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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 00:49:21 UTC

Update Date

2021-09-26 22:57:35 UTC

HMDB ID

HMDB0247731

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))-

Description

12-(chloromethyl)-12-hydroxy-3,4-dimethyl-11-oxo-10-oxatricyclo[6.4.0.0¹,⁵]dodeca-2,6-diene-7-carboxylic acid belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring. 12-(chloromethyl)-12-hydroxy-3,4-dimethyl-11-oxo-10-oxatricyclo[6.4.0.0¹,⁵]dodeca-2,6-diene-7-carboxylic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1s-(1alpha,4aalpha,6abeta,7alpha,9ar*))- is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))- 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

HMDB0247731
     RDKit          3D
Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexa...
 38 40  0  0  0  0  0  0  0  0999 V2000
   -3.5275   -0.2878   -0.8325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1363   -0.2239   -0.3135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1008   -0.7710   -0.9328 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1199   -0.5096   -0.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7882    0.6981   -0.6960 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8569    0.4124   -1.7113 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6402   -0.8570   -2.3318 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4213   -1.9614   -1.5348 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5840   -3.1206   -1.9639 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9829   -1.7242   -0.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1579   -1.5255    0.6069 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2190   -2.9235    0.3838 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2870   -4.3697    0.3578 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.2630    1.4313    0.4794 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2878    2.4949    0.5192 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8612    2.8684   -0.5251 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6119    3.0776    1.7178 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6284    1.0001    1.5496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3469   -0.0718    1.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7292    0.4377    0.9268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8136    1.9206    0.8138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1338   -0.8550   -0.1181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5892   -0.7836   -1.8241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9218    0.7224   -0.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0640   -1.3282   -1.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0124    1.3429   -1.1965 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8768    0.4028   -1.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8130    1.1734   -2.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7063   -2.3382    0.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1520   -2.7742    1.4123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6255   -3.1609   -0.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5520    4.0664    1.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7816    1.3741    2.5864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3197   -0.8436    2.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3775    0.1015    1.7843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6718    2.2780    1.4102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0219    2.1804   -0.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9200    2.4468    1.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
  5 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 14 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20  2  1  0
 10  4  1  0
 19  4  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
 20 35  1  0
 21 36  1  0
 21 37  1  0
 21 38  1  0
M  END


  Mrv1533004201501032D          

 21 23  0  0  0  0            999 V2000
    0.0001    0.0944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8032   -0.0944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4280    0.4444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6167    1.2475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4389    1.3162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7582    0.5555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5372    0.2839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6915   -0.5266    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0667   -1.0654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2209   -1.8759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2877   -0.7937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4628   -0.8049    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1554   -1.6081    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3841   -1.9007    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    2.1335    0.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9447   -0.7864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1226   -0.8551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6949   -1.5605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8666    2.0217    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6914    2.0040    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4694    2.7448    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
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 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
 11 15  1  0  0  0  0
  3 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  2 17  1  0  0  0  0
 17 18  1  0  0  0  0
  5 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0247731

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1C2C=C(C3COC(=O)C(O)(CCl)C23C=C1C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H17ClO5/c1-7-4-14-10(8(7)2)3-9(12(17)18)11(14)5-21-13(19)15(14,20)6-16/h3-4,8,10-11,20H,5-6H2,1-2H3,(H,17,18)

> <INCHI_KEY>
JIBVJJZCSYJNBC-UHFFFAOYSA-N

> <FORMULA>
C15H17ClO5

> <MOLECULAR_WEIGHT>
312.75

> <EXACT_MASS>
312.0764513

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
30.092742080429204

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
12-(chloromethyl)-12-hydroxy-3,4-dimethyl-11-oxo-10-oxatricyclo[6.4.0.0¹,⁵]dodeca-2,6-diene-7-carboxylic acid

> <ALOGPS_LOGP>
1.42

> <JCHEM_LOGP>
1.0617438743333338

> <ALOGPS_LOGS>
-2.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.238033029722954

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.364000325931734

> <JCHEM_PKA_STRONGEST_BASIC>
-4.444980954089197

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
76.2598

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.54e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
12-(chloromethyl)-12-hydroxy-3,4-dimethyl-11-oxo-10-oxatricyclo[6.4.0.0¹,⁵]dodeca-2,6-diene-7-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0247731
     RDKit          3D
Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexa...
 38 40  0  0  0  0  0  0  0  0999 V2000
   -3.5275   -0.2878   -0.8325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1363   -0.2239   -0.3135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1008   -0.7710   -0.9328 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1199   -0.5096   -0.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7882    0.6981   -0.6960 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8569    0.4124   -1.7113 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6402   -0.8570   -2.3318 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4213   -1.9614   -1.5348 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5840   -3.1206   -1.9639 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9829   -1.7242   -0.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1579   -1.5255    0.6069 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2190   -2.9235    0.3838 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2870   -4.3697    0.3578 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.2630    1.4313    0.4794 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2878    2.4949    0.5192 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8612    2.8684   -0.5251 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6119    3.0776    1.7178 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6284    1.0001    1.5496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3469   -0.0718    1.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7292    0.4377    0.9268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8136    1.9206    0.8138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1338   -0.8550   -0.1181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5892   -0.7836   -1.8241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9218    0.7224   -0.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0640   -1.3282   -1.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0124    1.3429   -1.1965 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8768    0.4028   -1.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8130    1.1734   -2.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7063   -2.3382    0.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1520   -2.7742    1.4123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6255   -3.1609   -0.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5520    4.0664    1.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7816    1.3741    2.5864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3197   -0.8436    2.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3775    0.1015    1.7843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6718    2.2780    1.4102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0219    2.1804   -0.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9200    2.4468    1.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
  5 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 14 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20  2  1  0
 10  4  1  0
 19  4  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
 20 35  1  0
 21 36  1  0
 21 37  1  0
 21 38  1  0
M  END

HEADER    PROTEIN                                 20-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-APR-15         0                                  
HETATM    1  C   UNK     0       0.000   0.176   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.499  -0.176   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.666   0.830   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.018   2.329   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.553   2.457   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.149   1.037   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.603   0.530   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.891  -0.983   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.725  -1.989   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       6.012  -3.502   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.270  -1.482   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.731  -1.502   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.023  -3.002   0.000  0.00  0.00           C+0
HETATM   14 Cl   UNK     0       2.584  -3.548   0.000  0.00  0.00          Cl+0
HETATM   15  C   UNK     0       3.982   0.031   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.630  -1.468   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.096  -1.596   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.297  -2.913   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.351   3.774   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.891   3.741   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       4.610   5.124   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4   15                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   19                                                  
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13   15                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13                                                            
CONECT   15   11    3    6   16                                             
CONECT   16   15   17                                                       
CONECT   17   16    2   18                                                  
CONECT   18   17                                                            
CONECT   19    5   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   46    0
END

COMPND    HMDB0247731
HETATM    1  C1  UNL     1      -3.527  -0.288  -0.832  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.136  -0.224  -0.313  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.101  -0.771  -0.933  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.120  -0.510  -0.130  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.788   0.698  -0.696  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.857   0.412  -1.711  1.00  0.00           C  
HETATM    7  O1  UNL     1       1.640  -0.857  -2.332  1.00  0.00           O  
HETATM    8  C7  UNL     1       1.421  -1.961  -1.535  1.00  0.00           C  
HETATM    9  O2  UNL     1       1.584  -3.121  -1.964  1.00  0.00           O  
HETATM   10  C8  UNL     1       0.983  -1.724  -0.140  1.00  0.00           C  
HETATM   11  O3  UNL     1       2.158  -1.525   0.607  1.00  0.00           O  
HETATM   12  C9  UNL     1       0.219  -2.923   0.384  1.00  0.00           C  
HETATM   13 CL1  UNL     1       1.287  -4.370   0.358  1.00  0.00          CL  
HETATM   14  C10 UNL     1       1.263   1.431   0.479  1.00  0.00           C  
HETATM   15  C11 UNL     1       2.288   2.495   0.519  1.00  0.00           C  
HETATM   16  O4  UNL     1       2.861   2.868  -0.525  1.00  0.00           O  
HETATM   17  O5  UNL     1       2.612   3.078   1.718  1.00  0.00           O  
HETATM   18  C12 UNL     1       0.628   1.000   1.550  1.00  0.00           C  
HETATM   19  C13 UNL     1      -0.347  -0.072   1.230  1.00  0.00           C  
HETATM   20  C14 UNL     1      -1.729   0.438   0.927  1.00  0.00           C  
HETATM   21  C15 UNL     1      -1.814   1.921   0.814  1.00  0.00           C  
HETATM   22  H1  UNL     1      -4.134  -0.855  -0.118  1.00  0.00           H  
HETATM   23  H2  UNL     1      -3.589  -0.784  -1.824  1.00  0.00           H  
HETATM   24  H3  UNL     1      -3.922   0.722  -0.926  1.00  0.00           H  
HETATM   25  H4  UNL     1      -1.064  -1.328  -1.864  1.00  0.00           H  
HETATM   26  H5  UNL     1       0.012   1.343  -1.197  1.00  0.00           H  
HETATM   27  H6  UNL     1       2.877   0.403  -1.296  1.00  0.00           H  
HETATM   28  H7  UNL     1       1.813   1.173  -2.515  1.00  0.00           H  
HETATM   29  H8  UNL     1       2.706  -2.338   0.495  1.00  0.00           H  
HETATM   30  H9  UNL     1      -0.152  -2.774   1.412  1.00  0.00           H  
HETATM   31  H10 UNL     1      -0.626  -3.161  -0.294  1.00  0.00           H  
HETATM   32  H11 UNL     1       2.552   4.066   1.915  1.00  0.00           H  
HETATM   33  H12 UNL     1       0.782   1.374   2.586  1.00  0.00           H  
HETATM   34  H13 UNL     1      -0.320  -0.844   2.001  1.00  0.00           H  
HETATM   35  H14 UNL     1      -2.378   0.102   1.784  1.00  0.00           H  
HETATM   36  H15 UNL     1      -2.672   2.278   1.410  1.00  0.00           H  
HETATM   37  H16 UNL     1      -2.022   2.180  -0.246  1.00  0.00           H  
HETATM   38  H17 UNL     1      -0.920   2.447   1.204  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    3   20
CONECT    3    4   25
CONECT    4    5   10   19
CONECT    5    6   14   26
CONECT    6    7   27   28
CONECT    7    8
CONECT    8    9    9   10
CONECT   10   11   12
CONECT   11   29
CONECT   12   13   30   31
CONECT   14   15   18   18
CONECT   15   16   16   17
CONECT   17   32
CONECT   18   19   33
CONECT   19   20   34
CONECT   20   21   35
CONECT   21   36   37   38
END

HMDB0247731
     RDKit          3D
Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexa...
 38 40  0  0  0  0  0  0  0  0999 V2000
   -3.5275   -0.2878   -0.8325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1363   -0.2239   -0.3135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1008   -0.7710   -0.9328 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1199   -0.5096   -0.1304 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7882    0.6981   -0.6960 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8569    0.4124   -1.7113 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6402   -0.8570   -2.3318 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4213   -1.9614   -1.5348 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5840   -3.1206   -1.9639 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9829   -1.7242   -0.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1579   -1.5255    0.6069 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2190   -2.9235    0.3838 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2870   -4.3697    0.3578 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.2630    1.4313    0.4794 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2878    2.4949    0.5192 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8612    2.8684   -0.5251 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6119    3.0776    1.7178 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6284    1.0001    1.5496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3469   -0.0718    1.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7292    0.4377    0.9268 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8136    1.9206    0.8138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1338   -0.8550   -0.1181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5892   -0.7836   -1.8241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9218    0.7224   -0.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0640   -1.3282   -1.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0124    1.3429   -1.1965 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8768    0.4028   -1.2960 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8130    1.1734   -2.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7063   -2.3382    0.4947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1520   -2.7742    1.4123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6255   -3.1609   -0.2938 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5520    4.0664    1.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7816    1.3741    2.5864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3197   -0.8436    2.0009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3775    0.1015    1.7843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6718    2.2780    1.4102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0219    2.1804   -0.2462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9200    2.4468    1.2037 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
  5 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 14 18  2  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
 20  2  1  0
 10  4  1  0
 19  4  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 17 32  1  0
 18 33  1  0
 19 34  1  0
 20 35  1  0
 21 36  1  0
 21 37  1  0
 21 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
12-(Chloromethyl)-12-hydroxy-3,4-dimethyl-11-oxo-10-oxatricyclo[6.4.0.0,]dodeca-2,6-diene-7-carboxylate	Generator
12-(Chloromethyl)-12-hydroxy-3,4-dimethyl-11-oxo-10-oxatricyclo[6.4.0.0¹,⁵]dodeca-2,6-diene-7-carboxylate	Generator

Chemical Formula

C₁₅H₁₇ClO₅

Average Molecular Weight

312.75

Monoisotopic Molecular Weight

312.0764513

IUPAC Name

12-(chloromethyl)-12-hydroxy-3,4-dimethyl-11-oxo-10-oxatricyclo[6.4.0.0¹,⁵]dodeca-2,6-diene-7-carboxylic acid

Traditional Name

12-(chloromethyl)-12-hydroxy-3,4-dimethyl-11-oxo-10-oxatricyclo[6.4.0.0¹,⁵]dodeca-2,6-diene-7-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC1C2C=C(C3COC(=O)C(O)(CCl)C23C=C1C)C(O)=O

InChI Identifier

InChI=1S/C15H17ClO5/c1-7-4-14-10(8(7)2)3-9(12(17)18)11(14)5-21-13(19)15(14,20)6-16/h3-4,8,10-11,20H,5-6H2,1-2H3,(H,17,18)

InChI Key

JIBVJJZCSYJNBC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as terpene lactones. These are prenol lipids containing a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Terpene lactones

Alternative Parents

Substituents

Terpene lactone
Iridoid-skeleton
Monoterpenoid
Delta valerolactone
Delta_valerolactone
Dicarboxylic acid or derivatives
Oxane
Tertiary alcohol
Carboxylic acid ester
Chlorohydrin
Halohydrin
Lactone
Organoheterocyclic compound
Carboxylic acid derivative
Carboxylic acid
Oxacycle
Alcohol
Organic oxygen compound
Organochloride
Alkyl chloride
Organooxygen compound
Carbonyl group
Organohalogen compound
Organic oxide
Hydrocarbon derivative
Alkyl halide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (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	1.42	ALOGPS
logP	1.06	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	4.36	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	76.26 m³·mol⁻¹	ChemAxon
Polarizability	30.09 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]-	201.599	30932474
DeepCCS	[M+Na]+	177.165	30932474
AllCCS	[M+H]+	167.2	32859911
AllCCS	[M+H-H2O]+	164.0	32859911
AllCCS	[M+NH4]+	170.2	32859911
AllCCS	[M+Na]+	171.1	32859911
AllCCS	[M-H]-	171.1	32859911
AllCCS	[M+Na-2H]-	171.0	32859911
AllCCS	[M+HCOO]-	171.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))-	CC1C2C=C(C3COC(=O)C(O)(CCl)C23C=C1C)C(O)=O	3942.4	Standard polar	33892256
Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))-	CC1C2C=C(C3COC(=O)C(O)(CCl)C23C=C1C)C(O)=O	2212.6	Standard non polar	33892256
Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))-	CC1C2C=C(C3COC(=O)C(O)(CCl)C23C=C1C)C(O)=O	2534.9	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 - Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))- GC-MS (Non-derivatized) - 70eV, Positive	splash10-004r-3930000000-daa58afaa83713f10749	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))- GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))- GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))- GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))- GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))- GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))- GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))- GC-MS (TBDMS_2_1) - 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 - Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))- 10V, Negative-QTOF	splash10-03yi-0098000000-1c95a1ec2daccaf678c0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))- 20V, Negative-QTOF	splash10-014j-0090000000-b600be7d72684714e5af	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))- 40V, Negative-QTOF	splash10-014i-2191000000-832d4d53807229581ce2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))- 10V, Positive-QTOF	splash10-03dj-0059000000-0c6d5e1f73eb307d45b4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))- 20V, Positive-QTOF	splash10-0002-0091000000-c8e3c26b0d77afbe00ee	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))- 40V, Positive-QTOF	splash10-0udu-1491000000-52acb88e5ef280d39380	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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 Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))- (HMDB0247731)

MOL for HMDB0247731 (Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))-)

3D MOL for HMDB0247731 (Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))-)

3D SDF for HMDB0247731 (Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))-)

3D-SDF for HMDB0247731 (Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))-)

PDB for HMDB0247731 (Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))-)

3D PDB for HMDB0247731 (Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))-)

SMILES for HMDB0247731 (Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))-)

INCHI for HMDB0247731 (Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))-)

Structure for HMDB0247731 (Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))-)

3D Structure for HMDB0247731 (Pentaleno(1,6a-c)pyran-5-carboxylic acid, 1-(chloromethyl)-1,2,4,4a,6a,7-hexahydro-1-hydroxy-7,8-dimethyl-2-oxo-, (1S-(1alpha,4aalpha,6abeta,7alpha,9aR*))-)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra