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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:48:58 UTC

Update Date

2022-03-07 02:55:24 UTC

HMDB ID

HMDB0037565

Secondary Accession Numbers

HMDB37565

Metabolite Identification

Common Name

Artenolide

Description

Artenolide belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom. Artenolide is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, artenolide has been detected, but not quantified in, alcoholic beverages and herbs and spices. This could make artenolide a potential biomarker for the consumption of these foods.

Structure

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


  Mrv0541 01111303302D          

 38 44  0  0  0  0            999 V2000
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   -2.5655    0.4645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.2814    0.0998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.6608   -1.2140    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  9 15  1  1  0  0  0
 24 26  1  1  0  0  0
M  END

HMDB0037565
     RDKit          3D
Artenolide
 78 84  0  0  0  0  0  0  0  0999 V2000
    5.8330   -1.8335    1.7641 C   0  0  0  0  0  0  0  0  0  0  0  0
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 37 77  1  0
 38 78  1  6
M  END


  Mrv0541 01111303302D          

 38 44  0  0  0  0            999 V2000
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    3.1185    0.8377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9166    0.8228    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4033   -3.3168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1334   -1.6771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2744    2.1768    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8528   -0.3978    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  8  1  0  0  0  0
  7 10  1  0  0  0  0
  9  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  1  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  4  8  2  0  0  0  0
  7  8  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 15 12  1  0  0  0  0
  9 10  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 14 15  1  0  0  0  0
 13 22  1  0  0  0  0
 21 16  1  0  0  0  0
 16 17  1  0  0  0  0
 13 17  1  0  0  0  0
 13 18  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 22 23  1  0  0  0  0
 24 25  1  0  0  0  0
 25 19  1  0  0  0  0
 22 21  2  0  0  0  0
 24 23  1  0  0  0  0
 23 27  1  6  0  0  0
 27 28  1  0  0  0  0
 26 28  1  0  0  0  0
 12 29  2  0  0  0  0
  6 30  1  0  0  0  0
  5 31  1  0  0  0  0
  1 32  1  0  0  0  0
 20 33  1  6  0  0  0
 20 34  1  1  0  0  0
 28 35  2  0  0  0  0
 26 36  1  6  0  0  0
  1 37  1  0  0  0  0
  6 38  1  0  0  0  0
  9 15  1  1  0  0  0
 24 26  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0037565

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@H]1[C@@H]2CC[C@](C)(O)C3=C([C@H]2OC1=O)C1(C)CC3C2(C1)[C@@H]1CCC(C)(O)C3=CC(O)C(C)(O)C3[C@H]1OC2=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H40O8/c1-13-14-6-8-28(4,35)19-17-11-26(2,21(19)22(14)37-24(13)32)12-30(17)15-7-9-27(3,34)16-10-18(31)29(5,36)20(16)23(15)38-25(30)33/h10,13-15,17-18,20,22-23,31,34-36H,6-9,11-12H2,1-5H3/t13-,14-,15+,17?,18?,20?,22-,23-,26?,27?,28-,29?,30?/m0/s1

> <INCHI_KEY>
INWDFSUZZFAFBJ-HXCFRXSLSA-N

> <FORMULA>
C30H40O8

> <MOLECULAR_WEIGHT>
528.6338

> <EXACT_MASS>
528.272318256

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
56.75771215884217

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3'S,3aS,6'S,7'S,9bS,10'S)-6,8,9,10'-tetrahydroxy-1',6,6',9,10'-pentamethyl-3a,4,5,6,8,9,9a,9b-octahydro-2H-4'-oxaspiro[azuleno[4,5-b]furan-3,13'-tetracyclo[10.2.1.0²,¹¹.0³,⁷]pentadecan]-2'(11')-ene-2,5'-dione

> <ALOGPS_LOGP>
1.92

> <JCHEM_LOGP>
0.6177365656666659

> <ALOGPS_LOGS>
-3.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.069743925053078

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.237474328021904

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0509277625983344

> <JCHEM_POLAR_SURFACE_AREA>
133.52

> <JCHEM_REFRACTIVITY>
136.77770000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.82e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3'S,3aS,6'S,7'S,9bS,10'S)-6,8,9,10'-tetrahydroxy-1',6,6',9,10'-pentamethyl-3a,4,5,8,9a,9b-hexahydro-4'-oxaspiro[azuleno[4,5-b]furan-3,13'-tetracyclo[10.2.1.0²,¹¹.0³,⁷]pentadecan]-2'(11')-ene-2,5'-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0037565
     RDKit          3D
Artenolide
 78 84  0  0  0  0  0  0  0  0999 V2000
    5.8330   -1.8335    1.7641 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6365   -2.2274    0.9298 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9237   -2.2909   -0.5084 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9068   -2.8434   -1.0686 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8942   -1.6147   -1.1902 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9036   -1.2137   -0.2760 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1820    0.0153   -0.7033 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4226    0.7406    0.1224 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6693    1.6959   -0.7324 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8723    2.1085   -1.6191 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1493    0.6497   -2.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3240    0.4849   -2.8800 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8175    0.3459   -2.6809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1816    1.0258   -1.7792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8986    2.1293   -2.5070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4709    2.8147   -3.5021 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1145    2.2237   -1.8511 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5208    0.8528   -1.6691 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6664    0.7340   -0.7321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5028   -0.4547    0.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9295   -0.2082    1.3745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4201    1.1927    1.4355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9684    1.7293    2.6399 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7832    1.8601    0.2423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6536    2.9863   -0.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5411    2.3434    0.6505 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9773   -1.8153   -0.1597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1259   -2.7879    0.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9159   -2.1664    0.6521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5751   -1.9594   -1.6078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2886   -1.2242   -1.9100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2595    0.1420   -1.2542 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2684    0.7206    1.5940 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2627    1.6576    2.2674 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0088    1.1912    1.9409 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4516   -0.6692    2.1620 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8709   -1.1150    2.2486 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6618   -1.0423    0.9951 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6990   -1.5141    1.1517 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6067   -0.9898    2.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0931   -2.6984    2.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1643   -3.1611    1.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1770   -2.0576   -0.2065 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2263    2.5257   -0.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6858    2.4878   -0.9954 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5896    2.7429   -2.4464 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1801   -0.3731   -3.5648 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4365    1.3786   -3.5379 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2352    0.4231   -2.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7221   -0.7540   -2.6915 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7575    0.7620   -3.6959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8596    0.5359   -2.6851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6392    0.6244   -1.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9432   -0.8688    2.2346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5349    1.1936    1.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1537    1.0437    3.3359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7229    2.7714   -0.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3548    3.9020    0.2654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5017    3.1784   -1.3550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5420    2.6084    1.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9464   -3.7675   -0.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0179   -2.3576   -0.4403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3758   -2.8671    1.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1166   -2.9840    1.1619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3788   -3.0369   -1.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4033   -1.6795   -2.2899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4743   -1.8817   -1.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2595   -1.0625   -3.0041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1981   -0.0307   -0.1724 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7959    2.6608    2.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1749    1.8106    1.6933 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4722    1.2622    3.2601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2407    0.9183    2.8720 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0398   -0.6476    3.1916 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8275   -1.3829    1.5883 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8509   -2.1842    2.5797 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3556   -0.5647    3.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3085   -0.1444    0.9008 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 20 27  1  0
 27 28  1  0
 27 29  1  0
 27 30  1  0
 30 31  1  0
 31 32  1  0
  8 33  1  0
 33 34  1  0
 33 35  1  6
 33 36  1  0
 36 37  1  0
 37 38  1  0
 38  2  1  0
 38  6  1  0
 11  7  1  0
 32 14  1  0
 14  9  1  0
 32 18  1  0
 24 19  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  2 42  1  1
  6 43  1  1
  9 44  1  0
 10 45  1  0
 10 46  1  0
 12 47  1  0
 12 48  1  0
 12 49  1  0
 13 50  1  0
 13 51  1  0
 18 52  1  6
 19 53  1  0
 21 54  1  0
 22 55  1  0
 23 56  1  0
 25 57  1  0
 25 58  1  0
 25 59  1  0
 26 60  1  0
 28 61  1  0
 28 62  1  0
 28 63  1  0
 29 64  1  0
 30 65  1  0
 30 66  1  0
 31 67  1  0
 31 68  1  0
 32 69  1  1
 34 70  1  0
 34 71  1  0
 34 72  1  0
 35 73  1  0
 36 74  1  0
 36 75  1  0
 37 76  1  0
 37 77  1  0
 38 78  1  6
M  END

HEADER    PROTEIN                                 11-JAN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-JAN-13         0                                  
HETATM    1  C   UNK     0      -1.282   2.730   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.950   1.082   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.231   2.443   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.931   2.146   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.789   0.867   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.838  -0.344   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.392   0.186   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.450   1.725   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.335  -0.330   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.153  -0.728   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.233  -2.266   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       0.204  -2.818   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.734  -3.363   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.864  -4.198   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.173  -1.621   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.089  -0.956   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.537  -2.394   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.653  -4.901   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.080   0.260   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.541   0.202   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.627  -1.037   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.025  -2.524   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.437  -3.140   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.798  -2.420   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       9.084  -0.907   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.943  -3.451   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       7.785  -4.697   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       9.316  -4.858   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       0.603  -4.305   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -4.258  -1.825   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -6.328   0.809   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -1.681   4.217   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.821   1.564   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       7.311   1.536   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      10.086  -6.191   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      11.449  -3.131   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -0.512   4.063   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -5.325  -0.743   0.000  0.00  0.00           O+0
CONECT    1    8    3   32   37                                             
CONECT    2    9    3                                                       
CONECT    3    2    1                                                       
CONECT    4    5    8                                                       
CONECT    5    4    6   31                                                  
CONECT    6    5    7   30   38                                             
CONECT    7   10    6    8                                                  
CONECT    8    1    4    7                                                  
CONECT    9    2   10   15                                                  
CONECT   10    7   11    9                                                  
CONECT   11   10   12                                                       
CONECT   12   11   15   29                                                  
CONECT   13   14   22   17   18                                             
CONECT   14   13   15                                                       
CONECT   15   12   16   14    9                                             
CONECT   16   15   21   17                                                  
CONECT   17   16   13                                                       
CONECT   18   13                                                            
CONECT   19   20   25                                                       
CONECT   20   19   21   33   34                                             
CONECT   21   16   20   22                                                  
CONECT   22   13   23   21                                                  
CONECT   23   22   24   27                                                  
CONECT   24   25   23   26                                                  
CONECT   25   24   19                                                       
CONECT   26   28   36   24                                                  
CONECT   27   23   28                                                       
CONECT   28   27   26   35                                                  
CONECT   29   12                                                            
CONECT   30    6                                                            
CONECT   31    5                                                            
CONECT   32    1                                                            
CONECT   33   20                                                            
CONECT   34   20                                                            
CONECT   35   28                                                            
CONECT   36   26                                                            
CONECT   37    1                                                            
CONECT   38    6                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   88    0
END

COMPND    HMDB0037565
HETATM    1  C1  UNL     1       5.833  -1.834   1.764  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.636  -2.227   0.930  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.924  -2.291  -0.508  1.00  0.00           C  
HETATM    4  O1  UNL     1       5.907  -2.843  -1.069  1.00  0.00           O  
HETATM    5  O2  UNL     1       3.894  -1.615  -1.190  1.00  0.00           O  
HETATM    6  C4  UNL     1       2.904  -1.214  -0.276  1.00  0.00           C  
HETATM    7  C5  UNL     1       2.182   0.015  -0.703  1.00  0.00           C  
HETATM    8  C6  UNL     1       1.423   0.741   0.122  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.669   1.696  -0.732  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.872   2.108  -1.619  1.00  0.00           C  
HETATM   11  C9  UNL     1       2.149   0.650  -2.031  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.324   0.485  -2.880  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.817   0.346  -2.681  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.182   1.026  -1.779  1.00  0.00           C  
HETATM   15  C13 UNL     1      -0.899   2.129  -2.507  1.00  0.00           C  
HETATM   16  O3  UNL     1      -0.471   2.815  -3.502  1.00  0.00           O  
HETATM   17  O4  UNL     1      -2.114   2.224  -1.851  1.00  0.00           O  
HETATM   18  C14 UNL     1      -2.521   0.853  -1.669  1.00  0.00           C  
HETATM   19  C15 UNL     1      -3.666   0.734  -0.732  1.00  0.00           C  
HETATM   20  C16 UNL     1      -3.503  -0.455   0.129  1.00  0.00           C  
HETATM   21  C17 UNL     1      -3.929  -0.208   1.374  1.00  0.00           C  
HETATM   22  C18 UNL     1      -4.420   1.193   1.435  1.00  0.00           C  
HETATM   23  O5  UNL     1      -3.968   1.729   2.640  1.00  0.00           O  
HETATM   24  C19 UNL     1      -3.783   1.860   0.242  1.00  0.00           C  
HETATM   25  C20 UNL     1      -4.654   2.986  -0.292  1.00  0.00           C  
HETATM   26  O6  UNL     1      -2.541   2.343   0.650  1.00  0.00           O  
HETATM   27  C21 UNL     1      -2.977  -1.815  -0.160  1.00  0.00           C  
HETATM   28  C22 UNL     1      -4.126  -2.788   0.074  1.00  0.00           C  
HETATM   29  O7  UNL     1      -1.916  -2.166   0.652  1.00  0.00           O  
HETATM   30  C23 UNL     1      -2.575  -1.959  -1.608  1.00  0.00           C  
HETATM   31  C24 UNL     1      -1.289  -1.224  -1.910  1.00  0.00           C  
HETATM   32  C25 UNL     1      -1.260   0.142  -1.254  1.00  0.00           C  
HETATM   33  C26 UNL     1       1.268   0.721   1.594  1.00  0.00           C  
HETATM   34  C27 UNL     1       2.263   1.658   2.267  1.00  0.00           C  
HETATM   35  O8  UNL     1       0.009   1.191   1.941  1.00  0.00           O  
HETATM   36  C28 UNL     1       1.452  -0.669   2.162  1.00  0.00           C  
HETATM   37  C29 UNL     1       2.871  -1.115   2.249  1.00  0.00           C  
HETATM   38  C30 UNL     1       3.662  -1.042   0.995  1.00  0.00           C  
HETATM   39  H1  UNL     1       6.699  -1.514   1.152  1.00  0.00           H  
HETATM   40  H2  UNL     1       5.607  -0.990   2.454  1.00  0.00           H  
HETATM   41  H3  UNL     1       6.093  -2.698   2.434  1.00  0.00           H  
HETATM   42  H4  UNL     1       4.164  -3.161   1.256  1.00  0.00           H  
HETATM   43  H5  UNL     1       2.177  -2.058  -0.207  1.00  0.00           H  
HETATM   44  H6  UNL     1       0.226   2.526  -0.224  1.00  0.00           H  
HETATM   45  H7  UNL     1       2.686   2.488  -0.995  1.00  0.00           H  
HETATM   46  H8  UNL     1       1.590   2.743  -2.446  1.00  0.00           H  
HETATM   47  H9  UNL     1       3.180  -0.373  -3.565  1.00  0.00           H  
HETATM   48  H10 UNL     1       3.436   1.379  -3.538  1.00  0.00           H  
HETATM   49  H11 UNL     1       4.235   0.423  -2.280  1.00  0.00           H  
HETATM   50  H12 UNL     1       0.722  -0.754  -2.691  1.00  0.00           H  
HETATM   51  H13 UNL     1       0.757   0.762  -3.696  1.00  0.00           H  
HETATM   52  H14 UNL     1      -2.860   0.536  -2.685  1.00  0.00           H  
HETATM   53  H15 UNL     1      -4.639   0.624  -1.269  1.00  0.00           H  
HETATM   54  H16 UNL     1      -3.943  -0.869   2.235  1.00  0.00           H  
HETATM   55  H17 UNL     1      -5.535   1.194   1.378  1.00  0.00           H  
HETATM   56  H18 UNL     1      -4.154   1.044   3.336  1.00  0.00           H  
HETATM   57  H19 UNL     1      -5.723   2.771  -0.085  1.00  0.00           H  
HETATM   58  H20 UNL     1      -4.355   3.902   0.265  1.00  0.00           H  
HETATM   59  H21 UNL     1      -4.502   3.178  -1.355  1.00  0.00           H  
HETATM   60  H22 UNL     1      -2.542   2.608   1.607  1.00  0.00           H  
HETATM   61  H23 UNL     1      -3.946  -3.767  -0.399  1.00  0.00           H  
HETATM   62  H24 UNL     1      -5.018  -2.358  -0.440  1.00  0.00           H  
HETATM   63  H25 UNL     1      -4.376  -2.867   1.149  1.00  0.00           H  
HETATM   64  H26 UNL     1      -2.117  -2.984   1.162  1.00  0.00           H  
HETATM   65  H27 UNL     1      -2.379  -3.037  -1.781  1.00  0.00           H  
HETATM   66  H28 UNL     1      -3.403  -1.679  -2.290  1.00  0.00           H  
HETATM   67  H29 UNL     1      -0.474  -1.882  -1.543  1.00  0.00           H  
HETATM   68  H30 UNL     1      -1.260  -1.063  -3.004  1.00  0.00           H  
HETATM   69  H31 UNL     1      -1.198  -0.031  -0.172  1.00  0.00           H  
HETATM   70  H32 UNL     1       1.796   2.661   2.415  1.00  0.00           H  
HETATM   71  H33 UNL     1       3.175   1.811   1.693  1.00  0.00           H  
HETATM   72  H34 UNL     1       2.472   1.262   3.260  1.00  0.00           H  
HETATM   73  H35 UNL     1      -0.241   0.918   2.872  1.00  0.00           H  
HETATM   74  H36 UNL     1       1.040  -0.648   3.192  1.00  0.00           H  
HETATM   75  H37 UNL     1       0.827  -1.383   1.588  1.00  0.00           H  
HETATM   76  H38 UNL     1       2.851  -2.184   2.580  1.00  0.00           H  
HETATM   77  H39 UNL     1       3.356  -0.565   3.087  1.00  0.00           H  
HETATM   78  H40 UNL     1       4.308  -0.144   0.901  1.00  0.00           H  
CONECT    1    2   39   40   41
CONECT    2    3   38   42
CONECT    3    4    4    5
CONECT    5    6
CONECT    6    7   38   43
CONECT    7    8    8   11
CONECT    8    9   33
CONECT    9   10   14   44
CONECT   10   11   45   46
CONECT   11   12   13
CONECT   12   47   48   49
CONECT   13   14   50   51
CONECT   14   15   32
CONECT   15   16   16   17
CONECT   17   18
CONECT   18   19   32   52
CONECT   19   20   24   53
CONECT   20   21   21   27
CONECT   21   22   54
CONECT   22   23   24   55
CONECT   23   56
CONECT   24   25   26
CONECT   25   57   58   59
CONECT   26   60
CONECT   27   28   29   30
CONECT   28   61   62   63
CONECT   29   64
CONECT   30   31   65   66
CONECT   31   32   67   68
CONECT   32   69
CONECT   33   34   35   36
CONECT   34   70   71   72
CONECT   35   73
CONECT   36   37   74   75
CONECT   37   38   76   77
CONECT   38   78
END

HMDB0037565
     RDKit          3D
Artenolide
 78 84  0  0  0  0  0  0  0  0999 V2000
    5.8330   -1.8335    1.7641 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6365   -2.2274    0.9298 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9237   -2.2909   -0.5084 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9068   -2.8434   -1.0686 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8942   -1.6147   -1.1902 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9036   -1.2137   -0.2760 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1820    0.0153   -0.7033 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4226    0.7406    0.1224 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6693    1.6959   -0.7324 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8723    2.1085   -1.6191 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1493    0.6497   -2.0306 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3240    0.4849   -2.8800 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8175    0.3459   -2.6809 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1816    1.0258   -1.7792 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8986    2.1293   -2.5070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4709    2.8147   -3.5021 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1145    2.2237   -1.8511 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5208    0.8528   -1.6691 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6664    0.7340   -0.7321 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5028   -0.4547    0.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9295   -0.2082    1.3745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4201    1.1927    1.4355 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9684    1.7293    2.6399 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7832    1.8601    0.2423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6536    2.9863   -0.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5411    2.3434    0.6505 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9773   -1.8153   -0.1597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1259   -2.7879    0.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9159   -2.1664    0.6521 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5751   -1.9594   -1.6078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2886   -1.2242   -1.9100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2595    0.1420   -1.2542 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2684    0.7206    1.5940 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2627    1.6576    2.2674 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0088    1.1912    1.9409 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4516   -0.6692    2.1620 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8709   -1.1150    2.2486 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6618   -1.0423    0.9951 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6990   -1.5141    1.1517 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6067   -0.9898    2.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0931   -2.6984    2.4340 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1643   -3.1611    1.2560 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1770   -2.0576   -0.2065 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2263    2.5257   -0.2240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6858    2.4878   -0.9954 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5896    2.7429   -2.4464 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1801   -0.3731   -3.5648 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4365    1.3786   -3.5379 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2352    0.4231   -2.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7221   -0.7540   -2.6915 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7575    0.7620   -3.6959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8596    0.5359   -2.6851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6392    0.6244   -1.2691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9432   -0.8688    2.2346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5349    1.1936    1.3782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1537    1.0437    3.3359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7229    2.7714   -0.0851 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3548    3.9020    0.2654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5017    3.1784   -1.3550 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5420    2.6084    1.6068 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9464   -3.7675   -0.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0179   -2.3576   -0.4403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3758   -2.8671    1.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1166   -2.9840    1.1619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3788   -3.0369   -1.7811 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4033   -1.6795   -2.2899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4743   -1.8817   -1.5427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2595   -1.0625   -3.0041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1981   -0.0307   -0.1724 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7959    2.6608    2.4149 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1749    1.8106    1.6933 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4722    1.2622    3.2601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2407    0.9183    2.8720 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0398   -0.6476    3.1916 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8275   -1.3829    1.5883 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8509   -2.1842    2.5797 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3556   -0.5647    3.0872 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3085   -0.1444    0.9008 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 20 27  1  0
 27 28  1  0
 27 29  1  0
 27 30  1  0
 30 31  1  0
 31 32  1  0
  8 33  1  0
 33 34  1  0
 33 35  1  6
 33 36  1  0
 36 37  1  0
 37 38  1  0
 38  2  1  0
 38  6  1  0
 11  7  1  0
 32 14  1  0
 14  9  1  0
 32 18  1  0
 24 19  1  0
  1 39  1  0
  1 40  1  0
  1 41  1  0
  2 42  1  1
  6 43  1  1
  9 44  1  0
 10 45  1  0
 10 46  1  0
 12 47  1  0
 12 48  1  0
 12 49  1  0
 13 50  1  0
 13 51  1  0
 18 52  1  6
 19 53  1  0
 21 54  1  0
 22 55  1  0
 23 56  1  0
 25 57  1  0
 25 58  1  0
 25 59  1  0
 26 60  1  0
 28 61  1  0
 28 62  1  0
 28 63  1  0
 29 64  1  0
 30 65  1  0
 30 66  1  0
 31 67  1  0
 31 68  1  0
 32 69  1  1
 34 70  1  0
 34 71  1  0
 34 72  1  0
 35 73  1  0
 36 74  1  0
 36 75  1  0
 37 76  1  0
 37 77  1  0
 38 78  1  6
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₃₀H₄₀O₈

Average Molecular Weight

528.6338

Monoisotopic Molecular Weight

528.272318256

IUPAC Name

(3'S,3aS,6'S,7'S,9bS,10'S)-6,8,9,10'-tetrahydroxy-1',6,6',9,10'-pentamethyl-3a,4,5,6,8,9,9a,9b-octahydro-2H-4'-oxaspiro[azuleno[4,5-b]furan-3,13'-tetracyclo[10.2.1.0²,¹¹.0³,⁷]pentadecan]-2'(11')-ene-2,5'-dione

Traditional Name

(3'S,3aS,6'S,7'S,9bS,10'S)-6,8,9,10'-tetrahydroxy-1',6,6',9,10'-pentamethyl-3a,4,5,8,9a,9b-hexahydro-4'-oxaspiro[azuleno[4,5-b]furan-3,13'-tetracyclo[10.2.1.0²,¹¹.0³,⁷]pentadecan]-2'(11')-ene-2,5'-dione

CAS Registry Number

113807-34-4

SMILES

C[C@H]1[C@@H]2CC[C@](C)(O)C3=C([C@H]2OC1=O)C1(C)CC3C2(C1)[C@@H]1CCC(C)(O)C3=CC(O)C(C)(O)C3[C@H]1OC2=O

InChI Identifier

InChI=1S/C30H40O8/c1-13-14-6-8-28(4,35)19-17-11-26(2,21(19)22(14)37-24(13)32)12-30(17)15-7-9-27(3,34)16-10-18(31)29(5,36)20(16)23(15)38-25(30)33/h10,13-15,17-18,20,22-23,31,34-36H,6-9,11-12H2,1-5H3/t13-,14-,15+,17?,18?,20?,22-,23-,26?,27?,28-,29?,30?/m0/s1

InChI Key

INWDFSUZZFAFBJ-HXCFRXSLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gamma butyrolactones. Gamma butyrolactones are compounds containing a gamma butyrolactone moiety, which consists of an aliphatic five-member ring with four carbon atoms, one oxygen atom, and bears a ketone group on the carbon adjacent to the oxygen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Lactones

Sub Class

Gamma butyrolactones

Direct Parent

Gamma butyrolactones

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: HMDB0037565)

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037565)

Source

Endogenous

Endogenous (HMDB: HMDB0037565)

Plant

Plant (HMDB: HMDB0037565)

Exogenous

Food

Food (HMDB: HMDB0037565)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Beverage

Alcoholic beverage

Alcoholic beverages (FooDB: FOOD00854)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0037565)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0037565)

Nutrient

Nutrient (HMDB: HMDB0037565)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0037565)

Emulsifier (HMDB: HMDB0037565)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	163 - 174 °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	0.18 g/L	ALOGPS
logP	1.92	ALOGPS
logP	0.62	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	13.24	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	133.52 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	136.78 m³·mol⁻¹	ChemAxon
Polarizability	56.76 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	225.8	30932474
DeepCCS	[M-H]-	223.904	30932474
DeepCCS	[M-2H]-	257.356	30932474
DeepCCS	[M+Na]+	231.587	30932474
AllCCS	[M+H]+	221.0	32859911
AllCCS	[M+H-H2O]+	219.6	32859911
AllCCS	[M+NH4]+	222.3	32859911
AllCCS	[M+Na]+	222.7	32859911
AllCCS	[M-H]-	220.2	32859911
AllCCS	[M+Na-2H]-	222.2	32859911
AllCCS	[M+HCOO]-	224.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Artenolide	C[C@H]1[C@@H]2CC[C@](C)(O)C3=C([C@H]2OC1=O)C1(C)CC3C2(C1)[C@@H]1CCC(C)(O)C3=CC(O)C(C)(O)C3[C@H]1OC2=O	4156.0	Standard polar	33892256
Artenolide	C[C@H]1[C@@H]2CC[C@](C)(O)C3=C([C@H]2OC1=O)C1(C)CC3C2(C1)[C@@H]1CCC(C)(O)C3=CC(O)C(C)(O)C3[C@H]1OC2=O	3746.3	Standard non polar	33892256
Artenolide	C[C@H]1[C@@H]2CC[C@](C)(O)C3=C([C@H]2OC1=O)C1(C)CC3C2(C1)[C@@H]1CCC(C)(O)C3=CC(O)C(C)(O)C3[C@H]1OC2=O	4399.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Artenolide,1TMS,isomer #1	C[C@@H]1C(=O)O[C@@H]2C3=C(C4CC3(C)CC43C(=O)O[C@@H]4C5C(=CC(O)C5(C)O)C(C)(O)CC[C@H]43)[C@@](C)(O[Si](C)(C)C)CC[C@@H]12	4013.0	Semi standard non polar	33892256
Artenolide,1TMS,isomer #2	C[C@@H]1C(=O)O[C@@H]2C3=C(C4CC3(C)CC43C(=O)O[C@@H]4C5C(=CC(O)C5(C)O)C(C)(O[Si](C)(C)C)CC[C@H]43)[C@@](C)(O)CC[C@@H]12	4027.3	Semi standard non polar	33892256
Artenolide,1TMS,isomer #3	C[C@@H]1C(=O)O[C@@H]2C3=C(C4CC3(C)CC43C(=O)O[C@@H]4C5C(=CC(O[Si](C)(C)C)C5(C)O)C(C)(O)CC[C@H]43)[C@@](C)(O)CC[C@@H]12	4036.6	Semi standard non polar	33892256
Artenolide,1TMS,isomer #4	C[C@@H]1C(=O)O[C@@H]2C3=C(C4CC3(C)CC43C(=O)O[C@@H]4C5C(=CC(O)C5(C)O[Si](C)(C)C)C(C)(O)CC[C@H]43)[C@@](C)(O)CC[C@@H]12	4010.0	Semi standard non polar	33892256
Artenolide,2TMS,isomer #1	C[C@@H]1C(=O)O[C@@H]2C3=C(C4CC3(C)CC43C(=O)O[C@@H]4C5C(=CC(O[Si](C)(C)C)C5(C)O)C(C)(O)CC[C@H]43)[C@@](C)(O[Si](C)(C)C)CC[C@@H]12	3973.0	Semi standard non polar	33892256
Artenolide,2TMS,isomer #2	C[C@@H]1C(=O)O[C@@H]2C3=C(C4CC3(C)CC43C(=O)O[C@@H]4C5C(=CC(O)C5(C)O[Si](C)(C)C)C(C)(O)CC[C@H]43)[C@@](C)(O[Si](C)(C)C)CC[C@@H]12	3949.0	Semi standard non polar	33892256
Artenolide,2TMS,isomer #3	C[C@@H]1C(=O)O[C@@H]2C3=C(C4CC3(C)CC43C(=O)O[C@@H]4C5C(=CC(O)C5(C)O)C(C)(O[Si](C)(C)C)CC[C@H]43)[C@@](C)(O[Si](C)(C)C)CC[C@@H]12	3981.2	Semi standard non polar	33892256
Artenolide,2TMS,isomer #4	C[C@@H]1C(=O)O[C@@H]2C3=C(C4CC3(C)CC43C(=O)O[C@@H]4C5C(=CC(O[Si](C)(C)C)C5(C)O)C(C)(O[Si](C)(C)C)CC[C@H]43)[C@@](C)(O)CC[C@@H]12	4009.9	Semi standard non polar	33892256
Artenolide,2TMS,isomer #5	C[C@@H]1C(=O)O[C@@H]2C3=C(C4CC3(C)CC43C(=O)O[C@@H]4C5C(=CC(O)C5(C)O[Si](C)(C)C)C(C)(O[Si](C)(C)C)CC[C@H]43)[C@@](C)(O)CC[C@@H]12	3988.2	Semi standard non polar	33892256
Artenolide,2TMS,isomer #6	C[C@@H]1C(=O)O[C@@H]2C3=C(C4CC3(C)CC43C(=O)O[C@@H]4C5C(=CC(O[Si](C)(C)C)C5(C)O[Si](C)(C)C)C(C)(O)CC[C@H]43)[C@@](C)(O)CC[C@@H]12	3970.5	Semi standard non polar	33892256
Artenolide,3TMS,isomer #1	C[C@@H]1C(=O)O[C@@H]2C3=C(C4CC3(C)CC43C(=O)O[C@@H]4C5C(=CC(O[Si](C)(C)C)C5(C)O[Si](C)(C)C)C(C)(O)CC[C@H]43)[C@@](C)(O[Si](C)(C)C)CC[C@@H]12	3898.2	Semi standard non polar	33892256
Artenolide,3TMS,isomer #2	C[C@@H]1C(=O)O[C@@H]2C3=C(C4CC3(C)CC43C(=O)O[C@@H]4C5C(=CC(O[Si](C)(C)C)C5(C)O)C(C)(O[Si](C)(C)C)CC[C@H]43)[C@@](C)(O[Si](C)(C)C)CC[C@@H]12	3949.0	Semi standard non polar	33892256
Artenolide,3TMS,isomer #3	C[C@@H]1C(=O)O[C@@H]2C3=C(C4CC3(C)CC43C(=O)O[C@@H]4C5C(=CC(O)C5(C)O[Si](C)(C)C)C(C)(O[Si](C)(C)C)CC[C@H]43)[C@@](C)(O[Si](C)(C)C)CC[C@@H]12	3930.9	Semi standard non polar	33892256
Artenolide,3TMS,isomer #4	C[C@@H]1C(=O)O[C@@H]2C3=C(C4CC3(C)CC43C(=O)O[C@@H]4C5C(=CC(O[Si](C)(C)C)C5(C)O[Si](C)(C)C)C(C)(O[Si](C)(C)C)CC[C@H]43)[C@@](C)(O)CC[C@@H]12	3938.1	Semi standard non polar	33892256
Artenolide,4TMS,isomer #1	C[C@@H]1C(=O)O[C@@H]2C3=C(C4CC3(C)CC43C(=O)O[C@@H]4C5C(=CC(O[Si](C)(C)C)C5(C)O[Si](C)(C)C)C(C)(O[Si](C)(C)C)CC[C@H]43)[C@@](C)(O[Si](C)(C)C)CC[C@@H]12	3879.9	Semi standard non polar	33892256
Artenolide,1TBDMS,isomer #1	C[C@@H]1C(=O)O[C@@H]2C3=C(C4CC3(C)CC43C(=O)O[C@@H]4C5C(=CC(O)C5(C)O)C(C)(O)CC[C@H]43)[C@@](C)(O[Si](C)(C)C(C)(C)C)CC[C@@H]12	4237.1	Semi standard non polar	33892256
Artenolide,1TBDMS,isomer #2	C[C@@H]1C(=O)O[C@@H]2C3=C(C4CC3(C)CC43C(=O)O[C@@H]4C5C(=CC(O)C5(C)O)C(C)(O[Si](C)(C)C(C)(C)C)CC[C@H]43)[C@@](C)(O)CC[C@@H]12	4249.5	Semi standard non polar	33892256
Artenolide,1TBDMS,isomer #3	C[C@@H]1C(=O)O[C@@H]2C3=C(C4CC3(C)CC43C(=O)O[C@@H]4C5C(=CC(O[Si](C)(C)C(C)(C)C)C5(C)O)C(C)(O)CC[C@H]43)[C@@](C)(O)CC[C@@H]12	4257.2	Semi standard non polar	33892256
Artenolide,1TBDMS,isomer #4	C[C@@H]1C(=O)O[C@@H]2C3=C(C4CC3(C)CC43C(=O)O[C@@H]4C5C(=CC(O)C5(C)O[Si](C)(C)C(C)(C)C)C(C)(O)CC[C@H]43)[C@@](C)(O)CC[C@@H]12	4227.2	Semi standard non polar	33892256
Artenolide,2TBDMS,isomer #1	C[C@@H]1C(=O)O[C@@H]2C3=C(C4CC3(C)CC43C(=O)O[C@@H]4C5C(=CC(O[Si](C)(C)C(C)(C)C)C5(C)O)C(C)(O)CC[C@H]43)[C@@](C)(O[Si](C)(C)C(C)(C)C)CC[C@@H]12	4420.1	Semi standard non polar	33892256
Artenolide,2TBDMS,isomer #2	C[C@@H]1C(=O)O[C@@H]2C3=C(C4CC3(C)CC43C(=O)O[C@@H]4C5C(=CC(O)C5(C)O[Si](C)(C)C(C)(C)C)C(C)(O)CC[C@H]43)[C@@](C)(O[Si](C)(C)C(C)(C)C)CC[C@@H]12	4395.1	Semi standard non polar	33892256
Artenolide,2TBDMS,isomer #3	C[C@@H]1C(=O)O[C@@H]2C3=C(C4CC3(C)CC43C(=O)O[C@@H]4C5C(=CC(O)C5(C)O)C(C)(O[Si](C)(C)C(C)(C)C)CC[C@H]43)[C@@](C)(O[Si](C)(C)C(C)(C)C)CC[C@@H]12	4430.8	Semi standard non polar	33892256
Artenolide,2TBDMS,isomer #4	C[C@@H]1C(=O)O[C@@H]2C3=C(C4CC3(C)CC43C(=O)O[C@@H]4C5C(=CC(O[Si](C)(C)C(C)(C)C)C5(C)O)C(C)(O[Si](C)(C)C(C)(C)C)CC[C@H]43)[C@@](C)(O)CC[C@@H]12	4455.7	Semi standard non polar	33892256
Artenolide,2TBDMS,isomer #5	C[C@@H]1C(=O)O[C@@H]2C3=C(C4CC3(C)CC43C(=O)O[C@@H]4C5C(=CC(O)C5(C)O[Si](C)(C)C(C)(C)C)C(C)(O[Si](C)(C)C(C)(C)C)CC[C@H]43)[C@@](C)(O)CC[C@@H]12	4435.0	Semi standard non polar	33892256
Artenolide,2TBDMS,isomer #6	C[C@@H]1C(=O)O[C@@H]2C3=C(C4CC3(C)CC43C(=O)O[C@@H]4C5C(=CC(O[Si](C)(C)C(C)(C)C)C5(C)O[Si](C)(C)C(C)(C)C)C(C)(O)CC[C@H]43)[C@@](C)(O)CC[C@@H]12	4415.6	Semi standard non polar	33892256
Artenolide,3TBDMS,isomer #1	C[C@@H]1C(=O)O[C@@H]2C3=C(C4CC3(C)CC43C(=O)O[C@@H]4C5C(=CC(O[Si](C)(C)C(C)(C)C)C5(C)O[Si](C)(C)C(C)(C)C)C(C)(O)CC[C@H]43)[C@@](C)(O[Si](C)(C)C(C)(C)C)CC[C@@H]12	4567.0	Semi standard non polar	33892256
Artenolide,3TBDMS,isomer #2	C[C@@H]1C(=O)O[C@@H]2C3=C(C4CC3(C)CC43C(=O)O[C@@H]4C5C(=CC(O[Si](C)(C)C(C)(C)C)C5(C)O)C(C)(O[Si](C)(C)C(C)(C)C)CC[C@H]43)[C@@](C)(O[Si](C)(C)C(C)(C)C)CC[C@@H]12	4616.1	Semi standard non polar	33892256
Artenolide,3TBDMS,isomer #3	C[C@@H]1C(=O)O[C@@H]2C3=C(C4CC3(C)CC43C(=O)O[C@@H]4C5C(=CC(O)C5(C)O[Si](C)(C)C(C)(C)C)C(C)(O[Si](C)(C)C(C)(C)C)CC[C@H]43)[C@@](C)(O[Si](C)(C)C(C)(C)C)CC[C@@H]12	4596.2	Semi standard non polar	33892256
Artenolide,3TBDMS,isomer #4	C[C@@H]1C(=O)O[C@@H]2C3=C(C4CC3(C)CC43C(=O)O[C@@H]4C5C(=CC(O[Si](C)(C)C(C)(C)C)C5(C)O[Si](C)(C)C(C)(C)C)C(C)(O[Si](C)(C)C(C)(C)C)CC[C@H]43)[C@@](C)(O)CC[C@@H]12	4613.6	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 - Artenolide GC-MS (Non-derivatized) - 70eV, Positive	splash10-03e9-2542960000-e0654ebd9aabaa6cc9fd	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artenolide GC-MS (2 TMS) - 70eV, Positive	splash10-0a4i-1142319000-88ca1ae018b7c90acb63	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artenolide GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artenolide GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artenolide GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artenolide GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artenolide GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artenolide GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artenolide GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artenolide GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artenolide GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artenolide GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artenolide GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artenolide GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artenolide GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artenolide GC-MS (TMS_4_1) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artenolide GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artenolide GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artenolide GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artenolide GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artenolide GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artenolide GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artenolide GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artenolide GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Artenolide GC-MS (TBDMS_2_5) - 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 - Artenolide 10V, Positive-QTOF	splash10-03dl-0000790000-254a5a0d94f09a8b8a31	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artenolide 20V, Positive-QTOF	splash10-01pc-0000920000-405763960f7e14365792	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artenolide 40V, Positive-QTOF	splash10-0fkj-0490800000-8b31ccfdc0f94966950a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artenolide 10V, Negative-QTOF	splash10-0059-0000590000-284c858ca84a8c6da2d9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artenolide 20V, Negative-QTOF	splash10-0a7i-0000960000-5cee860ce5b34f9a2dc9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artenolide 40V, Negative-QTOF	splash10-000j-0031900000-409221c0f8056b3989f3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artenolide 10V, Negative-QTOF	splash10-004i-0000190000-530a2616fd547564c764	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artenolide 20V, Negative-QTOF	splash10-004i-0000290000-253bfa45a9e250240a47	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artenolide 40V, Negative-QTOF	splash10-056r-0300890000-020c71a02fd4ec897070	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artenolide 10V, Positive-QTOF	splash10-01tc-0000490000-2d79a9dba67f08520337	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artenolide 20V, Positive-QTOF	splash10-0929-0102950000-5f9ecd9972ed1129ecf4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Artenolide 40V, Positive-QTOF	splash10-014r-1198400000-6ab4da09a7e055d31d04	2021-09-22	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

FDB016649

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752206

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

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Artenolide (HMDB0037565)

MOL for HMDB0037565 (Artenolide)

3D MOL for HMDB0037565 (Artenolide)

3D SDF for HMDB0037565 (Artenolide)

3D-SDF for HMDB0037565 (Artenolide)

PDB for HMDB0037565 (Artenolide)

3D PDB for HMDB0037565 (Artenolide)

SMILES for HMDB0037565 (Artenolide)

INCHI for HMDB0037565 (Artenolide)

Structure for HMDB0037565 (Artenolide)

3D Structure for HMDB0037565 (Artenolide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra