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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:47:57 UTC

Update Date

2022-03-07 02:53:14 UTC

HMDB ID

HMDB0032116

Secondary Accession Numbers

HMDB32116

Metabolite Identification

Common Name

Helinorbisabone

Description

Helinorbisabone belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring. Based on a literature review a small amount of articles have been published on Helinorbisabone.

Structure

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

HMDB0032116
     RDKit          3D
Helinorbisabone
 36 36  0  0  0  0  0  0  0  0999 V2000
   -5.3591    0.0766    0.2563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8839   -0.7962   -0.8436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7213   -1.3242   -1.6067 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4731   -1.0586   -1.0543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5862   -0.4760   -0.2651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1239   -0.7246   -0.4325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9489   -2.0558    0.1538 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3767    0.2202    0.5207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8769    1.6163    0.0218 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0689    0.1415    0.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6652    0.5394   -0.8734 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0720    0.5431   -0.9470 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7335    0.9399   -2.1206 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8312    0.1601    0.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3069    0.1609   -0.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006   -0.2264    1.3213 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8280   -0.2291    1.3951 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2402   -0.6204    2.5694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4496   -0.1270    0.4297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8189   -0.1859    1.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2643    1.1536    0.0541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1145   -1.7176   -1.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9081    0.1962    0.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7409   -0.7594   -1.4338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1828   -1.9424    1.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7671    0.1296    1.5114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1100    1.5189   -1.0649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0187    2.2935    0.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7769    1.8745    0.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1266    0.8787   -1.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7470    0.9494   -2.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6946    1.1500   -0.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6279   -0.5195   -0.8277 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7636   -0.2844    0.9290 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8224   -0.5246    2.1732 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7733   -0.9704    3.3694 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 17 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  5 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
 11 30  1  0
 13 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 18 36  1  0
M  END


  Mrv0541 05061306222D          

 18 18  0  0  0  0            999 V2000
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    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
    0.0000    0.0000    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   -3.7125    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   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    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
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  8  1  1  0  0  0  0
  8  6  2  0  0  0  0
  9  2  1  0  0  0  0
  9  4  1  0  0  0  0
 10  3  1  0  0  0  0
 11  7  1  0  0  0  0
 11 10  1  0  0  0  0
 12  5  1  0  0  0  0
 12 10  1  0  0  0  0
 13  7  2  0  0  0  0
 13  8  1  0  0  0  0
 14  6  1  0  0  0  0
 14 11  2  0  0  0  0
 15  9  2  0  0  0  0
 16 12  1  0  0  0  0
 17 13  1  0  0  0  0
 18 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032116

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C(O)\C=C\C(C)=O)C1=C(O)C=C(C)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H18O4/c1-8-6-14(18)11(7-13(8)17)10(3)12(16)5-4-9(2)15/h4-7,10,12,16-18H,1-3H3/b5-4+

> <INCHI_KEY>
QUWXRNSZOIJARN-SNAWJCMRSA-N

> <FORMULA>
C14H18O4

> <MOLECULAR_WEIGHT>
250.2903

> <EXACT_MASS>
250.120509064

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
26.681393961457164

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3E)-6-(2,5-dihydroxy-4-methylphenyl)-5-hydroxyhept-3-en-2-one

> <ALOGPS_LOGP>
1.97

> <JCHEM_LOGP>
2.312601618

> <ALOGPS_LOGS>
-2.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.904399229945337

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.08087454063762

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0667078249940625

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
70.80310000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.75e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3E)-6-(2,5-dihydroxy-4-methylphenyl)-5-hydroxyhept-3-en-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0032116
     RDKit          3D
Helinorbisabone
 36 36  0  0  0  0  0  0  0  0999 V2000
   -5.3591    0.0766    0.2563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8839   -0.7962   -0.8436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7213   -1.3242   -1.6067 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4731   -1.0586   -1.0543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5862   -0.4760   -0.2651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1239   -0.7246   -0.4325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9489   -2.0558    0.1538 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3767    0.2202    0.5207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8769    1.6163    0.0218 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0689    0.1415    0.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6652    0.5394   -0.8734 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0720    0.5431   -0.9470 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7335    0.9399   -2.1206 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8312    0.1601    0.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3069    0.1609   -0.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006   -0.2264    1.3213 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8280   -0.2291    1.3951 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2402   -0.6204    2.5694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4496   -0.1270    0.4297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8189   -0.1859    1.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2643    1.1536    0.0541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1145   -1.7176   -1.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9081    0.1962    0.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7409   -0.7594   -1.4338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1828   -1.9424    1.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7671    0.1296    1.5114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1100    1.5189   -1.0649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0187    2.2935    0.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7769    1.8745    0.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1266    0.8787   -1.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7470    0.9494   -2.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6946    1.1500   -0.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6279   -0.5195   -0.8277 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7636   -0.2844    0.9290 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8224   -0.5246    2.1732 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7733   -0.9704    3.3694 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 17 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  5 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
 11 30  1  0
 13 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 18 36  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       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4    5    9                                                       
CONECT    5    4   12                                                       
CONECT    6    8   14                                                       
CONECT    7   11   13                                                       
CONECT    8    1    6   13                                                  
CONECT    9    2    4   15                                                  
CONECT   10    3   11   12                                                  
CONECT   11    7   10   14                                                  
CONECT   12    5   10   16                                                  
CONECT   13    7    8   17                                                  
CONECT   14    6   11   18                                                  
CONECT   15    9                                                            
CONECT   16   12                                                            
CONECT   17   13                                                            
CONECT   18   14                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0032116
HETATM    1  C1  UNL     1      -5.359   0.077   0.256  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.884  -0.796  -0.844  1.00  0.00           C  
HETATM    3  O1  UNL     1      -5.721  -1.324  -1.607  1.00  0.00           O  
HETATM    4  C3  UNL     1      -3.473  -1.059  -1.054  1.00  0.00           C  
HETATM    5  C4  UNL     1      -2.586  -0.476  -0.265  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.124  -0.725  -0.433  1.00  0.00           C  
HETATM    7  O2  UNL     1      -0.949  -2.056   0.154  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.377   0.220   0.521  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.877   1.616   0.022  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.069   0.141   0.321  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.665   0.539  -0.873  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.072   0.543  -0.947  1.00  0.00           C  
HETATM   13  O3  UNL     1       3.734   0.940  -2.121  1.00  0.00           O  
HETATM   14  C11 UNL     1       3.831   0.160   0.144  1.00  0.00           C  
HETATM   15  C12 UNL     1       5.307   0.161  -0.002  1.00  0.00           C  
HETATM   16  C13 UNL     1       3.201  -0.226   1.321  1.00  0.00           C  
HETATM   17  C14 UNL     1       1.828  -0.229   1.395  1.00  0.00           C  
HETATM   18  O4  UNL     1       1.240  -0.620   2.569  1.00  0.00           O  
HETATM   19  H1  UNL     1      -6.450  -0.127   0.430  1.00  0.00           H  
HETATM   20  H2  UNL     1      -4.819  -0.186   1.207  1.00  0.00           H  
HETATM   21  H3  UNL     1      -5.264   1.154   0.054  1.00  0.00           H  
HETATM   22  H4  UNL     1      -3.115  -1.718  -1.833  1.00  0.00           H  
HETATM   23  H5  UNL     1      -2.908   0.196   0.522  1.00  0.00           H  
HETATM   24  H6  UNL     1      -0.741  -0.759  -1.434  1.00  0.00           H  
HETATM   25  H7  UNL     1      -1.183  -1.942   1.133  1.00  0.00           H  
HETATM   26  H8  UNL     1      -0.767   0.130   1.511  1.00  0.00           H  
HETATM   27  H9  UNL     1      -1.110   1.519  -1.065  1.00  0.00           H  
HETATM   28  H10 UNL     1      -0.019   2.294   0.195  1.00  0.00           H  
HETATM   29  H11 UNL     1      -1.777   1.874   0.552  1.00  0.00           H  
HETATM   30  H12 UNL     1       1.127   0.879  -1.737  1.00  0.00           H  
HETATM   31  H13 UNL     1       4.747   0.949  -2.152  1.00  0.00           H  
HETATM   32  H14 UNL     1       5.695   1.150  -0.232  1.00  0.00           H  
HETATM   33  H15 UNL     1       5.628  -0.520  -0.828  1.00  0.00           H  
HETATM   34  H16 UNL     1       5.764  -0.284   0.929  1.00  0.00           H  
HETATM   35  H17 UNL     1       3.822  -0.525   2.173  1.00  0.00           H  
HETATM   36  H18 UNL     1       1.773  -0.970   3.369  1.00  0.00           H  
CONECT    1    2   19   20   21
CONECT    2    3    3    4
CONECT    4    5    5   22
CONECT    5    6   23
CONECT    6    7    8   24
CONECT    7   25
CONECT    8    9   10   26
CONECT    9   27   28   29
CONECT   10   11   11   17
CONECT   11   12   30
CONECT   12   13   14   14
CONECT   13   31
CONECT   14   15   16
CONECT   15   32   33   34
CONECT   16   17   17   35
CONECT   17   18
CONECT   18   36
END

HMDB0032116
     RDKit          3D
Helinorbisabone
 36 36  0  0  0  0  0  0  0  0999 V2000
   -5.3591    0.0766    0.2563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8839   -0.7962   -0.8436 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7213   -1.3242   -1.6067 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4731   -1.0586   -1.0543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5862   -0.4760   -0.2651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1239   -0.7246   -0.4325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9489   -2.0558    0.1538 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3767    0.2202    0.5207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8769    1.6163    0.0218 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0689    0.1415    0.3214 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6652    0.5394   -0.8734 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0720    0.5431   -0.9470 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7335    0.9399   -2.1206 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8312    0.1601    0.1443 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3069    0.1609   -0.0024 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2006   -0.2264    1.3213 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8280   -0.2291    1.3951 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2402   -0.6204    2.5694 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4496   -0.1270    0.4297 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8189   -0.1859    1.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2643    1.1536    0.0541 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1145   -1.7176   -1.8332 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9081    0.1962    0.5220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7409   -0.7594   -1.4338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1828   -1.9424    1.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7671    0.1296    1.5114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1100    1.5189   -1.0649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0187    2.2935    0.1949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7769    1.8745    0.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1266    0.8787   -1.7365 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7470    0.9494   -2.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6946    1.1500   -0.2320 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6279   -0.5195   -0.8277 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7636   -0.2844    0.9290 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8224   -0.5246    2.1732 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7733   -0.9704    3.3694 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 17 18  1  0
 17 10  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  5 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
  9 29  1  0
 11 30  1  0
 13 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 18 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₄H₁₈O₄

Average Molecular Weight

250.2903

Monoisotopic Molecular Weight

250.120509064

IUPAC Name

(3E)-6-(2,5-dihydroxy-4-methylphenyl)-5-hydroxyhept-3-en-2-one

Traditional Name

(3E)-6-(2,5-dihydroxy-4-methylphenyl)-5-hydroxyhept-3-en-2-one

CAS Registry Number

201288-95-1

SMILES

CC(C(O)\C=C\C(C)=O)C1=C(O)C=C(C)C(O)=C1

InChI Identifier

InChI=1S/C14H18O4/c1-8-6-14(18)11(7-13(8)17)10(3)12(16)5-4-9(2)15/h4-7,10,12,16-18H,1-3H3/b5-4+

InChI Key

QUWXRNSZOIJARN-SNAWJCMRSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as aromatic monoterpenoids. These are monoterpenoids containing at least one aromatic ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Aromatic monoterpenoids

Alternative Parents

Substituents

P-cymene
Aromatic monoterpenoid
Monocyclic monoterpenoid
Hydroquinone
M-cresol
O-cresol
1-hydroxy-2-unsubstituted benzenoid
Phenol
Toluene
Benzenoid
Monocyclic benzene moiety
Alpha,beta-unsaturated ketone
Enone
Acryloyl-group
Ketone
Secondary alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Alcohol
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0032116)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032116)

Source

Endogenous

Endogenous (HMDB: HMDB0032116)

Animal

Animal (HMDB: HMDB0032116)

Exogenous

Food

Food (HMDB: HMDB0032116)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0032116)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0032116)

Cellular process

Cell signaling (HMDB: HMDB0032116)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0032116)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0032116)

Nutrient

Nutrient (HMDB: HMDB0032116)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0032116)

Emulsifier (HMDB: HMDB0032116)

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	0.58 g/L	ALOGPS
logP	1.97	ALOGPS
logP	2.31	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	10.08	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	70.8 m³·mol⁻¹	ChemAxon
Polarizability	26.68 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
DeepCCS	[M+H]+	168.348	30932474
DeepCCS	[M-H]-	165.99	30932474
DeepCCS	[M-2H]-	198.877	30932474
DeepCCS	[M+Na]+	174.441	30932474
AllCCS	[M+H]+	159.1	32859911
AllCCS	[M+H-H2O]+	155.4	32859911
AllCCS	[M+NH4]+	162.6	32859911
AllCCS	[M+Na]+	163.6	32859911
AllCCS	[M-H]-	160.6	32859911
AllCCS	[M+Na-2H]-	161.0	32859911
AllCCS	[M+HCOO]-	161.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Helinorbisabone	CC(C(O)\C=C\C(C)=O)C1=C(O)C=C(C)C(O)=C1	3815.3	Standard polar	33892256
Helinorbisabone	CC(C(O)\C=C\C(C)=O)C1=C(O)C=C(C)C(O)=C1	2212.5	Standard non polar	33892256
Helinorbisabone	CC(C(O)\C=C\C(C)=O)C1=C(O)C=C(C)C(O)=C1	2347.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Helinorbisabone,1TMS,isomer #1	CC(=O)/C=C/C(O[Si](C)(C)C)C(C)C1=CC(O)=C(C)C=C1O	2263.6	Semi standard non polar	33892256
Helinorbisabone,1TMS,isomer #2	CC(=O)/C=C/C(O)C(C)C1=CC(O)=C(C)C=C1O[Si](C)(C)C	2257.2	Semi standard non polar	33892256
Helinorbisabone,1TMS,isomer #3	CC(=O)/C=C/C(O)C(C)C1=CC(O[Si](C)(C)C)=C(C)C=C1O	2227.3	Semi standard non polar	33892256
Helinorbisabone,1TMS,isomer #4	C=C(/C=C/C(O)C(C)C1=CC(O)=C(C)C=C1O)O[Si](C)(C)C	2351.6	Semi standard non polar	33892256
Helinorbisabone,2TMS,isomer #1	CC(=O)/C=C/C(O[Si](C)(C)C)C(C)C1=CC(O[Si](C)(C)C)=C(C)C=C1O	2210.5	Semi standard non polar	33892256
Helinorbisabone,2TMS,isomer #2	CC(=O)/C=C/C(O[Si](C)(C)C)C(C)C1=CC(O)=C(C)C=C1O[Si](C)(C)C	2225.0	Semi standard non polar	33892256
Helinorbisabone,2TMS,isomer #3	C=C(/C=C/C(O[Si](C)(C)C)C(C)C1=CC(O)=C(C)C=C1O)O[Si](C)(C)C	2328.4	Semi standard non polar	33892256
Helinorbisabone,2TMS,isomer #4	CC(=O)/C=C/C(O)C(C)C1=CC(O[Si](C)(C)C)=C(C)C=C1O[Si](C)(C)C	2229.5	Semi standard non polar	33892256
Helinorbisabone,2TMS,isomer #5	C=C(/C=C/C(O)C(C)C1=CC(O)=C(C)C=C1O[Si](C)(C)C)O[Si](C)(C)C	2301.0	Semi standard non polar	33892256
Helinorbisabone,2TMS,isomer #6	C=C(/C=C/C(O)C(C)C1=CC(O[Si](C)(C)C)=C(C)C=C1O)O[Si](C)(C)C	2282.1	Semi standard non polar	33892256
Helinorbisabone,3TMS,isomer #1	CC(=O)/C=C/C(O[Si](C)(C)C)C(C)C1=CC(O[Si](C)(C)C)=C(C)C=C1O[Si](C)(C)C	2218.9	Semi standard non polar	33892256
Helinorbisabone,3TMS,isomer #2	C=C(/C=C/C(O[Si](C)(C)C)C(C)C1=CC(O[Si](C)(C)C)=C(C)C=C1O)O[Si](C)(C)C	2271.2	Semi standard non polar	33892256
Helinorbisabone,3TMS,isomer #3	C=C(/C=C/C(O[Si](C)(C)C)C(C)C1=CC(O)=C(C)C=C1O[Si](C)(C)C)O[Si](C)(C)C	2264.7	Semi standard non polar	33892256
Helinorbisabone,3TMS,isomer #4	C=C(/C=C/C(O)C(C)C1=CC(O[Si](C)(C)C)=C(C)C=C1O[Si](C)(C)C)O[Si](C)(C)C	2262.9	Semi standard non polar	33892256
Helinorbisabone,4TMS,isomer #1	C=C(/C=C/C(O[Si](C)(C)C)C(C)C1=CC(O[Si](C)(C)C)=C(C)C=C1O[Si](C)(C)C)O[Si](C)(C)C	2263.7	Semi standard non polar	33892256
Helinorbisabone,4TMS,isomer #1	C=C(/C=C/C(O[Si](C)(C)C)C(C)C1=CC(O[Si](C)(C)C)=C(C)C=C1O[Si](C)(C)C)O[Si](C)(C)C	2316.0	Standard non polar	33892256
Helinorbisabone,1TBDMS,isomer #1	CC(=O)/C=C/C(O[Si](C)(C)C(C)(C)C)C(C)C1=CC(O)=C(C)C=C1O	2567.9	Semi standard non polar	33892256
Helinorbisabone,1TBDMS,isomer #2	CC(=O)/C=C/C(O)C(C)C1=CC(O)=C(C)C=C1O[Si](C)(C)C(C)(C)C	2549.8	Semi standard non polar	33892256
Helinorbisabone,1TBDMS,isomer #3	CC(=O)/C=C/C(O)C(C)C1=CC(O[Si](C)(C)C(C)(C)C)=C(C)C=C1O	2505.5	Semi standard non polar	33892256
Helinorbisabone,1TBDMS,isomer #4	C=C(/C=C/C(O)C(C)C1=CC(O)=C(C)C=C1O)O[Si](C)(C)C(C)(C)C	2617.7	Semi standard non polar	33892256
Helinorbisabone,2TBDMS,isomer #1	CC(=O)/C=C/C(O[Si](C)(C)C(C)(C)C)C(C)C1=CC(O[Si](C)(C)C(C)(C)C)=C(C)C=C1O	2786.7	Semi standard non polar	33892256
Helinorbisabone,2TBDMS,isomer #2	CC(=O)/C=C/C(O[Si](C)(C)C(C)(C)C)C(C)C1=CC(O)=C(C)C=C1O[Si](C)(C)C(C)(C)C	2775.3	Semi standard non polar	33892256
Helinorbisabone,2TBDMS,isomer #3	C=C(/C=C/C(O[Si](C)(C)C(C)(C)C)C(C)C1=CC(O)=C(C)C=C1O)O[Si](C)(C)C(C)(C)C	2869.7	Semi standard non polar	33892256
Helinorbisabone,2TBDMS,isomer #4	CC(=O)/C=C/C(O)C(C)C1=CC(O[Si](C)(C)C(C)(C)C)=C(C)C=C1O[Si](C)(C)C(C)(C)C	2789.5	Semi standard non polar	33892256
Helinorbisabone,2TBDMS,isomer #5	C=C(/C=C/C(O)C(C)C1=CC(O)=C(C)C=C1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2844.4	Semi standard non polar	33892256
Helinorbisabone,2TBDMS,isomer #6	C=C(/C=C/C(O)C(C)C1=CC(O[Si](C)(C)C(C)(C)C)=C(C)C=C1O)O[Si](C)(C)C(C)(C)C	2825.6	Semi standard non polar	33892256
Helinorbisabone,3TBDMS,isomer #1	CC(=O)/C=C/C(O[Si](C)(C)C(C)(C)C)C(C)C1=CC(O[Si](C)(C)C(C)(C)C)=C(C)C=C1O[Si](C)(C)C(C)(C)C	2966.8	Semi standard non polar	33892256
Helinorbisabone,3TBDMS,isomer #2	C=C(/C=C/C(O[Si](C)(C)C(C)(C)C)C(C)C1=CC(O[Si](C)(C)C(C)(C)C)=C(C)C=C1O)O[Si](C)(C)C(C)(C)C	3035.8	Semi standard non polar	33892256
Helinorbisabone,3TBDMS,isomer #3	C=C(/C=C/C(O[Si](C)(C)C(C)(C)C)C(C)C1=CC(O)=C(C)C=C1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3009.9	Semi standard non polar	33892256
Helinorbisabone,3TBDMS,isomer #4	C=C(/C=C/C(O)C(C)C1=CC(O[Si](C)(C)C(C)(C)C)=C(C)C=C1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3042.2	Semi standard non polar	33892256
Helinorbisabone,4TBDMS,isomer #1	C=C(/C=C/C(O[Si](C)(C)C(C)(C)C)C(C)C1=CC(O[Si](C)(C)C(C)(C)C)=C(C)C=C1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3188.4	Semi standard non polar	33892256
Helinorbisabone,4TBDMS,isomer #1	C=C(/C=C/C(O[Si](C)(C)C(C)(C)C)C(C)C1=CC(O[Si](C)(C)C(C)(C)C)=C(C)C=C1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	3067.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Helinorbisabone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0uxr-7930000000-06ae271e48b9cafde6f8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Helinorbisabone GC-MS (3 TMS) - 70eV, Positive	splash10-0udi-4122900000-1052a30aecc18a4e2a3f	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Helinorbisabone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Helinorbisabone 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 - Helinorbisabone 10V, Positive-QTOF	splash10-0f89-0190000000-b14ecd1b460248361eed	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Helinorbisabone 20V, Positive-QTOF	splash10-0fsi-1960000000-60b7b0cf49b45ee73db4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Helinorbisabone 40V, Positive-QTOF	splash10-0gb9-4920000000-bc37ff594f6fd046a965	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Helinorbisabone 10V, Negative-QTOF	splash10-0002-0190000000-3bfe04af472e7caab67a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Helinorbisabone 20V, Negative-QTOF	splash10-05i1-2950000000-55acbf8f34b5e3f11595	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Helinorbisabone 40V, Negative-QTOF	splash10-0kmi-5900000000-b55324811e09b4ca4ea1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Helinorbisabone 10V, Negative-QTOF	splash10-0002-0190000000-7b2c3b5869bc5cd5b5b7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Helinorbisabone 20V, Negative-QTOF	splash10-0ugs-2900000000-4e1171fbca97b89ce06c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Helinorbisabone 40V, Negative-QTOF	splash10-00ei-3900000000-c9925f87a88248cdc78e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Helinorbisabone 10V, Positive-QTOF	splash10-0zgi-0940000000-b40ec97a1ff7d64f53a2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Helinorbisabone 20V, Positive-QTOF	splash10-0ar0-3920000000-cc6c4b1fc3f143d48506	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Helinorbisabone 40V, Positive-QTOF	splash10-000x-8900000000-dddb1e7870eb588b3e4c	2021-09-23	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

FDB008838

KNApSAcK ID

C00058002

Chemspider ID

8786036

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10610669

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 Helinorbisabone (HMDB0032116)

MOL for HMDB0032116 (Helinorbisabone)

3D MOL for HMDB0032116 (Helinorbisabone)

3D SDF for HMDB0032116 (Helinorbisabone)

3D-SDF for HMDB0032116 (Helinorbisabone)

PDB for HMDB0032116 (Helinorbisabone)

3D PDB for HMDB0032116 (Helinorbisabone)

SMILES for HMDB0032116 (Helinorbisabone)

INCHI for HMDB0032116 (Helinorbisabone)

Structure for HMDB0032116 (Helinorbisabone)

3D Structure for HMDB0032116 (Helinorbisabone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra