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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:24:20 UTC

Update Date

2022-03-07 02:56:03 UTC

HMDB ID

HMDB0039052

Secondary Accession Numbers

HMDB39052

Metabolite Identification

Common Name

(4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one

Description

(4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Based on a literature review a small amount of articles have been published on (4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one.

Structure

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

HMDB0039052
     RDKit          3D
(4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one
 29 29  0  0  0  0  0  0  0  0999 V2000
    3.9962   -0.0080    0.0731 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5240   -0.2321   -0.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8323   -0.9258    0.8169 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3933   -1.0956    0.6005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2816    0.1933    0.1372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7324   -0.1265   -0.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2828   -0.6027    1.2690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8346   -1.1511   -0.9944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5543    1.0583   -0.4873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1934    1.5992   -1.6935 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3907    0.7705   -1.0560 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8050    0.3220   -1.2037 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4016    0.4165   -2.3200 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5353   -0.3634   -0.8122 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3269   -0.4886    1.0128 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1829    1.0685    0.1786 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3456   -1.3388    1.6584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0597   -1.4863    1.5060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1791   -1.8405   -0.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2150    0.8822    1.0311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7561   -0.0681    2.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2095   -1.7008    1.3381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3692   -0.3331    1.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9904   -2.0259   -0.5916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6087    0.7007   -0.5771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5725    1.8511    0.2859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5704    2.5214   -1.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4306    1.8799   -0.9235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1131    0.5235   -2.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
  5 11  1  0
 11 12  1  0
 12 13  2  0
 12  2  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  0
  7 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
M  END

Uroterpenolone
  Mrv1572001071617202D          

 13 13  0  0  0  0            999 V2000
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   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
    1.4290    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1435    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  3  9  1  0  0  0  0
  8 10  2  0  0  0  0
  2 11  1  0  0  0  0
 11 12  1  0  0  0  0
  2 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0039052

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=CCC(CC1=O)C(C)(O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C10H16O3/c1-7-3-4-8(5-9(7)12)10(2,13)6-11/h3,8,11,13H,4-6H2,1-2H3

> <INCHI_KEY>
AOKPDATZUBLDMG-UHFFFAOYSA-N

> <FORMULA>
C10H16O3

> <MOLECULAR_WEIGHT>
184.235

> <EXACT_MASS>
184.109944375

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
20.125158555899873

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-(1,2-dihydroxypropan-2-yl)-2-methylcyclohex-2-en-1-one

> <ALOGPS_LOGP>
0.34

> <JCHEM_LOGP>
0.4601041796666663

> <ALOGPS_LOGS>
-0.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.369784832465708

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.853689427826627

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0720816513479257

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
50.6988

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.97e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-(1,2-dihydroxypropan-2-yl)-2-methylcyclohex-2-en-1-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0039052
     RDKit          3D
(4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one
 29 29  0  0  0  0  0  0  0  0999 V2000
    3.9962   -0.0080    0.0731 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5240   -0.2321   -0.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8323   -0.9258    0.8169 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3933   -1.0956    0.6005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2816    0.1933    0.1372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7324   -0.1265   -0.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2828   -0.6027    1.2690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8346   -1.1511   -0.9944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5543    1.0583   -0.4873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1934    1.5992   -1.6935 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3907    0.7705   -1.0560 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8050    0.3220   -1.2037 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4016    0.4165   -2.3200 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5353   -0.3634   -0.8122 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3269   -0.4886    1.0128 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1829    1.0685    0.1786 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3456   -1.3388    1.6584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0597   -1.4863    1.5060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1791   -1.8405   -0.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2150    0.8822    1.0311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7561   -0.0681    2.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2095   -1.7008    1.3381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3692   -0.3331    1.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9904   -2.0259   -0.5916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6087    0.7007   -0.5771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5725    1.8511    0.2859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5704    2.5214   -1.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4306    1.8799   -0.9235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1131    0.5235   -2.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
  5 11  1  0
 11 12  1  0
 12 13  2  0
 12  2  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  0
  7 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
M  END

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Uroterpenolone                                    
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   3.850   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       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.334   5.390   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11   13                                             
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10                                                  
CONECT    9    8    3                                                       
CONECT   10    8                                                            
CONECT   11    2   12                                                       
CONECT   12   11                                                            
CONECT   13    2                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

COMPND    HMDB0039052
HETATM    1  C1  UNL     1       3.996  -0.008   0.073  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.524  -0.232  -0.067  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.832  -0.926   0.817  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.393  -1.096   0.601  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.282   0.193   0.137  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.732  -0.126  -0.066  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.283  -0.603   1.269  1.00  0.00           C  
HETATM    8  O1  UNL     1      -1.835  -1.151  -0.994  1.00  0.00           O  
HETATM    9  C8  UNL     1      -2.554   1.058  -0.487  1.00  0.00           C  
HETATM   10  O2  UNL     1      -2.193   1.599  -1.693  1.00  0.00           O  
HETATM   11  C9  UNL     1       0.391   0.770  -1.056  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.805   0.322  -1.204  1.00  0.00           C  
HETATM   13  O3  UNL     1       2.402   0.417  -2.320  1.00  0.00           O  
HETATM   14  H1  UNL     1       4.535  -0.363  -0.812  1.00  0.00           H  
HETATM   15  H2  UNL     1       4.327  -0.489   1.013  1.00  0.00           H  
HETATM   16  H3  UNL     1       4.183   1.069   0.179  1.00  0.00           H  
HETATM   17  H4  UNL     1       2.346  -1.339   1.658  1.00  0.00           H  
HETATM   18  H5  UNL     1      -0.060  -1.486   1.506  1.00  0.00           H  
HETATM   19  H6  UNL     1       0.179  -1.841  -0.214  1.00  0.00           H  
HETATM   20  H7  UNL     1      -0.215   0.882   1.031  1.00  0.00           H  
HETATM   21  H8  UNL     1      -1.756  -0.068   2.085  1.00  0.00           H  
HETATM   22  H9  UNL     1      -2.209  -1.701   1.338  1.00  0.00           H  
HETATM   23  H10 UNL     1      -3.369  -0.333   1.376  1.00  0.00           H  
HETATM   24  H11 UNL     1      -1.990  -2.026  -0.592  1.00  0.00           H  
HETATM   25  H12 UNL     1      -3.609   0.701  -0.577  1.00  0.00           H  
HETATM   26  H13 UNL     1      -2.573   1.851   0.286  1.00  0.00           H  
HETATM   27  H14 UNL     1      -2.570   2.521  -1.733  1.00  0.00           H  
HETATM   28  H15 UNL     1       0.431   1.880  -0.924  1.00  0.00           H  
HETATM   29  H16 UNL     1      -0.113   0.523  -2.015  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3    3   12
CONECT    3    4   17
CONECT    4    5   18   19
CONECT    5    6   11   20
CONECT    6    7    8    9
CONECT    7   21   22   23
CONECT    8   24
CONECT    9   10   25   26
CONECT   10   27
CONECT   11   12   28   29
CONECT   12   13   13
END

HMDB0039052
     RDKit          3D
(4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one
 29 29  0  0  0  0  0  0  0  0999 V2000
    3.9962   -0.0080    0.0731 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5240   -0.2321   -0.0667 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8323   -0.9258    0.8169 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3933   -1.0956    0.6005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2816    0.1933    0.1372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7324   -0.1265   -0.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2828   -0.6027    1.2690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8346   -1.1511   -0.9944 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5543    1.0583   -0.4873 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1934    1.5992   -1.6935 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3907    0.7705   -1.0560 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8050    0.3220   -1.2037 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4016    0.4165   -2.3200 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5353   -0.3634   -0.8122 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3269   -0.4886    1.0128 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1829    1.0685    0.1786 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3456   -1.3388    1.6584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0597   -1.4863    1.5060 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1791   -1.8405   -0.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2150    0.8822    1.0311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7561   -0.0681    2.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2095   -1.7008    1.3381 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3692   -0.3331    1.3760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9904   -2.0259   -0.5916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6087    0.7007   -0.5771 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5725    1.8511    0.2859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5704    2.5214   -1.7330 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4306    1.8799   -0.9235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1131    0.5235   -2.0154 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
  5 11  1  0
 11 12  1  0
 12 13  2  0
 12  2  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  0
  4 18  1  0
  4 19  1  0
  5 20  1  0
  7 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
M  END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₀H₁₆O₃

Average Molecular Weight

184.235

Monoisotopic Molecular Weight

184.109944375

IUPAC Name

5-(1,2-dihydroxypropan-2-yl)-2-methylcyclohex-2-en-1-one

Traditional Name

5-(1,2-dihydroxypropan-2-yl)-2-methylcyclohex-2-en-1-one

CAS Registry Number

402593-42-4

SMILES

CC1=CCC(CC1=O)C(C)(O)CO

InChI Identifier

InChI=1S/C10H16O3/c1-7-3-4-8(5-9(7)12)10(2,13)6-11/h3,8,11,13H,4-6H2,1-2H3

InChI Key

AOKPDATZUBLDMG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Menthane monoterpenoids

Alternative Parents

Substituents

P-menthane monoterpenoid
Monocyclic monoterpenoid
Cyclohexenone
Tertiary alcohol
Cyclic ketone
Ketone
1,2-diol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Source

Endogenous

Endogenous (HMDB: HMDB0039052)

Exogenous

Exogenous (HMDB: HMDB0039052)

Food

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	19.7 g/L	ALOGPS
logP	0.34	ALOGPS
logP	0.46	ChemAxon
logS	-0.97	ALOGPS
pKa (Strongest Acidic)	13.85	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	50.7 m³·mol⁻¹	ChemAxon
Polarizability	20.13 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	143.448	31661259
DarkChem	[M-H]-	140.097	31661259
DeepCCS	[M+H]+	143.795	30932474
DeepCCS	[M-H]-	140.435	30932474
DeepCCS	[M-2H]-	177.458	30932474
DeepCCS	[M+Na]+	152.997	30932474
AllCCS	[M+H]+	140.8	32859911
AllCCS	[M+H-H2O]+	136.6	32859911
AllCCS	[M+NH4]+	144.7	32859911
AllCCS	[M+Na]+	145.8	32859911
AllCCS	[M-H]-	143.3	32859911
AllCCS	[M+Na-2H]-	144.4	32859911
AllCCS	[M+HCOO]-	145.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one	CC1=CCC(CC1=O)C(C)(O)CO	2472.2	Standard polar	33892256
(4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one	CC1=CCC(CC1=O)C(C)(O)CO	1544.0	Standard non polar	33892256
(4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one	CC1=CCC(CC1=O)C(C)(O)CO	1659.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one,1TMS,isomer #1	CC1=CCC(C(C)(CO)O[Si](C)(C)C)CC1=O	1755.6	Semi standard non polar	33892256
(4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one,1TMS,isomer #2	CC1=CCC(C(C)(O)CO[Si](C)(C)C)CC1=O	1748.9	Semi standard non polar	33892256
(4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one,1TMS,isomer #3	CC1=CCC(C(C)(O)CO)C=C1O[Si](C)(C)C	1792.9	Semi standard non polar	33892256
(4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one,2TMS,isomer #1	CC1=CCC(C(C)(CO[Si](C)(C)C)O[Si](C)(C)C)CC1=O	1852.4	Semi standard non polar	33892256
(4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one,2TMS,isomer #2	CC1=CCC(C(C)(CO)O[Si](C)(C)C)C=C1O[Si](C)(C)C	1835.2	Semi standard non polar	33892256
(4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one,2TMS,isomer #3	CC1=CCC(C(C)(O)CO[Si](C)(C)C)C=C1O[Si](C)(C)C	1829.7	Semi standard non polar	33892256
(4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one,3TMS,isomer #1	CC1=CCC(C(C)(CO[Si](C)(C)C)O[Si](C)(C)C)C=C1O[Si](C)(C)C	1860.9	Semi standard non polar	33892256
(4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one,3TMS,isomer #1	CC1=CCC(C(C)(CO[Si](C)(C)C)O[Si](C)(C)C)C=C1O[Si](C)(C)C	1792.8	Standard non polar	33892256
(4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one,1TBDMS,isomer #1	CC1=CCC(C(C)(CO)O[Si](C)(C)C(C)(C)C)CC1=O	2006.0	Semi standard non polar	33892256
(4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one,1TBDMS,isomer #2	CC1=CCC(C(C)(O)CO[Si](C)(C)C(C)(C)C)CC1=O	2005.0	Semi standard non polar	33892256
(4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one,1TBDMS,isomer #3	CC1=CCC(C(C)(O)CO)C=C1O[Si](C)(C)C(C)(C)C	2045.0	Semi standard non polar	33892256
(4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one,2TBDMS,isomer #1	CC1=CCC(C(C)(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)CC1=O	2332.3	Semi standard non polar	33892256
(4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one,2TBDMS,isomer #2	CC1=CCC(C(C)(CO)O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	2303.3	Semi standard non polar	33892256
(4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one,2TBDMS,isomer #3	CC1=CCC(C(C)(O)CO[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	2291.5	Semi standard non polar	33892256
(4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one,3TBDMS,isomer #1	CC1=CCC(C(C)(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	2563.0	Semi standard non polar	33892256
(4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one,3TBDMS,isomer #1	CC1=CCC(C(C)(CO[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C)C=C1O[Si](C)(C)C(C)(C)C	2346.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-053u-9400000000-b7e2e86236cbf4b750f8	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one GC-MS (2 TMS) - 70eV, Positive	splash10-0iti-9473000000-8353f7bc072726278a8c	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-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 - (4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one 10V, Positive-QTOF	splash10-000i-0900000000-670835a2885600fc95f0	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one 20V, Positive-QTOF	splash10-0671-3900000000-ef5a599ace7164e683f5	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one 40V, Positive-QTOF	splash10-0ue9-9200000000-aaa717e5042f8053bf34	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one 10V, Negative-QTOF	splash10-001i-0900000000-3d9acee6e699739da89a	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one 20V, Negative-QTOF	splash10-0pc0-1900000000-e73309bc510409076813	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one 40V, Negative-QTOF	splash10-0a4i-9800000000-dada2e76fc8d3f3f8a47	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one 10V, Negative-QTOF	splash10-0a59-3900000000-62d15329e27365456522	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one 20V, Negative-QTOF	splash10-0f89-2900000000-83f5ad925fad273584b8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one 40V, Negative-QTOF	splash10-0a4l-9100000000-8dce7224627f066977a5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one 10V, Positive-QTOF	splash10-00ks-3900000000-4aad8deb5d5875943b51	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one 20V, Positive-QTOF	splash10-053s-9400000000-16611941503d0491eddb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one 40V, Positive-QTOF	splash10-0006-9000000000-4ba8fce8d19780b482cf	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB018550

KNApSAcK ID

Not Available

Chemspider ID

35014729

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

73120805

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 (4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one (HMDB0039052)

MOL for HMDB0039052 ((4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one)

3D MOL for HMDB0039052 ((4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one)

3D SDF for HMDB0039052 ((4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one)

3D-SDF for HMDB0039052 ((4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one)

PDB for HMDB0039052 ((4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one)

3D PDB for HMDB0039052 ((4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one)

SMILES for HMDB0039052 ((4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one)

INCHI for HMDB0039052 ((4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one)

Structure for HMDB0039052 ((4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one)

3D Structure for HMDB0039052 ((4S,8R)-8,9-Dihydroxy-p-menth-1(6)-en-2-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra