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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:48:26 UTC

Update Date

2022-03-07 02:56:11 UTC

HMDB ID

HMDB0039376

Secondary Accession Numbers

HMDB39376

Metabolite Identification

Common Name

Methyl dihydrophaseate

Description

Methyl dihydrophaseate belongs to the class of organic compounds known as abscisic acids and derivatives. These are terpene compounds containing the abscisic acid moiety, which is characterized by a 3-methylpenta-2,4-dienoic acid attached to the C1 carbon of a 4-oxocyclohex-2-ene moiety. Based on a literature review a small amount of articles have been published on Methyl dihydrophaseate.

Structure

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

HMDB0039376
     RDKit          3D
Methyl dihydrophaseate
 45 46  0  0  0  0  0  0  0  0999 V2000
    6.0780    2.0191   -0.9910 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8431    1.4613   -0.5725 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6806    0.7315    0.5805 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7196    0.5697    1.2841 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4184    0.1713    0.9915 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3159    0.3213    0.2814 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3862    1.0896   -0.9742 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0920   -0.2865    0.7879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0845   -0.2266    0.1973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2841   -0.8689    0.7717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0242   -1.7243    1.8071 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9841   -1.6413   -0.3504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3482   -2.9612   -0.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3857   -1.7045    0.2235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5805   -0.5796    0.9826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3951    0.1245    1.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2737    0.7786    2.3897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3632    1.1381   -0.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5193    0.5718   -1.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8677    0.7290   -1.7891 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0384   -0.8149   -1.6047 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1990    1.7553   -2.0601 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9550    3.1303   -0.9243 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9357    1.6403   -0.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3851   -0.4034    1.9388 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4087    1.1764   -1.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0643    0.6097   -1.7370 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6770    2.1682   -0.7984 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1473   -0.8413    1.7388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1653    0.3062   -0.7277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6425   -1.3090    2.5978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8372   -2.9563   -1.5488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5310   -3.1102    0.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0386   -3.8222   -0.5144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4234   -2.5871    0.9077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1486   -1.8091   -0.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0649    0.0320    3.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5838    1.6457    2.4159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2835    1.2059    2.6546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1762    1.8842    0.1917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4178    1.7087    0.0626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9484    1.2343   -2.1203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0796    1.6798   -1.5818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0535   -0.9038   -2.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7630   -1.3325   -2.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 16 10  1  0
 21 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  7 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
 11 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 17 37  1  0
 17 38  1  0
 17 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
 21 44  1  0
 21 45  1  0
M  END


  Mrv0541 02241211562D          

 21 22  0  0  0  0            999 V2000
   -2.8581    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8581   -0.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1442   -1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4318   -0.8245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4318    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1442    0.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5569   -0.3032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9737   -0.8864    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5733   -1.2371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1442    1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7165   -1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7165    0.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0013    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7138    0.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4290    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7138    1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1442    0.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8595    0.0007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1442    1.2371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7165   -0.4119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5733    0.4147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  2  9  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  8  1  0  0  0  0
  4 11  1  0  0  0  0
  5  6  1  0  0  0  0
  5 12  1  0  0  0  0
  5 20  1  0  0  0  0
  6  7  1  0  0  0  0
  6 10  1  0  0  0  0
  7  8  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  2  0  0  0  0
 18 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0039376

> <DATABASE_NAME>
hmdb

> <SMILES>
COC(=O)\C=C(/C)\C=C\C1(O)C2(C)COC1(C)CC(O)C2

> <INCHI_IDENTIFIER>
InChI=1S/C16H24O5/c1-11(7-13(18)20-4)5-6-16(19)14(2)8-12(17)9-15(16,3)21-10-14/h5-7,12,17,19H,8-10H2,1-4H3/b6-5+,11-7+

> <INCHI_KEY>
QNMHUZMKLBWTQM-LCAICKDSSA-N

> <FORMULA>
C16H24O5

> <MOLECULAR_WEIGHT>
296.3588

> <EXACT_MASS>
296.162373878

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
32.066902507995394

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (2E,4E)-5-{3,8-dihydroxy-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-8-yl}-3-methylpenta-2,4-dienoate

> <ALOGPS_LOGP>
0.85

> <JCHEM_LOGP>
0.8817213306666671

> <ALOGPS_LOGS>
-2.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.15046660811451

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.890714828183388

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7397165799455063

> <JCHEM_POLAR_SURFACE_AREA>
75.99

> <JCHEM_REFRACTIVITY>
79.773

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.89e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2E,4E)-5-{3,8-dihydroxy-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-8-yl}-3-methylpenta-2,4-dienoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0039376
     RDKit          3D
Methyl dihydrophaseate
 45 46  0  0  0  0  0  0  0  0999 V2000
    6.0780    2.0191   -0.9910 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8431    1.4613   -0.5725 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6806    0.7315    0.5805 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7196    0.5697    1.2841 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4184    0.1713    0.9915 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3159    0.3213    0.2814 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3862    1.0896   -0.9742 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0920   -0.2865    0.7879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0845   -0.2266    0.1973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2841   -0.8689    0.7717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0242   -1.7243    1.8071 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9841   -1.6413   -0.3504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3482   -2.9612   -0.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3857   -1.7045    0.2235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5805   -0.5796    0.9826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3951    0.1245    1.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2737    0.7786    2.3897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3632    1.1381   -0.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5193    0.5718   -1.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8677    0.7290   -1.7891 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0384   -0.8149   -1.6047 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1990    1.7553   -2.0601 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9550    3.1303   -0.9243 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9357    1.6403   -0.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3851   -0.4034    1.9388 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4087    1.1764   -1.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0643    0.6097   -1.7370 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6770    2.1682   -0.7984 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1473   -0.8413    1.7388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1653    0.3062   -0.7277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6425   -1.3090    2.5978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8372   -2.9563   -1.5488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5310   -3.1102    0.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0386   -3.8222   -0.5144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4234   -2.5871    0.9077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1486   -1.8091   -0.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0649    0.0320    3.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5838    1.6457    2.4159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2835    1.2059    2.6546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1762    1.8842    0.1917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4178    1.7087    0.0626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9484    1.2343   -2.1203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0796    1.6798   -1.5818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0535   -0.9038   -2.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7630   -1.3325   -2.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 16 10  1  0
 21 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  7 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
 11 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 17 37  1  0
 17 38  1  0
 17 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
 21 44  1  0
 21 45  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      -5.335   0.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.335  -1.539   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.003  -2.309   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.673  -1.539   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.673   0.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.003   0.769   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.773  -0.566   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.684  -1.655   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -6.670  -2.309   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -4.003   2.309   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.337  -2.309   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.337   0.769   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.002   0.001   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.332   0.769   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.667   0.001   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.332   2.309   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.003   0.769   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.338   0.001   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.003   2.309   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -1.337  -0.769   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.670   0.774   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3    9                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    8   11                                             
CONECT    5    4    6   12   20                                             
CONECT    6    1    5    7   10                                             
CONECT    7    6    8                                                       
CONECT    8    4    7                                                       
CONECT    9    2                                                            
CONECT   10    6                                                            
CONECT   11    4                                                            
CONECT   12    5   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14   17                                                       
CONECT   16   14                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17   21                                                       
CONECT   19   17                                                            
CONECT   20    5                                                            
CONECT   21   18                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0039376
HETATM    1  C1  UNL     1       6.078   2.019  -0.991  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.843   1.461  -0.572  1.00  0.00           O  
HETATM    3  C2  UNL     1       4.681   0.731   0.580  1.00  0.00           C  
HETATM    4  O2  UNL     1       5.720   0.570   1.284  1.00  0.00           O  
HETATM    5  C3  UNL     1       3.418   0.171   0.992  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.316   0.321   0.281  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.386   1.090  -0.974  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.092  -0.287   0.788  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.085  -0.227   0.197  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.284  -0.869   0.772  1.00  0.00           C  
HETATM   11  O3  UNL     1      -1.024  -1.724   1.807  1.00  0.00           O  
HETATM   12  C9  UNL     1      -1.984  -1.641  -0.350  1.00  0.00           C  
HETATM   13  C10 UNL     1      -1.348  -2.961  -0.556  1.00  0.00           C  
HETATM   14  C11 UNL     1      -3.386  -1.705   0.224  1.00  0.00           C  
HETATM   15  O4  UNL     1      -3.580  -0.580   0.983  1.00  0.00           O  
HETATM   16  C12 UNL     1      -2.395   0.124   1.067  1.00  0.00           C  
HETATM   17  C13 UNL     1      -2.274   0.779   2.390  1.00  0.00           C  
HETATM   18  C14 UNL     1      -2.363   1.138  -0.047  1.00  0.00           C  
HETATM   19  C15 UNL     1      -2.519   0.572  -1.405  1.00  0.00           C  
HETATM   20  O5  UNL     1      -3.868   0.729  -1.789  1.00  0.00           O  
HETATM   21  C16 UNL     1      -2.038  -0.815  -1.605  1.00  0.00           C  
HETATM   22  H1  UNL     1       6.199   1.755  -2.060  1.00  0.00           H  
HETATM   23  H2  UNL     1       5.955   3.130  -0.924  1.00  0.00           H  
HETATM   24  H3  UNL     1       6.936   1.640  -0.431  1.00  0.00           H  
HETATM   25  H4  UNL     1       3.385  -0.403   1.939  1.00  0.00           H  
HETATM   26  H5  UNL     1       1.409   1.176  -1.511  1.00  0.00           H  
HETATM   27  H6  UNL     1       3.064   0.610  -1.737  1.00  0.00           H  
HETATM   28  H7  UNL     1       2.677   2.168  -0.798  1.00  0.00           H  
HETATM   29  H8  UNL     1       1.147  -0.841   1.739  1.00  0.00           H  
HETATM   30  H9  UNL     1      -0.165   0.306  -0.728  1.00  0.00           H  
HETATM   31  H10 UNL     1      -0.642  -1.309   2.598  1.00  0.00           H  
HETATM   32  H11 UNL     1      -0.837  -2.956  -1.549  1.00  0.00           H  
HETATM   33  H12 UNL     1      -0.531  -3.110   0.190  1.00  0.00           H  
HETATM   34  H13 UNL     1      -2.039  -3.822  -0.514  1.00  0.00           H  
HETATM   35  H14 UNL     1      -3.423  -2.587   0.908  1.00  0.00           H  
HETATM   36  H15 UNL     1      -4.149  -1.809  -0.594  1.00  0.00           H  
HETATM   37  H16 UNL     1      -2.065   0.032   3.178  1.00  0.00           H  
HETATM   38  H17 UNL     1      -1.584   1.646   2.416  1.00  0.00           H  
HETATM   39  H18 UNL     1      -3.284   1.206   2.655  1.00  0.00           H  
HETATM   40  H19 UNL     1      -3.176   1.884   0.192  1.00  0.00           H  
HETATM   41  H20 UNL     1      -1.418   1.709   0.063  1.00  0.00           H  
HETATM   42  H21 UNL     1      -1.948   1.234  -2.120  1.00  0.00           H  
HETATM   43  H22 UNL     1      -4.080   1.680  -1.582  1.00  0.00           H  
HETATM   44  H23 UNL     1      -1.053  -0.904  -2.109  1.00  0.00           H  
HETATM   45  H24 UNL     1      -2.763  -1.332  -2.292  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6    6   25
CONECT    6    7    8
CONECT    7   26   27   28
CONECT    8    9    9   29
CONECT    9   10   30
CONECT   10   11   12   16
CONECT   11   31
CONECT   12   13   14   21
CONECT   13   32   33   34
CONECT   14   15   35   36
CONECT   15   16
CONECT   16   17   18
CONECT   17   37   38   39
CONECT   18   19   40   41
CONECT   19   20   21   42
CONECT   20   43
CONECT   21   44   45
END

HMDB0039376
     RDKit          3D
Methyl dihydrophaseate
 45 46  0  0  0  0  0  0  0  0999 V2000
    6.0780    2.0191   -0.9910 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8431    1.4613   -0.5725 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6806    0.7315    0.5805 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7196    0.5697    1.2841 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4184    0.1713    0.9915 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3159    0.3213    0.2814 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3862    1.0896   -0.9742 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0920   -0.2865    0.7879 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0845   -0.2266    0.1973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2841   -0.8689    0.7717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0242   -1.7243    1.8071 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9841   -1.6413   -0.3504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3482   -2.9612   -0.5557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3857   -1.7045    0.2235 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5805   -0.5796    0.9826 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3951    0.1245    1.0670 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2737    0.7786    2.3897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3632    1.1381   -0.0470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5193    0.5718   -1.4049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8677    0.7290   -1.7891 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0384   -0.8149   -1.6047 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1990    1.7553   -2.0601 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9550    3.1303   -0.9243 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9357    1.6403   -0.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3851   -0.4034    1.9388 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4087    1.1764   -1.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0643    0.6097   -1.7370 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6770    2.1682   -0.7984 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1473   -0.8413    1.7388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1653    0.3062   -0.7277 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6425   -1.3090    2.5978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8372   -2.9563   -1.5488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5310   -3.1102    0.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0386   -3.8222   -0.5144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4234   -2.5871    0.9077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1486   -1.8091   -0.5942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0649    0.0320    3.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5838    1.6457    2.4159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2835    1.2059    2.6546 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1762    1.8842    0.1917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4178    1.7087    0.0626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9484    1.2343   -2.1203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0796    1.6798   -1.5818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0535   -0.9038   -2.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7630   -1.3325   -2.2924 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 19 21  1  0
 16 10  1  0
 21 12  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  5 25  1  0
  7 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
 11 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 14 36  1  0
 17 37  1  0
 17 38  1  0
 17 39  1  0
 18 40  1  0
 18 41  1  0
 19 42  1  0
 20 43  1  0
 21 44  1  0
 21 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Methyl dihydrophaseic acid	Generator
Methyl (2E,4E)-5-{3,8-dihydroxy-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-8-yl}-3-methylpenta-2,4-dienoic acid	HMDB

Chemical Formula

C₁₆H₂₄O₅

Average Molecular Weight

296.3588

Monoisotopic Molecular Weight

296.162373878

IUPAC Name

methyl (2E,4E)-5-{3,8-dihydroxy-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-8-yl}-3-methylpenta-2,4-dienoate

Traditional Name

methyl (2E,4E)-5-{3,8-dihydroxy-1,5-dimethyl-6-oxabicyclo[3.2.1]octan-8-yl}-3-methylpenta-2,4-dienoate

CAS Registry Number

Not Available

SMILES

COC(=O)\C=C(/C)\C=C\C1(O)C2(C)COC1(C)CC(O)C2

InChI Identifier

InChI=1S/C16H24O5/c1-11(7-13(18)20-4)5-6-16(19)14(2)8-12(17)9-15(16,3)21-10-14/h5-7,12,17,19H,8-10H2,1-4H3/b6-5+,11-7+

InChI Key

QNMHUZMKLBWTQM-LCAICKDSSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as abscisic acids and derivatives. These are terpene compounds containing the abscisic acid moiety, which is characterized by a 3-methylpenta-2,4-dienoic acid attached to the C1 carbon of a 4-oxocyclohex-2-ene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Abscisic acids and derivatives

Alternative Parents

Substituents

Abscisic acid
Fatty acid ester
Oxepane
Fatty acyl
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Carboxylic acid ester
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Alcohol
Hydrocarbon derivative
Organooxygen compound
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

Cell membrane (HMDB: HMDB0039376)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039376)

Source

Endogenous

Endogenous (HMDB: HMDB0039376)

Plant

Fabaceae (HMDB: HMDB0039376)

Animal

Animal (HMDB: HMDB0039376)

Exogenous

Food

Food (HMDB: HMDB0039376)

Pulse

Pulses (FooDB: FOOD00867)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0039376)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0039376)

Cellular process

Cell signaling (HMDB: HMDB0039376)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0039376)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0039376)

Nutrient

Nutrient (HMDB: HMDB0039376)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0039376)

Emulsifier (HMDB: HMDB0039376)

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	0.69 g/L	ALOGPS
logP	0.85	ALOGPS
logP	0.88	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	12.89	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	79.77 m³·mol⁻¹	ChemAxon
Polarizability	32.07 Å³	ChemAxon
Number of Rings	2	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
DarkChem	[M+H]+	172.403	31661259
DarkChem	[M-H]-	166.722	31661259
DeepCCS	[M+H]+	172.255	30932474
DeepCCS	[M-H]-	169.897	30932474
DeepCCS	[M-2H]-	203.753	30932474
DeepCCS	[M+Na]+	178.967	30932474
AllCCS	[M+H]+	171.1	32859911
AllCCS	[M+H-H2O]+	167.9	32859911
AllCCS	[M+NH4]+	174.0	32859911
AllCCS	[M+Na]+	174.9	32859911
AllCCS	[M-H]-	175.0	32859911
AllCCS	[M+Na-2H]-	175.5	32859911
AllCCS	[M+HCOO]-	176.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methyl dihydrophaseate	COC(=O)\C=C(/C)\C=C\C1(O)C2(C)COC1(C)CC(O)C2	3471.1	Standard polar	33892256
Methyl dihydrophaseate	COC(=O)\C=C(/C)\C=C\C1(O)C2(C)COC1(C)CC(O)C2	2081.6	Standard non polar	33892256
Methyl dihydrophaseate	COC(=O)\C=C(/C)\C=C\C1(O)C2(C)COC1(C)CC(O)C2	2251.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Methyl dihydrophaseate,1TMS,isomer #1	COC(=O)/C=C(C)/C=C/C1(O[Si](C)(C)C)C2(C)COC1(C)CC(O)C2	2285.4	Semi standard non polar	33892256
Methyl dihydrophaseate,1TMS,isomer #2	COC(=O)/C=C(C)/C=C/C1(O)C2(C)COC1(C)CC(O[Si](C)(C)C)C2	2202.7	Semi standard non polar	33892256
Methyl dihydrophaseate,2TMS,isomer #1	COC(=O)/C=C(C)/C=C/C1(O[Si](C)(C)C)C2(C)COC1(C)CC(O[Si](C)(C)C)C2	2302.5	Semi standard non polar	33892256
Methyl dihydrophaseate,1TBDMS,isomer #1	COC(=O)/C=C(C)/C=C/C1(O[Si](C)(C)C(C)(C)C)C2(C)COC1(C)CC(O)C2	2518.2	Semi standard non polar	33892256
Methyl dihydrophaseate,1TBDMS,isomer #2	COC(=O)/C=C(C)/C=C/C1(O)C2(C)COC1(C)CC(O[Si](C)(C)C(C)(C)C)C2	2434.7	Semi standard non polar	33892256
Methyl dihydrophaseate,2TBDMS,isomer #1	COC(=O)/C=C(C)/C=C/C1(O[Si](C)(C)C(C)(C)C)C2(C)COC1(C)CC(O[Si](C)(C)C(C)(C)C)C2	2759.0	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 - Methyl dihydrophaseate GC-MS (Non-derivatized) - 70eV, Positive	splash10-05rr-5390000000-02a737f3a83ccd2d4416	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl dihydrophaseate GC-MS (2 TMS) - 70eV, Positive	splash10-004i-9308700000-dfe3cac23dbaa2d8979b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methyl dihydrophaseate 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 - Methyl dihydrophaseate 10V, Positive-QTOF	splash10-002b-0090000000-7560892519218b314e63	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl dihydrophaseate 20V, Positive-QTOF	splash10-0kmi-0190000000-56aa9a680af0b05d4462	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl dihydrophaseate 40V, Positive-QTOF	splash10-0v4i-5690000000-0e013368aa33038d3460	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl dihydrophaseate 10V, Negative-QTOF	splash10-0002-0190000000-3712d8e921e3124f90a2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl dihydrophaseate 20V, Negative-QTOF	splash10-01r2-1190000000-77182059440c4a8aa411	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl dihydrophaseate 40V, Negative-QTOF	splash10-00m1-1390000000-29459ab61a82bcbdf2ed	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl dihydrophaseate 10V, Negative-QTOF	splash10-03di-0090000000-71363ffde0a15445e5bd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl dihydrophaseate 20V, Negative-QTOF	splash10-00rb-0390000000-cae8a29d43fafcb7f50a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl dihydrophaseate 40V, Negative-QTOF	splash10-0udi-1930000000-ec7c026ac5154576fcee	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl dihydrophaseate 10V, Positive-QTOF	splash10-002b-0290000000-f4403ea918e0c1a89977	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl dihydrophaseate 20V, Positive-QTOF	splash10-0fka-1970000000-afdc258117db6bce1e42	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methyl dihydrophaseate 40V, Positive-QTOF	splash10-0f75-9260000000-c4febc5d1c2c1334e992	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

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

FDB018940

KNApSAcK ID

Not Available

Chemspider ID

35014785

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752623

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

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Methyl dihydrophaseate (HMDB0039376)

MOL for HMDB0039376 (Methyl dihydrophaseate)

3D MOL for HMDB0039376 (Methyl dihydrophaseate)

3D SDF for HMDB0039376 (Methyl dihydrophaseate)

3D-SDF for HMDB0039376 (Methyl dihydrophaseate)

PDB for HMDB0039376 (Methyl dihydrophaseate)

3D PDB for HMDB0039376 (Methyl dihydrophaseate)

SMILES for HMDB0039376 (Methyl dihydrophaseate)

INCHI for HMDB0039376 (Methyl dihydrophaseate)

Structure for HMDB0039376 (Methyl dihydrophaseate)

3D Structure for HMDB0039376 (Methyl dihydrophaseate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra