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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:31:25 UTC

Update Date

2022-03-07 02:56:05 UTC

HMDB ID

HMDB0039155

Secondary Accession Numbers

HMDB39155

Metabolite Identification

Common Name

ar-Artemisene

Description

ar-Artemisene belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a small amount of articles have been published on ar-Artemisene.

Structure

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

HMDB0039155
     RDKit          3D
ar-Artemisene
 50 50  0  0  0  0  0  0  0  0999 V2000
    2.1815   -0.3824   -1.9339 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7783   -0.1948   -0.6932 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6710    0.3294    0.3702 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0497    0.5816   -0.1685 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0922   -0.0434    0.3349 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4917    0.1412   -0.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3695    0.6536    0.9843 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0829   -1.1676   -0.6365 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3794   -0.5270   -0.3370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3019    0.7269    0.1524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7461    0.4718    0.5350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5698   -0.0357   -0.5992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5834    0.9700   -1.7509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9799   -0.1728   -0.1470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6345   -1.3876   -0.2295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9504   -1.5017    0.1961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6306   -0.4070    0.7091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0432   -0.5087    1.1713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9649    0.7982    0.7853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6704    0.8915    0.3618 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1978   -0.1510   -2.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5127   -0.7634   -2.6833 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2509    1.2860    0.7968 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7444   -0.3779    1.2042 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2261    1.2789   -0.9798 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9372   -0.7440    1.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5570    0.8562   -0.9807 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5059    1.7593    0.8807 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3857    0.2035    0.9725 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9509    0.4603    1.9903 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5439   -1.5568   -1.5155 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1165   -0.9153   -0.9829 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1919   -1.8984    0.1745 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3817   -1.2955    0.4847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1859   -0.9377   -1.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2525    1.1615    0.9986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2941    1.4517   -0.6883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7245   -0.3155    1.3199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1720    1.4262    0.8898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2016   -1.0110   -0.9740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9075    0.6179   -2.5483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6017    1.0421   -2.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3226    1.9808   -1.3816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0977   -2.2363   -0.6305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4674   -2.4510    0.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6462    0.3454    0.7983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4325   -1.4725    0.7818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0373   -0.4869    2.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5033    1.6553    1.1889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1820    1.8526    0.4372 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  2  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  2  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 14  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 13 43  1  0
 15 44  1  0
 16 45  1  0
 18 46  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
 20 50  1  0
M  END


  Mrv0541 05061310532D          

 20 20  0  0  0  0            999 V2000
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8  6  2  0  0  0  0
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  7  1  0  0  0  0
 14 12  1  0  0  0  0
 15 13  2  0  0  0  0
 16  1  1  0  0  0  0
 16  2  1  0  0  0  0
 16  8  1  0  0  0  0
 17  3  2  0  0  0  0
 17  9  1  0  0  0  0
 17 10  1  0  0  0  0
 18  4  1  0  0  0  0
 18 12  2  0  0  0  0
 18 13  1  0  0  0  0
 19  5  1  0  0  0  0
 19 11  1  0  0  0  0
 20 14  2  0  0  0  0
 20 15  1  0  0  0  0
 20 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0039155

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H30/c1-16(2)8-6-9-17(3)10-7-11-19(5)20-14-12-18(4)13-15-20/h6,8,12-16,19H,3,7,9-11H2,1-2,4-5H3/b8-6+

> <INCHI_KEY>
KVCMFLFVCBKBMA-SOFGYWHQSA-N

> <FORMULA>
C20H30

> <MOLECULAR_WEIGHT>
270.4522

> <EXACT_MASS>
270.23475096

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
35.20211185377226

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1-methyl-4-[(8E)-10-methyl-6-methylideneundec-8-en-2-yl]benzene

> <ALOGPS_LOGP>
7.51

> <JCHEM_LOGP>
7.152696400999999

> <ALOGPS_LOGS>
-6.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
92.08929999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.64e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-methyl-4-[(8E)-10-methyl-6-methylideneundec-8-en-2-yl]benzene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0039155
     RDKit          3D
ar-Artemisene
 50 50  0  0  0  0  0  0  0  0999 V2000
    2.1815   -0.3824   -1.9339 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7783   -0.1948   -0.6932 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6710    0.3294    0.3702 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0497    0.5816   -0.1685 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0922   -0.0434    0.3349 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4917    0.1412   -0.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3695    0.6536    0.9843 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0829   -1.1676   -0.6365 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3794   -0.5270   -0.3370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3019    0.7269    0.1524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7461    0.4718    0.5350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5698   -0.0357   -0.5992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5834    0.9700   -1.7509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9799   -0.1728   -0.1470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6345   -1.3876   -0.2295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9504   -1.5017    0.1961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6306   -0.4070    0.7091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0432   -0.5087    1.1713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9649    0.7982    0.7853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6704    0.8915    0.3618 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1978   -0.1510   -2.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5127   -0.7634   -2.6833 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2509    1.2860    0.7968 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7444   -0.3779    1.2042 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2261    1.2789   -0.9798 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9372   -0.7440    1.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5570    0.8562   -0.9807 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5059    1.7593    0.8807 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3857    0.2035    0.9725 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9509    0.4603    1.9903 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5439   -1.5568   -1.5155 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1165   -0.9153   -0.9829 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1919   -1.8984    0.1745 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3817   -1.2955    0.4847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1859   -0.9377   -1.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2525    1.1615    0.9986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2941    1.4517   -0.6883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7245   -0.3155    1.3199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1720    1.4262    0.8898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2016   -1.0110   -0.9740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9075    0.6179   -2.5483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6017    1.0421   -2.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3226    1.9808   -1.3816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0977   -2.2363   -0.6305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4674   -2.4510    0.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6462    0.3454    0.7983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4325   -1.4725    0.7818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0373   -0.4869    2.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5033    1.6553    1.1889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1820    1.8526    0.4372 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  2  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  2  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 14  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 13 43  1  0
 15 44  1  0
 16 45  1  0
 18 46  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
 20 50  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      20.005  -3.850   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.671   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.003  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002  -1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669  -1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.337  -1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      18.672  -1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      17.338  -3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.338  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      16.004  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      18.672  -3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.671  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      16.004  -1.540   0.000  0.00  0.00           C+0
CONECT    1   16                                                            
CONECT    2   16                                                            
CONECT    3   17                                                            
CONECT    4   18                                                            
CONECT    5   19                                                            
CONECT    6    8    9                                                       
CONECT    7   10   11                                                       
CONECT    8    6   16                                                       
CONECT    9    6   17                                                       
CONECT   10    7   17                                                       
CONECT   11    7   19                                                       
CONECT   12   14   18                                                       
CONECT   13   15   18                                                       
CONECT   14   12   20                                                       
CONECT   15   13   20                                                       
CONECT   16    1    2    8                                                  
CONECT   17    3    9   10                                                  
CONECT   18    4   12   13                                                  
CONECT   19    5   11   20                                                  
CONECT   20   14   15   19                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

COMPND    HMDB0039155
HETATM    1  C1  UNL     1       2.181  -0.382  -1.934  1.00  0.00           C  
HETATM    2  C2  UNL     1       1.778  -0.195  -0.693  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.671   0.329   0.370  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.050   0.582  -0.168  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.092  -0.043   0.335  1.00  0.00           C  
HETATM    6  C6  UNL     1       6.492   0.141  -0.132  1.00  0.00           C  
HETATM    7  C7  UNL     1       7.370   0.654   0.984  1.00  0.00           C  
HETATM    8  C8  UNL     1       7.083  -1.168  -0.637  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.379  -0.527  -0.337  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.302   0.727   0.152  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.746   0.472   0.535  1.00  0.00           C  
HETATM   12  C12 UNL     1      -2.570  -0.036  -0.599  1.00  0.00           C  
HETATM   13  C13 UNL     1      -2.583   0.970  -1.751  1.00  0.00           C  
HETATM   14  C14 UNL     1      -3.980  -0.173  -0.147  1.00  0.00           C  
HETATM   15  C15 UNL     1      -4.634  -1.388  -0.229  1.00  0.00           C  
HETATM   16  C16 UNL     1      -5.950  -1.502   0.196  1.00  0.00           C  
HETATM   17  C17 UNL     1      -6.631  -0.407   0.709  1.00  0.00           C  
HETATM   18  C18 UNL     1      -8.043  -0.509   1.171  1.00  0.00           C  
HETATM   19  C19 UNL     1      -5.965   0.798   0.785  1.00  0.00           C  
HETATM   20  C20 UNL     1      -4.670   0.892   0.362  1.00  0.00           C  
HETATM   21  H1  UNL     1       3.198  -0.151  -2.205  1.00  0.00           H  
HETATM   22  H2  UNL     1       1.513  -0.763  -2.683  1.00  0.00           H  
HETATM   23  H3  UNL     1       2.251   1.286   0.797  1.00  0.00           H  
HETATM   24  H4  UNL     1       2.744  -0.378   1.204  1.00  0.00           H  
HETATM   25  H5  UNL     1       4.226   1.279  -0.980  1.00  0.00           H  
HETATM   26  H6  UNL     1       4.937  -0.744   1.146  1.00  0.00           H  
HETATM   27  H7  UNL     1       6.557   0.856  -0.981  1.00  0.00           H  
HETATM   28  H8  UNL     1       7.506   1.759   0.881  1.00  0.00           H  
HETATM   29  H9  UNL     1       8.386   0.203   0.972  1.00  0.00           H  
HETATM   30  H10 UNL     1       6.951   0.460   1.990  1.00  0.00           H  
HETATM   31  H11 UNL     1       6.544  -1.557  -1.515  1.00  0.00           H  
HETATM   32  H12 UNL     1       8.116  -0.915  -0.983  1.00  0.00           H  
HETATM   33  H13 UNL     1       7.192  -1.898   0.174  1.00  0.00           H  
HETATM   34  H14 UNL     1       0.382  -1.295   0.485  1.00  0.00           H  
HETATM   35  H15 UNL     1      -0.186  -0.938  -1.212  1.00  0.00           H  
HETATM   36  H16 UNL     1       0.252   1.162   0.999  1.00  0.00           H  
HETATM   37  H17 UNL     1      -0.294   1.452  -0.688  1.00  0.00           H  
HETATM   38  H18 UNL     1      -1.724  -0.315   1.320  1.00  0.00           H  
HETATM   39  H19 UNL     1      -2.172   1.426   0.890  1.00  0.00           H  
HETATM   40  H20 UNL     1      -2.202  -1.011  -0.974  1.00  0.00           H  
HETATM   41  H21 UNL     1      -1.908   0.618  -2.548  1.00  0.00           H  
HETATM   42  H22 UNL     1      -3.602   1.042  -2.207  1.00  0.00           H  
HETATM   43  H23 UNL     1      -2.323   1.981  -1.382  1.00  0.00           H  
HETATM   44  H24 UNL     1      -4.098  -2.236  -0.630  1.00  0.00           H  
HETATM   45  H25 UNL     1      -6.467  -2.451   0.134  1.00  0.00           H  
HETATM   46  H26 UNL     1      -8.646   0.345   0.798  1.00  0.00           H  
HETATM   47  H27 UNL     1      -8.432  -1.472   0.782  1.00  0.00           H  
HETATM   48  H28 UNL     1      -8.037  -0.487   2.279  1.00  0.00           H  
HETATM   49  H29 UNL     1      -6.503   1.655   1.189  1.00  0.00           H  
HETATM   50  H30 UNL     1      -4.182   1.853   0.437  1.00  0.00           H  
CONECT    1    2    2   21   22
CONECT    2    3    9
CONECT    3    4   23   24
CONECT    4    5    5   25
CONECT    5    6   26
CONECT    6    7    8   27
CONECT    7   28   29   30
CONECT    8   31   32   33
CONECT    9   10   34   35
CONECT   10   11   36   37
CONECT   11   12   38   39
CONECT   12   13   14   40
CONECT   13   41   42   43
CONECT   14   15   15   20
CONECT   15   16   44
CONECT   16   17   17   45
CONECT   17   18   19
CONECT   18   46   47   48
CONECT   19   20   20   49
CONECT   20   50
END

HMDB0039155
     RDKit          3D
ar-Artemisene
 50 50  0  0  0  0  0  0  0  0999 V2000
    2.1815   -0.3824   -1.9339 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7783   -0.1948   -0.6932 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6710    0.3294    0.3702 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0497    0.5816   -0.1685 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0922   -0.0434    0.3349 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4917    0.1412   -0.1322 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3695    0.6536    0.9843 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0829   -1.1676   -0.6365 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3794   -0.5270   -0.3370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3019    0.7269    0.1524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7461    0.4718    0.5350 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5698   -0.0357   -0.5992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5834    0.9700   -1.7509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9799   -0.1728   -0.1470 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6345   -1.3876   -0.2295 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9504   -1.5017    0.1961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6306   -0.4070    0.7091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0432   -0.5087    1.1713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9649    0.7982    0.7853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6704    0.8915    0.3618 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1978   -0.1510   -2.2051 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5127   -0.7634   -2.6833 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2509    1.2860    0.7968 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7444   -0.3779    1.2042 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2261    1.2789   -0.9798 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9372   -0.7440    1.1460 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5570    0.8562   -0.9807 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5059    1.7593    0.8807 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3857    0.2035    0.9725 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9509    0.4603    1.9903 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5439   -1.5568   -1.5155 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1165   -0.9153   -0.9829 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1919   -1.8984    0.1745 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3817   -1.2955    0.4847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1859   -0.9377   -1.2117 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2525    1.1615    0.9986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2941    1.4517   -0.6883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7245   -0.3155    1.3199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1720    1.4262    0.8898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2016   -1.0110   -0.9740 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9075    0.6179   -2.5483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6017    1.0421   -2.2070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3226    1.9808   -1.3816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0977   -2.2363   -0.6305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4674   -2.4510    0.1336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6462    0.3454    0.7983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4325   -1.4725    0.7818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0373   -0.4869    2.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5033    1.6553    1.1889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1820    1.8526    0.4372 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  2  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  2  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 17 19  1  0
 19 20  2  0
 20 14  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  4 25  1  0
  5 26  1  0
  6 27  1  0
  7 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
  8 33  1  0
  9 34  1  0
  9 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 13 41  1  0
 13 42  1  0
 13 43  1  0
 15 44  1  0
 16 45  1  0
 18 46  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
 20 50  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₀H₃₀

Average Molecular Weight

270.4522

Monoisotopic Molecular Weight

270.23475096

IUPAC Name

1-methyl-4-[(8E)-10-methyl-6-methylideneundec-8-en-2-yl]benzene

Traditional Name

1-methyl-4-[(8E)-10-methyl-6-methylideneundec-8-en-2-yl]benzene

CAS Registry Number

6089-98-1

SMILES

CC(C)\C=C\CC(=C)CCCC(C)C1=CC=C(C)C=C1

InChI Identifier

InChI=1S/C20H30/c1-16(2)8-6-9-17(3)10-7-11-19(5)20-14-12-18(4)13-15-20/h6,8,12-16,19H,3,7,9-11H2,1-2,4-5H3/b8-6+

InChI Key

KVCMFLFVCBKBMA-SOFGYWHQSA-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

Bisabolane sesquiterpenoid
Sesquiterpenoid
P-cymene
Toluene
Benzenoid
Monocyclic benzene moiety
Aromatic hydrocarbon
Branched unsaturated hydrocarbon
Cyclic olefin
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039155)

Source

Endogenous

Endogenous (HMDB: HMDB0039155)

Plant

Plant (HMDB: HMDB0039155)

Animal

Animal (HMDB: HMDB0039155)

Exogenous

Food

Food (HMDB: HMDB0039155)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Exogenous (HMDB: HMDB0039155)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0039155)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0039155)

Lipid metabolism pathway (HMDB: HMDB0039155)

Cellular process

Cell signaling (HMDB: HMDB0039155)

Biochemical process

Lipid transport (HMDB: HMDB0039155)

Role

Biological role

Energy source (HMDB: HMDB0039155)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0039155)

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	4.6e-05 g/L	ALOGPS
logP	7.51	ALOGPS
logP	7.15	ChemAxon
logS	-6.8	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	92.09 m³·mol⁻¹	ChemAxon
Polarizability	35.2 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	171.719	31661259
DarkChem	[M-H]-	170.417	31661259
DeepCCS	[M+H]+	181.092	30932474
DeepCCS	[M-H]-	178.734	30932474
DeepCCS	[M-2H]-	211.62	30932474
DeepCCS	[M+Na]+	187.185	30932474
AllCCS	[M+H]+	172.4	32859911
AllCCS	[M+H-H2O]+	168.9	32859911
AllCCS	[M+NH4]+	175.6	32859911
AllCCS	[M+Na]+	176.5	32859911
AllCCS	[M-H]-	175.7	32859911
AllCCS	[M+Na-2H]-	176.4	32859911
AllCCS	[M+HCOO]-	177.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	10.35 minutes	32390414
Predicted by Siyang on May 30, 2022	28.0265 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.57 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	37.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3230.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	983.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	365.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	625.1 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	563.7 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1300.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	1107.0 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	183.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2491.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	936.5 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	2283.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	881.6 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	643.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	617.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	679.8 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
ar-Artemisene	CC(C)\C=C\CC(=C)CCCC(C)C1=CC=C(C)C=C1	2285.8	Standard polar	33892256
ar-Artemisene	CC(C)\C=C\CC(=C)CCCC(C)C1=CC=C(C)C=C1	1911.6	Standard non polar	33892256
ar-Artemisene	CC(C)\C=C\CC(=C)CCCC(C)C1=CC=C(C)C=C1	1849.7	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 - ar-Artemisene GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-1920000000-705eda5f6c02f9d5ee5a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - ar-Artemisene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - ar-Artemisene 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 - ar-Artemisene 10V, Positive-QTOF	splash10-00di-1290000000-cb5b721064e6b49ea6e8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ar-Artemisene 20V, Positive-QTOF	splash10-00xr-3930000000-1bd409dbb409fa4ec12a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ar-Artemisene 40V, Positive-QTOF	splash10-0gb9-9700000000-83d42e2dbe39b6732aac	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ar-Artemisene 10V, Negative-QTOF	splash10-014i-0090000000-8fb990c6200021285910	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ar-Artemisene 20V, Negative-QTOF	splash10-014i-0090000000-a0e19a8f0bf861f32976	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ar-Artemisene 40V, Negative-QTOF	splash10-1009-4970000000-8169a2b3a1583f280226	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ar-Artemisene 10V, Positive-QTOF	splash10-00sl-4930000000-b02fb6d3bf95949ce0f2	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ar-Artemisene 20V, Positive-QTOF	splash10-0006-9600000000-e187ac5dfcfe1e1cf28c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ar-Artemisene 40V, Positive-QTOF	splash10-00kf-9800000000-001e121fc3cbbf7ec9b7	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ar-Artemisene 10V, Negative-QTOF	splash10-014i-0090000000-6e8153dfb4c02b21ea4a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ar-Artemisene 20V, Negative-QTOF	splash10-014i-0290000000-072ac02d5b512cb45686	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ar-Artemisene 40V, Negative-QTOF	splash10-00kf-8920000000-bbe22a99814b499e2336	2021-09-25	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

FDB018675

KNApSAcK ID

C00055291

Chemspider ID

35014754

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752566

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 ar-Artemisene (HMDB0039155)

MOL for HMDB0039155 (ar-Artemisene)

3D MOL for HMDB0039155 (ar-Artemisene)

3D SDF for HMDB0039155 (ar-Artemisene)

3D-SDF for HMDB0039155 (ar-Artemisene)

PDB for HMDB0039155 (ar-Artemisene)

3D PDB for HMDB0039155 (ar-Artemisene)

SMILES for HMDB0039155 (ar-Artemisene)

INCHI for HMDB0039155 (ar-Artemisene)

Structure for HMDB0039155 (ar-Artemisene)

3D Structure for HMDB0039155 (ar-Artemisene)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra