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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:44:11 UTC

Update Date

2022-03-07 02:54:58 UTC

HMDB ID

HMDB0036578

Secondary Accession Numbers

HMDB36578

Metabolite Identification

Common Name

Cyperotundone

Description

Cyperotundone, also known as articulone or cyperenone, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a significant number of articles have been published on Cyperotundone.

Structure

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

HMDB0036578
     RDKit          3D
Cyperotundone
 40 42  0  0  0  0  0  0  0  0999 V2000
    2.4140   -0.5564    2.5076 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7066   -0.0639    1.5352 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4127    0.7260    1.5913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2292    0.1975    0.3347 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9318   -0.0246   -0.6106 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0294   -0.1737    0.0923 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4250   -0.4184   -0.3949 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3767    0.0328   -1.9759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718    0.5117   -1.8043 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9031   -0.7456   -1.7311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3188   -1.7180   -0.7356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0618   -1.0075    0.5485 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5653   -1.9232    1.6407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9963    1.2104   -0.4618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1445    2.4451   -0.6225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3289    1.5601    0.1039 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3148   -1.0960    2.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0971   -0.4236    3.5249 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7141    1.7858    1.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1519    0.5088    2.5096 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3461   -0.8356   -1.4288 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9469   -1.1818    0.2220 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9990    0.5244   -0.4909 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8772    0.7970   -2.6089 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4140   -0.9618   -2.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4078    1.1435   -2.6212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7927   -1.2409   -2.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9708   -0.5706   -1.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1574   -2.4475   -0.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4482   -2.2611   -1.1333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0689   -0.6400    0.9104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4160   -2.3632    1.4421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2867   -2.7929    1.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6730   -1.4559    2.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9326    2.2213   -0.4974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3542    2.9713   -1.5925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4231    3.1438    0.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5011    2.6550   -0.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3327    1.4378    1.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1656    1.0297   -0.3505 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  4  3  1  1
  4  5  1  0
  5  6  2  0
  6  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  9 14  1  0
 14 15  1  0
 14 16  1  0
  6  2  1  0
 12  4  1  0
 14  4  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  7 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  6
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  1
 13 32  1  0
 13 33  1  0
 13 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
M  END

  Mrv0541 06301305362D          

 16 18  0  0  0  0            999 V2000
    0.0000    1.2282    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7433    0.8703    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4125   -0.5791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9269    0.0660    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7433    0.8703    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9269    0.0660    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7019   -0.2336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6587   -1.0574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8618   -1.2709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.5791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5661   -2.0411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2998   -1.5766    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3883    1.3846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1225    0.2496    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2900    0.9640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0910   -0.5473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  6  1  0  0  0  0
 10  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  1  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  6 10  1  0  0  0  0
  9 11  1  0  0  0  0
  8 12  2  0  0  0  0
  2 13  1  6  0  0  0
  6 14  1  1  0  0  0
  4 14  1  1  0  0  0
 14 15  1  1  0  0  0
 14 16  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0036578

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@@H]1CC[C@@H]2CC3=C(C)C(=C)C[C@]13C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C16H24/c1-10-9-16-11(2)6-7-13(15(16,4)5)8-14(16)12(10)3/h11,13H,1,6-9H2,2-5H3/t11-,13-,16+/m1/s1

> <INCHI_KEY>
CASPQMNSCBDWDR-KFNAQCHYSA-N

> <FORMULA>
C16H24

> <MOLECULAR_WEIGHT>
216.3618

> <EXACT_MASS>
216.187800768

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
26.954988807413038

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,7R,10R)-4,10,11,11-tetramethyl-3-methylidenetricyclo[5.3.1.0¹,⁵]undec-4-ene

> <ALOGPS_LOGP>
5.63

> <JCHEM_LOGP>
3.9968736469999997

> <ALOGPS_LOGS>
-4.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
69.7539

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.22e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,7R,10R)-4,10,11,11-tetramethyl-3-methylidenetricyclo[5.3.1.0¹,⁵]undec-4-ene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0036578
     RDKit          3D
Cyperotundone
 40 42  0  0  0  0  0  0  0  0999 V2000
    2.4140   -0.5564    2.5076 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7066   -0.0639    1.5352 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4127    0.7260    1.5913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2292    0.1975    0.3347 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9318   -0.0246   -0.6106 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0294   -0.1737    0.0923 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4250   -0.4184   -0.3949 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3767    0.0328   -1.9759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718    0.5117   -1.8043 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9031   -0.7456   -1.7311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3188   -1.7180   -0.7356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0618   -1.0075    0.5485 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5653   -1.9232    1.6407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9963    1.2104   -0.4618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1445    2.4451   -0.6225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3289    1.5601    0.1039 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3148   -1.0960    2.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0971   -0.4236    3.5249 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7141    1.7858    1.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1519    0.5088    2.5096 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3461   -0.8356   -1.4288 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9469   -1.1818    0.2220 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9990    0.5244   -0.4909 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8772    0.7970   -2.6089 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4140   -0.9618   -2.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4078    1.1435   -2.6212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7927   -1.2409   -2.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9708   -0.5706   -1.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1574   -2.4475   -0.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4482   -2.2611   -1.1333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0689   -0.6400    0.9104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4160   -2.3632    1.4421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2867   -2.7929    1.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6730   -1.4559    2.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9326    2.2213   -0.4974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3542    2.9713   -1.5925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4231    3.1438    0.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5011    2.6550   -0.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3327    1.4378    1.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1656    1.0297   -0.3505 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  4  3  1  1
  4  5  1  0
  5  6  2  0
  6  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  9 14  1  0
 14 15  1  0
 14 16  1  0
  6  2  1  0
 12  4  1  0
 14  4  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  7 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  6
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  1
 13 32  1  0
 13 33  1  0
 13 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
M  END

HEADER    PROTEIN                                 30-JUN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUN-13         0                                  
HETATM    1  C   UNK     0       0.000   2.293   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.387   1.625   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.770  -1.081   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.730   0.123   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.387   1.625   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.730   0.123   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.177  -0.436   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.096  -1.974   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.609  -2.372   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.770  -1.081   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.057  -3.810   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.293  -2.943   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.591   2.585   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.229   0.466   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.541   1.799   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.170  -1.022   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    6   13                                                  
CONECT    3   10    4                                                       
CONECT    4    3    5   14                                                  
CONECT    5    4    1                                                       
CONECT    6    2    7   10   14                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    3    9    6                                                  
CONECT   11    9                                                            
CONECT   12    8                                                            
CONECT   13    2                                                            
CONECT   14    6    4   15   16                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

COMPND    HMDB0036578
HETATM    1  C1  UNL     1       2.414  -0.556   2.508  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.707  -0.064   1.535  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.413   0.726   1.591  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.229   0.198   0.335  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.932  -0.025  -0.611  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.029  -0.174   0.092  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.425  -0.418  -0.395  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.377   0.033  -1.976  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.072   0.512  -1.804  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.903  -0.746  -1.731  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.319  -1.718  -0.736  1.00  0.00           C  
HETATM   12  C12 UNL     1      -1.062  -1.008   0.548  1.00  0.00           C  
HETATM   13  C13 UNL     1      -0.565  -1.923   1.641  1.00  0.00           C  
HETATM   14  C14 UNL     1      -0.996   1.210  -0.462  1.00  0.00           C  
HETATM   15  C15 UNL     1      -0.145   2.445  -0.623  1.00  0.00           C  
HETATM   16  C16 UNL     1      -2.329   1.560   0.104  1.00  0.00           C  
HETATM   17  H1  UNL     1       3.315  -1.096   2.297  1.00  0.00           H  
HETATM   18  H2  UNL     1       2.097  -0.424   3.525  1.00  0.00           H  
HETATM   19  H3  UNL     1       0.714   1.786   1.486  1.00  0.00           H  
HETATM   20  H4  UNL     1      -0.152   0.509   2.510  1.00  0.00           H  
HETATM   21  H5  UNL     1       3.346  -0.836  -1.429  1.00  0.00           H  
HETATM   22  H6  UNL     1       3.947  -1.182   0.222  1.00  0.00           H  
HETATM   23  H7  UNL     1       3.999   0.524  -0.491  1.00  0.00           H  
HETATM   24  H8  UNL     1       0.877   0.797  -2.609  1.00  0.00           H  
HETATM   25  H9  UNL     1       0.414  -0.962  -2.424  1.00  0.00           H  
HETATM   26  H10 UNL     1      -1.408   1.144  -2.621  1.00  0.00           H  
HETATM   27  H11 UNL     1      -1.793  -1.241  -2.740  1.00  0.00           H  
HETATM   28  H12 UNL     1      -2.971  -0.571  -1.600  1.00  0.00           H  
HETATM   29  H13 UNL     1      -2.157  -2.448  -0.523  1.00  0.00           H  
HETATM   30  H14 UNL     1      -0.448  -2.261  -1.133  1.00  0.00           H  
HETATM   31  H15 UNL     1      -2.069  -0.640   0.910  1.00  0.00           H  
HETATM   32  H16 UNL     1       0.416  -2.363   1.442  1.00  0.00           H  
HETATM   33  H17 UNL     1      -1.287  -2.793   1.656  1.00  0.00           H  
HETATM   34  H18 UNL     1      -0.673  -1.456   2.639  1.00  0.00           H  
HETATM   35  H19 UNL     1       0.933   2.221  -0.497  1.00  0.00           H  
HETATM   36  H20 UNL     1      -0.354   2.971  -1.592  1.00  0.00           H  
HETATM   37  H21 UNL     1      -0.423   3.144   0.195  1.00  0.00           H  
HETATM   38  H22 UNL     1      -2.501   2.655  -0.114  1.00  0.00           H  
HETATM   39  H23 UNL     1      -2.333   1.438   1.226  1.00  0.00           H  
HETATM   40  H24 UNL     1      -3.166   1.030  -0.350  1.00  0.00           H  
CONECT    1    2    2   17   18
CONECT    2    3    6
CONECT    3    4   19   20
CONECT    4    5   12   14
CONECT    5    6    6    8
CONECT    6    7
CONECT    7   21   22   23
CONECT    8    9   24   25
CONECT    9   10   14   26
CONECT   10   11   27   28
CONECT   11   12   29   30
CONECT   12   13   31
CONECT   13   32   33   34
CONECT   14   15   16
CONECT   15   35   36   37
CONECT   16   38   39   40
END

HMDB0036578
     RDKit          3D
Cyperotundone
 40 42  0  0  0  0  0  0  0  0999 V2000
    2.4140   -0.5564    2.5076 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7066   -0.0639    1.5352 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4127    0.7260    1.5913 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2292    0.1975    0.3347 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9318   -0.0246   -0.6106 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0294   -0.1737    0.0923 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4250   -0.4184   -0.3949 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3767    0.0328   -1.9759 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0718    0.5117   -1.8043 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9031   -0.7456   -1.7311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3188   -1.7180   -0.7356 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0618   -1.0075    0.5485 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5653   -1.9232    1.6407 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9963    1.2104   -0.4618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1445    2.4451   -0.6225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3289    1.5601    0.1039 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3148   -1.0960    2.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0971   -0.4236    3.5249 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7141    1.7858    1.4862 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1519    0.5088    2.5096 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3461   -0.8356   -1.4288 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9469   -1.1818    0.2220 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9990    0.5244   -0.4909 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8772    0.7970   -2.6089 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4140   -0.9618   -2.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4078    1.1435   -2.6212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7927   -1.2409   -2.7403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9708   -0.5706   -1.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1574   -2.4475   -0.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4482   -2.2611   -1.1333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0689   -0.6400    0.9104 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4160   -2.3632    1.4421 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2867   -2.7929    1.6557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6730   -1.4559    2.6386 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9326    2.2213   -0.4974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3542    2.9713   -1.5925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4231    3.1438    0.1947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5011    2.6550   -0.1139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3327    1.4378    1.2259 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1656    1.0297   -0.3505 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  4  3  1  1
  4  5  1  0
  5  6  2  0
  6  7  1  0
  5  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
  9 14  1  0
 14 15  1  0
 14 16  1  0
  6  2  1  0
 12  4  1  0
 14  4  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  7 21  1  0
  7 22  1  0
  7 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  6
 10 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 12 31  1  1
 13 32  1  0
 13 33  1  0
 13 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Articulone	HMDB
Cyperenone	HMDB
Isopatchoulenone	HMDB

Chemical Formula

C₁₆H₂₄

Average Molecular Weight

216.3618

Monoisotopic Molecular Weight

216.187800768

IUPAC Name

(1R,7R,10R)-4,10,11,11-tetramethyl-3-methylidenetricyclo[5.3.1.0¹,⁵]undec-4-ene

Traditional Name

(1R,7R,10R)-4,10,11,11-tetramethyl-3-methylidenetricyclo[5.3.1.0¹,⁵]undec-4-ene

CAS Registry Number

3466-15-7

SMILES

C[C@@H]1CC[C@@H]2CC3=C(C)C(=C)C[C@]13C2(C)C

InChI Identifier

InChI=1S/C16H24/c1-10-9-16-11(2)6-7-13(15(16,4)5)8-14(16)12(10)3/h11,13H,1,6-9H2,2-5H3/t11-,13-,16+/m1/s1

InChI Key

CASPQMNSCBDWDR-KFNAQCHYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Patchoulane sesquiterpenoid
Sesquiterpenoid
Branched unsaturated hydrocarbon
Polycyclic hydrocarbon
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0036578)
Membrane (HMDB: HMDB0036578)

Source

Exogenous

Exogenous (HMDB: HMDB0036578)

Food

Vegetable

Root vegetable

Root vegetables (FooDB: FOOD00873)

Endogenous

Endogenous (HMDB: HMDB0036578)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	46 - 47.5 °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	0.012 g/L	ALOGPS
logP	5.63	ALOGPS
logP	4	ChemAxon
logS	-4.2	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	69.75 m³·mol⁻¹	ChemAxon
Polarizability	26.95 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]+	152.53	31661259
DarkChem	[M-H]-	149.957	31661259
DeepCCS	[M-2H]-	192.68	30932474
DeepCCS	[M+Na]+	167.805	30932474
AllCCS	[M+H]+	149.7	32859911
AllCCS	[M+H-H2O]+	145.9	32859911
AllCCS	[M+NH4]+	153.3	32859911
AllCCS	[M+Na]+	154.3	32859911
AllCCS	[M-H]-	161.7	32859911
AllCCS	[M+Na-2H]-	161.8	32859911
AllCCS	[M+HCOO]-	162.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cyperotundone	C[C@@H]1CC[C@@H]2CC3=C(C)C(=C)C[C@]13C2(C)C	1758.2	Standard polar	33892256
Cyperotundone	C[C@@H]1CC[C@@H]2CC3=C(C)C(=C)C[C@]13C2(C)C	1488.4	Standard non polar	33892256
Cyperotundone	C[C@@H]1CC[C@@H]2CC3=C(C)C(=C)C[C@]13C2(C)C	1507.7	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cyperotundone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0zg0-1930000000-08e2dd60dbe06c293525	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cyperotundone 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 - Cyperotundone 10V, Positive-QTOF	splash10-014i-0190000000-df10cc334b2b94ac7107	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyperotundone 20V, Positive-QTOF	splash10-014i-1970000000-4e3b87716b4be929fe3f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyperotundone 40V, Positive-QTOF	splash10-0f79-3910000000-74a31a9b1245c4ca48ff	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyperotundone 10V, Negative-QTOF	splash10-014i-0090000000-3af05bc04f3cf1f962a7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyperotundone 20V, Negative-QTOF	splash10-014i-0090000000-65a6f7424c6127387be8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyperotundone 40V, Negative-QTOF	splash10-0002-0910000000-5be62bec5fd4cac7fa1b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyperotundone 10V, Positive-QTOF	splash10-014i-0090000000-1f496f5ccc0d51d2fcf5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyperotundone 20V, Positive-QTOF	splash10-014i-0190000000-0d96915e43415561f31d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyperotundone 40V, Positive-QTOF	splash10-014i-0190000000-50a0299b086f453859c0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyperotundone 10V, Negative-QTOF	splash10-014i-0090000000-1a33d3c7cd01cb07892e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyperotundone 20V, Negative-QTOF	splash10-014i-0090000000-1a33d3c7cd01cb07892e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cyperotundone 40V, Negative-QTOF	splash10-014i-0090000000-ebb810b08b3780e86475	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Cyperotundone

METLIN ID

Not Available

PubChem Compound

131752013

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1564211

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 Cyperotundone (HMDB0036578)

MOL for HMDB0036578 (Cyperotundone)

3D MOL for HMDB0036578 (Cyperotundone)

3D SDF for HMDB0036578 (Cyperotundone)

3D-SDF for HMDB0036578 (Cyperotundone)

PDB for HMDB0036578 (Cyperotundone)

3D PDB for HMDB0036578 (Cyperotundone)

SMILES for HMDB0036578 (Cyperotundone)

INCHI for HMDB0036578 (Cyperotundone)

Structure for HMDB0036578 (Cyperotundone)

3D Structure for HMDB0036578 (Cyperotundone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra