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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 08:06:12 UTC

Update Date

2021-09-26 23:02:41 UTC

HMDB ID

HMDB0250946

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Dehydrocostus lactone

Description

Dehydrocostus lactone 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. Dehydrocostus lactone 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 ). Dehydrocostus lactone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Dehydrocostus lactone 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

HMDB0250946
     RDKit          3D
Dehydrocostus lactone
 35 37  0  0  0  0  0  0  0  0999 V2000
    3.9899   -0.2680   -0.8050 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7889   -0.7460   -0.5602 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4987   -1.9481    0.2163 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3725   -2.7301    0.7053 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0933   -2.0721    0.3170 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6155   -0.7688    0.2007 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4578   -0.2471   -0.9678 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3561    1.2045   -1.1764 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8125    2.0045   -0.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6415    1.8134    0.1953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4515    2.7747   -0.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2388    0.6209    0.8464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7228    0.5337    0.7532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9105   -0.9676    1.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7421   -1.6200    0.4007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5905   -2.9188    0.2481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8247   -0.5770   -0.0274 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8733   -0.7312   -0.4474 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0955    0.6326   -1.3933 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0100   -0.2136    1.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1893   -0.8117   -1.9055 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6664    1.3818   -2.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3151    1.6948   -1.4939 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0221    3.0889   -0.2744 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4147    1.7830    0.8606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5211    2.7151   -0.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0227    3.6447   -0.6771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8400    0.5307    1.8635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0198    0.7511   -0.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2540    1.1320    1.5029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8702   -1.3263    0.6740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8102   -1.0401    2.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3456   -3.6443    0.6053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7381   -3.3865   -0.2297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0278   -0.2892   -1.0824 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  1  0
 15 16  2  3
 15 17  1  0
  7  2  1  0
 17 12  1  0
 17  6  1  0
  1 18  1  0
  1 19  1  0
  6 20  1  0
  7 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
M  END


  Mrv0541 02241223402D          

 17 19  0  0  0  0            999 V2000
    0.2477   -2.3109    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0833   -1.4852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7424   -1.3201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0727   -0.5773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7424    0.1647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0833    0.3299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7424   -0.1647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7424   -0.9897    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4859   -1.2379    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9807   -0.5773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4859    0.0826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7333    0.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9807    0.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1549    0.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6595    1.4859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1647    1.1557    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8246    2.3109    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2  8  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5 14  1  0  0  0  0
  6  7  1  0  0  0  0
  6 16  1  0  0  0  0
  7  8  1  0  0  0  0
  7 11  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0250946

> <DATABASE_NAME>
hmdb

> <SMILES>
C=C1CCC2C1C1OC(=O)C(=C)C1CCC2=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H18O2/c1-8-4-7-12-10(3)15(16)17-14(12)13-9(2)5-6-11(8)13/h11-14H,1-7H2

> <INCHI_KEY>
NETSQGRTUNRXEO-UHFFFAOYSA-N

> <FORMULA>
C15H18O2

> <MOLECULAR_WEIGHT>
230.3022

> <EXACT_MASS>
230.13067982

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
25.799447386308486

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,6,9-trimethylidene-dodecahydroazuleno[4,5-b]furan-2-one

> <ALOGPS_LOGP>
2.84

> <JCHEM_LOGP>
3.075255217333333

> <ALOGPS_LOGS>
-3.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.865903641179668

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
65.97139999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.98e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,6,9-trimethylidene-octahydroazuleno[4,5-b]furan-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0250946
     RDKit          3D
Dehydrocostus lactone
 35 37  0  0  0  0  0  0  0  0999 V2000
    3.9899   -0.2680   -0.8050 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7889   -0.7460   -0.5602 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4987   -1.9481    0.2163 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3725   -2.7301    0.7053 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0933   -2.0721    0.3170 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6155   -0.7688    0.2007 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4578   -0.2471   -0.9678 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3561    1.2045   -1.1764 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8125    2.0045   -0.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6415    1.8134    0.1953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4515    2.7747   -0.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2388    0.6209    0.8464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7228    0.5337    0.7532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9105   -0.9676    1.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7421   -1.6200    0.4007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5905   -2.9188    0.2481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8247   -0.5770   -0.0274 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8733   -0.7312   -0.4474 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0955    0.6326   -1.3933 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0100   -0.2136    1.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1893   -0.8117   -1.9055 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6664    1.3818   -2.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3151    1.6948   -1.4939 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0221    3.0889   -0.2744 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4147    1.7830    0.8606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5211    2.7151   -0.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0227    3.6447   -0.6771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8400    0.5307    1.8635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0198    0.7511   -0.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2540    1.1320    1.5029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8702   -1.3263    0.6740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8102   -1.0401    2.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3456   -3.6443    0.6053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7381   -3.3865   -0.2297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0278   -0.2892   -1.0824 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  1  0
 15 16  2  3
 15 17  1  0
  7  2  1  0
 17 12  1  0
 17  6  1  0
  1 18  1  0
  1 19  1  0
  6 20  1  0
  7 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       0.462  -4.314   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.155  -2.772   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.386  -2.464   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.002  -1.078   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.386   0.307   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.155   0.616   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.386  -0.307   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.386  -1.847   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.774  -2.311   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.697  -1.078   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.774   0.154   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.235   1.695   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.697   1.695   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.156   1.695   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.231   2.774   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.307   2.157   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -1.539   4.314   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7   16                                                  
CONECT    7    6    8   11                                                  
CONECT    8    2    7    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11    7   10   12                                                  
CONECT   12   11                                                            
CONECT   13   14                                                            
CONECT   14    5   13   15                                                  
CONECT   15   14   16   17                                                  
CONECT   16    6   15                                                       
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

COMPND    HMDB0250946
HETATM    1  C1  UNL     1       3.990  -0.268  -0.805  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.789  -0.746  -0.560  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.499  -1.948   0.216  1.00  0.00           C  
HETATM    4  O1  UNL     1       3.372  -2.730   0.705  1.00  0.00           O  
HETATM    5  O2  UNL     1       1.093  -2.072   0.317  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.615  -0.769   0.201  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.458  -0.247  -0.968  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.356   1.205  -1.176  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.813   2.005  -0.042  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.642   1.813   0.195  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.452   2.775  -0.203  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.239   0.621   0.846  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.723   0.534   0.753  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.910  -0.968   1.053  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.742  -1.620   0.401  1.00  0.00           C  
HETATM   16  C14 UNL     1      -1.591  -2.919   0.248  1.00  0.00           C  
HETATM   17  C15 UNL     1      -0.825  -0.577  -0.027  1.00  0.00           C  
HETATM   18  H1  UNL     1       4.873  -0.731  -0.447  1.00  0.00           H  
HETATM   19  H2  UNL     1       4.096   0.633  -1.393  1.00  0.00           H  
HETATM   20  H3  UNL     1       1.010  -0.214   1.099  1.00  0.00           H  
HETATM   21  H4  UNL     1       1.189  -0.812  -1.905  1.00  0.00           H  
HETATM   22  H5  UNL     1       0.666   1.382  -2.056  1.00  0.00           H  
HETATM   23  H6  UNL     1       2.315   1.695  -1.494  1.00  0.00           H  
HETATM   24  H7  UNL     1       1.022   3.089  -0.274  1.00  0.00           H  
HETATM   25  H8  UNL     1       1.415   1.783   0.861  1.00  0.00           H  
HETATM   26  H9  UNL     1      -2.521   2.715  -0.069  1.00  0.00           H  
HETATM   27  H10 UNL     1      -1.023   3.645  -0.677  1.00  0.00           H  
HETATM   28  H11 UNL     1      -0.840   0.531   1.864  1.00  0.00           H  
HETATM   29  H12 UNL     1      -3.020   0.751  -0.294  1.00  0.00           H  
HETATM   30  H13 UNL     1      -3.254   1.132   1.503  1.00  0.00           H  
HETATM   31  H14 UNL     1      -3.870  -1.326   0.674  1.00  0.00           H  
HETATM   32  H15 UNL     1      -2.810  -1.040   2.163  1.00  0.00           H  
HETATM   33  H16 UNL     1      -2.346  -3.644   0.605  1.00  0.00           H  
HETATM   34  H17 UNL     1      -0.738  -3.387  -0.230  1.00  0.00           H  
HETATM   35  H18 UNL     1      -1.028  -0.289  -1.082  1.00  0.00           H  
CONECT    1    2    2   18   19
CONECT    2    3    7
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   17   20
CONECT    7    8   21
CONECT    8    9   22   23
CONECT    9   10   24   25
CONECT   10   11   11   12
CONECT   11   26   27
CONECT   12   13   17   28
CONECT   13   14   29   30
CONECT   14   15   31   32
CONECT   15   16   16   17
CONECT   16   33   34
CONECT   17   35
END

HMDB0250946
     RDKit          3D
Dehydrocostus lactone
 35 37  0  0  0  0  0  0  0  0999 V2000
    3.9899   -0.2680   -0.8050 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7889   -0.7460   -0.5602 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4987   -1.9481    0.2163 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3725   -2.7301    0.7053 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0933   -2.0721    0.3170 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6155   -0.7688    0.2007 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4578   -0.2471   -0.9678 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3561    1.2045   -1.1764 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8125    2.0045   -0.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6415    1.8134    0.1953 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4515    2.7747   -0.2030 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2388    0.6209    0.8464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7228    0.5337    0.7532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9105   -0.9676    1.0528 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7421   -1.6200    0.4007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5905   -2.9188    0.2481 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8247   -0.5770   -0.0274 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8733   -0.7312   -0.4474 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0955    0.6326   -1.3933 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0100   -0.2136    1.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1893   -0.8117   -1.9055 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6664    1.3818   -2.0556 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3151    1.6948   -1.4939 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0221    3.0889   -0.2744 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4147    1.7830    0.8606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5211    2.7151   -0.0687 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0227    3.6447   -0.6771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8400    0.5307    1.8635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0198    0.7511   -0.2943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2540    1.1320    1.5029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8702   -1.3263    0.6740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8102   -1.0401    2.1626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3456   -3.6443    0.6053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7381   -3.3865   -0.2297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0278   -0.2892   -1.0824 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  1  0
 15 16  2  3
 15 17  1  0
  7  2  1  0
 17 12  1  0
 17  6  1  0
  1 18  1  0
  1 19  1  0
  6 20  1  0
  7 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
 14 31  1  0
 14 32  1  0
 16 33  1  0
 16 34  1  0
 17 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
dehydro-Alpha-Curcumene	ChEMBL
dehydro-a-Curcumene	Generator
dehydro-α-curcumene	Generator

Chemical Formula

C₁₅H₁₈O₂

Average Molecular Weight

230.3022

Monoisotopic Molecular Weight

230.13067982

IUPAC Name

3,6,9-trimethylidene-dodecahydroazuleno[4,5-b]furan-2-one

Traditional Name

3,6,9-trimethylidene-octahydroazuleno[4,5-b]furan-2-one

CAS Registry Number

Not Available

SMILES

C=C1CCC2C1C1OC(=O)C(=C)C1CCC2=C

InChI Identifier

InChI=1S/C15H18O2/c1-8-4-7-12-10(3)15(16)17-14(12)13-9(2)5-6-11(8)13/h11-14H,1-7H2

InChI Key

NETSQGRTUNRXEO-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
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

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Sweet bay (FooDB: FOOD00097)

Vegetable

Root vegetable

Burdock (FooDB: FOOD00017)

Process

Not Available

Role

Biological role

Industrial application

Agriculture

Pesticide

Insecticide

pesticide (HMDB: HMDB0250946)

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	2.84	ALOGPS
logP	3.08	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	65.97 m³·mol⁻¹	ChemAxon
Polarizability	25.8 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	155.947	30932474
DeepCCS	[M-H]-	153.589	30932474
DeepCCS	[M-2H]-	186.928	30932474
DeepCCS	[M+Na]+	162.04	30932474
AllCCS	[M+H]+	154.6	32859911
AllCCS	[M+H-H2O]+	150.8	32859911
AllCCS	[M+NH4]+	158.2	32859911
AllCCS	[M+Na]+	159.3	32859911
AllCCS	[M-H]-	158.8	32859911
AllCCS	[M+Na-2H]-	158.6	32859911
AllCCS	[M+HCOO]-	158.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dehydrocostus lactone	C=C1CCC2C1C1OC(=O)C(=C)C1CCC2=C	2601.2	Standard polar	33892256
Dehydrocostus lactone	C=C1CCC2C1C1OC(=O)C(=C)C1CCC2=C	1913.9	Standard non polar	33892256
Dehydrocostus lactone	C=C1CCC2C1C1OC(=O)C(=C)C1CCC2=C	2022.6	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 - Dehydrocostus lactone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0kdi-3930000000-3f00fd3e8749a79d1168	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydrocostus lactone 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 - Dehydrocostus lactone 10V, Positive-QTOF	splash10-001i-0390000000-5532b639b679c69b3d1a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrocostus lactone 20V, Positive-QTOF	splash10-053r-0930000000-beee5323db3a04c22af1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrocostus lactone 40V, Positive-QTOF	splash10-0zfr-9510000000-1f46379e5f54b341dbaf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrocostus lactone 10V, Negative-QTOF	splash10-004i-0290000000-ce97bd6be29026142474	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrocostus lactone 20V, Negative-QTOF	splash10-004r-0790000000-d0706a3090bdb6efb867	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrocostus lactone 40V, Negative-QTOF	splash10-1000-8900000000-036b2ebe798d073d9a38	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrocostus lactone 10V, Positive-QTOF	splash10-001i-0090000000-88e5e1b462dfdf06b4e5	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrocostus lactone 20V, Positive-QTOF	splash10-001i-0590000000-bcadd3d8315920fa3b32	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrocostus lactone 40V, Positive-QTOF	splash10-056r-6910000000-d6e397454b0e47563534	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrocostus lactone 10V, Negative-QTOF	splash10-004i-0090000000-fb2ff0c6ce4213f1f376	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrocostus lactone 20V, Negative-QTOF	splash10-004i-0290000000-299ce8142782da5e202f	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrocostus lactone 40V, Negative-QTOF	splash10-0zi0-0960000000-fdcd7a87ddd805d5854a	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

FDB004098

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

4426320

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 Dehydrocostus lactone (HMDB0250946)

MOL for HMDB0250946 (Dehydrocostus lactone)

3D MOL for HMDB0250946 (Dehydrocostus lactone)

3D SDF for HMDB0250946 (Dehydrocostus lactone)

3D-SDF for HMDB0250946 (Dehydrocostus lactone)

PDB for HMDB0250946 (Dehydrocostus lactone)

3D PDB for HMDB0250946 (Dehydrocostus lactone)

SMILES for HMDB0250946 (Dehydrocostus lactone)

INCHI for HMDB0250946 (Dehydrocostus lactone)

Structure for HMDB0250946 (Dehydrocostus lactone)

3D Structure for HMDB0250946 (Dehydrocostus lactone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra