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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:35:53 UTC

Update Date

2022-03-07 02:54:56 UTC

HMDB ID

HMDB0036456

Secondary Accession Numbers

HMDB36456

Metabolite Identification

Common Name

10-Hydroxy-3-methoxy-1,3,5,7-cadinatetraen-9-one

Description

10-Hydroxy-3-methoxy-1,3,5,7-cadinatetraen-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 small amount of articles have been published on 10-Hydroxy-3-methoxy-1,3,5,7-cadinatetraen-9-one.

Structure

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

HMDB0036456
     RDKit          3D
10-Hydroxy-3-methoxy-1,3,5,7-cadinatetraen-9-one
 39 40  0  0  0  0  0  0  0  0999 V2000
    4.7690   -0.0686   -0.0468 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7689    0.9324   -0.0286 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4146    0.6399    0.0379 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9097   -0.6352    0.0924 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5608   -0.9282    0.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3286    0.1196    0.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1770    1.4277    0.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5273    1.6919    0.0499 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0115    3.1084   -0.0073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7672   -0.0677    0.2520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6938    1.0581    0.2638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1384    0.6220    0.4662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6524    1.9225   -0.9710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2601   -1.2896    0.3202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3762   -2.4474    0.3148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9098   -3.6019    0.4037 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0722   -2.3208    0.2126 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6398   -3.1562   -0.9222 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6447   -2.8642    1.3915 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6540    0.3931   -0.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0128   -0.2774    1.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4635   -0.9660   -0.5993 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5917   -1.4808    0.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4840    2.2876    0.1292 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2625    3.3995    1.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9456    3.1756   -0.6052 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2355    3.7877   -0.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4589    1.6932    1.1561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5399    0.0861   -0.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2683    0.0682    1.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7253    1.5762    0.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6079    1.8234   -1.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8588    1.6248   -1.6921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5749    3.0099   -0.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3434   -1.4333    0.3814 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5741   -3.6871   -0.6214 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8448   -2.5373   -1.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1022   -3.9241   -1.2192 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0099   -2.7620    2.1514 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 10 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
  8  3  1  0
 17  5  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  7 24  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 18 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
M  END


  Mrv0541 05061309092D          

 19 20  0  0  0  0            999 V2000
    4.2868    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    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
    4.1027   -1.0445    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
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    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
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    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
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0421   -1.0445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  9  1  1  0  0  0  0
  9  2  1  0  0  0  0
 10  3  1  0  0  0  0
 10  6  1  0  0  0  0
 11  7  2  0  0  0  0
 11  9  1  0  0  0  0
 12  6  2  0  0  0  0
 12 11  1  0  0  0  0
 13  8  2  0  0  0  0
 13 12  1  0  0  0  0
 14  8  1  0  0  0  0
 14 10  2  0  0  0  0
 15  7  1  0  0  0  0
 16  4  1  0  0  0  0
 16 13  1  0  0  0  0
 16 15  1  0  0  0  0
 17 15  2  0  0  0  0
 18 16  1  0  0  0  0
 19  5  1  0  0  0  0
 19 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036456

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(C)C=C2C(=CC(=O)C(C)(O)C2=C1)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C16H20O3/c1-9(2)11-7-15(17)16(4,18)13-8-14(19-5)10(3)6-12(11)13/h6-9,18H,1-5H3

> <INCHI_KEY>
VMEKKHYIQYOLHA-UHFFFAOYSA-N

> <FORMULA>
C16H20O3

> <MOLECULAR_WEIGHT>
260.3282

> <EXACT_MASS>
260.141244506

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
29.211003241922743

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-hydroxy-7-methoxy-1,6-dimethyl-4-(propan-2-yl)-1,2-dihydronaphthalen-2-one

> <ALOGPS_LOGP>
2.97

> <JCHEM_LOGP>
3.431145701666666

> <ALOGPS_LOGS>
-3.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.480489827677381

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9008337493739136

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
76.26239999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.79e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-hydroxy-4-isopropyl-7-methoxy-1,6-dimethylnaphthalen-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036456
     RDKit          3D
10-Hydroxy-3-methoxy-1,3,5,7-cadinatetraen-9-one
 39 40  0  0  0  0  0  0  0  0999 V2000
    4.7690   -0.0686   -0.0468 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7689    0.9324   -0.0286 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4146    0.6399    0.0379 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9097   -0.6352    0.0924 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5608   -0.9282    0.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3286    0.1196    0.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1770    1.4277    0.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5273    1.6919    0.0499 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0115    3.1084   -0.0073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7672   -0.0677    0.2520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6938    1.0581    0.2638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1384    0.6220    0.4662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6524    1.9225   -0.9710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2601   -1.2896    0.3202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3762   -2.4474    0.3148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9098   -3.6019    0.4037 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0722   -2.3208    0.2126 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6398   -3.1562   -0.9222 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6447   -2.8642    1.3915 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6540    0.3931   -0.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0128   -0.2774    1.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4635   -0.9660   -0.5993 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5917   -1.4808    0.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4840    2.2876    0.1292 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2625    3.3995    1.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9456    3.1756   -0.6052 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2355    3.7877   -0.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4589    1.6932    1.1561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5399    0.0861   -0.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2683    0.0682    1.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7253    1.5762    0.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6079    1.8234   -1.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8588    1.6248   -1.6921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5749    3.0099   -0.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3434   -1.4333    0.3814 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5741   -3.6871   -0.6214 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8448   -2.5373   -1.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1022   -3.9241   -1.2192 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0099   -2.7620    2.1514 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 10 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
  8  3  1  0
 17  5  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  7 24  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 18 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  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       8.002   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.658  -1.950   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.679  -1.950   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4   16                                                            
CONECT    5   19                                                            
CONECT    6   10   12                                                       
CONECT    7   11   15                                                       
CONECT    8   13   14                                                       
CONECT    9    1    2   11                                                  
CONECT   10    3    6   14                                                  
CONECT   11    7    9   12                                                  
CONECT   12    6   11   13                                                  
CONECT   13    8   12   16                                                  
CONECT   14    8   10   19                                                  
CONECT   15    7   16   17                                                  
CONECT   16    4   13   15   18                                             
CONECT   17   15                                                            
CONECT   18   16                                                            
CONECT   19    5   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

COMPND    HMDB0036456
HETATM    1  C1  UNL     1       4.769  -0.069  -0.047  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.769   0.932  -0.029  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.415   0.640   0.038  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.910  -0.635   0.092  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.561  -0.928   0.159  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.329   0.120   0.171  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.177   1.428   0.116  1.00  0.00           C  
HETATM    8  C7  UNL     1       1.527   1.692   0.050  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.012   3.108  -0.007  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.767  -0.068   0.252  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.694   1.058   0.264  1.00  0.00           C  
HETATM   12  C11 UNL     1      -4.138   0.622   0.466  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.652   1.923  -0.971  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.260  -1.290   0.320  1.00  0.00           C  
HETATM   15  C14 UNL     1      -1.376  -2.447   0.315  1.00  0.00           C  
HETATM   16  O2  UNL     1      -1.910  -3.602   0.404  1.00  0.00           O  
HETATM   17  C15 UNL     1       0.072  -2.321   0.213  1.00  0.00           C  
HETATM   18  C16 UNL     1       0.640  -3.156  -0.922  1.00  0.00           C  
HETATM   19  O3  UNL     1       0.645  -2.864   1.392  1.00  0.00           O  
HETATM   20  H1  UNL     1       5.654   0.393  -0.554  1.00  0.00           H  
HETATM   21  H2  UNL     1       5.013  -0.277   1.026  1.00  0.00           H  
HETATM   22  H3  UNL     1       4.463  -0.966  -0.599  1.00  0.00           H  
HETATM   23  H4  UNL     1       2.592  -1.481   0.084  1.00  0.00           H  
HETATM   24  H5  UNL     1      -0.484   2.288   0.129  1.00  0.00           H  
HETATM   25  H6  UNL     1       2.262   3.399   1.048  1.00  0.00           H  
HETATM   26  H7  UNL     1       2.946   3.176  -0.605  1.00  0.00           H  
HETATM   27  H8  UNL     1       1.235   3.788  -0.396  1.00  0.00           H  
HETATM   28  H9  UNL     1      -2.459   1.693   1.156  1.00  0.00           H  
HETATM   29  H10 UNL     1      -4.540   0.086  -0.417  1.00  0.00           H  
HETATM   30  H11 UNL     1      -4.268   0.068   1.414  1.00  0.00           H  
HETATM   31  H12 UNL     1      -4.725   1.576   0.572  1.00  0.00           H  
HETATM   32  H13 UNL     1      -3.608   1.823  -1.563  1.00  0.00           H  
HETATM   33  H14 UNL     1      -1.859   1.625  -1.692  1.00  0.00           H  
HETATM   34  H15 UNL     1      -2.575   3.010  -0.740  1.00  0.00           H  
HETATM   35  H16 UNL     1      -3.343  -1.433   0.381  1.00  0.00           H  
HETATM   36  H17 UNL     1       1.574  -3.687  -0.621  1.00  0.00           H  
HETATM   37  H18 UNL     1       0.845  -2.537  -1.831  1.00  0.00           H  
HETATM   38  H19 UNL     1      -0.102  -3.924  -1.219  1.00  0.00           H  
HETATM   39  H20 UNL     1       0.010  -2.762   2.151  1.00  0.00           H  
CONECT    1    2   20   21   22
CONECT    2    3
CONECT    3    4    4    8
CONECT    4    5   23
CONECT    5    6    6   17
CONECT    6    7   10
CONECT    7    8    8   24
CONECT    8    9
CONECT    9   25   26   27
CONECT   10   11   14   14
CONECT   11   12   13   28
CONECT   12   29   30   31
CONECT   13   32   33   34
CONECT   14   15   35
CONECT   15   16   16   17
CONECT   17   18   19
CONECT   18   36   37   38
CONECT   19   39
END

HMDB0036456
     RDKit          3D
10-Hydroxy-3-methoxy-1,3,5,7-cadinatetraen-9-one
 39 40  0  0  0  0  0  0  0  0999 V2000
    4.7690   -0.0686   -0.0468 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7689    0.9324   -0.0286 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4146    0.6399    0.0379 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9097   -0.6352    0.0924 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5608   -0.9282    0.1585 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3286    0.1196    0.1706 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1770    1.4277    0.1156 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5273    1.6919    0.0499 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0115    3.1084   -0.0073 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7672   -0.0677    0.2520 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6938    1.0581    0.2638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1384    0.6220    0.4662 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6524    1.9225   -0.9710 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2601   -1.2896    0.3202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3762   -2.4474    0.3148 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9098   -3.6019    0.4037 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0722   -2.3208    0.2126 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6398   -3.1562   -0.9222 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6447   -2.8642    1.3915 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6540    0.3931   -0.5537 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0128   -0.2774    1.0262 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4635   -0.9660   -0.5993 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5917   -1.4808    0.0842 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4840    2.2876    0.1292 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2625    3.3995    1.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9456    3.1756   -0.6052 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2355    3.7877   -0.3956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4589    1.6932    1.1561 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5399    0.0861   -0.4167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2683    0.0682    1.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7253    1.5762    0.5722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6079    1.8234   -1.5628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8588    1.6248   -1.6921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5749    3.0099   -0.7402 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3434   -1.4333    0.3814 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5741   -3.6871   -0.6214 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8448   -2.5373   -1.8307 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1022   -3.9241   -1.2192 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0099   -2.7620    2.1514 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  6 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 10 14  2  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
  8  3  1  0
 17  5  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  4 23  1  0
  7 24  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 13 34  1  0
 14 35  1  0
 18 36  1  0
 18 37  1  0
 18 38  1  0
 19 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Lacinilene C 7-methyl ether	HMDB

Chemical Formula

C₁₆H₂₀O₃

Average Molecular Weight

260.3282

Monoisotopic Molecular Weight

260.141244506

IUPAC Name

1-hydroxy-7-methoxy-1,6-dimethyl-4-(propan-2-yl)-1,2-dihydronaphthalen-2-one

Traditional Name

1-hydroxy-4-isopropyl-7-methoxy-1,6-dimethylnaphthalen-2-one

CAS Registry Number

72843-51-7

SMILES

COC1=C(C)C=C2C(=CC(=O)C(C)(O)C2=C1)C(C)C

InChI Identifier

InChI=1S/C16H20O3/c1-9(2)11-7-15(17)16(4,18)13-8-14(19-5)10(3)6-12(11)13/h6-9,18H,1-5H3

InChI Key

VMEKKHYIQYOLHA-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

Sesquiterpenoid
Cadinane sesquiterpenoid
Naphthalene
Anisole
Alkyl aryl ether
Acyloin
Benzenoid
Tertiary alcohol
Cyclic ketone
Ketone
Ether
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036456)

Source

Endogenous

Endogenous (HMDB: HMDB0036456)

Animal

Animal (HMDB: HMDB0036456)

Exogenous

Food

Food (HMDB: HMDB0036456)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Exogenous (HMDB: HMDB0036456)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036456)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036456)

Lipid metabolism pathway (HMDB: HMDB0036456)

Cellular process

Cell signaling (HMDB: HMDB0036456)

Biochemical process

Lipid transport (HMDB: HMDB0036456)

Role

Biological role

Energy source (HMDB: HMDB0036456)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	100 - 102 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	31.4 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.038 g/L	ALOGPS
logP	2.97	ALOGPS
logP	3.43	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	12.48	ChemAxon
pKa (Strongest Basic)	-3.9	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	2	ChemAxon
Refractivity	76.26 m³·mol⁻¹	ChemAxon
Polarizability	29.21 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	161.822	31661259
DarkChem	[M-H]-	161.66	31661259
DeepCCS	[M+H]+	166.354	30932474
DeepCCS	[M-H]-	163.996	30932474
DeepCCS	[M-2H]-	197.531	30932474
DeepCCS	[M+Na]+	172.758	30932474
AllCCS	[M+H]+	159.4	32859911
AllCCS	[M+H-H2O]+	155.8	32859911
AllCCS	[M+NH4]+	162.8	32859911
AllCCS	[M+Na]+	163.8	32859911
AllCCS	[M-H]-	167.3	32859911
AllCCS	[M+Na-2H]-	167.4	32859911
AllCCS	[M+HCOO]-	167.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	7.12 minutes	32390414
Predicted by Siyang on May 30, 2022	16.4591 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.21 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2185.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	471.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	195.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	244.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	143.3 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	708.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	773.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	84.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1387.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	520.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1598.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	462.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	406.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	356.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	455.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	7.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
10-Hydroxy-3-methoxy-1,3,5,7-cadinatetraen-9-one	COC1=C(C)C=C2C(=CC(=O)C(C)(O)C2=C1)C(C)C	3069.3	Standard polar	33892256
10-Hydroxy-3-methoxy-1,3,5,7-cadinatetraen-9-one	COC1=C(C)C=C2C(=CC(=O)C(C)(O)C2=C1)C(C)C	2128.7	Standard non polar	33892256
10-Hydroxy-3-methoxy-1,3,5,7-cadinatetraen-9-one	COC1=C(C)C=C2C(=CC(=O)C(C)(O)C2=C1)C(C)C	1993.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
10-Hydroxy-3-methoxy-1,3,5,7-cadinatetraen-9-one,1TMS,isomer #1	COC1=CC2=C(C=C1C)C(C(C)C)=CC(=O)C2(C)O[Si](C)(C)C	2109.6	Semi standard non polar	33892256
10-Hydroxy-3-methoxy-1,3,5,7-cadinatetraen-9-one,1TBDMS,isomer #1	COC1=CC2=C(C=C1C)C(C(C)C)=CC(=O)C2(C)O[Si](C)(C)C(C)(C)C	2364.8	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 10-Hydroxy-3-methoxy-1,3,5,7-cadinatetraen-9-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-0390000000-a90e6a008363d84d20de	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 10-Hydroxy-3-methoxy-1,3,5,7-cadinatetraen-9-one GC-MS (1 TMS) - 70eV, Positive	splash10-01bi-5094000000-3aa4adb7c61ed9ebcd66	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 10-Hydroxy-3-methoxy-1,3,5,7-cadinatetraen-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 - 10-Hydroxy-3-methoxy-1,3,5,7-cadinatetraen-9-one 10V, Positive-QTOF	splash10-03di-0090000000-3ea2f77a95613a44a151	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Hydroxy-3-methoxy-1,3,5,7-cadinatetraen-9-one 20V, Positive-QTOF	splash10-02t9-1190000000-e7be24840ef82c259aa4	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Hydroxy-3-methoxy-1,3,5,7-cadinatetraen-9-one 40V, Positive-QTOF	splash10-0gbi-3690000000-7b2836146e7a107e3dd2	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Hydroxy-3-methoxy-1,3,5,7-cadinatetraen-9-one 10V, Negative-QTOF	splash10-0a4i-0090000000-1cda8f57dfee6c992864	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Hydroxy-3-methoxy-1,3,5,7-cadinatetraen-9-one 20V, Negative-QTOF	splash10-0a4i-0090000000-a542b5e5da0350b32bc6	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Hydroxy-3-methoxy-1,3,5,7-cadinatetraen-9-one 40V, Negative-QTOF	splash10-0gy6-0390000000-b866f5bfa2ffe14faeef	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Hydroxy-3-methoxy-1,3,5,7-cadinatetraen-9-one 10V, Positive-QTOF	splash10-01ox-0090000000-d3321739480447ca44cc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Hydroxy-3-methoxy-1,3,5,7-cadinatetraen-9-one 20V, Positive-QTOF	splash10-0udi-0190000000-ff424f7dd3f8a247ff2d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Hydroxy-3-methoxy-1,3,5,7-cadinatetraen-9-one 40V, Positive-QTOF	splash10-0006-7940000000-64760aa7648665c82532	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Hydroxy-3-methoxy-1,3,5,7-cadinatetraen-9-one 10V, Negative-QTOF	splash10-0a4i-0090000000-4be38e911cfdd5146146	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Hydroxy-3-methoxy-1,3,5,7-cadinatetraen-9-one 20V, Negative-QTOF	splash10-0a4i-0090000000-43c2c91130d456998ff6	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10-Hydroxy-3-methoxy-1,3,5,7-cadinatetraen-9-one 40V, Negative-QTOF	splash10-0a4l-0290000000-6fc27f48d98f26dc7489	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB015345

KNApSAcK ID

Not Available

Chemspider ID

2744555

KEGG Compound ID

C09695

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3504625

PDB ID

Not Available

ChEBI ID

172504

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1855291

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 ]
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Showing metabocard for 10-Hydroxy-3-methoxy-1,3,5,7-cadinatetraen-9-one (HMDB0036456)

MOL for HMDB0036456 (10-Hydroxy-3-methoxy-1,3,5,7-cadinatetraen-9-one)

3D MOL for HMDB0036456 (10-Hydroxy-3-methoxy-1,3,5,7-cadinatetraen-9-one)

3D SDF for HMDB0036456 (10-Hydroxy-3-methoxy-1,3,5,7-cadinatetraen-9-one)

3D-SDF for HMDB0036456 (10-Hydroxy-3-methoxy-1,3,5,7-cadinatetraen-9-one)

PDB for HMDB0036456 (10-Hydroxy-3-methoxy-1,3,5,7-cadinatetraen-9-one)

3D PDB for HMDB0036456 (10-Hydroxy-3-methoxy-1,3,5,7-cadinatetraen-9-one)

SMILES for HMDB0036456 (10-Hydroxy-3-methoxy-1,3,5,7-cadinatetraen-9-one)

INCHI for HMDB0036456 (10-Hydroxy-3-methoxy-1,3,5,7-cadinatetraen-9-one)

Structure for HMDB0036456 (10-Hydroxy-3-methoxy-1,3,5,7-cadinatetraen-9-one)

3D Structure for HMDB0036456 (10-Hydroxy-3-methoxy-1,3,5,7-cadinatetraen-9-one)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra