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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:43:14 UTC

Update Date

2022-03-07 02:54:57 UTC

HMDB ID

HMDB0036564

Secondary Accession Numbers

HMDB36564

Metabolite Identification

Common Name

Sugiol

Description

Sugiol belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Based on a literature review a significant number of articles have been published on Sugiol.

Structure

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

HMDB0036564
     RDKit          3D
Sugiol
 50 52  0  0  0  0  0  0  0  0999 V2000
    5.2894   -0.5093    0.1419 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3933    0.6542    0.6546 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5915    0.7315    2.1620 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9794    0.3368    0.3168 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1234   -0.4178    1.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8086   -0.5580    0.6017 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3116    0.0188   -0.5455 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1969    0.7785   -1.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5165    0.9464   -0.8494 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3849    1.7252   -1.5857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0307   -0.1922   -1.0922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7320   -1.1376   -2.3060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5495    1.0466   -1.6952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5914    1.7870   -0.8829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7055    0.7930   -0.6342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1180   -0.1950    0.3557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7375    0.5586    1.5805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2379   -1.1576    0.6933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9766   -0.9699   -0.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3737   -1.8280    0.7965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1591   -1.3118    1.4151 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1185   -1.4641    2.6369 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1133   -0.4604   -0.9823 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3215   -0.2020    0.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9886   -1.4713    0.5101 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7129    1.5655    0.2071 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1493    1.6113    2.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2861   -0.1448    2.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6930    0.6007    2.7545 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4748   -0.8769    1.9579 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9698    1.3031   -2.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0870    2.1592   -2.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3389   -2.0989   -1.9094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7317   -1.3473   -2.7260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1099   -0.6564   -3.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0603    0.8242   -2.6744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7989    1.8107   -1.9401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9952    2.5746   -1.5421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1711    2.2175    0.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9172    0.3200   -1.6344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6143    1.2378   -0.2067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5045    1.3779    1.7068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7170    0.9509    1.5785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8567   -0.1055    2.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9460   -2.2155    0.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5404   -1.0813    1.7553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1500   -1.0038    0.0576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5370   -1.7071   -0.9237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1204   -1.9418    1.6496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1891   -2.8755    0.4988 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  7 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
  9  4  1  0
 19 11  1  0
 21  6  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  5 30  1  0
  8 31  1  0
 10 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 15 41  1  0
 17 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 20 49  1  0
 20 50  1  0
M  END

  Mrv0541 05061309122D          

 22 24  0  0  0  0            999 V2000
    4.5375    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1877    0.6534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2692    0.1231    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1250    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    3.0789    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.4934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
  8  6  1  0  0  0  0
 12  1  1  0  0  0  0
 12  2  1  0  0  0  0
 13  9  2  0  0  0  0
 13 12  1  0  0  0  0
 14  9  1  0  0  0  0
 15 10  1  0  0  0  0
 15 14  2  0  0  0  0
 16 10  2  0  0  0  0
 16 13  1  0  0  0  0
 17 11  1  0  0  0  0
 17 14  1  0  0  0  0
 18 11  1  0  0  0  0
 19  3  1  0  0  0  0
 19  4  1  0  0  0  0
 19  7  1  0  0  0  0
 19 18  1  0  0  0  0
 20  5  1  0  0  0  0
 20  8  1  0  0  0  0
 20 15  1  0  0  0  0
 20 18  1  0  0  0  0
 21 16  1  0  0  0  0
 22 17  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036564

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C1=CC2=C(C=C1O)C1(C)CCCC(C)(C)C1CC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O2/c1-12(2)13-9-14-15(10-16(13)21)20(5)8-6-7-19(3,4)18(20)11-17(14)22/h9-10,12,18,21H,6-8,11H2,1-5H3

> <INCHI_KEY>
IPEHJNRNYPOFII-UHFFFAOYSA-N

> <FORMULA>
C20H28O2

> <MOLECULAR_WEIGHT>
300.4351

> <EXACT_MASS>
300.20893014

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
35.83194849880883

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-hydroxy-1,1,4a-trimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthren-9-one

> <ALOGPS_LOGP>
5.36

> <JCHEM_LOGP>
5.1091314536666665

> <ALOGPS_LOGS>
-4.93

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.055672861393557

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.193583684739075

> <JCHEM_PKA_STRONGEST_BASIC>
-6.688690083150029

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
90.49419999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.52e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-hydroxy-7-isopropyl-1,1,4a-trimethyl-3,4,10,10a-tetrahydro-2H-phenanthren-9-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0036564
     RDKit          3D
Sugiol
 50 52  0  0  0  0  0  0  0  0999 V2000
    5.2894   -0.5093    0.1419 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3933    0.6542    0.6546 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5915    0.7315    2.1620 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9794    0.3368    0.3168 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1234   -0.4178    1.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8086   -0.5580    0.6017 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3116    0.0188   -0.5455 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1969    0.7785   -1.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5165    0.9464   -0.8494 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3849    1.7252   -1.5857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0307   -0.1922   -1.0922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7320   -1.1376   -2.3060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5495    1.0466   -1.6952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5914    1.7870   -0.8829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7055    0.7930   -0.6342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1180   -0.1950    0.3557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7375    0.5586    1.5805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2379   -1.1576    0.6933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9766   -0.9699   -0.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3737   -1.8280    0.7965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1591   -1.3118    1.4151 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1185   -1.4641    2.6369 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1133   -0.4604   -0.9823 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3215   -0.2020    0.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9886   -1.4713    0.5101 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7129    1.5655    0.2071 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1493    1.6113    2.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2861   -0.1448    2.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6930    0.6007    2.7545 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4748   -0.8769    1.9579 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9698    1.3031   -2.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0870    2.1592   -2.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3389   -2.0989   -1.9094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7317   -1.3473   -2.7260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1099   -0.6564   -3.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0603    0.8242   -2.6744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7989    1.8107   -1.9401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9952    2.5746   -1.5421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1711    2.2175    0.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9172    0.3200   -1.6344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6143    1.2378   -0.2067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5045    1.3779    1.7068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7170    0.9509    1.5785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8567   -0.1055    2.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9460   -2.2155    0.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5404   -1.0813    1.7553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1500   -1.0038    0.0576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5370   -1.7071   -0.9237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1204   -1.9418    1.6496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1891   -2.8755    0.4988 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  7 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
  9  4  1  0
 19 11  1  0
 21  6  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  5 30  1  0
  8 31  1  0
 10 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 15 41  1  0
 17 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 20 49  1  0
 20 50  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       8.470   4.414   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.470   1.746   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.217   1.220   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.503   0.230   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.310   4.414   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.770   4.414   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.540   3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.770   4.414   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.390   1.746   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.850   4.414   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.540   0.413   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.700   3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.160   3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.850   1.746   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.080   3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.390   4.414   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.080   0.413   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.770   1.746   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.770   1.746   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.540   3.080   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.160   5.747   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       3.850  -0.921   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   12                                                            
CONECT    3   19                                                            
CONECT    4   19                                                            
CONECT    5   20                                                            
CONECT    6    7    8                                                       
CONECT    7    6   19                                                       
CONECT    8    6   20                                                       
CONECT    9   13   14                                                       
CONECT   10   15   16                                                       
CONECT   11   17   18                                                       
CONECT   12    1    2   13                                                  
CONECT   13    9   12   16                                                  
CONECT   14    9   15   17                                                  
CONECT   15   10   14   20                                                  
CONECT   16   10   13   21                                                  
CONECT   17   11   14   22                                                  
CONECT   18   11   19   20                                                  
CONECT   19    3    4    7   18                                             
CONECT   20    5    8   15   18                                             
CONECT   21   16                                                            
CONECT   22   17                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

COMPND    HMDB0036564
HETATM    1  C1  UNL     1       5.289  -0.509   0.142  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.393   0.654   0.655  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.591   0.731   2.162  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.979   0.337   0.317  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.123  -0.418   1.047  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.809  -0.558   0.602  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.312   0.019  -0.546  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.197   0.778  -1.263  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.517   0.946  -0.849  1.00  0.00           C  
HETATM   10  O1  UNL     1       3.385   1.725  -1.586  1.00  0.00           O  
HETATM   11  C10 UNL     1      -1.031  -0.192  -1.092  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.732  -1.138  -2.306  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.550   1.047  -1.695  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.591   1.787  -0.883  1.00  0.00           C  
HETATM   15  C14 UNL     1      -3.705   0.793  -0.634  1.00  0.00           C  
HETATM   16  C15 UNL     1      -3.118  -0.195   0.356  1.00  0.00           C  
HETATM   17  C16 UNL     1      -2.738   0.559   1.580  1.00  0.00           C  
HETATM   18  C17 UNL     1      -4.238  -1.158   0.693  1.00  0.00           C  
HETATM   19  C18 UNL     1      -1.977  -0.970  -0.258  1.00  0.00           C  
HETATM   20  C19 UNL     1      -1.374  -1.828   0.796  1.00  0.00           C  
HETATM   21  C20 UNL     1      -0.159  -1.312   1.415  1.00  0.00           C  
HETATM   22  O2  UNL     1       0.119  -1.464   2.637  1.00  0.00           O  
HETATM   23  H1  UNL     1       5.113  -0.460  -0.982  1.00  0.00           H  
HETATM   24  H2  UNL     1       6.321  -0.202   0.297  1.00  0.00           H  
HETATM   25  H3  UNL     1       4.989  -1.471   0.510  1.00  0.00           H  
HETATM   26  H4  UNL     1       4.713   1.566   0.207  1.00  0.00           H  
HETATM   27  H5  UNL     1       5.149   1.611   2.499  1.00  0.00           H  
HETATM   28  H6  UNL     1       5.286  -0.145   2.424  1.00  0.00           H  
HETATM   29  H7  UNL     1       3.693   0.601   2.755  1.00  0.00           H  
HETATM   30  H8  UNL     1       2.475  -0.877   1.958  1.00  0.00           H  
HETATM   31  H9  UNL     1       0.970   1.303  -2.195  1.00  0.00           H  
HETATM   32  H10 UNL     1       3.087   2.159  -2.432  1.00  0.00           H  
HETATM   33  H11 UNL     1      -0.339  -2.099  -1.909  1.00  0.00           H  
HETATM   34  H12 UNL     1      -1.732  -1.347  -2.726  1.00  0.00           H  
HETATM   35  H13 UNL     1      -0.110  -0.656  -3.042  1.00  0.00           H  
HETATM   36  H14 UNL     1      -2.060   0.824  -2.674  1.00  0.00           H  
HETATM   37  H15 UNL     1      -0.799   1.811  -1.940  1.00  0.00           H  
HETATM   38  H16 UNL     1      -2.995   2.575  -1.542  1.00  0.00           H  
HETATM   39  H17 UNL     1      -2.171   2.218   0.038  1.00  0.00           H  
HETATM   40  H18 UNL     1      -3.917   0.320  -1.634  1.00  0.00           H  
HETATM   41  H19 UNL     1      -4.614   1.238  -0.207  1.00  0.00           H  
HETATM   42  H20 UNL     1      -3.505   1.378   1.707  1.00  0.00           H  
HETATM   43  H21 UNL     1      -1.717   0.951   1.579  1.00  0.00           H  
HETATM   44  H22 UNL     1      -2.857  -0.106   2.473  1.00  0.00           H  
HETATM   45  H23 UNL     1      -3.946  -2.216   0.510  1.00  0.00           H  
HETATM   46  H24 UNL     1      -4.540  -1.081   1.755  1.00  0.00           H  
HETATM   47  H25 UNL     1      -5.150  -1.004   0.058  1.00  0.00           H  
HETATM   48  H26 UNL     1      -2.537  -1.707  -0.924  1.00  0.00           H  
HETATM   49  H27 UNL     1      -2.120  -1.942   1.650  1.00  0.00           H  
HETATM   50  H28 UNL     1      -1.189  -2.876   0.499  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3    4   26
CONECT    3   27   28   29
CONECT    4    5    5    9
CONECT    5    6   30
CONECT    6    7    7   21
CONECT    7    8   11
CONECT    8    9    9   31
CONECT    9   10
CONECT   10   32
CONECT   11   12   13   19
CONECT   12   33   34   35
CONECT   13   14   36   37
CONECT   14   15   38   39
CONECT   15   16   40   41
CONECT   16   17   18   19
CONECT   17   42   43   44
CONECT   18   45   46   47
CONECT   19   20   48
CONECT   20   21   49   50
CONECT   21   22   22
END

HMDB0036564
     RDKit          3D
Sugiol
 50 52  0  0  0  0  0  0  0  0999 V2000
    5.2894   -0.5093    0.1419 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3933    0.6542    0.6546 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5915    0.7315    2.1620 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9794    0.3368    0.3168 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1234   -0.4178    1.0474 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8086   -0.5580    0.6017 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3116    0.0188   -0.5455 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1969    0.7785   -1.2631 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5165    0.9464   -0.8494 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3849    1.7252   -1.5857 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0307   -0.1922   -1.0922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7320   -1.1376   -2.3060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5495    1.0466   -1.6952 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5914    1.7870   -0.8829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7055    0.7930   -0.6342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1180   -0.1950    0.3557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7375    0.5586    1.5805 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2379   -1.1576    0.6933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9766   -0.9699   -0.2584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3737   -1.8280    0.7965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1591   -1.3118    1.4151 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1185   -1.4641    2.6369 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1133   -0.4604   -0.9823 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3215   -0.2020    0.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9886   -1.4713    0.5101 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7129    1.5655    0.2071 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1493    1.6113    2.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2861   -0.1448    2.4238 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6930    0.6007    2.7545 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4748   -0.8769    1.9579 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9698    1.3031   -2.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0870    2.1592   -2.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3389   -2.0989   -1.9094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7317   -1.3473   -2.7260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1099   -0.6564   -3.0417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0603    0.8242   -2.6744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7989    1.8107   -1.9401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9952    2.5746   -1.5421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1711    2.2175    0.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9172    0.3200   -1.6344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6143    1.2378   -0.2067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5045    1.3779    1.7068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7170    0.9509    1.5785 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8567   -0.1055    2.4734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9460   -2.2155    0.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5404   -1.0813    1.7553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1500   -1.0038    0.0576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5370   -1.7071   -0.9237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1204   -1.9418    1.6496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1891   -2.8755    0.4988 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  7 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
  9  4  1  0
 19 11  1  0
 21  6  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  3 29  1  0
  5 30  1  0
  8 31  1  0
 10 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 15 41  1  0
 17 42  1  0
 17 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  0
 20 49  1  0
 20 50  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-Sugiol	HMDB
12-Hydroxy-13-isopropyl-podocarpa-8,11,13-trien-7-one	HMDB
7-Oxoferruginol	HMDB
Isomicropinic acid	HMDB

Chemical Formula

C₂₀H₂₈O₂

Average Molecular Weight

300.4351

Monoisotopic Molecular Weight

300.20893014

IUPAC Name

6-hydroxy-1,1,4a-trimethyl-7-(propan-2-yl)-1,2,3,4,4a,9,10,10a-octahydrophenanthren-9-one

Traditional Name

6-hydroxy-7-isopropyl-1,1,4a-trimethyl-3,4,10,10a-tetrahydro-2H-phenanthren-9-one

CAS Registry Number

511-05-7

SMILES

CC(C)C1=CC2=C(C=C1O)C1(C)CCCC(C)(C)C1CC2=O

InChI Identifier

InChI=1S/C20H28O2/c1-12(2)13-9-14-15(10-16(13)21)20(5)8-6-7-19(3,4)18(20)11-17(14)22/h9-10,12,18,21H,6-8,11H2,1-5H3

InChI Key

IPEHJNRNYPOFII-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Diterpenoid
Abietane diterpenoid
Phenanthrene
Hydrophenanthrene
Tetralin
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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: HMDB0036564)

Source

Endogenous

Endogenous (HMDB: HMDB0036564)

Plant

Plant (HMDB: HMDB0036564)

Animal

Animal (HMDB: HMDB0036564)

Exogenous

Food

Food (HMDB: HMDB0036564)

Fruit

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0036564)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036564)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036564)

Lipid metabolism pathway (HMDB: HMDB0036564)

Cellular process

Cell signaling (HMDB: HMDB0036564)

Biochemical process

Lipid transport (HMDB: HMDB0036564)

Role

Biological role

Energy source (HMDB: HMDB0036564)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036564)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	295 - 297 °C	Not Available
Boiling Point	437.20 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	0.21 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	6.770 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0035 g/L	ALOGPS
logP	5.36	ALOGPS
logP	5.11	ChemAxon
logS	-4.9	ALOGPS
pKa (Strongest Acidic)	8.19	ChemAxon
pKa (Strongest Basic)	-6.7	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	1	ChemAxon
Refractivity	90.49 m³·mol⁻¹	ChemAxon
Polarizability	35.83 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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
DarkChem	[M+H]+	171.594	31661259
DarkChem	[M-H]-	171.743	31661259
DeepCCS	[M+H]+	179.076	30932474
DeepCCS	[M-H]-	176.718	30932474
DeepCCS	[M-2H]-	209.706	30932474
DeepCCS	[M+Na]+	185.17	30932474
AllCCS	[M+H]+	172.6	32859911
AllCCS	[M+H-H2O]+	169.4	32859911
AllCCS	[M+NH4]+	175.5	32859911
AllCCS	[M+Na]+	176.4	32859911
AllCCS	[M-H]-	184.0	32859911
AllCCS	[M+Na-2H]-	184.3	32859911
AllCCS	[M+HCOO]-	184.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Sugiol	CC(C)C1=CC2=C(C=C1O)C1(C)CCCC(C)(C)C1CC2=O	3202.7	Standard polar	33892256
Sugiol	CC(C)C1=CC2=C(C=C1O)C1(C)CCCC(C)(C)C1CC2=O	2501.7	Standard non polar	33892256
Sugiol	CC(C)C1=CC2=C(C=C1O)C1(C)CCCC(C)(C)C1CC2=O	2643.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Sugiol,1TMS,isomer #1	CC(C)C1=CC2=C(C=C1O[Si](C)(C)C)C1(C)CCCC(C)(C)C1CC2=O	2520.6	Semi standard non polar	33892256
Sugiol,1TBDMS,isomer #1	CC(C)C1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)C1(C)CCCC(C)(C)C1CC2=O	2762.2	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 - Sugiol GC-MS (Non-derivatized) - 70eV, Positive	splash10-052r-1090000000-282839b8e3dc1c8105a3	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sugiol GC-MS (1 TMS) - 70eV, Positive	splash10-0a4i-1219000000-1e5c0208b9f7f7872eb6	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Sugiol 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 - Sugiol 10V, Positive-QTOF	splash10-0udi-0039000000-172a8bfa3470d4598f54	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sugiol 20V, Positive-QTOF	splash10-0k9i-3893000000-356b0302e81378e4e589	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sugiol 40V, Positive-QTOF	splash10-067i-7290000000-15d87e44ea62abbeff21	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sugiol 10V, Negative-QTOF	splash10-0002-0090000000-9eba4ff173f915b579b3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sugiol 20V, Negative-QTOF	splash10-0002-0090000000-a2d638c6fc01ce9ee1ac	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sugiol 40V, Negative-QTOF	splash10-00lr-1190000000-bdce3d396babd4a68188	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sugiol 10V, Positive-QTOF	splash10-0udi-0019000000-76f84d789b3006bfe268	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sugiol 20V, Positive-QTOF	splash10-0w2j-0953000000-d2226252a3789a459cdb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sugiol 40V, Positive-QTOF	splash10-000i-5890000000-1a5d547dd9a0f4ed1d37	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sugiol 10V, Negative-QTOF	splash10-0002-0090000000-344a11f406f20d02412c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sugiol 20V, Negative-QTOF	splash10-0002-0090000000-00b1ba4f29d6302dd272	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Sugiol 40V, Negative-QTOF	splash10-001r-0290000000-0be7aaadbf0d9fe09d08	2021-09-23	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

FDB015468

KNApSAcK ID

C00031398

Chemspider ID

242417

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Sugiol

METLIN ID

Not Available

PubChem Compound

275529

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1443571

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 Sugiol (HMDB0036564)

MOL for HMDB0036564 (Sugiol)

3D MOL for HMDB0036564 (Sugiol)

3D SDF for HMDB0036564 (Sugiol)

3D-SDF for HMDB0036564 (Sugiol)

PDB for HMDB0036564 (Sugiol)

3D PDB for HMDB0036564 (Sugiol)

SMILES for HMDB0036564 (Sugiol)

INCHI for HMDB0036564 (Sugiol)

Structure for HMDB0036564 (Sugiol)

3D Structure for HMDB0036564 (Sugiol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra