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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:41:30 UTC

Update Date

2022-03-07 02:53:54 UTC

HMDB ID

HMDB0033917

Secondary Accession Numbers

HMDB33917

Metabolite Identification

Common Name

4-Hydroxy-3-methoxy-2,10-bisaboladien-9-one

Description

4-Hydroxy-3-methoxy-2,10-bisaboladien-9-one belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a significant number of articles have been published on 4-Hydroxy-3-methoxy-2,10-bisaboladien-9-one.

Structure

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

HMDB0033917
     RDKit          3D
4-Hydroxy-3-methoxy-2,10-bisaboladien-9-one
 45 45  0  0  0  0  0  0  0  0999 V2000
   -4.3573   -1.4508    2.1062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9154   -1.2612    0.8362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9711   -0.3196    0.6287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6783   -0.7614    0.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9158    0.3523   -0.6307 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5773    0.3279   -0.3312 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8394    0.4311    1.1459 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2434   -0.8273   -1.0129 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6961   -0.9279   -0.7982 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2370   -1.9958   -1.2359 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5441    0.0451   -0.1577 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8385   -0.1478   -0.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7014    0.8863    0.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4991   -1.3625   -0.5347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4072    1.7109   -0.3073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6797    1.9669   -0.0760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6210    0.8261   -0.1519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9326    0.4040   -1.5607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7932    1.1518    0.5300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6152   -1.7472    2.8506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2383   -2.1303    2.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7602   -0.4530    2.4534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7341    0.1375    1.6371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0469   -1.2288    0.7951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9055   -1.5494   -0.7408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9910    0.2571   -1.7515 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9767    1.2601   -0.7841 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1855    1.4424    1.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0710    0.2587    1.7637 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5868   -0.3087    1.4658 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1211   -0.6736   -2.1210 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8192   -1.8126   -0.7146 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1537    0.9922    0.2390 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4937    1.1586   -0.0440 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0628    0.4948    1.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0720    1.7795    0.8446 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4165   -1.4652   -1.6493 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6061   -1.3245   -0.3002 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1421   -2.2668   -0.0010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6996    2.5249   -0.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9660    2.9824    0.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3524   -0.4950   -1.8735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0086    0.1353   -1.5897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7835    1.2347   -2.2608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3687    1.7488   -0.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  3
 12 13  1  0
 12 14  1  0
  5 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 17  3  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
 11 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 18 42  1  0
 18 43  1  0
 18 44  1  0
 19 45  1  0
M  END


  Mrv0541 05061307262D          

 19 19  0  0  0  0            999 V2000
   -2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4199    1.9579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  2  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 11  8  2  0  0  0  0
 12  3  1  0  0  0  0
 12  9  1  0  0  0  0
 13  6  1  0  0  0  0
 13 10  1  0  0  0  0
 13 12  1  0  0  0  0
 14  8  1  0  0  0  0
 14  9  1  0  0  0  0
 15 10  1  0  0  0  0
 16  4  1  0  0  0  0
 16  7  1  0  0  0  0
 16 15  1  0  0  0  0
 17 14  2  0  0  0  0
 18 16  1  0  0  0  0
 19  5  1  0  0  0  0
 19 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033917

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1CC(C=CC1(C)O)C(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(4,18)15(10-13)19-5/h6-8,12-13,15,18H,9-10H2,1-5H3

> <INCHI_KEY>
OJBJKMUUDWTVQL-UHFFFAOYSA-N

> <FORMULA>
C16H26O3

> <MOLECULAR_WEIGHT>
266.3758

> <EXACT_MASS>
266.188194698

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
30.86051543790051

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-(4-hydroxy-5-methoxy-4-methylcyclohex-2-en-1-yl)-2-methylhept-2-en-4-one

> <ALOGPS_LOGP>
2.41

> <JCHEM_LOGP>
2.7823273850000003

> <ALOGPS_LOGS>
-3.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.684409562353643

> <JCHEM_PKA_STRONGEST_BASIC>
-3.374239257426515

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
79.1079

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.90e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-(4-hydroxy-5-methoxy-4-methylcyclohex-2-en-1-yl)-2-methylhept-2-en-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0033917
     RDKit          3D
4-Hydroxy-3-methoxy-2,10-bisaboladien-9-one
 45 45  0  0  0  0  0  0  0  0999 V2000
   -4.3573   -1.4508    2.1062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9154   -1.2612    0.8362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9711   -0.3196    0.6287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6783   -0.7614    0.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9158    0.3523   -0.6307 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5773    0.3279   -0.3312 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8394    0.4311    1.1459 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2434   -0.8273   -1.0129 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6961   -0.9279   -0.7982 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2370   -1.9958   -1.2359 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5441    0.0451   -0.1577 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8385   -0.1478   -0.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7014    0.8863    0.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4991   -1.3625   -0.5347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4072    1.7109   -0.3073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6797    1.9669   -0.0760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6210    0.8261   -0.1519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9326    0.4040   -1.5607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7932    1.1518    0.5300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6152   -1.7472    2.8506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2383   -2.1303    2.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7602   -0.4530    2.4534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7341    0.1375    1.6371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0469   -1.2288    0.7951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9055   -1.5494   -0.7408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9910    0.2571   -1.7515 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9767    1.2601   -0.7841 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1855    1.4424    1.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0710    0.2587    1.7637 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5868   -0.3087    1.4658 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1211   -0.6736   -2.1210 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8192   -1.8126   -0.7146 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1537    0.9922    0.2390 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4937    1.1586   -0.0440 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0628    0.4948    1.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0720    1.7795    0.8446 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4165   -1.4652   -1.6493 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6061   -1.3245   -0.3002 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1421   -2.2668   -0.0010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6996    2.5249   -0.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9660    2.9824    0.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3524   -0.4950   -1.8735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0086    0.1353   -1.5897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7835    1.2347   -2.2608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3687    1.7488   -0.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  3
 12 13  1  0
 12 14  1  0
  5 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 17  3  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
 11 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 18 42  1  0
 18 43  1  0
 18 44  1  0
 19 45  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.784   3.655   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       2.324   3.490   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4   16                                                            
CONECT    5   19                                                            
CONECT    6    7   13                                                       
CONECT    7    6   16                                                       
CONECT    8   11   14                                                       
CONECT    9   12   14                                                       
CONECT   10   13   15                                                       
CONECT   11    1    2    8                                                  
CONECT   12    3    9   13                                                  
CONECT   13    6   10   12                                                  
CONECT   14    8    9   17                                                  
CONECT   15   10   16   19                                                  
CONECT   16    4    7   15   18                                             
CONECT   17   14                                                            
CONECT   18   16                                                            
CONECT   19    5   15                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

COMPND    HMDB0033917
HETATM    1  C1  UNL     1      -4.357  -1.451   2.106  1.00  0.00           C  
HETATM    2  O1  UNL     1      -3.915  -1.261   0.836  1.00  0.00           O  
HETATM    3  C2  UNL     1      -2.971  -0.320   0.629  1.00  0.00           C  
HETATM    4  C3  UNL     1      -1.678  -0.761   0.011  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.916   0.352  -0.631  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.577   0.328  -0.331  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.839   0.431   1.146  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.243  -0.827  -1.013  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.696  -0.928  -0.798  1.00  0.00           C  
HETATM   10  O2  UNL     1       3.237  -1.996  -1.236  1.00  0.00           O  
HETATM   11  C9  UNL     1       3.544   0.045  -0.158  1.00  0.00           C  
HETATM   12  C10 UNL     1       4.838  -0.148  -0.024  1.00  0.00           C  
HETATM   13  C11 UNL     1       5.701   0.886   0.651  1.00  0.00           C  
HETATM   14  C12 UNL     1       5.499  -1.362  -0.535  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.407   1.711  -0.307  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.680   1.967  -0.076  1.00  0.00           C  
HETATM   17  C15 UNL     1      -3.621   0.826  -0.152  1.00  0.00           C  
HETATM   18  C16 UNL     1      -3.933   0.404  -1.561  1.00  0.00           C  
HETATM   19  O3  UNL     1      -4.793   1.152   0.530  1.00  0.00           O  
HETATM   20  H1  UNL     1      -3.615  -1.747   2.851  1.00  0.00           H  
HETATM   21  H2  UNL     1      -5.238  -2.130   2.094  1.00  0.00           H  
HETATM   22  H3  UNL     1      -4.760  -0.453   2.453  1.00  0.00           H  
HETATM   23  H4  UNL     1      -2.734   0.138   1.637  1.00  0.00           H  
HETATM   24  H5  UNL     1      -1.047  -1.229   0.795  1.00  0.00           H  
HETATM   25  H6  UNL     1      -1.906  -1.549  -0.741  1.00  0.00           H  
HETATM   26  H7  UNL     1      -0.991   0.257  -1.752  1.00  0.00           H  
HETATM   27  H8  UNL     1       0.977   1.260  -0.784  1.00  0.00           H  
HETATM   28  H9  UNL     1       1.185   1.442   1.453  1.00  0.00           H  
HETATM   29  H10 UNL     1      -0.071   0.259   1.764  1.00  0.00           H  
HETATM   30  H11 UNL     1       1.587  -0.309   1.466  1.00  0.00           H  
HETATM   31  H12 UNL     1       1.121  -0.674  -2.121  1.00  0.00           H  
HETATM   32  H13 UNL     1       0.819  -1.813  -0.715  1.00  0.00           H  
HETATM   33  H14 UNL     1       3.154   0.992   0.239  1.00  0.00           H  
HETATM   34  H15 UNL     1       6.494   1.159  -0.044  1.00  0.00           H  
HETATM   35  H16 UNL     1       6.063   0.495   1.625  1.00  0.00           H  
HETATM   36  H17 UNL     1       5.072   1.779   0.845  1.00  0.00           H  
HETATM   37  H18 UNL     1       5.416  -1.465  -1.649  1.00  0.00           H  
HETATM   38  H19 UNL     1       6.606  -1.324  -0.300  1.00  0.00           H  
HETATM   39  H20 UNL     1       5.142  -2.267  -0.001  1.00  0.00           H  
HETATM   40  H21 UNL     1      -0.700   2.525  -0.261  1.00  0.00           H  
HETATM   41  H22 UNL     1      -2.966   2.982   0.154  1.00  0.00           H  
HETATM   42  H23 UNL     1      -3.352  -0.495  -1.874  1.00  0.00           H  
HETATM   43  H24 UNL     1      -5.009   0.135  -1.590  1.00  0.00           H  
HETATM   44  H25 UNL     1      -3.783   1.235  -2.261  1.00  0.00           H  
HETATM   45  H26 UNL     1      -5.369   1.749  -0.040  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3
CONECT    3    4   17   23
CONECT    4    5   24   25
CONECT    5    6   15   26
CONECT    6    7    8   27
CONECT    7   28   29   30
CONECT    8    9   31   32
CONECT    9   10   10   11
CONECT   11   12   12   33
CONECT   12   13   14
CONECT   13   34   35   36
CONECT   14   37   38   39
CONECT   15   16   16   40
CONECT   16   17   41
CONECT   17   18   19
CONECT   18   42   43   44
CONECT   19   45
END

HMDB0033917
     RDKit          3D
4-Hydroxy-3-methoxy-2,10-bisaboladien-9-one
 45 45  0  0  0  0  0  0  0  0999 V2000
   -4.3573   -1.4508    2.1062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9154   -1.2612    0.8362 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9711   -0.3196    0.6287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6783   -0.7614    0.0114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9158    0.3523   -0.6307 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5773    0.3279   -0.3312 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8394    0.4311    1.1459 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2434   -0.8273   -1.0129 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6961   -0.9279   -0.7982 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2370   -1.9958   -1.2359 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5441    0.0451   -0.1577 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8385   -0.1478   -0.0240 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7014    0.8863    0.6511 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4991   -1.3625   -0.5347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4072    1.7109   -0.3073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6797    1.9669   -0.0760 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6210    0.8261   -0.1519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9326    0.4040   -1.5607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7932    1.1518    0.5300 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6152   -1.7472    2.8506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2383   -2.1303    2.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7602   -0.4530    2.4534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7341    0.1375    1.6371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0469   -1.2288    0.7951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9055   -1.5494   -0.7408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9910    0.2571   -1.7515 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9767    1.2601   -0.7841 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1855    1.4424    1.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0710    0.2587    1.7637 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5868   -0.3087    1.4658 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1211   -0.6736   -2.1210 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8192   -1.8126   -0.7146 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1537    0.9922    0.2390 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4937    1.1586   -0.0440 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0628    0.4948    1.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0720    1.7795    0.8446 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4165   -1.4652   -1.6493 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6061   -1.3245   -0.3002 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1421   -2.2668   -0.0010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6996    2.5249   -0.2605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9660    2.9824    0.1538 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3524   -0.4950   -1.8735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0086    0.1353   -1.5897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7835    1.2347   -2.2608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3687    1.7488   -0.0402 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  3
 12 13  1  0
 12 14  1  0
  5 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 17  3  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  4 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
 11 33  1  0
 13 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 16 41  1  0
 18 42  1  0
 18 43  1  0
 18 44  1  0
 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

6-(4-hydroxy-5-methoxy-4-methylcyclohex-2-en-1-yl)-2-methylhept-2-en-4-one

Traditional Name

6-(4-hydroxy-5-methoxy-4-methylcyclohex-2-en-1-yl)-2-methylhept-2-en-4-one

CAS Registry Number

Not Available

SMILES

COC1CC(C=CC1(C)O)C(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(4,18)15(10-13)19-5/h6-8,12-13,15,18H,9-10H2,1-5H3

InChI Key

OJBJKMUUDWTVQL-UHFFFAOYSA-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
Tertiary alcohol
Ketone
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

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0033917)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033917)

Source

Endogenous

Endogenous (HMDB: HMDB0033917)

Plant

Plant (HMDB: HMDB0033917)

Animal

Animal (HMDB: HMDB0033917)

Exogenous

Food

Food (HMDB: HMDB0033917)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0033917)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0033917)

Cellular process

Cell signaling (HMDB: HMDB0033917)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0033917)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0033917)

Nutrient

Nutrient (HMDB: HMDB0033917)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0033917)

Emulsifier (HMDB: HMDB0033917)

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	0.19 g/L	ALOGPS
logP	2.41	ALOGPS
logP	2.78	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	13.68	ChemAxon
pKa (Strongest Basic)	-3.4	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	30.86 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
DarkChem	[M+H]+	163.968	31661259
DarkChem	[M-H]-	164.976	31661259
DeepCCS	[M+H]+	173.522	30932474
DeepCCS	[M-H]-	171.164	30932474
DeepCCS	[M-2H]-	204.05	30932474
DeepCCS	[M+Na]+	179.615	30932474
AllCCS	[M+H]+	165.8	32859911
AllCCS	[M+H-H2O]+	162.4	32859911
AllCCS	[M+NH4]+	169.0	32859911
AllCCS	[M+Na]+	170.0	32859911
AllCCS	[M-H]-	170.9	32859911
AllCCS	[M+Na-2H]-	171.7	32859911
AllCCS	[M+HCOO]-	172.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxy-3-methoxy-2,10-bisaboladien-9-one	COC1CC(C=CC1(C)O)C(C)CC(=O)C=C(C)C	2887.0	Standard polar	33892256
4-Hydroxy-3-methoxy-2,10-bisaboladien-9-one	COC1CC(C=CC1(C)O)C(C)CC(=O)C=C(C)C	1805.5	Standard non polar	33892256
4-Hydroxy-3-methoxy-2,10-bisaboladien-9-one	COC1CC(C=CC1(C)O)C(C)CC(=O)C=C(C)C	1885.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxy-3-methoxy-2,10-bisaboladien-9-one,1TMS,isomer #1	COC1CC(C(C)CC(=O)C=C(C)C)C=CC1(C)O[Si](C)(C)C	1972.8	Semi standard non polar	33892256
4-Hydroxy-3-methoxy-2,10-bisaboladien-9-one,1TMS,isomer #2	COC1CC(C(C)C=C(C=C(C)C)O[Si](C)(C)C)C=CC1(C)O	2062.1	Semi standard non polar	33892256
4-Hydroxy-3-methoxy-2,10-bisaboladien-9-one,2TMS,isomer #1	COC1CC(C(C)C=C(C=C(C)C)O[Si](C)(C)C)C=CC1(C)O[Si](C)(C)C	2086.0	Semi standard non polar	33892256
4-Hydroxy-3-methoxy-2,10-bisaboladien-9-one,2TMS,isomer #1	COC1CC(C(C)C=C(C=C(C)C)O[Si](C)(C)C)C=CC1(C)O[Si](C)(C)C	1998.4	Standard non polar	33892256
4-Hydroxy-3-methoxy-2,10-bisaboladien-9-one,1TBDMS,isomer #1	COC1CC(C(C)CC(=O)C=C(C)C)C=CC1(C)O[Si](C)(C)C(C)(C)C	2203.9	Semi standard non polar	33892256
4-Hydroxy-3-methoxy-2,10-bisaboladien-9-one,1TBDMS,isomer #2	COC1CC(C(C)C=C(C=C(C)C)O[Si](C)(C)C(C)(C)C)C=CC1(C)O	2300.9	Semi standard non polar	33892256
4-Hydroxy-3-methoxy-2,10-bisaboladien-9-one,2TBDMS,isomer #1	COC1CC(C(C)C=C(C=C(C)C)O[Si](C)(C)C(C)(C)C)C=CC1(C)O[Si](C)(C)C(C)(C)C	2551.4	Semi standard non polar	33892256
4-Hydroxy-3-methoxy-2,10-bisaboladien-9-one,2TBDMS,isomer #1	COC1CC(C(C)C=C(C=C(C)C)O[Si](C)(C)C(C)(C)C)C=CC1(C)O[Si](C)(C)C(C)(C)C	2448.8	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-3-methoxy-2,10-bisaboladien-9-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-053r-9350000000-e52d526f873269de038b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-3-methoxy-2,10-bisaboladien-9-one GC-MS (1 TMS) - 70eV, Positive	splash10-05ai-9142000000-7f9fd9556555a0aef374	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 4-Hydroxy-3-methoxy-2,10-bisaboladien-9-one 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 - 4-Hydroxy-3-methoxy-2,10-bisaboladien-9-one 10V, Positive-QTOF	splash10-014i-0290000000-609717258f1d2757fb26	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxy-2,10-bisaboladien-9-one 20V, Positive-QTOF	splash10-00lr-5970000000-51ac4523187d72ee09f1	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxy-2,10-bisaboladien-9-one 40V, Positive-QTOF	splash10-0le9-9300000000-86e9c0a58cd2b2f75a81	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxy-2,10-bisaboladien-9-one 10V, Negative-QTOF	splash10-014i-1090000000-d9894bd097c022cf205e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxy-2,10-bisaboladien-9-one 20V, Negative-QTOF	splash10-066s-6190000000-faa4c7955753dfa76602	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxy-2,10-bisaboladien-9-one 40V, Negative-QTOF	splash10-0a4j-9230000000-394afbbdd45b85012ad2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxy-2,10-bisaboladien-9-one 10V, Positive-QTOF	splash10-014i-0930000000-86776c2a2455e056a340	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxy-2,10-bisaboladien-9-one 20V, Positive-QTOF	splash10-0udj-3920000000-b81bc03f79476e7a3fbb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxy-2,10-bisaboladien-9-one 40V, Positive-QTOF	splash10-0kal-9800000000-26f4726c0758bd0da872	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxy-2,10-bisaboladien-9-one 10V, Negative-QTOF	splash10-0159-0090000000-832f399352a880473838	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxy-2,10-bisaboladien-9-one 20V, Negative-QTOF	splash10-0gc1-3590000000-1de9d50d4968b68d0c69	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxy-3-methoxy-2,10-bisaboladien-9-one 40V, Negative-QTOF	splash10-03xs-2690000000-6ec6eb4ca87cfa16aba3	2021-09-24	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

FDB012115

KNApSAcK ID

Not Available

Chemspider ID

35013677

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131751504

PDB ID

Not Available

ChEBI ID

138776

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 4-Hydroxy-3-methoxy-2,10-bisaboladien-9-one (HMDB0033917)

MOL for HMDB0033917 (4-Hydroxy-3-methoxy-2,10-bisaboladien-9-one)

3D MOL for HMDB0033917 (4-Hydroxy-3-methoxy-2,10-bisaboladien-9-one)

3D SDF for HMDB0033917 (4-Hydroxy-3-methoxy-2,10-bisaboladien-9-one)

3D-SDF for HMDB0033917 (4-Hydroxy-3-methoxy-2,10-bisaboladien-9-one)

PDB for HMDB0033917 (4-Hydroxy-3-methoxy-2,10-bisaboladien-9-one)

3D PDB for HMDB0033917 (4-Hydroxy-3-methoxy-2,10-bisaboladien-9-one)

SMILES for HMDB0033917 (4-Hydroxy-3-methoxy-2,10-bisaboladien-9-one)

INCHI for HMDB0033917 (4-Hydroxy-3-methoxy-2,10-bisaboladien-9-one)

Structure for HMDB0033917 (4-Hydroxy-3-methoxy-2,10-bisaboladien-9-one)

3D Structure for HMDB0033917 (4-Hydroxy-3-methoxy-2,10-bisaboladien-9-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra