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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-03-07 21:32:11 UTC

Update Date

2022-03-07 03:17:36 UTC

HMDB ID

HMDB0059836

Secondary Accession Numbers

HMDB59836

Metabolite Identification

Common Name

Cabreuva oxide D

Description

Cabreuva oxide D belongs to the class of organic compounds known as benzopyrans. These are organic compounds containing a benzene ring fused to a pyran ring. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds. Cabreuva oxide D is an extremely weak basic (essentially neutral) compound (based on its pKa). These are terpenes with three consecutive isoprene units.

Structure

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

HMDB0059836
     RDKit          3D
Cabreuva oxide D
 40 41  0  0  0  0  0  0  0  0999 V2000
   -3.7794   -0.2143   -1.4374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4892   -0.4698   -1.6257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6772   -0.8134   -0.4290 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2961   -2.0997    0.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2536   -1.1252   -0.7635 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5477   -0.9093    0.5264 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9132   -1.4541    0.4375 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9068   -0.6943    0.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3253   -1.2071   -0.0684 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5892    0.7046   -0.3106 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6265    1.3707    0.6365 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4635    0.5115    1.0078 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8542    1.1127    0.5875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7835    1.9621   -0.6406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2842    2.0601    1.7233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8440    0.1530    0.5228 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2542   -0.2463   -0.4628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4442    0.0470   -2.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1025   -0.4145   -2.6293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6855   -2.9857   -0.1191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3471   -2.0541    1.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3038   -2.2779   -0.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1601   -0.5951   -1.6131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1623   -2.2126   -0.9798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0040   -1.5756    1.2534 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0847   -2.4912    0.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2995   -2.2558   -0.4572 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6821   -1.2845    0.9843 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9274   -0.5405   -0.6940 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1815    0.6742   -1.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5442    1.2594   -0.4022 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3466    2.3394    0.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2187    1.6466    1.5348 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4358    0.4595    2.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7209    1.8367   -1.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0542    1.7778   -1.3026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7557    3.0688   -0.4077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5017    2.8228    1.9099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5983    1.5090    2.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1652    2.6050    1.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  3  2  1  6
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
 16  3  1  0
 12  6  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  4 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  1
  7 26  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  1
 14 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 15 40  1  0
M  END

  Mrv0541 03071314322D          

 18 19  0  0  0  0            999 V2000
    4.9151    0.0762    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3276   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8545    0.3627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3848   -0.5558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  2  0  0  0  0
  8  7  1  0  0  0  0
 11  2  1  0  0  0  0
 11  7  1  0  0  0  0
 11  9  2  0  0  0  0
 12  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13  8  1  0  0  0  0
 13 12  1  0  0  0  0
 14  3  1  0  0  0  0
 14  4  1  0  0  0  0
 14 13  1  0  0  0  0
 15  5  1  1  0  0  0
 15  6  1  6  0  0  0
 15 10  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  1  0  0  0  0
 12 17  1  1  0  0  0
 13 18  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0059836

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O/c1-6-15(5)10-12-9-11(2)7-8-13(12)14(3,4)16-15/h6,9,12-13H,1,7-8,10H2,2-5H3/t12-,13-,15+/m1/s1

> <INCHI_KEY>
NIGRJVWIKNICMW-NFAWXSAZSA-N

> <FORMULA>
C15H24O

> <MOLECULAR_WEIGHT>
220.3505

> <EXACT_MASS>
220.18271539

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
26.454992339215423

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R,4aS,8aR)-3-ethenyl-1,1,3,6-tetramethyl-3,4,4a,7,8,8a-hexahydro-1H-2-benzopyran

> <ALOGPS_LOGP>
4.34

> <JCHEM_LOGP>
3.702503786333333

> <ALOGPS_LOGS>
-4.57

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2336200062683504

> <JCHEM_POLAR_SURFACE_AREA>
9.23

> <JCHEM_REFRACTIVITY>
69.50120000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.97e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4aS,8aR)-3-ethenyl-1,1,3,6-tetramethyl-4a,7,8,8a-tetrahydro-4H-2-benzopyran

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0059836
     RDKit          3D
Cabreuva oxide D
 40 41  0  0  0  0  0  0  0  0999 V2000
   -3.7794   -0.2143   -1.4374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4892   -0.4698   -1.6257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6772   -0.8134   -0.4290 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2961   -2.0997    0.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2536   -1.1252   -0.7635 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5477   -0.9093    0.5264 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9132   -1.4541    0.4375 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9068   -0.6943    0.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3253   -1.2071   -0.0684 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5892    0.7046   -0.3106 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6265    1.3707    0.6365 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4635    0.5115    1.0078 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8542    1.1127    0.5875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7835    1.9621   -0.6406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2842    2.0601    1.7233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8440    0.1530    0.5228 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2542   -0.2463   -0.4628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4442    0.0470   -2.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1025   -0.4145   -2.6293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6855   -2.9857   -0.1191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3471   -2.0541    1.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3038   -2.2779   -0.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1601   -0.5951   -1.6131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1623   -2.2126   -0.9798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0040   -1.5756    1.2534 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0847   -2.4912    0.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2995   -2.2558   -0.4572 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6821   -1.2845    0.9843 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9274   -0.5405   -0.6940 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1815    0.6742   -1.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5442    1.2594   -0.4022 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3466    2.3394    0.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2187    1.6466    1.5348 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4358    0.4595    2.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7209    1.8367   -1.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0542    1.7778   -1.3026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7557    3.0688   -0.4077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5017    2.8228    1.9099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5983    1.5090    2.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1652    2.6050    1.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  3  2  1  6
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
 16  3  1  0
 12  6  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  4 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  1
  7 26  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  1
 14 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 15 40  1  0
M  END

HEADER    PROTEIN                                 07-MAR-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-MAR-13         0                                  
HETATM    1  C   UNK     0       9.175   0.142   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.345  -4.260   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.325  -4.260   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.195   0.677   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.185  -1.037   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.668  -2.310   0.000  0.00  0.00           O+0
HETATM   17  H   UNK     0       4.001   0.770   0.000  0.00  0.00           H+0
HETATM   18  H   UNK     0       4.001  -3.850   0.000  0.00  0.00           H+0
CONECT    1    6                                                            
CONECT    2   11                                                            
CONECT    3   14                                                            
CONECT    4   14                                                            
CONECT    5   15                                                            
CONECT    6    1   15                                                       
CONECT    7    8   11                                                       
CONECT    8    7   13                                                       
CONECT    9   11   12                                                       
CONECT   10   12   15                                                       
CONECT   11    2    7    9                                                  
CONECT   12    9   10   13   17                                             
CONECT   13    8   12   14   18                                             
CONECT   14    3    4   13   16                                             
CONECT   15    5    6   10   16                                             
CONECT   16   14   15                                                       
CONECT   17   12                                                            
CONECT   18   13                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0059836
HETATM    1  C1  UNL     1      -3.779  -0.214  -1.437  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.489  -0.470  -1.626  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.677  -0.813  -0.429  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.296  -2.100   0.139  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.254  -1.125  -0.764  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.548  -0.909   0.526  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.913  -1.454   0.438  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.907  -0.694   0.039  1.00  0.00           C  
HETATM    9  C9  UNL     1       4.325  -1.207  -0.068  1.00  0.00           C  
HETATM   10  C10 UNL     1       2.589   0.705  -0.311  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.627   1.371   0.636  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.463   0.512   1.008  1.00  0.00           C  
HETATM   13  C13 UNL     1      -0.854   1.113   0.587  1.00  0.00           C  
HETATM   14  C14 UNL     1      -0.783   1.962  -0.641  1.00  0.00           C  
HETATM   15  C15 UNL     1      -1.284   2.060   1.723  1.00  0.00           C  
HETATM   16  O1  UNL     1      -1.844   0.153   0.523  1.00  0.00           O  
HETATM   17  H1  UNL     1      -4.254  -0.246  -0.463  1.00  0.00           H  
HETATM   18  H2  UNL     1      -4.444   0.047  -2.273  1.00  0.00           H  
HETATM   19  H3  UNL     1      -2.103  -0.415  -2.629  1.00  0.00           H  
HETATM   20  H4  UNL     1      -1.685  -2.986  -0.119  1.00  0.00           H  
HETATM   21  H5  UNL     1      -2.347  -2.054   1.244  1.00  0.00           H  
HETATM   22  H6  UNL     1      -3.304  -2.278  -0.260  1.00  0.00           H  
HETATM   23  H7  UNL     1       0.160  -0.595  -1.613  1.00  0.00           H  
HETATM   24  H8  UNL     1      -0.162  -2.213  -0.980  1.00  0.00           H  
HETATM   25  H9  UNL     1      -0.004  -1.576   1.253  1.00  0.00           H  
HETATM   26  H10 UNL     1       2.085  -2.491   0.704  1.00  0.00           H  
HETATM   27  H11 UNL     1       4.300  -2.256  -0.457  1.00  0.00           H  
HETATM   28  H12 UNL     1       4.682  -1.284   0.984  1.00  0.00           H  
HETATM   29  H13 UNL     1       4.927  -0.541  -0.694  1.00  0.00           H  
HETATM   30  H14 UNL     1       2.181   0.674  -1.364  1.00  0.00           H  
HETATM   31  H15 UNL     1       3.544   1.259  -0.402  1.00  0.00           H  
HETATM   32  H16 UNL     1       1.347   2.339   0.172  1.00  0.00           H  
HETATM   33  H17 UNL     1       2.219   1.647   1.535  1.00  0.00           H  
HETATM   34  H18 UNL     1       0.436   0.460   2.116  1.00  0.00           H  
HETATM   35  H19 UNL     1      -1.721   1.837  -1.233  1.00  0.00           H  
HETATM   36  H20 UNL     1       0.054   1.778  -1.303  1.00  0.00           H  
HETATM   37  H21 UNL     1      -0.756   3.069  -0.408  1.00  0.00           H  
HETATM   38  H22 UNL     1      -0.502   2.823   1.910  1.00  0.00           H  
HETATM   39  H23 UNL     1      -1.598   1.509   2.610  1.00  0.00           H  
HETATM   40  H24 UNL     1      -2.165   2.605   1.325  1.00  0.00           H  
CONECT    1    2    2   17   18
CONECT    2    3   19
CONECT    3    4    5   16
CONECT    4   20   21   22
CONECT    5    6   23   24
CONECT    6    7   12   25
CONECT    7    8    8   26
CONECT    8    9   10
CONECT    9   27   28   29
CONECT   10   11   30   31
CONECT   11   12   32   33
CONECT   12   13   34
CONECT   13   14   15   16
CONECT   14   35   36   37
CONECT   15   38   39   40
END

HMDB0059836
     RDKit          3D
Cabreuva oxide D
 40 41  0  0  0  0  0  0  0  0999 V2000
   -3.7794   -0.2143   -1.4374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4892   -0.4698   -1.6257 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6772   -0.8134   -0.4290 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2961   -2.0997    0.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2536   -1.1252   -0.7635 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5477   -0.9093    0.5264 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9132   -1.4541    0.4375 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9068   -0.6943    0.0389 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3253   -1.2071   -0.0684 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5892    0.7046   -0.3106 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6265    1.3707    0.6365 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4635    0.5115    1.0078 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8542    1.1127    0.5875 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7835    1.9621   -0.6406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2842    2.0601    1.7233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8440    0.1530    0.5228 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2542   -0.2463   -0.4628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4442    0.0470   -2.2729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1025   -0.4145   -2.6293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6855   -2.9857   -0.1191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3471   -2.0541    1.2438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3038   -2.2779   -0.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1601   -0.5951   -1.6131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1623   -2.2126   -0.9798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0040   -1.5756    1.2534 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0847   -2.4912    0.7040 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2995   -2.2558   -0.4572 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6821   -1.2845    0.9843 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9274   -0.5405   -0.6940 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1815    0.6742   -1.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5442    1.2594   -0.4022 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3466    2.3394    0.1722 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2187    1.6466    1.5348 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4358    0.4595    2.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7209    1.8367   -1.2329 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0542    1.7778   -1.3026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7557    3.0688   -0.4077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5017    2.8228    1.9099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5983    1.5090    2.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1652    2.6050    1.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  3  2  1  6
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13 16  1  0
 16  3  1  0
 12  6  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  4 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  1
  7 26  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  1
 14 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
 15 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄O

Average Molecular Weight

220.3505

Monoisotopic Molecular Weight

220.18271539

IUPAC Name

(3R,4aS,8aR)-3-ethenyl-1,1,3,6-tetramethyl-3,4,4a,7,8,8a-hexahydro-1H-2-benzopyran

Traditional Name

(3R,4aS,8aR)-3-ethenyl-1,1,3,6-tetramethyl-4a,7,8,8a-tetrahydro-4H-2-benzopyran

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H24O/c1-6-15(5)10-12-9-11(2)7-8-13(12)14(3,4)16-15/h6,9,12-13H,1,7-8,10H2,2-5H3/t12-,13-,15+/m1/s1

InChI Key

NIGRJVWIKNICMW-NFAWXSAZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzopyrans. These are organic compounds containing a benzene ring fused to a pyran ring. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

Not Available

Direct Parent

Benzopyrans

Alternative Parents

Substituents

Benzopyran
Oxane
Oxacycle
Ether
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0059836)

Source

Exogenous

Exogenous (HMDB: HMDB0059836)

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
Water Solubility	0.006 g/L	ALOGPS
logP	4.34	ALOGPS
logP	3.7	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	9.23 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	69.5 m³·mol⁻¹	ChemAxon
Polarizability	26.45 Å³	ChemAxon
Number of Rings	2	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
DarkChem	[M+H]+	154.45	31661259
DarkChem	[M-H]-	149.144	31661259
DeepCCS	[M-2H]-	188.597	30932474
DeepCCS	[M+Na]+	163.512	30932474
AllCCS	[M+H]+	151.2	32859911
AllCCS	[M+H-H2O]+	147.3	32859911
AllCCS	[M+NH4]+	154.7	32859911
AllCCS	[M+Na]+	155.8	32859911
AllCCS	[M-H]-	160.6	32859911
AllCCS	[M+Na-2H]-	161.1	32859911
AllCCS	[M+HCOO]-	161.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cabreuva oxide D	[H][C@@]12C[C@@](C)(OC(C)(C)[C@]1([H])CCC(C)=C2)C=C	1746.8	Standard polar	33892256
Cabreuva oxide D	[H][C@@]12C[C@@](C)(OC(C)(C)[C@]1([H])CCC(C)=C2)C=C	1451.2	Standard non polar	33892256
Cabreuva oxide D	[H][C@@]12C[C@@](C)(OC(C)(C)[C@]1([H])CCC(C)=C2)C=C	1440.5	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 - Cabreuva oxide D GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4l-4920000000-30ba83617a5f74be1fdd	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cabreuva oxide D 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 - Cabreuva oxide D 10V, Negative-QTOF	splash10-014i-1090000000-ec0becabc6ae72a10b0e	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cabreuva oxide D 20V, Negative-QTOF	splash10-014i-1790000000-9e1016b0d161b730d951	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cabreuva oxide D 40V, Negative-QTOF	splash10-0159-9700000000-8c064bd7020b2550627b	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cabreuva oxide D 10V, Negative-QTOF	splash10-014i-0090000000-4af4c4ee1c4acef7e18b	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cabreuva oxide D 20V, Negative-QTOF	splash10-0a4i-9310000000-8600a8022daa050b7c1d	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cabreuva oxide D 40V, Negative-QTOF	splash10-0a4i-3910000000-fc8c6a16f467a5ee667f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cabreuva oxide D 10V, Positive-QTOF	splash10-00di-2390000000-af3d3726e464dcccccb4	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cabreuva oxide D 20V, Positive-QTOF	splash10-014j-3910000000-724c3a563f700bf3a262	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cabreuva oxide D 40V, Positive-QTOF	splash10-1000-9400000000-03d4d8be53f56a8021e4	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cabreuva oxide D 10V, Positive-QTOF	splash10-000j-5900000000-1851144aedc76462782c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cabreuva oxide D 20V, Positive-QTOF	splash10-0f7a-4900000000-1ea805f35271cffd81b0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cabreuva oxide D 40V, Positive-QTOF	splash10-0pb9-9700000000-43c216d0bf034b72a7b8	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

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

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

21603104

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 Cabreuva oxide D (HMDB0059836)

MOL for HMDB0059836 (Cabreuva oxide D)

3D MOL for HMDB0059836 (Cabreuva oxide D)

3D SDF for HMDB0059836 (Cabreuva oxide D)

3D-SDF for HMDB0059836 (Cabreuva oxide D)

PDB for HMDB0059836 (Cabreuva oxide D)

3D PDB for HMDB0059836 (Cabreuva oxide D)

SMILES for HMDB0059836 (Cabreuva oxide D)

INCHI for HMDB0059836 (Cabreuva oxide D)

Structure for HMDB0059836 (Cabreuva oxide D)

3D Structure for HMDB0059836 (Cabreuva oxide D)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra