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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:48:36 UTC

Update Date

2022-03-07 02:55:00 UTC

HMDB ID

HMDB0036647

Secondary Accession Numbers

HMDB36647

Metabolite Identification

Common Name

Isocurcumenol

Description

Isocurcumenol belongs to the class of organic compounds known as guaianes. These are sesquiterpenoids with a structure based on the guaiane skeleton. Guaiane is a bicyclic compound consisting of a decahydroazulene moiety, substituted with two methyl groups and a 1-methylethyl group at the 1-, 4-, and 7-position, respectively. Isocurcumenol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

HMDB0036647
     RDKit          3D
Isocurcumenol
 39 41  0  0  0  0  0  0  0  0999 V2000
   -0.4146    2.8785    0.9323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5237    1.9751   -0.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4923    1.8966   -1.0783 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7063    0.4317   -1.4535 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4782    0.3790   -2.5845 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5257   -0.2167   -1.6721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0450   -0.3423   -0.4135 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0885   -0.7222    0.5013 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2690   -0.2676   -0.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5532   -0.4236   -0.0480 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9213   -1.1689    1.2007 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6378    0.0726   -0.9061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2567   -1.1754   -0.2761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0035   -2.6458   -0.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8658   -0.6692    1.0320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2948    0.7278    1.2451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6244    1.0318   -0.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4195    3.5634    0.9213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1242    2.9900    1.7452 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0570    2.3736   -1.9802 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4630    2.3072   -0.7907 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1485    1.0767   -3.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624   -1.8028    0.6162 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0409   -0.1851    1.4797 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6202   -2.2333    1.0331 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3498   -0.7691    2.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0157   -1.1129    1.3972 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8803   -0.6466   -1.7333 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5489    0.2213   -0.2907 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3953    1.0366   -1.4241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9202   -1.0233   -1.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3027   -3.0372   -0.8716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6847   -2.8996    0.9226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9693   -3.1652   -0.2789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9769   -0.6360    0.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5015   -1.3071    1.8470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6747    0.8106    2.1323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1675    1.4284    1.3765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3728    1.2492   -0.8308 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  3
 10 11  1  0
 10 12  1  0
  7 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17  2  1  0
  9  4  1  0
 17  7  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  5 22  1  0
  8 23  1  0
  8 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
M  END


  Mrv0541 05061309162D          

 17 19  0  0  0  0            999 V2000
    5.4747    0.4680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9456   -0.8371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2128    2.5839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1889   -1.0245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3047    0.1203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4007    0.9327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4643    1.8450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3421   -0.1770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8334   -0.0318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6159    1.8778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0493   -0.2234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2051    1.1159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0798    0.2735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6417    0.3596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8681    1.0949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6251    1.3913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2194    0.7541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  9  1  1  0  0  0  0
  9  2  1  0  0  0  0
 10  3  2  0  0  0  0
 10  7  1  0  0  0  0
 11  4  1  0  0  0  0
 11  5  1  0  0  0  0
 12  6  1  0  0  0  0
 12 10  1  0  0  0  0
 13  8  1  0  0  0  0
 13  9  2  0  0  0  0
 14  8  1  0  0  0  0
 14 11  1  0  0  0  0
 14 12  1  0  0  0  0
 15  7  1  0  0  0  0
 15 13  1  0  0  0  0
 16 15  1  0  0  0  0
 17 14  1  0  0  0  0
 17 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036647

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CCC2C(=C)CC3(O)OC12CC3=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O2/c1-9(2)13-8-14-11(4)5-6-12(14)10(3)7-15(13,16)17-14/h11-12,16H,3,5-8H2,1-2,4H3

> <INCHI_KEY>
DEBDFZGNZTYPMF-UHFFFAOYSA-N

> <FORMULA>
C15H22O2

> <MOLECULAR_WEIGHT>
234.334

> <EXACT_MASS>
234.161979948

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.073028199845503

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methyl-6-methylidene-9-(propan-2-ylidene)-11-oxatricyclo[6.2.1.0¹,⁵]undecan-8-ol

> <ALOGPS_LOGP>
2.37

> <JCHEM_LOGP>
2.815830776

> <ALOGPS_LOGS>
-2.65

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.405634743651454

> <JCHEM_PKA_STRONGEST_BASIC>
-4.3709753631268535

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
68.37049999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methyl-6-methylidene-9-(propan-2-ylidene)-11-oxatricyclo[6.2.1.0¹,⁵]undecan-8-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0036647
     RDKit          3D
Isocurcumenol
 39 41  0  0  0  0  0  0  0  0999 V2000
   -0.4146    2.8785    0.9323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5237    1.9751   -0.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4923    1.8966   -1.0783 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7063    0.4317   -1.4535 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4782    0.3790   -2.5845 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5257   -0.2167   -1.6721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0450   -0.3423   -0.4135 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0885   -0.7222    0.5013 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2690   -0.2676   -0.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5532   -0.4236   -0.0480 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9213   -1.1689    1.2007 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6378    0.0726   -0.9061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2567   -1.1754   -0.2761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0035   -2.6458   -0.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8658   -0.6692    1.0320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2948    0.7278    1.2451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6244    1.0318   -0.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4195    3.5634    0.9213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1242    2.9900    1.7452 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0570    2.3736   -1.9802 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4630    2.3072   -0.7907 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1485    1.0767   -3.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624   -1.8028    0.6162 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0409   -0.1851    1.4797 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6202   -2.2333    1.0331 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3498   -0.7691    2.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0157   -1.1129    1.3972 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8803   -0.6466   -1.7333 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5489    0.2213   -0.2907 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3953    1.0366   -1.4241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9202   -1.0233   -1.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3027   -3.0372   -0.8716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6847   -2.8996    0.9226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9693   -3.1652   -0.2789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9769   -0.6360    0.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5015   -1.3071    1.8470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6747    0.8106    2.1323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1675    1.4284    1.3765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3728    1.2492   -0.8308 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  3
 10 11  1  0
 10 12  1  0
  7 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17  2  1  0
  9  4  1  0
 17  7  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  5 22  1  0
  8 23  1  0
  8 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      10.219   0.874   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.232  -1.563   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.131   4.823   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.086  -1.912   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.435   0.225   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.615   1.741   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.467   3.444   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.239  -0.330   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.022  -0.059   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.883   3.505   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.825  -0.417   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.116   2.083   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.616   0.511   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.931   0.671   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.220   2.044   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.634   2.597   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       6.009   1.408   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4   11                                                            
CONECT    5    6   11                                                       
CONECT    6    5   12                                                       
CONECT    7   10   15                                                       
CONECT    8   13   14                                                       
CONECT    9    1    2   13                                                  
CONECT   10    3    7   12                                                  
CONECT   11    4    5   14                                                  
CONECT   12    6   10   14                                                  
CONECT   13    8    9   15                                                  
CONECT   14    8   11   12   17                                             
CONECT   15    7   13   16   17                                             
CONECT   16   15                                                            
CONECT   17   14   15                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

COMPND    HMDB0036647
HETATM    1  C1  UNL     1      -0.415   2.879   0.932  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.524   1.975  -0.008  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.492   1.897  -1.078  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.706   0.432  -1.454  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.478   0.379  -2.585  1.00  0.00           O  
HETATM    6  O2  UNL     1      -0.526  -0.217  -1.672  1.00  0.00           O  
HETATM    7  C5  UNL     1      -1.045  -0.342  -0.413  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.088  -0.722   0.501  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.269  -0.268  -0.286  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.553  -0.424  -0.048  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.921  -1.169   1.201  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.638   0.073  -0.906  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.257  -1.175  -0.276  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.004  -2.646  -0.107  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.866  -0.669   1.032  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.295   0.728   1.245  1.00  0.00           C  
HETATM   17  C15 UNL     1      -1.624   1.032  -0.040  1.00  0.00           C  
HETATM   18  H1  UNL     1       0.419   3.563   0.921  1.00  0.00           H  
HETATM   19  H2  UNL     1      -1.124   2.990   1.745  1.00  0.00           H  
HETATM   20  H3  UNL     1       0.057   2.374  -1.980  1.00  0.00           H  
HETATM   21  H4  UNL     1       1.463   2.307  -0.791  1.00  0.00           H  
HETATM   22  H5  UNL     1       1.149   1.077  -3.210  1.00  0.00           H  
HETATM   23  H6  UNL     1       0.162  -1.803   0.616  1.00  0.00           H  
HETATM   24  H7  UNL     1       0.041  -0.185   1.480  1.00  0.00           H  
HETATM   25  H8  UNL     1       2.620  -2.233   1.033  1.00  0.00           H  
HETATM   26  H9  UNL     1       2.350  -0.769   2.071  1.00  0.00           H  
HETATM   27  H10 UNL     1       4.016  -1.113   1.397  1.00  0.00           H  
HETATM   28  H11 UNL     1       3.880  -0.647  -1.733  1.00  0.00           H  
HETATM   29  H12 UNL     1       4.549   0.221  -0.291  1.00  0.00           H  
HETATM   30  H13 UNL     1       3.395   1.037  -1.424  1.00  0.00           H  
HETATM   31  H14 UNL     1      -2.920  -1.023  -1.130  1.00  0.00           H  
HETATM   32  H15 UNL     1      -1.303  -3.037  -0.872  1.00  0.00           H  
HETATM   33  H16 UNL     1      -1.685  -2.900   0.923  1.00  0.00           H  
HETATM   34  H17 UNL     1      -2.969  -3.165  -0.279  1.00  0.00           H  
HETATM   35  H18 UNL     1      -3.977  -0.636   0.960  1.00  0.00           H  
HETATM   36  H19 UNL     1      -2.502  -1.307   1.847  1.00  0.00           H  
HETATM   37  H20 UNL     1      -1.675   0.811   2.132  1.00  0.00           H  
HETATM   38  H21 UNL     1      -3.167   1.428   1.376  1.00  0.00           H  
HETATM   39  H22 UNL     1      -2.373   1.249  -0.831  1.00  0.00           H  
CONECT    1    2    2   18   19
CONECT    2    3   17
CONECT    3    4   20   21
CONECT    4    5    6    9
CONECT    5   22
CONECT    6    7
CONECT    7    8   13   17
CONECT    8    9   23   24
CONECT    9   10   10
CONECT   10   11   12
CONECT   11   25   26   27
CONECT   12   28   29   30
CONECT   13   14   15   31
CONECT   14   32   33   34
CONECT   15   16   35   36
CONECT   16   17   37   38
CONECT   17   39
END

HMDB0036647
     RDKit          3D
Isocurcumenol
 39 41  0  0  0  0  0  0  0  0999 V2000
   -0.4146    2.8785    0.9323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5237    1.9751   -0.0083 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4923    1.8966   -1.0783 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7063    0.4317   -1.4535 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4782    0.3790   -2.5845 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5257   -0.2167   -1.6721 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0450   -0.3423   -0.4135 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0885   -0.7222    0.5013 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2690   -0.2676   -0.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5532   -0.4236   -0.0480 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9213   -1.1689    1.2007 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6378    0.0726   -0.9061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2567   -1.1754   -0.2761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0035   -2.6458   -0.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8658   -0.6692    1.0320 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2948    0.7278    1.2451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6244    1.0318   -0.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4195    3.5634    0.9213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1242    2.9900    1.7452 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0570    2.3736   -1.9802 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4630    2.3072   -0.7907 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1485    1.0767   -3.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624   -1.8028    0.6162 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0409   -0.1851    1.4797 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6202   -2.2333    1.0331 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3498   -0.7691    2.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0157   -1.1129    1.3972 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8803   -0.6466   -1.7333 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5489    0.2213   -0.2907 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3953    1.0366   -1.4241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9202   -1.0233   -1.1300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3027   -3.0372   -0.8716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6847   -2.8996    0.9226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9693   -3.1652   -0.2789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9769   -0.6360    0.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5015   -1.3071    1.8470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6747    0.8106    2.1323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1675    1.4284    1.3765 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3728    1.2492   -0.8308 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  3
 10 11  1  0
 10 12  1  0
  7 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17  2  1  0
  9  4  1  0
 17  7  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  5 22  1  0
  8 23  1  0
  8 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
5,8-Epoxy-7(11),10(14)-guaiadien-8-ol	HMDB
Isocurcumenol	MeSH

Chemical Formula

C₁₅H₂₂O₂

Average Molecular Weight

234.334

Monoisotopic Molecular Weight

234.161979948

IUPAC Name

2-methyl-6-methylidene-9-(propan-2-ylidene)-11-oxatricyclo[6.2.1.0¹,⁵]undecan-8-ol

Traditional Name

2-methyl-6-methylidene-9-(propan-2-ylidene)-11-oxatricyclo[6.2.1.0¹,⁵]undecan-8-ol

CAS Registry Number

24063-71-6

SMILES

CC1CCC2C(=C)CC3(O)OC12CC3=C(C)C

InChI Identifier

InChI=1S/C15H22O2/c1-9(2)13-8-14-11(4)5-6-12(14)10(3)7-15(13,16)17-14/h11-12,16H,3,5-8H2,1-2,4H3

InChI Key

DEBDFZGNZTYPMF-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianes. These are sesquiterpenoids with a structure based on the guaiane skeleton. Guaiane is a bicyclic compound consisting of a decahydroazulene moiety, substituted with two methyl groups and a 1-methylethyl group at the 1-, 4-, and 7-position, respectively.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Guaianes

Alternative Parents

Not Available

Substituents

Not Available

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0036647)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036647)

Source

Endogenous

Endogenous (HMDB: HMDB0036647)

Animal

Animal (HMDB: HMDB0036647)

Exogenous

Food

Food (HMDB: HMDB0036647)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0036647)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0036647)

Cellular process

Cell signaling (HMDB: HMDB0036647)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0036647)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0036647)

Nutrient

Nutrient (HMDB: HMDB0036647)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036647)

Emulsifier (HMDB: HMDB0036647)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	139 - 141 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.52 g/L	ALOGPS
logP	2.37	ALOGPS
logP	2.82	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	11.41	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	68.37 m³·mol⁻¹	ChemAxon
Polarizability	27.07 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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]+	158.17	31661259
DarkChem	[M-H]-	151.446	31661259
DeepCCS	[M-2H]-	189.577	30932474
DeepCCS	[M+Na]+	165.142	30932474
AllCCS	[M+H]+	155.0	32859911
AllCCS	[M+H-H2O]+	151.2	32859911
AllCCS	[M+NH4]+	158.4	32859911
AllCCS	[M+Na]+	159.4	32859911
AllCCS	[M-H]-	162.2	32859911
AllCCS	[M+Na-2H]-	162.3	32859911
AllCCS	[M+HCOO]-	162.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isocurcumenol	CC1CCC2C(=C)CC3(O)OC12CC3=C(C)C	2361.3	Standard polar	33892256
Isocurcumenol	CC1CCC2C(=C)CC3(O)OC12CC3=C(C)C	1708.4	Standard non polar	33892256
Isocurcumenol	CC1CCC2C(=C)CC3(O)OC12CC3=C(C)C	1739.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isocurcumenol,1TMS,isomer #1	C=C1CC2(O[Si](C)(C)C)OC3(CC2=C(C)C)C(C)CCC13	1814.3	Semi standard non polar	33892256
Isocurcumenol,1TBDMS,isomer #1	C=C1CC2(O[Si](C)(C)C(C)(C)C)OC3(CC2=C(C)C)C(C)CCC13	2041.6	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 - Isocurcumenol GC-MS (Non-derivatized) - 70eV, Positive	splash10-066u-9450000000-0155648739bd0c9f2e13	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isocurcumenol GC-MS (1 TMS) - 70eV, Positive	splash10-007c-9030000000-8a290b7a6c56ae384df9	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isocurcumenol 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 - Isocurcumenol 10V, Positive-QTOF	splash10-000i-2090000000-99763a7e816918c2882a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocurcumenol 20V, Positive-QTOF	splash10-052r-9260000000-8986ab1f685941721341	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocurcumenol 40V, Positive-QTOF	splash10-0q29-9000000000-639cccc8969014a4450f	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocurcumenol 10V, Positive-QTOF	splash10-000i-2090000000-99763a7e816918c2882a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocurcumenol 20V, Positive-QTOF	splash10-052r-9260000000-8986ab1f685941721341	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocurcumenol 40V, Positive-QTOF	splash10-0q29-9000000000-639cccc8969014a4450f	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocurcumenol 10V, Negative-QTOF	splash10-001i-0090000000-02657c04ef3dad936d64	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocurcumenol 20V, Negative-QTOF	splash10-001i-0290000000-6caf1111326d1db8c558	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocurcumenol 40V, Negative-QTOF	splash10-0173-1910000000-8ab79d9593cace8231b0	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocurcumenol 10V, Negative-QTOF	splash10-001i-0090000000-02657c04ef3dad936d64	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocurcumenol 20V, Negative-QTOF	splash10-001i-0290000000-6caf1111326d1db8c558	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocurcumenol 40V, Negative-QTOF	splash10-0173-1910000000-8ab79d9593cace8231b0	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocurcumenol 10V, Positive-QTOF	splash10-000i-0090000000-2f85d9144addaa938e0f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocurcumenol 20V, Positive-QTOF	splash10-000i-0190000000-9aef1612e13c9ddd67a6	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocurcumenol 40V, Positive-QTOF	splash10-05mx-9730000000-fb7eb05dae44f05ea6d9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocurcumenol 10V, Negative-QTOF	splash10-001i-0090000000-9087f47ed0ae51229a17	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocurcumenol 20V, Negative-QTOF	splash10-001i-0090000000-9087f47ed0ae51229a17	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocurcumenol 40V, Negative-QTOF	splash10-0159-0960000000-0cf8779fb69e4e2bf7c2	2021-09-25	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

FDB015572

KNApSAcK ID

C00020352

Chemspider ID

4421957

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5255901

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 Isocurcumenol (HMDB0036647)

MOL for HMDB0036647 (Isocurcumenol)

3D MOL for HMDB0036647 (Isocurcumenol)

3D SDF for HMDB0036647 (Isocurcumenol)

3D-SDF for HMDB0036647 (Isocurcumenol)

PDB for HMDB0036647 (Isocurcumenol)

3D PDB for HMDB0036647 (Isocurcumenol)

SMILES for HMDB0036647 (Isocurcumenol)

INCHI for HMDB0036647 (Isocurcumenol)

Structure for HMDB0036647 (Isocurcumenol)

3D Structure for HMDB0036647 (Isocurcumenol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra