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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:59:37 UTC

Update Date

2022-03-07 02:55:52 UTC

HMDB ID

HMDB0038661

Secondary Accession Numbers

HMDB38661

Metabolite Identification

Common Name

Epidihydrophaseic acid

Description

Epidihydrophaseic acid 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 Epidihydrophaseic acid.

Structure

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

HMDB0038661
     RDKit          3D
Epidihydrophaseic acid
 42 43  0  0  0  0  0  0  0  0999 V2000
    3.3738   -1.2847   -0.5531 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9672   -0.4532    0.5915 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6192    0.0626    0.6735 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6543   -0.1281   -0.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6659    0.4677    0.0349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6388    1.7190    0.6006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5887   -0.4248    0.8456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9125   -1.1624    1.9353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1019   -1.3576   -0.2080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0025   -0.7397   -1.4290 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4998    0.5395   -1.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6935    0.9904   -2.4135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6410    1.4618   -0.9773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3817    1.2392    0.2798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7445    2.4795    0.8391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7379    0.4230    1.3213 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8656   -0.1935    1.5364 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2300   -0.6748    1.5202 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9857   -0.3648    2.4674 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7413   -1.4596    0.5117 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5859   -1.4864   -1.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6749   -2.2803   -0.1278 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2212   -0.8445   -1.1240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3888    0.6800    1.5648 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8356   -0.7182   -1.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3647    2.3688   -0.1177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7111   -0.5761    2.8391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5617   -2.0196    2.2345 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0151   -1.6281    1.5191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1154   -1.7340    0.0288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4449   -2.2728   -0.2134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3633    0.0666   -2.9639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1692    1.6319   -2.1567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3037    1.5738   -3.1551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3044    1.4325   -1.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2227    2.5091   -0.9752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3656    0.7484    0.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6971    2.6517    0.8235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4639   -0.2887    1.8147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3472    1.0434    2.1658 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5476    0.4187    2.3687 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9991   -2.4159    0.6554 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
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
  2 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 11  5  1  0
 16  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  6 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 20 42  1  0
M  END


  Mrv0541 02241210272D          

 20 21  0  0  0  0            999 V2000
   -2.5011    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5011   -0.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7872   -1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0748   -0.8244    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0748    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7872    0.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1998   -0.3032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6168   -0.8863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2162   -1.2371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7872    1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3597   -1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3597    0.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3555    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0707    0.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7858    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0707    1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5011    0.4119    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2162    0.0007    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5011    1.2371    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3597   -0.4119    0.0000 O   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
M  END
> <DATABASE_ID>
HMDB0038661

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O5/c1-10(6-12(17)18)4-5-15(19)13(2)7-11(16)8-14(15,3)20-9-13/h4-6,11,16,19H,7-9H2,1-3H3,(H,17,18)/b5-4+,10-6+

> <INCHI_KEY>
XIVFQYWMMJWUCD-UMCKCUICSA-N

> <FORMULA>
C15H22O5

> <MOLECULAR_WEIGHT>
282.3322

> <EXACT_MASS>
282.146723814

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
29.82195347282505

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
0.62

> <JCHEM_LOGP>
0.5024939413333337

> <ALOGPS_LOGS>
-2.40

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.89197458754585

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.566584044161994

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7397165799455063

> <JCHEM_POLAR_SURFACE_AREA>
86.99

> <JCHEM_REFRACTIVITY>
75.00389999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.13e+00 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0038661
     RDKit          3D
Epidihydrophaseic acid
 42 43  0  0  0  0  0  0  0  0999 V2000
    3.3738   -1.2847   -0.5531 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9672   -0.4532    0.5915 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6192    0.0626    0.6735 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6543   -0.1281   -0.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6659    0.4677    0.0349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6388    1.7190    0.6006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5887   -0.4248    0.8456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9125   -1.1624    1.9353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1019   -1.3576   -0.2080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0025   -0.7397   -1.4290 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4998    0.5395   -1.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6935    0.9904   -2.4135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6410    1.4618   -0.9773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3817    1.2392    0.2798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7445    2.4795    0.8391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7379    0.4230    1.3213 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8656   -0.1935    1.5364 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2300   -0.6748    1.5202 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9857   -0.3648    2.4674 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7413   -1.4596    0.5117 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5859   -1.4864   -1.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6749   -2.2803   -0.1278 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2212   -0.8445   -1.1240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3888    0.6800    1.5648 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8356   -0.7182   -1.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3647    2.3688   -0.1177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7111   -0.5761    2.8391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5617   -2.0196    2.2345 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0151   -1.6281    1.5191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1154   -1.7340    0.0288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4449   -2.2728   -0.2134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3633    0.0666   -2.9639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1692    1.6319   -2.1567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3037    1.5738   -3.1551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3044    1.4325   -1.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2227    2.5091   -0.9752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3656    0.7484    0.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6971    2.6517    0.8235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4639   -0.2887    1.8147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3472    1.0434    2.1658 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5476    0.4187    2.3687 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9991   -2.4159    0.6554 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
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
  2 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 11  5  1  0
 16  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  6 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 20 42  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      -4.669   0.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.669  -1.539   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.336  -2.309   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.006  -1.539   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.006   0.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.336   0.769   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.106  -0.566   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -3.018  -1.654   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -6.004  -2.309   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -3.336   2.309   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.671  -2.309   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.671   0.769   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.664   0.001   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.999   0.769   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.334   0.001   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.999   2.309   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.669   0.769   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.004   0.001   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.669   2.309   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      -0.671  -0.769   0.000  0.00  0.00           O+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                                                            
CONECT   19   17                                                            
CONECT   20    5                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0038661
HETATM    1  C1  UNL     1       3.374  -1.285  -0.553  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.967  -0.453   0.591  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.619   0.063   0.673  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.654  -0.128  -0.196  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.666   0.468   0.035  1.00  0.00           C  
HETATM    6  O1  UNL     1      -0.639   1.719   0.601  1.00  0.00           O  
HETATM    7  C6  UNL     1      -1.589  -0.425   0.846  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.913  -1.162   1.935  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.102  -1.358  -0.208  1.00  0.00           C  
HETATM   10  O2  UNL     1      -2.002  -0.740  -1.429  1.00  0.00           O  
HETATM   11  C9  UNL     1      -1.500   0.539  -1.241  1.00  0.00           C  
HETATM   12  C10 UNL     1      -0.694   0.990  -2.413  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.641   1.462  -0.977  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.382   1.239   0.280  1.00  0.00           C  
HETATM   15  O3  UNL     1      -3.744   2.480   0.839  1.00  0.00           O  
HETATM   16  C13 UNL     1      -2.738   0.423   1.321  1.00  0.00           C  
HETATM   17  C14 UNL     1       3.866  -0.194   1.536  1.00  0.00           C  
HETATM   18  C15 UNL     1       5.230  -0.675   1.520  1.00  0.00           C  
HETATM   19  O4  UNL     1       5.986  -0.365   2.467  1.00  0.00           O  
HETATM   20  O5  UNL     1       5.741  -1.460   0.512  1.00  0.00           O  
HETATM   21  H1  UNL     1       2.586  -1.486  -1.288  1.00  0.00           H  
HETATM   22  H2  UNL     1       3.675  -2.280  -0.128  1.00  0.00           H  
HETATM   23  H3  UNL     1       4.221  -0.845  -1.124  1.00  0.00           H  
HETATM   24  H4  UNL     1       1.389   0.680   1.565  1.00  0.00           H  
HETATM   25  H5  UNL     1       0.836  -0.718  -1.071  1.00  0.00           H  
HETATM   26  H6  UNL     1      -0.365   2.369  -0.118  1.00  0.00           H  
HETATM   27  H7  UNL     1      -0.711  -0.576   2.839  1.00  0.00           H  
HETATM   28  H8  UNL     1      -1.562  -2.020   2.234  1.00  0.00           H  
HETATM   29  H9  UNL     1       0.015  -1.628   1.519  1.00  0.00           H  
HETATM   30  H10 UNL     1      -3.115  -1.734   0.029  1.00  0.00           H  
HETATM   31  H11 UNL     1      -1.445  -2.273  -0.213  1.00  0.00           H  
HETATM   32  H12 UNL     1      -0.363   0.067  -2.964  1.00  0.00           H  
HETATM   33  H13 UNL     1       0.169   1.632  -2.157  1.00  0.00           H  
HETATM   34  H14 UNL     1      -1.304   1.574  -3.155  1.00  0.00           H  
HETATM   35  H15 UNL     1      -3.304   1.432  -1.890  1.00  0.00           H  
HETATM   36  H16 UNL     1      -2.223   2.509  -0.975  1.00  0.00           H  
HETATM   37  H17 UNL     1      -4.366   0.748   0.014  1.00  0.00           H  
HETATM   38  H18 UNL     1      -4.697   2.652   0.823  1.00  0.00           H  
HETATM   39  H19 UNL     1      -3.464  -0.289   1.815  1.00  0.00           H  
HETATM   40  H20 UNL     1      -2.347   1.043   2.166  1.00  0.00           H  
HETATM   41  H21 UNL     1       3.548   0.419   2.369  1.00  0.00           H  
HETATM   42  H22 UNL     1       5.999  -2.416   0.655  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   17   17
CONECT    3    4    4   24
CONECT    4    5   25
CONECT    5    6    7   11
CONECT    6   26
CONECT    7    8    9   16
CONECT    8   27   28   29
CONECT    9   10   30   31
CONECT   10   11
CONECT   11   12   13
CONECT   12   32   33   34
CONECT   13   14   35   36
CONECT   14   15   16   37
CONECT   15   38
CONECT   16   39   40
CONECT   17   18   41
CONECT   18   19   19   20
CONECT   20   42
END

HMDB0038661
     RDKit          3D
Epidihydrophaseic acid
 42 43  0  0  0  0  0  0  0  0999 V2000
    3.3738   -1.2847   -0.5531 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9672   -0.4532    0.5915 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6192    0.0626    0.6735 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6543   -0.1281   -0.1959 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6659    0.4677    0.0349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6388    1.7190    0.6006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5887   -0.4248    0.8456 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9125   -1.1624    1.9353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1019   -1.3576   -0.2080 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0025   -0.7397   -1.4290 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4998    0.5395   -1.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6935    0.9904   -2.4135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6410    1.4618   -0.9773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3817    1.2392    0.2798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7445    2.4795    0.8391 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7379    0.4230    1.3213 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8656   -0.1935    1.5364 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2300   -0.6748    1.5202 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9857   -0.3648    2.4674 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7413   -1.4596    0.5117 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5859   -1.4864   -1.2877 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6749   -2.2803   -0.1278 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2212   -0.8445   -1.1240 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3888    0.6800    1.5648 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8356   -0.7182   -1.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3647    2.3688   -0.1177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7111   -0.5761    2.8391 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5617   -2.0196    2.2345 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0151   -1.6281    1.5191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1154   -1.7340    0.0288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4449   -2.2728   -0.2134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3633    0.0666   -2.9639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1692    1.6319   -2.1567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3037    1.5738   -3.1551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3044    1.4325   -1.8901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2227    2.5091   -0.9752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3656    0.7484    0.0139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6971    2.6517    0.8235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4639   -0.2887    1.8147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3472    1.0434    2.1658 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5476    0.4187    2.3687 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9991   -2.4159    0.6554 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
  4  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
  2 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 11  5  1  0
 16  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  4 25  1  0
  6 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 20 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

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

Chemical Formula

C₁₅H₂₂O₅

Average Molecular Weight

282.3322

Monoisotopic Molecular Weight

282.146723814

IUPAC Name

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

Traditional Name

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

CAS Registry Number

60102-38-7

SMILES

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

InChI Identifier

InChI=1S/C15H22O5/c1-10(6-12(17)18)4-5-15(19)13(2)7-11(16)8-14(15,3)20-9-13/h4-6,11,16,19H,7-9H2,1-3H3,(H,17,18)/b5-4+,10-6+

InChI Key

XIVFQYWMMJWUCD-UMCKCUICSA-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
Medium-chain fatty acid
Branched fatty acid
Heterocyclic fatty acid
Hydroxy fatty acid
Oxepane
Methyl-branched fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Cyclic alcohol
Tertiary alcohol
Tetrahydrofuran
Secondary alcohol
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Oxacycle
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic oxide
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0038661)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038661)

Source

Endogenous

Endogenous (HMDB: HMDB0038661)

Plant

Fabaceae (HMDB: HMDB0038661)

Animal

Animal (HMDB: HMDB0038661)

Exogenous

Food

Food (HMDB: HMDB0038661)

Pulse

Pulses (FooDB: FOOD00867)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0038661)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0038661)

Cellular process

Cell signaling (HMDB: HMDB0038661)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0038661)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0038661)

Nutrient

Nutrient (HMDB: HMDB0038661)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0038661)

Emulsifier (HMDB: HMDB0038661)

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	2746 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.13 g/L	ALOGPS
logP	0.62	ALOGPS
logP	0.5	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	4.57	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	75 m³·mol⁻¹	ChemAxon
Polarizability	29.82 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]+	168.564	31661259
DarkChem	[M-H]-	161.984	31661259
DeepCCS	[M+H]+	185.65	30932474
DeepCCS	[M-H]-	183.293	30932474
DeepCCS	[M-2H]-	216.18	30932474
DeepCCS	[M+Na]+	191.744	30932474
AllCCS	[M+H]+	166.8	32859911
AllCCS	[M+H-H2O]+	163.5	32859911
AllCCS	[M+NH4]+	169.9	32859911
AllCCS	[M+Na]+	170.8	32859911
AllCCS	[M-H]-	170.3	32859911
AllCCS	[M+Na-2H]-	170.6	32859911
AllCCS	[M+HCOO]-	171.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Epidihydrophaseic acid	C\C(\C=C\C1(O)C2(C)COC1(C)CC(O)C2)=C/C(O)=O	3864.8	Standard polar	33892256
Epidihydrophaseic acid	C\C(\C=C\C1(O)C2(C)COC1(C)CC(O)C2)=C/C(O)=O	2101.9	Standard non polar	33892256
Epidihydrophaseic acid	C\C(\C=C\C1(O)C2(C)COC1(C)CC(O)C2)=C/C(O)=O	2332.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Epidihydrophaseic acid,1TMS,isomer #1	CC(/C=C/C1(O[Si](C)(C)C)C2(C)COC1(C)CC(O)C2)=C\C(=O)O	2356.0	Semi standard non polar	33892256
Epidihydrophaseic acid,1TMS,isomer #2	CC(/C=C/C1(O)C2(C)COC1(C)CC(O[Si](C)(C)C)C2)=C\C(=O)O	2279.6	Semi standard non polar	33892256
Epidihydrophaseic acid,1TMS,isomer #3	CC(/C=C/C1(O)C2(C)COC1(C)CC(O)C2)=C\C(=O)O[Si](C)(C)C	2290.8	Semi standard non polar	33892256
Epidihydrophaseic acid,2TMS,isomer #1	CC(/C=C/C1(O[Si](C)(C)C)C2(C)COC1(C)CC(O[Si](C)(C)C)C2)=C\C(=O)O	2354.0	Semi standard non polar	33892256
Epidihydrophaseic acid,2TMS,isomer #2	CC(/C=C/C1(O[Si](C)(C)C)C2(C)COC1(C)CC(O)C2)=C\C(=O)O[Si](C)(C)C	2383.1	Semi standard non polar	33892256
Epidihydrophaseic acid,2TMS,isomer #3	CC(/C=C/C1(O)C2(C)COC1(C)CC(O[Si](C)(C)C)C2)=C\C(=O)O[Si](C)(C)C	2293.8	Semi standard non polar	33892256
Epidihydrophaseic acid,3TMS,isomer #1	CC(/C=C/C1(O[Si](C)(C)C)C2(C)COC1(C)CC(O[Si](C)(C)C)C2)=C\C(=O)O[Si](C)(C)C	2369.0	Semi standard non polar	33892256
Epidihydrophaseic acid,1TBDMS,isomer #1	CC(/C=C/C1(O[Si](C)(C)C(C)(C)C)C2(C)COC1(C)CC(O)C2)=C\C(=O)O	2600.7	Semi standard non polar	33892256
Epidihydrophaseic acid,1TBDMS,isomer #2	CC(/C=C/C1(O)C2(C)COC1(C)CC(O[Si](C)(C)C(C)(C)C)C2)=C\C(=O)O	2532.6	Semi standard non polar	33892256
Epidihydrophaseic acid,1TBDMS,isomer #3	CC(/C=C/C1(O)C2(C)COC1(C)CC(O)C2)=C\C(=O)O[Si](C)(C)C(C)(C)C	2520.0	Semi standard non polar	33892256
Epidihydrophaseic acid,2TBDMS,isomer #1	CC(/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)=C\C(=O)O	2838.0	Semi standard non polar	33892256
Epidihydrophaseic acid,2TBDMS,isomer #2	CC(/C=C/C1(O[Si](C)(C)C(C)(C)C)C2(C)COC1(C)CC(O)C2)=C\C(=O)O[Si](C)(C)C(C)(C)C	2829.9	Semi standard non polar	33892256
Epidihydrophaseic acid,2TBDMS,isomer #3	CC(/C=C/C1(O)C2(C)COC1(C)CC(O[Si](C)(C)C(C)(C)C)C2)=C\C(=O)O[Si](C)(C)C(C)(C)C	2749.8	Semi standard non polar	33892256
Epidihydrophaseic acid,3TBDMS,isomer #1	CC(/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)=C\C(=O)O[Si](C)(C)C(C)(C)C	3046.2	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 - Epidihydrophaseic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-066r-6390000000-15205983f888cc8aae34	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epidihydrophaseic acid GC-MS (3 TMS) - 70eV, Positive	splash10-0040-6302900000-a7a26686149125abc0b3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epidihydrophaseic acid 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 - Epidihydrophaseic acid 10V, Positive-QTOF	splash10-0159-0090000000-39cb65eb76c4015dff61	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epidihydrophaseic acid 20V, Positive-QTOF	splash10-0600-0190000000-daee06671fa05492ff10	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epidihydrophaseic acid 40V, Positive-QTOF	splash10-0v4i-6790000000-f456e9d8a76408cfbc3e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epidihydrophaseic acid 10V, Negative-QTOF	splash10-001i-0190000000-e1034d3cd46d13509eac	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epidihydrophaseic acid 20V, Negative-QTOF	splash10-02ar-1190000000-4a1fd8d5a91c0ecc7487	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epidihydrophaseic acid 40V, Negative-QTOF	splash10-0a4u-2890000000-5341ed0e427da270bdee	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epidihydrophaseic acid 10V, Positive-QTOF	splash10-00lr-0390000000-4cc316c252175c5d394e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epidihydrophaseic acid 20V, Positive-QTOF	splash10-0kmj-0950000000-39116992931e3a59276b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epidihydrophaseic acid 40V, Positive-QTOF	splash10-0uyr-9370000000-ddad2b2a83ceaaab4ee6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epidihydrophaseic acid 10V, Negative-QTOF	splash10-000i-0090000000-928c8b2e97da03829ca9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epidihydrophaseic acid 20V, Negative-QTOF	splash10-0fl9-0980000000-0ba786ed6e3e0584caca	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epidihydrophaseic acid 40V, Negative-QTOF	splash10-0v6r-1890000000-94edf85aff1490729256	2021-09-25	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

FDB018060

KNApSAcK ID

C00033819

Chemspider ID

35014625

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14160513

PDB ID

Not Available

ChEBI ID

174701

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1870301

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 Epidihydrophaseic acid (HMDB0038661)

MOL for HMDB0038661 (Epidihydrophaseic acid)

3D MOL for HMDB0038661 (Epidihydrophaseic acid)

3D SDF for HMDB0038661 (Epidihydrophaseic acid)

3D-SDF for HMDB0038661 (Epidihydrophaseic acid)

PDB for HMDB0038661 (Epidihydrophaseic acid)

3D PDB for HMDB0038661 (Epidihydrophaseic acid)

SMILES for HMDB0038661 (Epidihydrophaseic acid)

INCHI for HMDB0038661 (Epidihydrophaseic acid)

Structure for HMDB0038661 (Epidihydrophaseic acid)

3D Structure for HMDB0038661 (Epidihydrophaseic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra