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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 05:56:02 UTC

Update Date

2021-09-23 05:56:02 UTC

HMDB ID

HMDB0302038

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3beta-Chlorodehydrocostuslactone

Description

3beta-chlorodehydrocostuslactone belongs to guaianolides and derivatives class of compounds. Those 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. 3beta-chlorodehydrocostuslactone is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 3beta-chlorodehydrocostuslactone can be found in sweet bay, which makes 3beta-chlorodehydrocostuslactone a potential biomarker for the consumption of this food product.

Structure

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

HMDB0302038
     RDKit          3D
3beta-Chlorodehydrocostuslactone
 35 37  0  0  0  0  0  0  0  0999 V2000
    4.0764   -0.0454   -0.0605 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8836   -0.5771   -0.0543 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5692   -1.9920    0.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3089   -2.9828   -0.2579 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3049   -2.0526    0.6423 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6451   -0.8054    0.5378 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5855    0.1223   -0.1814 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6229    1.5139    0.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5355    2.3075   -0.3513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6912    1.4686   -0.2467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5479    1.8765    0.6472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0188    0.2649   -1.0024 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4784    0.0458   -1.3056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9022   -1.1690   -0.5174 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4796   -0.9631    0.2472 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.8079   -1.3235    0.4697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9432   -1.6682    1.7286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5690   -1.0007   -0.3020 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2824    1.0064   -0.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9674   -0.6768    0.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4157   -0.4334    1.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3814    0.2164   -1.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5667    2.0284    0.2153 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4001    1.5298    1.4804 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8562    2.3327   -1.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4147    3.3064    0.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4676    1.3428    0.8059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3803    2.7527    1.2606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4931    0.3033   -2.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0876    0.9324   -1.0148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6378   -0.1703   -2.3991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8604   -2.0561   -1.1841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9303   -1.8676    2.1242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1218   -1.7729    2.4268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3997   -1.7940   -1.0279 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
 14 16  1  0
 16 17  2  3
 16 18  1  0
  7  2  1  0
 18 12  1  0
 18  6  1  0
  1 19  1  0
  1 20  1  0
  6 21  1  1
  7 22  1  6
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  6
 13 30  1  0
 13 31  1  0
 14 32  1  6
 17 33  1  0
 17 34  1  0
 18 35  1  6
M  END

  Mrv0541 02241212152D          

 22 24  0  0  0  0            999 V2000
   -1.0018    3.5730    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7451    3.2151    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9286    2.4108    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4143    1.7658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5893    1.7658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0749    2.4108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2585    3.2151    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4533    3.6382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0746    3.0954    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7503    2.3368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0793    4.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8910    4.3905    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3116    3.8113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8789    3.2790    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -2.5273    4.4599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7451    4.0401    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3411    1.6963    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7722    1.0225    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7883    2.7761    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5665    3.2151    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1291    3.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2786    5.2811    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  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
  6  7  1  0  0  0  0
 10  3  1  0  0  0  0
  3  2  1  0  0  0  0
  8  2  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 12  1  1  0  0  0  0
  1  7  1  0  0  0  0
  7 13  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  9 14  1  6  0  0  0
  8 15  2  0  0  0  0
  2 16  1  1  0  0  0
  3 17  1  1  0  0  0
  4 18  2  0  0  0  0
  1 19  1  6  0  0  0
  7 20  1  1  0  0  0
 13 21  2  0  0  0  0
 11 22  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302038

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]12CCC(=C)[C@]3([H])C[C@H](Cl)C(=C)[C@]3([H])[C@@]1([H])OC(=O)C2=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H17ClO2/c1-7-4-5-10-8(2)15(17)18-14(10)13-9(3)12(16)6-11(7)13/h10-14H,1-6H2/t10-,11-,12-,13-,14-/m0/s1

> <INCHI_KEY>
XVGIEOUYQLZGPH-PEDHHIEDSA-N

> <FORMULA>
C15H17ClO2

> <MOLECULAR_WEIGHT>
264.747

> <EXACT_MASS>
264.091707495

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
27.674533883306186

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3aS,6aR,8S,9aR,9bS)-8-chloro-3,6,9-trimethylidene-dodecahydroazuleno[4,5-b]furan-2-one

> <ALOGPS_LOGP>
3.14

> <JCHEM_LOGP>
3.1990360063333334

> <ALOGPS_LOGS>
-3.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.865905204973273

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
70.5379

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.20e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3aS,6aR,8S,9aR,9bS)-8-chloro-3,6,9-trimethylidene-octahydroazuleno[4,5-b]furan-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0302038
     RDKit          3D
3beta-Chlorodehydrocostuslactone
 35 37  0  0  0  0  0  0  0  0999 V2000
    4.0764   -0.0454   -0.0605 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8836   -0.5771   -0.0543 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5692   -1.9920    0.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3089   -2.9828   -0.2579 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3049   -2.0526    0.6423 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6451   -0.8054    0.5378 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5855    0.1223   -0.1814 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6229    1.5139    0.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5355    2.3075   -0.3513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6912    1.4686   -0.2467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5479    1.8765    0.6472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0188    0.2649   -1.0024 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4784    0.0458   -1.3056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9022   -1.1690   -0.5174 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4796   -0.9631    0.2472 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.8079   -1.3235    0.4697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9432   -1.6682    1.7286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5690   -1.0007   -0.3020 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2824    1.0064   -0.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9674   -0.6768    0.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4157   -0.4334    1.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3814    0.2164   -1.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5667    2.0284    0.2153 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4001    1.5298    1.4804 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8562    2.3327   -1.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4147    3.3064    0.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4676    1.3428    0.8059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3803    2.7527    1.2606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4931    0.3033   -2.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0876    0.9324   -1.0148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6378   -0.1703   -2.3991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8604   -2.0561   -1.1841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9303   -1.8676    2.1242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1218   -1.7729    2.4268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3997   -1.7940   -1.0279 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
 14 16  1  0
 16 17  2  3
 16 18  1  0
  7  2  1  0
 18 12  1  0
 18  6  1  0
  1 19  1  0
  1 20  1  0
  6 21  1  1
  7 22  1  6
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  6
 13 30  1  0
 13 31  1  0
 14 32  1  6
 17 33  1  0
 17 34  1  0
 18 35  1  6
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      -1.870   6.670   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.258   6.002   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.600   4.500   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.640   3.296   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.100   3.296   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.140   4.500   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.483   6.002   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.579   6.791   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.739   5.778   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.134   4.362   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.148   8.471   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.663   8.196   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.582   7.114   0.000  0.00  0.00           C+0
HETATM   14 Cl   UNK     0      -7.241   6.121   0.000  0.00  0.00          Cl+0
HETATM   15  C   UNK     0      -4.718   8.325   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0      -3.258   7.542   0.000  0.00  0.00           H+0
HETATM   17  H   UNK     0      -4.370   3.166   0.000  0.00  0.00           H+0
HETATM   18  C   UNK     0      -3.308   1.909   0.000  0.00  0.00           C+0
HETATM   19  H   UNK     0      -1.471   5.182   0.000  0.00  0.00           H+0
HETATM   20  H   UNK     0       1.057   6.002   0.000  0.00  0.00           H+0
HETATM   21  C   UNK     0       2.108   6.908   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.520   9.858   0.000  0.00  0.00           O+0
CONECT    1    2   12    7   19                                             
CONECT    2    1    3    8   16                                             
CONECT    3    4   10    2   17                                             
CONECT    4    3    5   18                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    1   13   20                                             
CONECT    8    2    9   15                                                  
CONECT    9    8   10   14                                                  
CONECT   10    3    9                                                       
CONECT   11   12   13   22                                                  
CONECT   12    1   11                                                       
CONECT   13    7   11   21                                                  
CONECT   14    9                                                            
CONECT   15    8                                                            
CONECT   16    2                                                            
CONECT   17    3                                                            
CONECT   18    4                                                            
CONECT   19    1                                                            
CONECT   20    7                                                            
CONECT   21   13                                                            
CONECT   22   11                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0302038
HETATM    1  C1  UNL     1       4.076  -0.045  -0.061  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.884  -0.577  -0.054  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.569  -1.992   0.078  1.00  0.00           C  
HETATM    4  O1  UNL     1       3.309  -2.983  -0.258  1.00  0.00           O  
HETATM    5  O2  UNL     1       1.305  -2.053   0.642  1.00  0.00           O  
HETATM    6  C4  UNL     1       0.645  -0.805   0.538  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.585   0.122  -0.181  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.623   1.514   0.397  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.535   2.308  -0.351  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.691   1.469  -0.247  1.00  0.00           C  
HETATM   11  C9  UNL     1      -1.548   1.876   0.647  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.019   0.265  -1.002  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.478   0.046  -1.306  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.902  -1.169  -0.517  1.00  0.00           C  
HETATM   15 CL1  UNL     1      -4.480  -0.963   0.247  1.00  0.00          CL  
HETATM   16  C13 UNL     1      -1.808  -1.323   0.470  1.00  0.00           C  
HETATM   17  C14 UNL     1      -1.943  -1.668   1.729  1.00  0.00           C  
HETATM   18  C15 UNL     1      -0.569  -1.001  -0.302  1.00  0.00           C  
HETATM   19  H1  UNL     1       4.282   1.006  -0.160  1.00  0.00           H  
HETATM   20  H2  UNL     1       4.967  -0.677   0.040  1.00  0.00           H  
HETATM   21  H3  UNL     1       0.416  -0.433   1.559  1.00  0.00           H  
HETATM   22  H4  UNL     1       1.381   0.216  -1.270  1.00  0.00           H  
HETATM   23  H5  UNL     1       2.567   2.028   0.215  1.00  0.00           H  
HETATM   24  H6  UNL     1       1.400   1.530   1.480  1.00  0.00           H  
HETATM   25  H7  UNL     1       0.856   2.333  -1.417  1.00  0.00           H  
HETATM   26  H8  UNL     1       0.415   3.306   0.092  1.00  0.00           H  
HETATM   27  H9  UNL     1      -2.468   1.343   0.806  1.00  0.00           H  
HETATM   28  H10 UNL     1      -1.380   2.753   1.261  1.00  0.00           H  
HETATM   29  H11 UNL     1      -0.493   0.303  -2.000  1.00  0.00           H  
HETATM   30  H12 UNL     1      -3.088   0.932  -1.015  1.00  0.00           H  
HETATM   31  H13 UNL     1      -2.638  -0.170  -2.399  1.00  0.00           H  
HETATM   32  H14 UNL     1      -2.860  -2.056  -1.184  1.00  0.00           H  
HETATM   33  H15 UNL     1      -2.930  -1.868   2.124  1.00  0.00           H  
HETATM   34  H16 UNL     1      -1.122  -1.773   2.427  1.00  0.00           H  
HETATM   35  H17 UNL     1      -0.400  -1.794  -1.028  1.00  0.00           H  
CONECT    1    2    2   19   20
CONECT    2    3    7
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   18   21
CONECT    7    8   22
CONECT    8    9   23   24
CONECT    9   10   25   26
CONECT   10   11   11   12
CONECT   11   27   28
CONECT   12   13   18   29
CONECT   13   14   30   31
CONECT   14   15   16   32
CONECT   16   17   17   18
CONECT   17   33   34
CONECT   18   35
END

HMDB0302038
     RDKit          3D
3beta-Chlorodehydrocostuslactone
 35 37  0  0  0  0  0  0  0  0999 V2000
    4.0764   -0.0454   -0.0605 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8836   -0.5771   -0.0543 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5692   -1.9920    0.0781 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3089   -2.9828   -0.2579 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3049   -2.0526    0.6423 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6451   -0.8054    0.5378 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5855    0.1223   -0.1814 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6229    1.5139    0.3970 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5355    2.3075   -0.3513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6912    1.4686   -0.2467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5479    1.8765    0.6472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0188    0.2649   -1.0024 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4784    0.0458   -1.3056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9022   -1.1690   -0.5174 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4796   -0.9631    0.2472 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -1.8079   -1.3235    0.4697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9432   -1.6682    1.7286 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5690   -1.0007   -0.3020 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2824    1.0064   -0.1601 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9674   -0.6768    0.0400 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4157   -0.4334    1.5592 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3814    0.2164   -1.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5667    2.0284    0.2153 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4001    1.5298    1.4804 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8562    2.3327   -1.4169 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4147    3.3064    0.0918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4676    1.3428    0.8059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3803    2.7527    1.2606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4931    0.3033   -2.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0876    0.9324   -1.0148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6378   -0.1703   -2.3991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8604   -2.0561   -1.1841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9303   -1.8676    2.1242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1218   -1.7729    2.4268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3997   -1.7940   -1.0279 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
 14 16  1  0
 16 17  2  3
 16 18  1  0
  7  2  1  0
 18 12  1  0
 18  6  1  0
  1 19  1  0
  1 20  1  0
  6 21  1  1
  7 22  1  6
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 11 27  1  0
 11 28  1  0
 12 29  1  6
 13 30  1  0
 13 31  1  0
 14 32  1  6
 17 33  1  0
 17 34  1  0
 18 35  1  6
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(3Abeta,6abeta,9abeta,9balpha)-3,6,9-trismethylene-8a-chlorododecahydroazuleno[4,5-b]furan-2-one	Generator
(3Abeta,6abeta,9abeta,9balpha)-3,6,9-trismethylene-8α-chlorododecahydroazuleno[4,5-b]furan-2-one	Generator
3b-Chlorodehydrocostuslactone	Generator
3Β-chlorodehydrocostuslactone	Generator

Chemical Formula

C₁₅H₁₇ClO₂

Average Molecular Weight

264.747

Monoisotopic Molecular Weight

264.091707495

IUPAC Name

(3aS,6aR,8S,9aR,9bS)-8-chloro-3,6,9-trimethylidene-dodecahydroazuleno[4,5-b]furan-2-one

Traditional Name

(3aS,6aR,8S,9aR,9bS)-8-chloro-3,6,9-trimethylidene-octahydroazuleno[4,5-b]furan-2-one

CAS Registry Number

Not Available

SMILES

[H][C@@]12CCC(=C)[C@]3([H])C[C@H](Cl)C(=C)[C@]3([H])[C@@]1([H])OC(=O)C2=C

InChI Identifier

InChI=1S/C15H17ClO2/c1-7-4-5-10-8(2)15(17)18-14(10)13-9(3)12(16)6-11(7)13/h10-14H,1-6H2/t10-,11-,12-,13-,14-/m0/s1

InChI Key

XVGIEOUYQLZGPH-PEDHHIEDSA-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
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Lactone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Organochloride
Organohalogen compound
Alkyl chloride
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alkyl halide
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0302038)

Food

Herb and spice

Herb

Sweet bay (FooDB: FOOD00097)

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	3.14	ALOGPS
logP	3.2	ChemAxon
logS	-3.5	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	70.54 m³·mol⁻¹	ChemAxon
Polarizability	27.67 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
AllCCS	[M+H]+	159.995	32859911
AllCCS	[M+H-H2O]+	156.492	32859911
AllCCS	[M+Na]+	164.178	32859911
AllCCS	[M+NH4]+	163.244	32859911
AllCCS	[M-H]-	162.715	32859911
AllCCS	[M+Na-2H]-	162.511	32859911
AllCCS	[M+HCOO]-	162.399	32859911
DeepCCS	[M-2H]-	196.767	30932474
DeepCCS	[M+Na]+	172.547	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3beta-Chlorodehydrocostuslactone 10V, Positive-QTOF	splash10-014i-0290000000-cd2fb1592ef834402660	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3beta-Chlorodehydrocostuslactone 20V, Positive-QTOF	splash10-014i-0980000000-a1d0ea5a34c07b1b1702	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3beta-Chlorodehydrocostuslactone 40V, Positive-QTOF	splash10-0zi0-8900000000-a1d4baa6de888e798e4e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3beta-Chlorodehydrocostuslactone 10V, Negative-QTOF	splash10-03di-0090000000-f0d9e36db776470bf4b2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3beta-Chlorodehydrocostuslactone 20V, Negative-QTOF	splash10-0400-0090000000-e020137d64a33c1490c4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3beta-Chlorodehydrocostuslactone 40V, Negative-QTOF	splash10-0uxu-9540000000-166e2bfbf536aadaef36	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3beta-Chlorodehydrocostuslactone 10V, Positive-QTOF	splash10-014i-0090000000-3bb50308f6a8d5bad4ab	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3beta-Chlorodehydrocostuslactone 20V, Positive-QTOF	splash10-014i-0190000000-025f06c17207dd089c65	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3beta-Chlorodehydrocostuslactone 40V, Positive-QTOF	splash10-0a4l-0920000000-c997eeb10e0dc4122d01	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3beta-Chlorodehydrocostuslactone 10V, Negative-QTOF	splash10-03di-0090000000-2d167fa136b10896c25f	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3beta-Chlorodehydrocostuslactone 20V, Negative-QTOF	splash10-01q9-8090000000-f9e421effefab2572c32	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3beta-Chlorodehydrocostuslactone 40V, Negative-QTOF	splash10-03di-2190000000-52b8a268b5106d0551e8	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001782

KNApSAcK ID

Not Available

Chemspider ID

8834671

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10659317

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

Not Available

Showing metabocard for 3beta-Chlorodehydrocostuslactone (HMDB0302038)

MOL for HMDB0302038 (3beta-Chlorodehydrocostuslactone)

3D MOL for HMDB0302038 (3beta-Chlorodehydrocostuslactone)

3D SDF for HMDB0302038 (3beta-Chlorodehydrocostuslactone)

3D-SDF for HMDB0302038 (3beta-Chlorodehydrocostuslactone)

PDB for HMDB0302038 (3beta-Chlorodehydrocostuslactone)

3D PDB for HMDB0302038 (3beta-Chlorodehydrocostuslactone)

SMILES for HMDB0302038 (3beta-Chlorodehydrocostuslactone)

INCHI for HMDB0302038 (3beta-Chlorodehydrocostuslactone)

Structure for HMDB0302038 (3beta-Chlorodehydrocostuslactone)

3D Structure for HMDB0302038 (3beta-Chlorodehydrocostuslactone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra