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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 19:04:00 UTC

Update Date

2021-09-23 19:04:00 UTC

HMDB ID

HMDB0302604

Secondary Accession Numbers

None

Metabolite Identification

Common Name

5-Hydroxy-4-methoxybisabola-2,10-dien-9-one

Description

5-hydroxy-4-methoxybisabola-2,10-dien-9-one is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. 5-hydroxy-4-methoxybisabola-2,10-dien-9-one is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 5-hydroxy-4-methoxybisabola-2,10-dien-9-one can be found in turmeric, which makes 5-hydroxy-4-methoxybisabola-2,10-dien-9-one a potential biomarker for the consumption of this food product.

Structure

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

HMDB0302604
     RDKit          3D
5-Hydroxy-4-methoxybisabola-2,10-dien-9-one
 45 45  0  0  0  0  0  0  0  0999 V2000
    5.5438   -0.8779    1.2025 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3643   -1.5279    0.9736 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4432   -0.8491    0.2145 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9553   -0.5151   -1.1653 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2760   -1.7885    0.0278 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0567   -1.3564   -0.2513 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8541    0.0958   -0.3799 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6003    0.4959   -0.2841 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6903    1.9874   -0.4397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4742   -0.1951   -1.2624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8737    0.2461   -1.0852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4041    1.1895   -1.7069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6972   -0.4813   -0.1052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9560   -0.1828    0.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6940   -0.9854    1.1512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6672    0.9225   -0.5615 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5642    0.7291    0.7997 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0131    0.4270    0.8792 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7232    1.5423    0.4150 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1731   -1.5717    1.8344 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4798    0.0573    1.7529 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1624   -0.6901    0.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3220   -0.9558   -1.9738 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9844   -0.8834   -1.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9867    0.5904   -1.3486 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4028   -2.8685    0.1186 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2506   -2.0563   -0.3771 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2629    0.4234   -1.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9989    0.2606    0.7437 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2862    2.3900   -0.8314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4462    2.2284   -1.1941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8737    2.5047    0.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4792   -1.3102   -1.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1736    0.0913   -2.2959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2653   -1.3148    0.4617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6755   -2.0475    0.8049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1921   -0.9133    2.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7407   -0.6684    1.2062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7395    0.9406   -0.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6647    0.6759   -1.6423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1694    1.8649   -0.3434 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3430    1.8115    0.7701 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0095    0.3527    1.7097 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2746    0.3141    1.9728 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7435    2.1865    1.1546 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  1
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  3
 14 15  1  0
 14 16  1  0
  7 17  1  0
 17 18  1  0
 18 19  1  0
 18  3  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  6
  8 29  1  1
  9 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 13 35  1  0
 15 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  1
 19 45  1  0
M  END


  Mrv0541 02241212462D          

 20 20  0  0  0  0            999 V2000
    1.1491    0.1179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4346   -0.2946    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4346   -1.1197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1491   -1.5322    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8636   -1.1197    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8636   -0.2946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2798    0.1179    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9943   -0.2946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9943   -1.1197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2798   -1.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2798    0.9429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2798   -2.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4346   -2.7697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9943   -2.7697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5781   -1.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7088   -1.5322    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1491   -2.3572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8636   -1.9447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5781   -2.3572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4346    0.5304    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  3  2  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  7 11  1  6  0  0  0
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  5 15  1  1  0  0  0
  9 16  2  0  0  0  0
  4 17  1  1  0  0  0
  5 18  1  6  0  0  0
 18 19  1  0  0  0  0
  2 20  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0302604

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]1(C[C@H](O)[C@@](C)(OC)C=C1)[C@@H](C)CC(=O)C=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C16H26O3/c1-11(2)8-14(17)9-12(3)13-6-7-16(4,19-5)15(18)10-13/h6-8,12-13,15,18H,9-10H2,1-5H3/t12-,13+,15-,16-/m0/s1

> <INCHI_KEY>
XQXANAYBQDKOBU-XRGAULLZSA-N

> <FORMULA>
C16H26O3

> <MOLECULAR_WEIGHT>
266.3758

> <EXACT_MASS>
266.188194698

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
31.001772831469026

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6S)-6-[(1R,4S,5S)-5-hydroxy-4-methoxy-4-methylcyclohex-2-en-1-yl]-2-methylhept-2-en-4-one

> <ALOGPS_LOGP>
2.32

> <JCHEM_LOGP>
2.7823273850000003

> <ALOGPS_LOGS>
-3.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.926576310934287

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2683155215973425

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
79.10789999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.58e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6S)-6-[(1R,4S,5S)-5-hydroxy-4-methoxy-4-methylcyclohex-2-en-1-yl]-2-methylhept-2-en-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302604
     RDKit          3D
5-Hydroxy-4-methoxybisabola-2,10-dien-9-one
 45 45  0  0  0  0  0  0  0  0999 V2000
    5.5438   -0.8779    1.2025 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3643   -1.5279    0.9736 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4432   -0.8491    0.2145 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9553   -0.5151   -1.1653 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2760   -1.7885    0.0278 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0567   -1.3564   -0.2513 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8541    0.0958   -0.3799 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6003    0.4959   -0.2841 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6903    1.9874   -0.4397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4742   -0.1951   -1.2624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8737    0.2461   -1.0852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4041    1.1895   -1.7069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6972   -0.4813   -0.1052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9560   -0.1828    0.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6940   -0.9854    1.1512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6672    0.9225   -0.5615 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5642    0.7291    0.7997 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0131    0.4270    0.8792 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7232    1.5423    0.4150 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1731   -1.5717    1.8344 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4798    0.0573    1.7529 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1624   -0.6901    0.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3220   -0.9558   -1.9738 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9844   -0.8834   -1.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9867    0.5904   -1.3486 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4028   -2.8685    0.1186 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2506   -2.0563   -0.3771 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2629    0.4234   -1.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9989    0.2606    0.7437 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2862    2.3900   -0.8314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4462    2.2284   -1.1941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8737    2.5047    0.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4792   -1.3102   -1.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1736    0.0913   -2.2959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2653   -1.3148    0.4617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6755   -2.0475    0.8049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1921   -0.9133    2.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7407   -0.6684    1.2062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7395    0.9406   -0.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6647    0.6759   -1.6423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1694    1.8649   -0.3434 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3430    1.8115    0.7701 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0095    0.3527    1.7097 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2746    0.3141    1.9728 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7435    2.1865    1.1546 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  1
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  3
 14 15  1  0
 14 16  1  0
  7 17  1  0
 17 18  1  0
 18 19  1  0
 18  3  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  6
  8 29  1  1
  9 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 13 35  1  0
 15 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  1
 19 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       2.145   0.220   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.811  -0.550   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.811  -2.090   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.145  -2.860   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.479  -2.090   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.479  -0.550   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.522   0.220   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.856  -0.550   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.856  -2.090   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.522  -2.860   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.522   1.760   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.522  -4.400   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.811  -5.170   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.856  -5.170   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.812  -2.860   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.190  -2.860   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       2.145  -4.400   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       3.479  -3.630   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.812  -4.400   0.000  0.00  0.00           C+0
HETATM   20  H   UNK     0       0.811   0.990   0.000  0.00  0.00           H+0
CONECT    1    2    6                                                       
CONECT    2    1    3    7   20                                             
CONECT    3    4    2                                                       
CONECT    4    3    5   17                                                  
CONECT    5    4    6   15   18                                             
CONECT    6    1    5                                                       
CONECT    7    2    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   12                                                       
CONECT   11    7                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    5                                                            
CONECT   16    9                                                            
CONECT   17    4                                                            
CONECT   18    5   19                                                       
CONECT   19   18                                                            
CONECT   20    2                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

COMPND    HMDB0302604
HETATM    1  C1  UNL     1       5.544  -0.878   1.203  1.00  0.00           C  
HETATM    2  O1  UNL     1       4.364  -1.528   0.974  1.00  0.00           O  
HETATM    3  C2  UNL     1       3.443  -0.849   0.215  1.00  0.00           C  
HETATM    4  C3  UNL     1       3.955  -0.515  -1.165  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.276  -1.788   0.028  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.057  -1.356  -0.251  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.854   0.096  -0.380  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.600   0.496  -0.284  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.690   1.987  -0.440  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.474  -0.195  -1.262  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.874   0.246  -1.085  1.00  0.00           C  
HETATM   12  O2  UNL     1      -3.404   1.189  -1.707  1.00  0.00           O  
HETATM   13  C11 UNL     1      -3.697  -0.481  -0.105  1.00  0.00           C  
HETATM   14  C12 UNL     1      -4.956  -0.183   0.138  1.00  0.00           C  
HETATM   15  C13 UNL     1      -5.694  -0.985   1.151  1.00  0.00           C  
HETATM   16  C14 UNL     1      -5.667   0.922  -0.562  1.00  0.00           C  
HETATM   17  C15 UNL     1       1.564   0.729   0.800  1.00  0.00           C  
HETATM   18  C16 UNL     1       3.013   0.427   0.879  1.00  0.00           C  
HETATM   19  O3  UNL     1       3.723   1.542   0.415  1.00  0.00           O  
HETATM   20  H1  UNL     1       6.173  -1.572   1.834  1.00  0.00           H  
HETATM   21  H2  UNL     1       5.480   0.057   1.753  1.00  0.00           H  
HETATM   22  H3  UNL     1       6.162  -0.690   0.300  1.00  0.00           H  
HETATM   23  H4  UNL     1       3.322  -0.956  -1.974  1.00  0.00           H  
HETATM   24  H5  UNL     1       4.984  -0.883  -1.350  1.00  0.00           H  
HETATM   25  H6  UNL     1       3.987   0.590  -1.349  1.00  0.00           H  
HETATM   26  H7  UNL     1       2.403  -2.868   0.119  1.00  0.00           H  
HETATM   27  H8  UNL     1       0.251  -2.056  -0.377  1.00  0.00           H  
HETATM   28  H9  UNL     1       1.263   0.423  -1.351  1.00  0.00           H  
HETATM   29  H10 UNL     1      -0.999   0.261   0.744  1.00  0.00           H  
HETATM   30  H11 UNL     1       0.286   2.390  -0.831  1.00  0.00           H  
HETATM   31  H12 UNL     1      -1.446   2.228  -1.194  1.00  0.00           H  
HETATM   32  H13 UNL     1      -0.874   2.505   0.533  1.00  0.00           H  
HETATM   33  H14 UNL     1      -1.479  -1.310  -1.142  1.00  0.00           H  
HETATM   34  H15 UNL     1      -1.174   0.091  -2.296  1.00  0.00           H  
HETATM   35  H16 UNL     1      -3.265  -1.315   0.462  1.00  0.00           H  
HETATM   36  H17 UNL     1      -5.675  -2.047   0.805  1.00  0.00           H  
HETATM   37  H18 UNL     1      -5.192  -0.913   2.157  1.00  0.00           H  
HETATM   38  H19 UNL     1      -6.741  -0.668   1.206  1.00  0.00           H  
HETATM   39  H20 UNL     1      -6.739   0.941  -0.231  1.00  0.00           H  
HETATM   40  H21 UNL     1      -5.665   0.676  -1.642  1.00  0.00           H  
HETATM   41  H22 UNL     1      -5.169   1.865  -0.343  1.00  0.00           H  
HETATM   42  H23 UNL     1       1.343   1.811   0.770  1.00  0.00           H  
HETATM   43  H24 UNL     1       1.009   0.353   1.710  1.00  0.00           H  
HETATM   44  H25 UNL     1       3.275   0.314   1.973  1.00  0.00           H  
HETATM   45  H26 UNL     1       3.743   2.186   1.155  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3
CONECT    3    4    5   18
CONECT    4   23   24   25
CONECT    5    6    6   26
CONECT    6    7   27
CONECT    7    8   17   28
CONECT    8    9   10   29
CONECT    9   30   31   32
CONECT   10   11   33   34
CONECT   11   12   12   13
CONECT   13   14   14   35
CONECT   14   15   16
CONECT   15   36   37   38
CONECT   16   39   40   41
CONECT   17   18   42   43
CONECT   18   19   44
CONECT   19   45
END

HMDB0302604
     RDKit          3D
5-Hydroxy-4-methoxybisabola-2,10-dien-9-one
 45 45  0  0  0  0  0  0  0  0999 V2000
    5.5438   -0.8779    1.2025 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3643   -1.5279    0.9736 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4432   -0.8491    0.2145 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.9553   -0.5151   -1.1653 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2760   -1.7885    0.0278 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0567   -1.3564   -0.2513 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8541    0.0958   -0.3799 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6003    0.4959   -0.2841 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6903    1.9874   -0.4397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4742   -0.1951   -1.2624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8737    0.2461   -1.0852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4041    1.1895   -1.7069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6972   -0.4813   -0.1052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9560   -0.1828    0.1382 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6940   -0.9854    1.1512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6672    0.9225   -0.5615 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5642    0.7291    0.7997 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0131    0.4270    0.8792 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7232    1.5423    0.4150 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1731   -1.5717    1.8344 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4798    0.0573    1.7529 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1624   -0.6901    0.3005 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3220   -0.9558   -1.9738 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9844   -0.8834   -1.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9867    0.5904   -1.3486 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4028   -2.8685    0.1186 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2506   -2.0563   -0.3771 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2629    0.4234   -1.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9989    0.2606    0.7437 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2862    2.3900   -0.8314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4462    2.2284   -1.1941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8737    2.5047    0.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4792   -1.3102   -1.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1736    0.0913   -2.2959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2653   -1.3148    0.4617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6755   -2.0475    0.8049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1921   -0.9133    2.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7407   -0.6684    1.2062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7395    0.9406   -0.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6647    0.6759   -1.6423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1694    1.8649   -0.3434 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3430    1.8115    0.7701 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0095    0.3527    1.7097 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2746    0.3141    1.9728 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7435    2.1865    1.1546 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  3  2  1  1
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  3
 14 15  1  0
 14 16  1  0
  7 17  1  0
 17 18  1  0
 18 19  1  0
 18  3  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  6
  8 29  1  1
  9 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 13 35  1  0
 15 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 16 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  1
 19 45  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₆H₂₆O₃

Average Molecular Weight

266.3758

Monoisotopic Molecular Weight

266.188194698

IUPAC Name

(6S)-6-[(1R,4S,5S)-5-hydroxy-4-methoxy-4-methylcyclohex-2-en-1-yl]-2-methylhept-2-en-4-one

Traditional Name

(6S)-6-[(1R,4S,5S)-5-hydroxy-4-methoxy-4-methylcyclohex-2-en-1-yl]-2-methylhept-2-en-4-one

CAS Registry Number

Not Available

SMILES

[H][C@@]1(C[C@H](O)[C@@](C)(OC)C=C1)[C@@H](C)CC(=O)C=C(C)C

InChI Identifier

InChI=1S/C16H26O3/c1-11(2)8-14(17)9-12(3)13-6-7-16(4,19-5)15(18)10-13/h6-8,12-13,15,18H,9-10H2,1-5H3/t12-,13+,15-,16-/m0/s1

InChI Key

XQXANAYBQDKOBU-XRGAULLZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Bisabolane sesquiterpenoid
Sesquiterpenoid
Acryloyl-group
Enone
Alpha,beta-unsaturated ketone
Ketone
Secondary alcohol
Dialkyl ether
Ether
Alcohol
Organic oxide
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Turmeric (FooDB: FOOD00068)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.32	ALOGPS
logP	2.78	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	13.93	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	79.11 m³·mol⁻¹	ChemAxon
Polarizability	31 Å³	ChemAxon
Number of Rings	1	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
AllCCS	[M+H]+	166.348	32859911
AllCCS	[M+H-H2O]+	162.915	32859911
AllCCS	[M+Na]+	170.449	32859911
AllCCS	[M+NH4]+	169.533	32859911
AllCCS	[M-H]-	170.84	32859911
AllCCS	[M+Na-2H]-	171.691	32859911
AllCCS	[M+HCOO]-	172.753	32859911
DeepCCS	[M+H]+	172.218	30932474
DeepCCS	[M-H]-	169.823	30932474
DeepCCS	[M-2H]-	203.317	30932474
DeepCCS	[M+Na]+	178.131	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5-Hydroxy-4-methoxybisabola-2,10-dien-9-one,2TMS,isomer #1	CO[C@@]1(C)C=C[C@@H]([C@@H](C)C=C(C=C(C)C)O[Si](C)(C)C)C[C@@H]1O[Si](C)(C)C	2060.7	Semi standard non polar	33892256
5-Hydroxy-4-methoxybisabola-2,10-dien-9-one,2TMS,isomer #1	CO[C@@]1(C)C=C[C@@H]([C@@H](C)C=C(C=C(C)C)O[Si](C)(C)C)C[C@@H]1O[Si](C)(C)C	2006.4	Standard non polar	33892256
5-Hydroxy-4-methoxybisabola-2,10-dien-9-one,2TMS,isomer #1	CO[C@@]1(C)C=C[C@@H]([C@@H](C)C=C(C=C(C)C)O[Si](C)(C)C)C[C@@H]1O[Si](C)(C)C	2285.3	Standard polar	33892256
5-Hydroxy-4-methoxybisabola-2,10-dien-9-one,2TBDMS,isomer #1	CO[C@@]1(C)C=C[C@@H]([C@@H](C)C=C(C=C(C)C)O[Si](C)(C)C(C)(C)C)C[C@@H]1O[Si](C)(C)C(C)(C)C	2499.0	Semi standard non polar	33892256
5-Hydroxy-4-methoxybisabola-2,10-dien-9-one,2TBDMS,isomer #1	CO[C@@]1(C)C=C[C@@H]([C@@H](C)C=C(C=C(C)C)O[Si](C)(C)C(C)(C)C)C[C@@H]1O[Si](C)(C)C(C)(C)C	2424.5	Standard non polar	33892256
5-Hydroxy-4-methoxybisabola-2,10-dien-9-one,2TBDMS,isomer #1	CO[C@@]1(C)C=C[C@@H]([C@@H](C)C=C(C=C(C)C)O[Si](C)(C)C(C)(C)C)C[C@@H]1O[Si](C)(C)C(C)(C)C	2507.3	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4-methoxybisabola-2,10-dien-9-one 10V, Positive-QTOF	splash10-014i-0290000000-8bbd1e696ff5758e8f12	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4-methoxybisabola-2,10-dien-9-one 20V, Positive-QTOF	splash10-00lr-5940000000-b8823ece2222b2a10ea4	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4-methoxybisabola-2,10-dien-9-one 40V, Positive-QTOF	splash10-0159-9300000000-8c1aa352789a67531736	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4-methoxybisabola-2,10-dien-9-one 10V, Negative-QTOF	splash10-014i-1090000000-db0fa6fdd28693301120	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4-methoxybisabola-2,10-dien-9-one 20V, Negative-QTOF	splash10-066s-6190000000-26595ff88f8264742e14	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4-methoxybisabola-2,10-dien-9-one 40V, Negative-QTOF	splash10-0a4j-9230000000-e08feb9b3cf9cad51192	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4-methoxybisabola-2,10-dien-9-one 10V, Negative-QTOF	splash10-014i-0090000000-ee459c988e055563bdde	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4-methoxybisabola-2,10-dien-9-one 20V, Negative-QTOF	splash10-014i-0590000000-d3f51100aa1fcba45979	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4-methoxybisabola-2,10-dien-9-one 40V, Negative-QTOF	splash10-0gc9-2940000000-125011ef90dd6de4c504	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4-methoxybisabola-2,10-dien-9-one 10V, Positive-QTOF	splash10-014r-1920000000-c290ac40b5fc3eed284d	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4-methoxybisabola-2,10-dien-9-one 20V, Positive-QTOF	splash10-0f79-4920000000-14a4f769757846beaa1a	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5-Hydroxy-4-methoxybisabola-2,10-dien-9-one 40V, Positive-QTOF	splash10-0a4l-9400000000-cfa9ce1abf1d2c8a4d99	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB005323

KNApSAcK ID

Not Available

Chemspider ID

59696359

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14633008

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 5-Hydroxy-4-methoxybisabola-2,10-dien-9-one (HMDB0302604)

MOL for HMDB0302604 (5-Hydroxy-4-methoxybisabola-2,10-dien-9-one)

3D MOL for HMDB0302604 (5-Hydroxy-4-methoxybisabola-2,10-dien-9-one)

3D SDF for HMDB0302604 (5-Hydroxy-4-methoxybisabola-2,10-dien-9-one)

3D-SDF for HMDB0302604 (5-Hydroxy-4-methoxybisabola-2,10-dien-9-one)

PDB for HMDB0302604 (5-Hydroxy-4-methoxybisabola-2,10-dien-9-one)

3D PDB for HMDB0302604 (5-Hydroxy-4-methoxybisabola-2,10-dien-9-one)

SMILES for HMDB0302604 (5-Hydroxy-4-methoxybisabola-2,10-dien-9-one)

INCHI for HMDB0302604 (5-Hydroxy-4-methoxybisabola-2,10-dien-9-one)

Structure for HMDB0302604 (5-Hydroxy-4-methoxybisabola-2,10-dien-9-one)

3D Structure for HMDB0302604 (5-Hydroxy-4-methoxybisabola-2,10-dien-9-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra