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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 19:03:30 UTC

Update Date

2021-09-23 19:03:30 UTC

HMDB ID

HMDB0302603

Secondary Accession Numbers

None

Metabolite Identification

Common Name

4-Hydroxybisabola-2,10-dien-9-one

Description

4-hydroxybisabola-2,10-dien-9-one is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. 4-hydroxybisabola-2,10-dien-9-one is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). 4-hydroxybisabola-2,10-dien-9-one can be found in turmeric, which makes 4-hydroxybisabola-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

HMDB0302603
     RDKit          3D
4-Hydroxybisabola-2,10-dien-9-one
 41 41  0  0  0  0  0  0  0  0999 V2000
   -3.2554    1.0754    0.7522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0448    0.1452   -0.0777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5155   -0.0349    0.2739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5292   -0.5083   -1.0787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2271   -0.5427   -1.6306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0585   -1.3375   -2.6579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9976    0.1774   -1.2415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0553   -0.8524   -0.6556 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6048   -1.5514    0.5378 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3271   -0.3152   -0.4149 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1370   -1.4274    0.1602 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3538   -1.1395    0.6016 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8393    0.2553    0.5004 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3084    0.4999   -0.9439 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9683    0.3532    1.3317 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7688    1.2069    0.8919 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3623    0.7915    0.6172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9123    1.4012    1.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0301    2.0059    0.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3663    0.6235    1.2092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8610    0.8037    0.8838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6143   -0.9654    0.8764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0573   -0.1335   -0.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2724   -1.1834   -1.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4987    0.4515   -2.2414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1164    1.0778   -0.6549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0671   -1.6294   -1.4673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7105   -1.6575    0.3681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4124   -1.0789    1.5056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2169   -2.6041    0.5402 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7808    0.1053   -1.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7870   -2.4524    0.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9981   -1.9320    1.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7969    1.3786   -1.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1035   -0.3748   -1.5944 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4066    0.7135   -0.9534 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7551    0.8126    2.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9553    2.1928    0.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9065    1.4259    1.9778 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9468    0.4158    1.6005 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7881    1.6828    0.2844 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  1
 13 16  1  0
 16 17  1  0
 17 10  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  6
  9 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  6
 11 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  1  0
M  END

  Mrv0541 02241212452D          

 18 18  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  0  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
    1.8636   -1.9447    0.0000 O   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
  5 17  1  6  0  0  0
  2 18  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0302603

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O2/c1-11(2)9-14(16)10-12(3)13-5-7-15(4,17)8-6-13/h5,7,9,12-13,17H,6,8,10H2,1-4H3/t12-,13+,15-/m0/s1

> <INCHI_KEY>
OZDOAMOSJAOPRV-GUTXKFCHSA-N

> <FORMULA>
C15H24O2

> <MOLECULAR_WEIGHT>
236.3499

> <EXACT_MASS>
236.177630012

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.947739111545957

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.72

> <JCHEM_LOGP>
3.214104488333332

> <ALOGPS_LOGS>
-3.18

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.171179579185342

> <JCHEM_PKA_STRONGEST_BASIC>
-1.411238094092449

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
72.99519999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.55e-01 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0302603
     RDKit          3D
4-Hydroxybisabola-2,10-dien-9-one
 41 41  0  0  0  0  0  0  0  0999 V2000
   -3.2554    1.0754    0.7522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0448    0.1452   -0.0777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5155   -0.0349    0.2739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5292   -0.5083   -1.0787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2271   -0.5427   -1.6306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0585   -1.3375   -2.6579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9976    0.1774   -1.2415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0553   -0.8524   -0.6556 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6048   -1.5514    0.5378 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3271   -0.3152   -0.4149 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1370   -1.4274    0.1602 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3538   -1.1395    0.6016 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8393    0.2553    0.5004 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3084    0.4999   -0.9439 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9683    0.3532    1.3317 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7688    1.2069    0.8919 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3623    0.7915    0.6172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9123    1.4012    1.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0301    2.0059    0.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3663    0.6235    1.2092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8610    0.8037    0.8838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6143   -0.9654    0.8764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0573   -0.1335   -0.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2724   -1.1834   -1.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4987    0.4515   -2.2414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1164    1.0778   -0.6549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0671   -1.6294   -1.4673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7105   -1.6575    0.3681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4124   -1.0789    1.5056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2169   -2.6041    0.5402 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7808    0.1053   -1.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7870   -2.4524    0.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9981   -1.9320    1.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7969    1.3786   -1.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1035   -0.3748   -1.5944 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4066    0.7135   -0.9534 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7551    0.8126    2.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9553    2.1928    0.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9065    1.4259    1.9778 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9468    0.4158    1.6005 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7881    1.6828    0.2844 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  1
 13 16  1  0
 16 17  1  0
 17 10  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  6
  9 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  6
 11 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  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       3.479  -3.630   0.000  0.00  0.00           O+0
HETATM   18  H   UNK     0       0.811   0.990   0.000  0.00  0.00           H+0
CONECT    1    2    6                                                       
CONECT    2    1    3    7   18                                             
CONECT    3    4    2                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   15   17                                             
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    5                                                            
CONECT   18    2                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0302603
HETATM    1  C1  UNL     1      -3.255   1.075   0.752  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.045   0.145  -0.078  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.516  -0.035   0.274  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.529  -0.508  -1.079  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.227  -0.543  -1.631  1.00  0.00           C  
HETATM    6  O1  UNL     1      -2.059  -1.338  -2.658  1.00  0.00           O  
HETATM    7  C6  UNL     1      -0.998   0.177  -1.242  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.055  -0.852  -0.656  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.605  -1.551   0.538  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.327  -0.315  -0.415  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.137  -1.427   0.160  1.00  0.00           C  
HETATM   12  C11 UNL     1       3.354  -1.140   0.602  1.00  0.00           C  
HETATM   13  C12 UNL     1       3.839   0.255   0.500  1.00  0.00           C  
HETATM   14  C13 UNL     1       4.308   0.500  -0.944  1.00  0.00           C  
HETATM   15  O2  UNL     1       4.968   0.353   1.332  1.00  0.00           O  
HETATM   16  C14 UNL     1       2.769   1.207   0.892  1.00  0.00           C  
HETATM   17  C15 UNL     1       1.362   0.791   0.617  1.00  0.00           C  
HETATM   18  H1  UNL     1      -3.912   1.401   1.623  1.00  0.00           H  
HETATM   19  H2  UNL     1      -3.030   2.006   0.198  1.00  0.00           H  
HETATM   20  H3  UNL     1      -2.366   0.623   1.209  1.00  0.00           H  
HETATM   21  H4  UNL     1      -5.861   0.804   0.884  1.00  0.00           H  
HETATM   22  H5  UNL     1      -5.614  -0.965   0.876  1.00  0.00           H  
HETATM   23  H6  UNL     1      -6.057  -0.133  -0.679  1.00  0.00           H  
HETATM   24  H7  UNL     1      -4.272  -1.183  -1.614  1.00  0.00           H  
HETATM   25  H8  UNL     1      -0.499   0.452  -2.241  1.00  0.00           H  
HETATM   26  H9  UNL     1      -1.116   1.078  -0.655  1.00  0.00           H  
HETATM   27  H10 UNL     1       0.067  -1.629  -1.467  1.00  0.00           H  
HETATM   28  H11 UNL     1      -1.711  -1.657   0.368  1.00  0.00           H  
HETATM   29  H12 UNL     1      -0.412  -1.079   1.506  1.00  0.00           H  
HETATM   30  H13 UNL     1      -0.217  -2.604   0.540  1.00  0.00           H  
HETATM   31  H14 UNL     1       1.781   0.105  -1.336  1.00  0.00           H  
HETATM   32  H15 UNL     1       1.787  -2.452   0.235  1.00  0.00           H  
HETATM   33  H16 UNL     1       3.998  -1.932   1.039  1.00  0.00           H  
HETATM   34  H17 UNL     1       3.797   1.379  -1.342  1.00  0.00           H  
HETATM   35  H18 UNL     1       4.103  -0.375  -1.594  1.00  0.00           H  
HETATM   36  H19 UNL     1       5.407   0.713  -0.953  1.00  0.00           H  
HETATM   37  H20 UNL     1       4.755   0.813   2.183  1.00  0.00           H  
HETATM   38  H21 UNL     1       2.955   2.193   0.391  1.00  0.00           H  
HETATM   39  H22 UNL     1       2.907   1.426   1.978  1.00  0.00           H  
HETATM   40  H23 UNL     1       0.947   0.416   1.601  1.00  0.00           H  
HETATM   41  H24 UNL     1       0.788   1.683   0.284  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    4    4
CONECT    3   21   22   23
CONECT    4    5   24
CONECT    5    6    6    7
CONECT    7    8   25   26
CONECT    8    9   10   27
CONECT    9   28   29   30
CONECT   10   11   17   31
CONECT   11   12   12   32
CONECT   12   13   33
CONECT   13   14   15   16
CONECT   14   34   35   36
CONECT   15   37
CONECT   16   17   38   39
CONECT   17   40   41
END

HMDB0302603
     RDKit          3D
4-Hydroxybisabola-2,10-dien-9-one
 41 41  0  0  0  0  0  0  0  0999 V2000
   -3.2554    1.0754    0.7522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0448    0.1452   -0.0777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5155   -0.0349    0.2739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5292   -0.5083   -1.0787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2271   -0.5427   -1.6306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0585   -1.3375   -2.6579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9976    0.1774   -1.2415 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0553   -0.8524   -0.6556 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6048   -1.5514    0.5378 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3271   -0.3152   -0.4149 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1370   -1.4274    0.1602 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3538   -1.1395    0.6016 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8393    0.2553    0.5004 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3084    0.4999   -0.9439 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9683    0.3532    1.3317 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7688    1.2069    0.8919 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3623    0.7915    0.6172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9123    1.4012    1.6228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0301    2.0059    0.1978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3663    0.6235    1.2092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8610    0.8037    0.8838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6143   -0.9654    0.8764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0573   -0.1335   -0.6786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2724   -1.1834   -1.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4987    0.4515   -2.2414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1164    1.0778   -0.6549 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0671   -1.6294   -1.4673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7105   -1.6575    0.3681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4124   -1.0789    1.5056 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2169   -2.6041    0.5402 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7808    0.1053   -1.3362 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7870   -2.4524    0.2355 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9981   -1.9320    1.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7969    1.3786   -1.3421 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1035   -0.3748   -1.5944 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4066    0.7135   -0.9534 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7551    0.8126    2.1833 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9553    2.1928    0.3914 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9065    1.4259    1.9778 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9468    0.4158    1.6005 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7881    1.6828    0.2844 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  1
 13 16  1  0
 16 17  1  0
 17 10  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  4 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  6
  9 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  6
 11 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄O₂

Average Molecular Weight

236.3499

Monoisotopic Molecular Weight

236.177630012

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H24O2/c1-11(2)9-14(16)10-12(3)13-5-7-15(4,17)8-6-13/h5,7,9,12-13,17H,6,8,10H2,1-4H3/t12-,13+,15-/m0/s1

InChI Key

OZDOAMOSJAOPRV-GUTXKFCHSA-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
Alpha,beta-unsaturated ketone
Tertiary alcohol
Enone
Acryloyl-group
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0302603)

Food

Herb and spice

Spice

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	2.72	ALOGPS
logP	3.21	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	18.17	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	73 m³·mol⁻¹	ChemAxon
Polarizability	27.95 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	157.675	32859911
AllCCS	[M+H-H2O]+	153.988	32859911
AllCCS	[M+Na]+	162.087	32859911
AllCCS	[M+NH4]+	161.101	32859911
AllCCS	[M-H]-	163.659	32859911
AllCCS	[M+Na-2H]-	164.456	32859911
AllCCS	[M+HCOO]-	165.45	32859911
DeepCCS	[M+H]+	160.433	30932474
DeepCCS	[M-H]-	158.038	30932474
DeepCCS	[M-2H]-	192.108	30932474
DeepCCS	[M+Na]+	166.779	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
4-Hydroxybisabola-2,10-dien-9-one,2TMS,isomer #1	CC(C)=CC(=C[C@H](C)[C@@H]1C=C[C@](C)(O[Si](C)(C)C)CC1)O[Si](C)(C)C	2008.5	Semi standard non polar	33892256
4-Hydroxybisabola-2,10-dien-9-one,2TMS,isomer #1	CC(C)=CC(=C[C@H](C)[C@@H]1C=C[C@](C)(O[Si](C)(C)C)CC1)O[Si](C)(C)C	1858.6	Standard non polar	33892256
4-Hydroxybisabola-2,10-dien-9-one,2TMS,isomer #1	CC(C)=CC(=C[C@H](C)[C@@H]1C=C[C@](C)(O[Si](C)(C)C)CC1)O[Si](C)(C)C	2224.4	Standard polar	33892256
4-Hydroxybisabola-2,10-dien-9-one,2TBDMS,isomer #1	CC(C)=CC(=C[C@H](C)[C@@H]1C=C[C@](C)(O[Si](C)(C)C(C)(C)C)CC1)O[Si](C)(C)C(C)(C)C	2461.6	Semi standard non polar	33892256
4-Hydroxybisabola-2,10-dien-9-one,2TBDMS,isomer #1	CC(C)=CC(=C[C@H](C)[C@@H]1C=C[C@](C)(O[Si](C)(C)C(C)(C)C)CC1)O[Si](C)(C)C(C)(C)C	2294.4	Standard non polar	33892256
4-Hydroxybisabola-2,10-dien-9-one,2TBDMS,isomer #1	CC(C)=CC(=C[C@H](C)[C@@H]1C=C[C@](C)(O[Si](C)(C)C(C)(C)C)CC1)O[Si](C)(C)C(C)(C)C	2412.9	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 - 4-Hydroxybisabola-2,10-dien-9-one 10V, Positive-QTOF	splash10-014r-0290000000-24c5c92df3badceaf21e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybisabola-2,10-dien-9-one 20V, Positive-QTOF	splash10-0fs9-6940000000-e8235f3c4eec5a808dae	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybisabola-2,10-dien-9-one 40V, Positive-QTOF	splash10-00lr-9400000000-e634fb42738307c968fe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybisabola-2,10-dien-9-one 10V, Negative-QTOF	splash10-000i-1090000000-d77c3af04b464eec8c19	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybisabola-2,10-dien-9-one 20V, Negative-QTOF	splash10-052r-8490000000-0fff8a778d456492155b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybisabola-2,10-dien-9-one 40V, Negative-QTOF	splash10-0a4i-9310000000-a96727f304d254192f12	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybisabola-2,10-dien-9-one 10V, Positive-QTOF	splash10-00dr-1910000000-910014d37f09ddc53ede	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybisabola-2,10-dien-9-one 20V, Positive-QTOF	splash10-0006-9700000000-1ace1b0334ddbc17b182	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybisabola-2,10-dien-9-one 40V, Positive-QTOF	splash10-0006-9200000000-ea940d38742d98a046d2	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybisabola-2,10-dien-9-one 10V, Negative-QTOF	splash10-000i-0090000000-29196d276b55245348a7	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybisabola-2,10-dien-9-one 20V, Negative-QTOF	splash10-000i-3690000000-4dfa2b3d59c7042690e7	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 4-Hydroxybisabola-2,10-dien-9-one 40V, Negative-QTOF	splash10-014i-6920000000-320712b9a62cb846fab0	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

FDB005319

KNApSAcK ID

Not Available

Chemspider ID

59696358

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14633004

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 4-Hydroxybisabola-2,10-dien-9-one (HMDB0302603)

MOL for HMDB0302603 (4-Hydroxybisabola-2,10-dien-9-one)

3D MOL for HMDB0302603 (4-Hydroxybisabola-2,10-dien-9-one)

3D SDF for HMDB0302603 (4-Hydroxybisabola-2,10-dien-9-one)

3D-SDF for HMDB0302603 (4-Hydroxybisabola-2,10-dien-9-one)

PDB for HMDB0302603 (4-Hydroxybisabola-2,10-dien-9-one)

3D PDB for HMDB0302603 (4-Hydroxybisabola-2,10-dien-9-one)

SMILES for HMDB0302603 (4-Hydroxybisabola-2,10-dien-9-one)

INCHI for HMDB0302603 (4-Hydroxybisabola-2,10-dien-9-one)

Structure for HMDB0302603 (4-Hydroxybisabola-2,10-dien-9-one)

3D Structure for HMDB0302603 (4-Hydroxybisabola-2,10-dien-9-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra