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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 01:11:25 UTC

Update Date

2022-03-07 02:56:18 UTC

HMDB ID

HMDB0039660

Secondary Accession Numbers

HMDB39660

Metabolite Identification

Common Name

Gossyvertin

Description

Gossyvertin 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 Gossyvertin.

Structure

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

HMDB0039660
     RDKit          3D
Gossyvertin
 38 39  0  0  0  0  0  0  0  0999 V2000
    4.7529   -0.2832   -0.7764 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8129   -0.2365    0.2374 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4297   -0.1202    0.1782 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7338   -1.2892    0.0966 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4364   -2.6053    0.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3575   -1.2245    0.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3541   -0.0462    0.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7391   -0.1345    0.1093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4484   -1.3968   -0.1730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3947   -1.7690    0.9743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5318   -0.9955   -1.2995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3998    1.0452    0.2612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7509    2.2579    0.3519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4441    3.4335    0.5025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3294    2.3384    0.2909 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2434    3.6375    0.3930 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5262    3.8099    0.3518 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3564    1.1512    0.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7446    1.0735    0.1987 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5236    2.1927    0.2828 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7281    0.1738   -0.4550 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4120    0.0772   -1.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9944   -1.3892   -0.9337 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9502   -2.8543   -0.8304 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1308   -2.5488    0.9745 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7318   -3.4290    0.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1766   -2.2102   -0.0207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9280   -2.1952   -0.6547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4966   -0.9527    1.6993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3757   -2.1172    0.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9890   -2.6203    1.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3344   -0.4381   -0.7992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8741   -1.9822   -1.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9522   -0.4989   -2.0594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4963    1.0445    0.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1271    4.3626    0.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2458    4.5568    0.4842 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5231    2.1823    0.3299 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  8 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 15 18  1  0
 18 19  2  0
 19 20  1  0
 19  3  1  0
 18  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  5 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 14 36  1  0
 16 37  1  0
 20 38  1  0
M  END


  Mrv0541 05061311182D          

 20 21  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
    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
    3.5724   -1.2375    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
    3.5724   -0.4125    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
    2.8579    0.0000    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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   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
    2.1434   -1.2375    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
  8  1  1  0  0  0  0
  8  2  1  0  0  0  0
  9  3  1  0  0  0  0
  9  5  2  0  0  0  0
 10  6  2  0  0  0  0
 10  8  1  0  0  0  0
 11  5  1  0  0  0  0
 11 10  1  0  0  0  0
 12  7  1  0  0  0  0
 13  6  1  0  0  0  0
 13 12  2  0  0  0  0
 14 11  2  0  0  0  0
 14 12  1  0  0  0  0
 15 14  1  0  0  0  0
 16  9  1  0  0  0  0
 16 15  2  0  0  0  0
 17  7  2  0  0  0  0
 18 13  1  0  0  0  0
 19 15  1  0  0  0  0
 20  4  1  0  0  0  0
 20 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0039660

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=C(O)C2=C(C=C1C)C(=CC(O)=C2C=O)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C16H18O4/c1-8(2)10-6-13(18)12(7-17)14-11(10)5-9(3)16(20-4)15(14)19/h5-8,18-19H,1-4H3

> <INCHI_KEY>
WDKQNEBNLKMOLB-UHFFFAOYSA-N

> <FORMULA>
C16H18O4

> <MOLECULAR_WEIGHT>
274.3117

> <EXACT_MASS>
274.120509064

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
29.678995182406286

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,8-dihydroxy-7-methoxy-6-methyl-4-(propan-2-yl)naphthalene-1-carbaldehyde

> <ALOGPS_LOGP>
3.59

> <JCHEM_LOGP>
4.318853548333333

> <ALOGPS_LOGS>
-3.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.452010974127015

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.148606079599551

> <JCHEM_PKA_STRONGEST_BASIC>
-4.8906343713885985

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
78.7492

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.27e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,8-dihydroxy-4-isopropyl-7-methoxy-6-methylnaphthalene-1-carbaldehyde

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0039660
     RDKit          3D
Gossyvertin
 38 39  0  0  0  0  0  0  0  0999 V2000
    4.7529   -0.2832   -0.7764 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8129   -0.2365    0.2374 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4297   -0.1202    0.1782 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7338   -1.2892    0.0966 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4364   -2.6053    0.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3575   -1.2245    0.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3541   -0.0462    0.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7391   -0.1345    0.1093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4484   -1.3968   -0.1730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3947   -1.7690    0.9743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5318   -0.9955   -1.2995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3998    1.0452    0.2612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7509    2.2579    0.3519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4441    3.4335    0.5025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3294    2.3384    0.2909 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2434    3.6375    0.3930 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5262    3.8099    0.3518 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3564    1.1512    0.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7446    1.0735    0.1987 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5236    2.1927    0.2828 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7281    0.1738   -0.4550 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4120    0.0772   -1.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9944   -1.3892   -0.9337 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9502   -2.8543   -0.8304 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1308   -2.5488    0.9745 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7318   -3.4290    0.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1766   -2.2102   -0.0207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9280   -2.1952   -0.6547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4966   -0.9527    1.6993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3757   -2.1172    0.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9890   -2.6203    1.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3344   -0.4381   -0.7992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8741   -1.9822   -1.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9522   -0.4989   -2.0594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4963    1.0445    0.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1271    4.3626    0.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2458    4.5568    0.4842 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5231    2.1823    0.3299 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  8 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 15 18  1  0
 18 19  2  0
 19 20  1  0
 19  3  1  0
 18  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  5 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 14 36  1  0
 16 37  1  0
 20 38  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       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    8                                                            
CONECT    3    9                                                            
CONECT    4   20                                                            
CONECT    5    9   11                                                       
CONECT    6   10   13                                                       
CONECT    7   12   17                                                       
CONECT    8    1    2   10                                                  
CONECT    9    3    5   16                                                  
CONECT   10    6    8   11                                                  
CONECT   11    5   10   14                                                  
CONECT   12    7   13   14                                                  
CONECT   13    6   12   18                                                  
CONECT   14   11   12   15                                                  
CONECT   15   14   16   19                                                  
CONECT   16    9   15   20                                                  
CONECT   17    7                                                            
CONECT   18   13                                                            
CONECT   19   15                                                            
CONECT   20    4   16                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

COMPND    HMDB0039660
HETATM    1  C1  UNL     1       4.753  -0.283  -0.776  1.00  0.00           C  
HETATM    2  O1  UNL     1       3.813  -0.237   0.237  1.00  0.00           O  
HETATM    3  C2  UNL     1       2.430  -0.120   0.178  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.734  -1.289   0.097  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.436  -2.605   0.092  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.357  -1.225   0.034  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.354  -0.046   0.053  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.739  -0.135   0.109  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.448  -1.397  -0.173  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.395  -1.769   0.974  1.00  0.00           C  
HETATM   11  C10 UNL     1      -3.532  -0.996  -1.300  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.400   1.045   0.261  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.751   2.258   0.352  1.00  0.00           C  
HETATM   14  O2  UNL     1      -2.444   3.434   0.502  1.00  0.00           O  
HETATM   15  C13 UNL     1      -0.329   2.338   0.291  1.00  0.00           C  
HETATM   16  C14 UNL     1       0.243   3.638   0.393  1.00  0.00           C  
HETATM   17  O3  UNL     1       1.526   3.810   0.352  1.00  0.00           O  
HETATM   18  C15 UNL     1       0.356   1.151   0.142  1.00  0.00           C  
HETATM   19  C16 UNL     1       1.745   1.074   0.199  1.00  0.00           C  
HETATM   20  O4  UNL     1       2.524   2.193   0.283  1.00  0.00           O  
HETATM   21  H1  UNL     1       5.728   0.174  -0.455  1.00  0.00           H  
HETATM   22  H2  UNL     1       4.412   0.077  -1.771  1.00  0.00           H  
HETATM   23  H3  UNL     1       4.994  -1.389  -0.934  1.00  0.00           H  
HETATM   24  H4  UNL     1       2.950  -2.854  -0.830  1.00  0.00           H  
HETATM   25  H5  UNL     1       3.131  -2.549   0.975  1.00  0.00           H  
HETATM   26  H6  UNL     1       1.732  -3.429   0.344  1.00  0.00           H  
HETATM   27  H7  UNL     1      -0.177  -2.210  -0.021  1.00  0.00           H  
HETATM   28  H8  UNL     1      -1.928  -2.195  -0.655  1.00  0.00           H  
HETATM   29  H9  UNL     1      -3.497  -0.953   1.699  1.00  0.00           H  
HETATM   30  H10 UNL     1      -4.376  -2.117   0.610  1.00  0.00           H  
HETATM   31  H11 UNL     1      -2.989  -2.620   1.549  1.00  0.00           H  
HETATM   32  H12 UNL     1      -4.334  -0.438  -0.799  1.00  0.00           H  
HETATM   33  H13 UNL     1      -3.874  -1.982  -1.656  1.00  0.00           H  
HETATM   34  H14 UNL     1      -2.952  -0.499  -2.059  1.00  0.00           H  
HETATM   35  H15 UNL     1      -3.496   1.044   0.317  1.00  0.00           H  
HETATM   36  H16 UNL     1      -2.127   4.363   0.570  1.00  0.00           H  
HETATM   37  H17 UNL     1      -0.246   4.557   0.484  1.00  0.00           H  
HETATM   38  H18 UNL     1       3.523   2.182   0.330  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3
CONECT    3    4    4   19
CONECT    4    5    6
CONECT    5   24   25   26
CONECT    6    7    7   27
CONECT    7    8   18
CONECT    8    9   12   12
CONECT    9   10   11   28
CONECT   10   29   30   31
CONECT   11   32   33   34
CONECT   12   13   35
CONECT   13   14   15   15
CONECT   14   36
CONECT   15   16   18
CONECT   16   17   17   37
CONECT   18   19   19
CONECT   19   20
CONECT   20   38
END

HMDB0039660
     RDKit          3D
Gossyvertin
 38 39  0  0  0  0  0  0  0  0999 V2000
    4.7529   -0.2832   -0.7764 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8129   -0.2365    0.2374 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4297   -0.1202    0.1782 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7338   -1.2892    0.0966 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4364   -2.6053    0.0917 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3575   -1.2245    0.0344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3541   -0.0462    0.0532 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7391   -0.1345    0.1093 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4484   -1.3968   -0.1730 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3947   -1.7690    0.9743 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5318   -0.9955   -1.2995 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3998    1.0452    0.2612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7509    2.2579    0.3519 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4441    3.4335    0.5025 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3294    2.3384    0.2909 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2434    3.6375    0.3930 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5262    3.8099    0.3518 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3564    1.1512    0.1422 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7446    1.0735    0.1987 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5236    2.1927    0.2828 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7281    0.1738   -0.4550 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4120    0.0772   -1.7706 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9944   -1.3892   -0.9337 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9502   -2.8543   -0.8304 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1308   -2.5488    0.9745 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7318   -3.4290    0.3443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1766   -2.2102   -0.0207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9280   -2.1952   -0.6547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4966   -0.9527    1.6993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3757   -2.1172    0.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9890   -2.6203    1.5492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3344   -0.4381   -0.7992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8741   -1.9822   -1.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9522   -0.4989   -2.0594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4963    1.0445    0.3168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1271    4.3626    0.5697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2458    4.5568    0.4842 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5231    2.1823    0.3299 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
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  8 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  2  0
 15 18  1  0
 18 19  2  0
 19 20  1  0
 19  3  1  0
 18  7  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  5 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 11 34  1  0
 12 35  1  0
 14 36  1  0
 16 37  1  0
 20 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,8-Dihydroxy-4-isopropyl-7-methoxy-6-methyl-1-naphthalenecarboxaldehyde	HMDB

Chemical Formula

C₁₆H₁₈O₄

Average Molecular Weight

274.3117

Monoisotopic Molecular Weight

274.120509064

IUPAC Name

2,8-dihydroxy-7-methoxy-6-methyl-4-(propan-2-yl)naphthalene-1-carbaldehyde

Traditional Name

2,8-dihydroxy-4-isopropyl-7-methoxy-6-methylnaphthalene-1-carbaldehyde

CAS Registry Number

60089-74-9

SMILES

COC1=C(O)C2=C(C=C1C)C(=CC(O)=C2C=O)C(C)C

InChI Identifier

InChI=1S/C16H18O4/c1-8(2)10-6-13(18)12(7-17)14-11(10)5-9(3)16(20-4)15(14)19/h5-8,18-19H,1-4H3

InChI Key

WDKQNEBNLKMOLB-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
2-naphthol
1-naphthol
Naphthalene
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Aryl-aldehyde
Benzenoid
Vinylogous acid
Ether
Aldehyde
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0039660)
Cell membrane (HMDB: HMDB0039660)

Cellular substructure

Extracellular (HMDB: HMDB0039660)
Membrane (HMDB: HMDB0039660)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039660)

Source

Endogenous

Endogenous (HMDB: HMDB0039660)

Animal

Animal (HMDB: HMDB0039660)

Exogenous

Food

Food (HMDB: HMDB0039660)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0039660)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0039660)

Cellular process

Cell signaling (HMDB: HMDB0039660)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0039660)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0039660)

Nutrient

Nutrient (HMDB: HMDB0039660)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0039660)

Emulsifier (HMDB: HMDB0039660)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	147 - 149 °C	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	0.073 g/L	ALOGPS
logP	3.59	ALOGPS
logP	4.32	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	8.15	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	78.75 m³·mol⁻¹	ChemAxon
Polarizability	29.68 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]+	162.992	31661259
DarkChem	[M-H]-	163.96	31661259
DeepCCS	[M+H]+	166.57	30932474
DeepCCS	[M-H]-	164.212	30932474
DeepCCS	[M-2H]-	197.714	30932474
DeepCCS	[M+Na]+	172.941	30932474
AllCCS	[M+H]+	161.9	32859911
AllCCS	[M+H-H2O]+	158.4	32859911
AllCCS	[M+NH4]+	165.2	32859911
AllCCS	[M+Na]+	166.1	32859911
AllCCS	[M-H]-	167.8	32859911
AllCCS	[M+Na-2H]-	167.6	32859911
AllCCS	[M+HCOO]-	167.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Gossyvertin	COC1=C(O)C2=C(C=C1C)C(=CC(O)=C2C=O)C(C)C	3292.9	Standard polar	33892256
Gossyvertin	COC1=C(O)C2=C(C=C1C)C(=CC(O)=C2C=O)C(C)C	2355.5	Standard non polar	33892256
Gossyvertin	COC1=C(O)C2=C(C=C1C)C(=CC(O)=C2C=O)C(C)C	2391.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Gossyvertin,1TMS,isomer #1	COC1=C(C)C=C2C(C(C)C)=CC(O)=C(C=O)C2=C1O[Si](C)(C)C	2275.8	Semi standard non polar	33892256
Gossyvertin,1TMS,isomer #2	COC1=C(C)C=C2C(C(C)C)=CC(O[Si](C)(C)C)=C(C=O)C2=C1O	2389.9	Semi standard non polar	33892256
Gossyvertin,2TMS,isomer #1	COC1=C(C)C=C2C(C(C)C)=CC(O[Si](C)(C)C)=C(C=O)C2=C1O[Si](C)(C)C	2367.1	Semi standard non polar	33892256
Gossyvertin,1TBDMS,isomer #1	COC1=C(C)C=C2C(C(C)C)=CC(O)=C(C=O)C2=C1O[Si](C)(C)C(C)(C)C	2513.9	Semi standard non polar	33892256
Gossyvertin,1TBDMS,isomer #2	COC1=C(C)C=C2C(C(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C(C=O)C2=C1O	2619.7	Semi standard non polar	33892256
Gossyvertin,2TBDMS,isomer #1	COC1=C(C)C=C2C(C(C)C)=CC(O[Si](C)(C)C(C)(C)C)=C(C=O)C2=C1O[Si](C)(C)C(C)(C)C	2808.7	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 - Gossyvertin GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a5d-0090000000-b8ff398df82dbb4729d6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gossyvertin GC-MS (2 TMS) - 70eV, Positive	splash10-0uk9-5309600000-ea09423e2101639012f4	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Gossyvertin 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 - Gossyvertin 10V, Positive-QTOF	splash10-004i-0090000000-9265bfd02f8624633c0f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gossyvertin 20V, Positive-QTOF	splash10-004i-0090000000-66a52143781295b62b52	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gossyvertin 40V, Positive-QTOF	splash10-0bvm-2790000000-4728ebd5ba17e0d1d1e5	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gossyvertin 10V, Negative-QTOF	splash10-00di-0090000000-a903075c308ae400b041	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gossyvertin 20V, Negative-QTOF	splash10-00di-0090000000-72e3bed7718aa3249f83	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gossyvertin 40V, Negative-QTOF	splash10-002f-0290000000-b80cee6533f064bbf162	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gossyvertin 10V, Negative-QTOF	splash10-00di-0090000000-b03c805fc5d67115d290	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gossyvertin 20V, Negative-QTOF	splash10-00di-0090000000-ce5bd3a29fef06d78987	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gossyvertin 40V, Negative-QTOF	splash10-0wos-0390000000-3ee98f14ef9853f15e9a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gossyvertin 10V, Positive-QTOF	splash10-004i-0090000000-88f9ab4b7858e89b39d0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gossyvertin 20V, Positive-QTOF	splash10-004i-0090000000-1e3aaaaac9b9e206ba3a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Gossyvertin 40V, Positive-QTOF	splash10-100c-4590000000-f7a931d0db65cfe4a408	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB019289

KNApSAcK ID

Not Available

Chemspider ID

162323

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

186727

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

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 Gossyvertin (HMDB0039660)

MOL for HMDB0039660 (Gossyvertin)

3D MOL for HMDB0039660 (Gossyvertin)

3D SDF for HMDB0039660 (Gossyvertin)

3D-SDF for HMDB0039660 (Gossyvertin)

PDB for HMDB0039660 (Gossyvertin)

3D PDB for HMDB0039660 (Gossyvertin)

SMILES for HMDB0039660 (Gossyvertin)

INCHI for HMDB0039660 (Gossyvertin)

Structure for HMDB0039660 (Gossyvertin)

3D Structure for HMDB0039660 (Gossyvertin)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra