248.322

> <EXACT_MASS>
248.141244504

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
26.80270032178945

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,5,9-trimethyl-11-oxotricyclo[6.3.0.0¹,⁵]undec-3-ene-3-carboxylic acid

> <ALOGPS_LOGP>
2.83

> <JCHEM_LOGP>
2.625567424

> <ALOGPS_LOGS>
-3.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.656996451339905

> <JCHEM_PKA_STRONGEST_BASIC>
-7.512800098939316

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
68.1048

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.87e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,5,9-trimethyl-11-oxotricyclo[6.3.0.0¹,⁵]undec-3-ene-3-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0258529
     RDKit          3D
Sodium suberogorgin
 38 40  0  0  0  0  0  0  0  0999 V2000
   -3.0322    1.7359    0.5912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6514    1.5742   -0.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7392    1.0146   -1.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9731   -0.2838   -1.3501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1644   -1.2122   -2.1296 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0562   -0.1350   -0.2238 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2038    0.6082   -0.5308 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6737    0.2799   -1.9130 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1156    0.0764    0.5298 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3699    0.7486    0.8562 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0943    0.2613    1.7514 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7735    1.8915    0.2135 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6266   -1.0277    1.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3288   -1.3828    0.4697 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5535   -2.5641   -0.4332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7436   -1.6440    1.4998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7845   -0.5640    1.2836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8999    0.5849    0.8069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9689    1.6583    1.6860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5355    2.6565    0.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6324    0.8718    0.2258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1304    2.5508    0.0165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2059    1.7060   -2.1285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7654    0.8009   -1.7272 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0424    1.7032   -0.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5642   -0.3916   -1.8289 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9735    1.2078   -2.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9098   -0.2082   -2.5299 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6097    1.9831   -0.3392 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1716   -1.5400    1.8732 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1449   -2.2510   -1.2927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3845   -3.0643   -0.7363 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1315   -3.3181    0.1513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3598   -1.5617    2.5367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1707   -2.6651    1.3815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3168   -0.3127    2.2190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4624   -0.8116    0.4455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3101    1.0241    1.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  9 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18  2  1  0
 14  6  1  0
 18  6  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 16 34  1  0
 16 35  1  0
 17 36  1  0
 17 37  1  0
 18 38  1  0
M  END

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       0.064  -1.357   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.529  -0.881   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.005   0.584   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.545   0.584   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.450   1.830   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.021  -0.881   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.496   0.584   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.972   2.049   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.036   0.584   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.512  -0.881   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.266  -1.786   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.512  -2.691   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.791  -3.251   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.251  -3.251   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.775  -1.786   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.942   1.830   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       6.315   3.237   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       8.473   1.669   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   11   15                                             
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10    6   12   13                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    2    6                                                  
CONECT   16    9   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

COMPND    HMDB0244376
HETATM    1  C1  UNL     1      -3.354   0.351   1.102  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.361  -0.227   0.137  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.350   0.576  -1.141  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.953   0.559  -1.597  1.00  0.00           C  
HETATM    5  O1  UNL     1      -0.574   0.814  -2.727  1.00  0.00           O  
HETATM    6  C5  UNL     1      -0.083   0.184  -0.471  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.972   1.179  -0.218  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.636   2.243   0.785  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.152   0.442   0.245  1.00  0.00           C  
HETATM   10  C9  UNL     1       3.275   1.039   0.945  1.00  0.00           C  
HETATM   11  O2  UNL     1       3.306   2.269   1.207  1.00  0.00           O  
HETATM   12  O3  UNL     1       4.341   0.271   1.342  1.00  0.00           O  
HETATM   13  C10 UNL     1       2.041  -0.829  -0.067  1.00  0.00           C  
HETATM   14  C11 UNL     1       0.749  -1.065  -0.782  1.00  0.00           C  
HETATM   15  C12 UNL     1       1.031  -1.211  -2.235  1.00  0.00           C  
HETATM   16  C13 UNL     1       0.051  -2.208  -0.149  1.00  0.00           C  
HETATM   17  C14 UNL     1      -0.523  -1.579   1.119  1.00  0.00           C  
HETATM   18  C15 UNL     1      -0.939  -0.196   0.676  1.00  0.00           C  
HETATM   19  H1  UNL     1      -4.167  -0.389   1.291  1.00  0.00           H  
HETATM   20  H2  UNL     1      -3.857   1.258   0.706  1.00  0.00           H  
HETATM   21  H3  UNL     1      -2.855   0.654   2.061  1.00  0.00           H  
HETATM   22  H4  UNL     1      -2.656  -1.269  -0.132  1.00  0.00           H  
HETATM   23  H5  UNL     1      -3.026   0.134  -1.897  1.00  0.00           H  
HETATM   24  H6  UNL     1      -2.690   1.629  -0.966  1.00  0.00           H  
HETATM   25  H7  UNL     1       1.232   1.677  -1.189  1.00  0.00           H  
HETATM   26  H8  UNL     1       0.920   1.968   1.816  1.00  0.00           H  
HETATM   27  H9  UNL     1      -0.423   2.554   0.683  1.00  0.00           H  
HETATM   28  H10 UNL     1       1.245   3.139   0.527  1.00  0.00           H  
HETATM   29  H11 UNL     1       4.528   0.098   2.333  1.00  0.00           H  
HETATM   30  H12 UNL     1       2.732  -1.629   0.130  1.00  0.00           H  
HETATM   31  H13 UNL     1       1.833  -1.978  -2.346  1.00  0.00           H  
HETATM   32  H14 UNL     1       1.500  -0.251  -2.581  1.00  0.00           H  
HETATM   33  H15 UNL     1       0.158  -1.401  -2.856  1.00  0.00           H  
HETATM   34  H16 UNL     1       0.803  -2.981   0.128  1.00  0.00           H  
HETATM   35  H17 UNL     1      -0.736  -2.672  -0.768  1.00  0.00           H  
HETATM   36  H18 UNL     1       0.311  -1.479   1.849  1.00  0.00           H  
HETATM   37  H19 UNL     1      -1.376  -2.155   1.496  1.00  0.00           H  
HETATM   38  H20 UNL     1      -0.891   0.482   1.544  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3   18   22
CONECT    3    4   23   24
CONECT    4    5    5    6
CONECT    6    7   14   18
CONECT    7    8    9   25
CONECT    8   26   27   28
CONECT    9   10   13   13
CONECT   10   11   11   12
CONECT   12   29
CONECT   13   14   30
CONECT   14   15   16
CONECT   15   31   32   33
CONECT   16   17   34   35
CONECT   17   18   36   37
CONECT   18   38
END

HMDB0258529
     RDKit          3D
Sodium suberogorgin
 38 40  0  0  0  0  0  0  0  0999 V2000
   -3.0322    1.7359    0.5912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6514    1.5742   -0.0226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7392    1.0146   -1.4280 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9731   -0.2838   -1.3501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1644   -1.2122   -2.1296 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0562   -0.1350   -0.2238 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2038    0.6082   -0.5308 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6737    0.2799   -1.9130 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1156    0.0764    0.5298 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3699    0.7486    0.8562 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0943    0.2613    1.7514 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7735    1.8915    0.2135 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6266   -1.0277    1.0822 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3288   -1.3828    0.4697 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5535   -2.5641   -0.4332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7436   -1.6440    1.4998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7845   -0.5640    1.2836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8999    0.5849    0.8069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9689    1.6583    1.6860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5355    2.6565    0.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6324    0.8718    0.2258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1304    2.5508    0.0165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2059    1.7060   -2.1285 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7654    0.8009   -1.7272 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0424    1.7032   -0.4201 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5642   -0.3916   -1.8289 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9735    1.2078   -2.4773 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9098   -0.2082   -2.5299 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6097    1.9831   -0.3392 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1716   -1.5400    1.8732 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1449   -2.2510   -1.2927 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3845   -3.0643   -0.7363 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1315   -3.3181    0.1513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3598   -1.5617    2.5367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1707   -2.6651    1.3815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3168   -0.3127    2.2190 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4624   -0.8116    0.4455 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3101    1.0241    1.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
  9 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18  2  1  0
 14  6  1  0
 18  6  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  2 22  1  0
  3 23  1  0
  3 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
 12 29  1  0
 13 30  1  0
 15 31  1  0
 15 32  1  0
 15 33  1  0
 16 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

Value	Source
2,5,9-Trimethyl-11-oxotricyclo[6.3.0.01,5]undec-3-ene-3-carboxylate	Generator
2,5,9-Trimethyl-11-oxotricyclo[6.3.0.0,]undec-3-ene-3-carboxylate	HMDB
Suberogorgin	HMDB
Sodium suberogorgin	HMDB

Chemical Formula

C₁₅H₂₀O₃

Average Molecular Weight

248.322

Monoisotopic Molecular Weight

248.141244504

IUPAC Name

2,5,9-trimethyl-11-oxotricyclo[6.3.0.0¹,⁵]undec-3-ene-3-carboxylic acid

Traditional Name

2,5,9-trimethyl-11-oxotricyclo[6.3.0.0¹,⁵]undec-3-ene-3-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1CC(=O)C23C(C)C(=CC2(C)CCC13)C(O)=O

InChI Identifier

InChI=1S/C15H20O3/c1-8-6-12(16)15-9(2)10(13(17)18)7-14(15,3)5-4-11(8)15/h7-9,11H,4-6H2,1-3H3,(H,17,18)

InChI Key

LFKSRWRSZVCLFJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as angular triquinanes. These are triquinane with a structure based on a [6.3.0.0^1,5] Undecane carbon skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Angular triquinanes

Alternative Parents

Substituents

Angular triquinane sesquiterpenoid
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

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	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.83	ALOGPS
logP	2.63	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	4.66	ChemAxon
pKa (Strongest Basic)	-7.5	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	68.1 m³·mol⁻¹	ChemAxon
Polarizability	26.8 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-2H]-	193.567	30932474
DeepCCS	[M+Na]+	169.132	30932474
AllCCS	[M+H]+	156.8	32859911
AllCCS	[M+H-H2O]+	153.2	32859911
AllCCS	[M+NH4]+	160.1	32859911
AllCCS	[M+Na]+	161.1	32859911
AllCCS	[M-H]-	163.9	32859911
AllCCS	[M+Na-2H]-	163.9	32859911
AllCCS	[M+HCOO]-	164.0	32859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2,5,9-Trimethyl-11-oxotricyclo[6.3.0.01,5]undec-3-ene-3-carboxylic acid,1TMS,isomer #1	CC1CC(=O)C23C(C)C(C(=O)O[Si](C)(C)C)=CC2(C)CCC13	1991.3	Semi standard non polar	33892256
2,5,9-Trimethyl-11-oxotricyclo[6.3.0.01,5]undec-3-ene-3-carboxylic acid,1TMS,isomer #1	CC1CC(=O)C23C(C)C(C(=O)O[Si](C)(C)C)=CC2(C)CCC13	2010.6	Standard non polar	33892256
2,5,9-Trimethyl-11-oxotricyclo[6.3.0.01,5]undec-3-ene-3-carboxylic acid,1TMS,isomer #1	CC1CC(=O)C23C(C)C(C(=O)O[Si](C)(C)C)=CC2(C)CCC13	2143.2	Standard polar	33892256
2,5,9-Trimethyl-11-oxotricyclo[6.3.0.01,5]undec-3-ene-3-carboxylic acid,1TMS,isomer #2	CC1C=C(O[Si](C)(C)C)C23C(C)C(C(=O)O)=CC2(C)CCC13	2054.2	Semi standard non polar	33892256
2,5,9-Trimethyl-11-oxotricyclo[6.3.0.01,5]undec-3-ene-3-carboxylic acid,1TMS,isomer #2	CC1C=C(O[Si](C)(C)C)C23C(C)C(C(=O)O)=CC2(C)CCC13	1822.3	Standard non polar	33892256
2,5,9-Trimethyl-11-oxotricyclo[6.3.0.01,5]undec-3-ene-3-carboxylic acid,1TMS,isomer #2	CC1C=C(O[Si](C)(C)C)C23C(C)C(C(=O)O)=CC2(C)CCC13	2244.7	Standard polar	33892256
2,5,9-Trimethyl-11-oxotricyclo[6.3.0.01,5]undec-3-ene-3-carboxylic acid,2TMS,isomer #1	CC1C=C(O[Si](C)(C)C)C23C(C)C(C(=O)O[Si](C)(C)C)=CC2(C)CCC13	2072.7	Semi standard non polar	33892256
2,5,9-Trimethyl-11-oxotricyclo[6.3.0.01,5]undec-3-ene-3-carboxylic acid,2TMS,isomer #1	CC1C=C(O[Si](C)(C)C)C23C(C)C(C(=O)O[Si](C)(C)C)=CC2(C)CCC13	1955.6	Standard non polar	33892256
2,5,9-Trimethyl-11-oxotricyclo[6.3.0.01,5]undec-3-ene-3-carboxylic acid,2TMS,isomer #1	CC1C=C(O[Si](C)(C)C)C23C(C)C(C(=O)O[Si](C)(C)C)=CC2(C)CCC13	2195.3	Standard polar	33892256
2,5,9-Trimethyl-11-oxotricyclo[6.3.0.01,5]undec-3-ene-3-carboxylic acid,2TBDMS,isomer #1	CC1C=C(O[Si](C)(C)C(C)(C)C)C23C(C)C(C(=O)O[Si](C)(C)C(C)(C)C)=CC2(C)CCC13	2512.4	Semi standard non polar	33892256
2,5,9-Trimethyl-11-oxotricyclo[6.3.0.01,5]undec-3-ene-3-carboxylic acid,2TBDMS,isomer #1	CC1C=C(O[Si](C)(C)C(C)(C)C)C23C(C)C(C(=O)O[Si](C)(C)C(C)(C)C)=CC2(C)CCC13	2308.9	Standard non polar	33892256
2,5,9-Trimethyl-11-oxotricyclo[6.3.0.01,5]undec-3-ene-3-carboxylic acid,2TBDMS,isomer #1	CC1C=C(O[Si](C)(C)C(C)(C)C)C23C(C)C(C(=O)O[Si](C)(C)C(C)(C)C)=CC2(C)CCC13	2474.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5,9-Trimethyl-11-oxotricyclo[6.3.0.01,5]undec-3-ene-3-carboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-053u-2290000000-c1eb4ba8b88a2f8f9189	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5,9-Trimethyl-11-oxotricyclo[6.3.0.01,5]undec-3-ene-3-carboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5,9-Trimethyl-11-oxotricyclo[6.3.0.01,5]undec-3-ene-3-carboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5,9-Trimethyl-11-oxotricyclo[6.3.0.01,5]undec-3-ene-3-carboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5,9-Trimethyl-11-oxotricyclo[6.3.0.01,5]undec-3-ene-3-carboxylic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2,5,9-Trimethyl-11-oxotricyclo[6.3.0.01,5]undec-3-ene-3-carboxylic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	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 - 2,5,9-Trimethyl-11-oxotricyclo[6.3.0.01,5]undec-3-ene-3-carboxylic acid 10V, Positive-QTOF	splash10-000t-0190000000-898b1f27f15c94b1eeab	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5,9-Trimethyl-11-oxotricyclo[6.3.0.01,5]undec-3-ene-3-carboxylic acid 20V, Positive-QTOF	splash10-001i-0390000000-0190a7a2bcaebcd70e7a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5,9-Trimethyl-11-oxotricyclo[6.3.0.01,5]undec-3-ene-3-carboxylic acid 40V, Positive-QTOF	splash10-0a4i-9830000000-949cfc01cf50371ac94a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5,9-Trimethyl-11-oxotricyclo[6.3.0.01,5]undec-3-ene-3-carboxylic acid 10V, Negative-QTOF	splash10-0002-0090000000-843bcf51babcb3ea206b	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5,9-Trimethyl-11-oxotricyclo[6.3.0.01,5]undec-3-ene-3-carboxylic acid 20V, Negative-QTOF	splash10-0002-0090000000-ad2c853d448948ce8626	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2,5,9-Trimethyl-11-oxotricyclo[6.3.0.01,5]undec-3-ene-3-carboxylic acid 40V, Negative-QTOF	splash10-0005-0090000000-49967aa50c407b38c68a	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

4479249

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5321540

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 2,5,9-Trimethyl-11-oxotricyclo[6.3.0.01,5]undec-3-ene-3-carboxylic acid (HMDB0244375)

MOL for HMDB0244375 (2,5,9-Trimethyl-11-oxotricyclo[6.3.0.01,5]undec-3-ene-3-carboxylic acid)

3D MOL for HMDB0244375 (2,5,9-Trimethyl-11-oxotricyclo[6.3.0.01,5]undec-3-ene-3-carboxylic acid)

3D SDF for HMDB0244375 (2,5,9-Trimethyl-11-oxotricyclo[6.3.0.01,5]undec-3-ene-3-carboxylic acid)

3D-SDF for HMDB0244375 (2,5,9-Trimethyl-11-oxotricyclo[6.3.0.01,5]undec-3-ene-3-carboxylic acid)

PDB for HMDB0244375 (2,5,9-Trimethyl-11-oxotricyclo[6.3.0.01,5]undec-3-ene-3-carboxylic acid)

3D PDB for HMDB0244375 (2,5,9-Trimethyl-11-oxotricyclo[6.3.0.01,5]undec-3-ene-3-carboxylic acid)

SMILES for HMDB0244375 (2,5,9-Trimethyl-11-oxotricyclo[6.3.0.01,5]undec-3-ene-3-carboxylic acid)

INCHI for HMDB0244375 (2,5,9-Trimethyl-11-oxotricyclo[6.3.0.01,5]undec-3-ene-3-carboxylic acid)

Structure for HMDB0244375 (2,5,9-Trimethyl-11-oxotricyclo[6.3.0.01,5]undec-3-ene-3-carboxylic acid)

3D Structure for HMDB0244375 (2,5,9-Trimethyl-11-oxotricyclo[6.3.0.01,5]undec-3-ene-3-carboxylic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra