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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:51:11 UTC

Update Date

2022-03-07 02:53:26 UTC

HMDB ID

HMDB0032685

Secondary Accession Numbers

HMDB32685

Metabolite Identification

Common Name

(14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide

Description

(14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring. Based on a literature review a significant number of articles have been published on (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide.

Structure

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


  Mrv0541 02241209132D          

 33 38  0  0  0  0            999 V2000
   -3.9184   -1.4702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9184   -2.2966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2036   -2.7098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4902   -2.2966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4902   -1.4702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2036   -1.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7753   -2.7098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0618   -2.2966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0618   -1.4702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7753   -1.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3500   -1.0584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3500   -0.2361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0618    0.1742    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7753   -0.2361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4310   -1.3118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9117   -0.6465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2036   -0.2321    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0178    0.7320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.0466    0.3575    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8537    0.5268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.5590    1.9247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8151    2.7098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9184    1.4813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4060   -0.0888    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2711    0.2170    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  2  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  5 19  1  0  0  0  0
  6 18  2  0  0  0  0
  7  8  1  0  0  0  0
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  9 11  1  0  0  0  0
 10 14  1  0  0  0  0
 11 12  1  0  0  0  0
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 11 33  1  0  0  0  0
 12 13  1  0  0  0  0
 12 17  1  0  0  0  0
 12 20  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 21  1  0  0  0  0
 17 22  1  0  0  0  0
 21 23  1  0  0  0  0
 21 24  1  0  0  0  0
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 26 27  1  0  0  0  0
 26 32  2  0  0  0  0
 27 28  2  0  0  0  0
 27 31  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
M  END

HMDB0032685
     RDKit          3D
(14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide
 69 74  0  0  0  0  0  0  0  0999 V2000
    5.0171   -2.8577    0.7652 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7086   -1.4321    0.4992 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2088    0.2618   -0.5325 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4136    0.3473   -1.8782 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3090    1.5867   -1.7498 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1740    1.9591   -0.2638 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5662    3.1960    0.0416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3404    1.7140   -0.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0160    2.6196   -1.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8396    1.6880    1.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2987    1.2058    1.1843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3814   -0.2004    0.6568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4094   -0.5754   -0.3802 C   0  0  0  0  0  0  0  0  0  0  0  0
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 33  2  1  0
 15  9  1  0
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 33 69  1  0
M  END


  Mrv0541 02241209132D          

 33 38  0  0  0  0            999 V2000
   -3.9184   -1.4702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
HMDB0032685

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1=C(C)C(=O)OC(C1)C1(C)OC23CCC1(O)C2(C)CCC1C3CC=C2C=CCC(=O)C12C

> <INCHI_IDENTIFIER>
InChI=1S/C28H36O5/c1-16-15-22(32-23(30)17(16)2)26(5)28(31)14-13-27(33-26)20-10-9-18-7-6-8-21(29)25(18,4)19(20)11-12-24(27,28)3/h6-7,9,19-20,22,31H,8,10-15H2,1-5H3

> <INCHI_KEY>
KOYNICXFSFFIPU-UHFFFAOYSA-N

> <FORMULA>
C28H36O5

> <MOLECULAR_WEIGHT>
452.5824

> <EXACT_MASS>
452.256274262

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
50.59744940399742

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
16-(4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-15-hydroxy-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]nonadeca-4,6-dien-9-one

> <ALOGPS_LOGP>
4.32

> <JCHEM_LOGP>
4.1624895173333325

> <ALOGPS_LOGS>
-5.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.354132419117398

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.192701016871212

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5879889332831096

> <JCHEM_POLAR_SURFACE_AREA>
72.83

> <JCHEM_REFRACTIVITY>
126.39549999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.75e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
16-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-15-hydroxy-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]nonadeca-4,6-dien-9-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0032685
     RDKit          3D
(14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide
 69 74  0  0  0  0  0  0  0  0999 V2000
    5.0171   -2.8577    0.7652 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7086   -1.4321    0.4992 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6099   -0.6673   -0.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9171   -1.2496   -0.4616 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3298    0.7585   -0.3707 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1922    1.4984   -0.9293 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0702    1.1951    0.0191 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0225    0.2446   -0.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7235    0.8222    0.5000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0423    1.3140    1.9043 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7481   -0.1347    0.4396 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2088    0.2618   -0.5325 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4136    0.3473   -1.8782 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3090    1.5867   -1.7498 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1740    1.9591   -0.2638 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5662    3.1960    0.0416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3404    1.7140   -0.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0160    2.6196   -1.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8396    1.6880    1.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2987    1.2058    1.1843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3814   -0.2004    0.6568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4094   -0.5754   -0.3802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0181   -0.7806   -1.7732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1612   -1.7077   -1.6651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0066   -1.5406   -0.6722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1280   -2.4595   -0.5767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0522   -2.4054    0.3651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9749   -1.3417    1.4234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5661   -0.8667    1.5542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0286   -0.8111    2.6601 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8443   -0.4678    0.3126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5402    0.7789   -0.1840 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3834   -0.9224    0.9141 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0018   -2.9479    1.3061 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2781   -3.3496    1.3961 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0998   -3.4497   -0.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7859   -2.1980   -1.0287 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5340   -0.5370   -1.0375 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4945   -1.5332    0.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9772   -0.1877   -1.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1289    1.5876    1.9819 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8667    0.5590    2.6775 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5215    2.2945    2.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9523   -0.5398   -2.2163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3772    0.5285   -2.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3358    1.4163   -2.0574 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8191    2.4103   -2.3105 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0400    3.7153   -0.6565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0037    3.0421   -0.6998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2035    2.2930   -2.0781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3941    3.5630   -1.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8330    2.6264    1.8021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3526    0.8353    1.8136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6274    1.2267    2.2703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9569    1.9282    0.6933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1905   -0.8585    1.5612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0108   -1.6220   -0.1658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2246   -1.2990   -2.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3533    0.1484   -2.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2783   -2.4890   -2.3902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2655   -3.2717   -1.3092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8758   -3.0918    0.4226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2735   -1.8299    2.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6667   -0.5429    1.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9172    1.3855    0.6682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4825    0.4067   -0.6881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0006    1.3303   -0.9459 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4507   -0.6130    1.9578 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5888   -1.7055    0.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
 31 32  1  0
  8 33  1  0
 33  2  1  0
 15  9  1  0
 31 21  1  0
 17 12  1  0
 31 25  1  0
 22 12  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  4 37  1  0
  4 38  1  0
  4 39  1  0
  8 40  1  0
 10 41  1  0
 10 42  1  0
 10 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 16 48  1  0
 18 49  1  0
 18 50  1  0
 18 51  1  0
 19 52  1  0
 19 53  1  0
 20 54  1  0
 20 55  1  0
 21 56  1  0
 22 57  1  0
 23 58  1  0
 23 59  1  0
 24 60  1  0
 26 61  1  0
 27 62  1  0
 28 63  1  0
 28 64  1  0
 32 65  1  0
 32 66  1  0
 32 67  1  0
 33 68  1  0
 33 69  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -7.314  -2.744   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.314  -4.287   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.980  -5.058   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.648  -4.287   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.648  -2.744   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.980  -1.976   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.314  -5.058   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.982  -4.287   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.982  -2.744   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.314  -1.976   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.653  -1.976   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.653  -0.441   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.982   0.325   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -3.314  -0.441   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.805  -2.449   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.702  -1.207   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.805   0.029   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -5.980  -0.433   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -4.648  -1.202   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.052   1.050   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.283   1.495   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.033   1.366   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.252   2.642   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.792   1.814   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.820   0.667   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.327   0.983   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.805   2.446   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.777   3.593   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       3.267   3.274   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.255   5.058   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.314   2.765   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.358  -0.166   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       2.373   0.405   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10   19                                             
CONECT    6    1    5   18                                                  
CONECT    7    4    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    5    9   14                                                  
CONECT   11    9   12   15   33                                             
CONECT   12   11   13   17   20                                             
CONECT   13   12   14                                                       
CONECT   14   10   13                                                       
CONECT   15   11   16                                                       
CONECT   16   15   17                                                       
CONECT   17   12   16   21   22                                             
CONECT   18    6                                                            
CONECT   19    5                                                            
CONECT   20   12                                                            
CONECT   21   17   23   24   33                                             
CONECT   22   17                                                            
CONECT   23   21                                                            
CONECT   24   21   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   32                                                  
CONECT   27   26   28   31                                                  
CONECT   28   27   29   30                                                  
CONECT   29   24   28                                                       
CONECT   30   28                                                            
CONECT   31   27                                                            
CONECT   32   26                                                            
CONECT   33   11   21                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   76    0
END

COMPND    HMDB0032685
HETATM    1  C1  UNL     1       5.017  -2.858   0.765  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.709  -1.432   0.499  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.610  -0.667  -0.084  1.00  0.00           C  
HETATM    4  C4  UNL     1       6.917  -1.250  -0.462  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.330   0.758  -0.371  1.00  0.00           C  
HETATM    6  O1  UNL     1       6.192   1.498  -0.929  1.00  0.00           O  
HETATM    7  O2  UNL     1       4.070   1.195   0.019  1.00  0.00           O  
HETATM    8  C6  UNL     1       3.022   0.245  -0.015  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.724   0.822   0.500  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.042   1.314   1.904  1.00  0.00           C  
HETATM   11  O3  UNL     1       0.748  -0.135   0.440  1.00  0.00           O  
HETATM   12  C9  UNL     1      -0.209   0.262  -0.532  1.00  0.00           C  
HETATM   13  C10 UNL     1       0.414   0.347  -1.878  1.00  0.00           C  
HETATM   14  C11 UNL     1       1.309   1.587  -1.750  1.00  0.00           C  
HETATM   15  C12 UNL     1       1.174   1.959  -0.264  1.00  0.00           C  
HETATM   16  O4  UNL     1       1.566   3.196   0.042  1.00  0.00           O  
HETATM   17  C13 UNL     1      -0.340   1.714  -0.135  1.00  0.00           C  
HETATM   18  C14 UNL     1      -1.016   2.620  -1.055  1.00  0.00           C  
HETATM   19  C15 UNL     1      -0.840   1.688   1.261  1.00  0.00           C  
HETATM   20  C16 UNL     1      -2.299   1.206   1.184  1.00  0.00           C  
HETATM   21  C17 UNL     1      -2.381  -0.200   0.657  1.00  0.00           C  
HETATM   22  C18 UNL     1      -1.409  -0.575  -0.380  1.00  0.00           C  
HETATM   23  C19 UNL     1      -2.018  -0.781  -1.773  1.00  0.00           C  
HETATM   24  C20 UNL     1      -3.161  -1.708  -1.665  1.00  0.00           C  
HETATM   25  C21 UNL     1      -4.007  -1.541  -0.672  1.00  0.00           C  
HETATM   26  C22 UNL     1      -5.128  -2.459  -0.577  1.00  0.00           C  
HETATM   27  C23 UNL     1      -6.052  -2.405   0.365  1.00  0.00           C  
HETATM   28  C24 UNL     1      -5.975  -1.342   1.423  1.00  0.00           C  
HETATM   29  C25 UNL     1      -4.566  -0.867   1.554  1.00  0.00           C  
HETATM   30  O5  UNL     1      -4.029  -0.811   2.660  1.00  0.00           O  
HETATM   31  C26 UNL     1      -3.844  -0.468   0.313  1.00  0.00           C  
HETATM   32  C27 UNL     1      -4.540   0.779  -0.184  1.00  0.00           C  
HETATM   33  C28 UNL     1       3.383  -0.922   0.914  1.00  0.00           C  
HETATM   34  H1  UNL     1       6.002  -2.948   1.306  1.00  0.00           H  
HETATM   35  H2  UNL     1       4.278  -3.350   1.396  1.00  0.00           H  
HETATM   36  H3  UNL     1       5.100  -3.450  -0.188  1.00  0.00           H  
HETATM   37  H4  UNL     1       6.786  -2.198  -1.029  1.00  0.00           H  
HETATM   38  H5  UNL     1       7.534  -0.537  -1.038  1.00  0.00           H  
HETATM   39  H6  UNL     1       7.495  -1.533   0.453  1.00  0.00           H  
HETATM   40  H7  UNL     1       2.977  -0.188  -1.005  1.00  0.00           H  
HETATM   41  H8  UNL     1       3.129   1.588   1.982  1.00  0.00           H  
HETATM   42  H9  UNL     1       1.867   0.559   2.678  1.00  0.00           H  
HETATM   43  H10 UNL     1       1.522   2.294   2.120  1.00  0.00           H  
HETATM   44  H11 UNL     1       0.952  -0.540  -2.216  1.00  0.00           H  
HETATM   45  H12 UNL     1      -0.377   0.528  -2.638  1.00  0.00           H  
HETATM   46  H13 UNL     1       2.336   1.416  -2.057  1.00  0.00           H  
HETATM   47  H14 UNL     1       0.819   2.410  -2.311  1.00  0.00           H  
HETATM   48  H15 UNL     1       2.040   3.715  -0.657  1.00  0.00           H  
HETATM   49  H16 UNL     1      -2.004   3.042  -0.700  1.00  0.00           H  
HETATM   50  H17 UNL     1      -1.204   2.293  -2.078  1.00  0.00           H  
HETATM   51  H18 UNL     1      -0.394   3.563  -1.155  1.00  0.00           H  
HETATM   52  H19 UNL     1      -0.833   2.626   1.802  1.00  0.00           H  
HETATM   53  H20 UNL     1      -0.353   0.835   1.814  1.00  0.00           H  
HETATM   54  H21 UNL     1      -2.627   1.227   2.270  1.00  0.00           H  
HETATM   55  H22 UNL     1      -2.957   1.928   0.693  1.00  0.00           H  
HETATM   56  H23 UNL     1      -2.191  -0.859   1.561  1.00  0.00           H  
HETATM   57  H24 UNL     1      -1.011  -1.622  -0.166  1.00  0.00           H  
HETATM   58  H25 UNL     1      -1.225  -1.299  -2.378  1.00  0.00           H  
HETATM   59  H26 UNL     1      -2.353   0.148  -2.226  1.00  0.00           H  
HETATM   60  H27 UNL     1      -3.278  -2.489  -2.390  1.00  0.00           H  
HETATM   61  H28 UNL     1      -5.266  -3.272  -1.309  1.00  0.00           H  
HETATM   62  H29 UNL     1      -6.876  -3.092   0.423  1.00  0.00           H  
HETATM   63  H30 UNL     1      -6.274  -1.830   2.374  1.00  0.00           H  
HETATM   64  H31 UNL     1      -6.667  -0.543   1.102  1.00  0.00           H  
HETATM   65  H32 UNL     1      -4.917   1.386   0.668  1.00  0.00           H  
HETATM   66  H33 UNL     1      -5.483   0.407  -0.688  1.00  0.00           H  
HETATM   67  H34 UNL     1      -4.001   1.330  -0.946  1.00  0.00           H  
HETATM   68  H35 UNL     1       3.451  -0.613   1.958  1.00  0.00           H  
HETATM   69  H36 UNL     1       2.589  -1.706   0.800  1.00  0.00           H  
CONECT    1    2   34   35   36
CONECT    2    3    3   33
CONECT    3    4    5
CONECT    4   37   38   39
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   33   40
CONECT    9   10   11   15
CONECT   10   41   42   43
CONECT   11   12
CONECT   12   13   17   22
CONECT   13   14   44   45
CONECT   14   15   46   47
CONECT   15   16   17
CONECT   16   48
CONECT   17   18   19
CONECT   18   49   50   51
CONECT   19   20   52   53
CONECT   20   21   54   55
CONECT   21   22   31   56
CONECT   22   23   57
CONECT   23   24   58   59
CONECT   24   25   25   60
CONECT   25   26   31
CONECT   26   27   27   61
CONECT   27   28   62
CONECT   28   29   63   64
CONECT   29   30   30   31
CONECT   31   32
CONECT   32   65   66   67
CONECT   33   68   69
END

HMDB0032685
     RDKit          3D
(14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide
 69 74  0  0  0  0  0  0  0  0999 V2000
    5.0171   -2.8577    0.7652 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7086   -1.4321    0.4992 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6099   -0.6673   -0.0837 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9171   -1.2496   -0.4616 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3298    0.7585   -0.3707 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1922    1.4984   -0.9293 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0702    1.1951    0.0191 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0225    0.2446   -0.0147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7235    0.8222    0.5000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0423    1.3140    1.9043 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7481   -0.1347    0.4396 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2088    0.2618   -0.5325 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4136    0.3473   -1.8782 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3090    1.5867   -1.7498 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1740    1.9591   -0.2638 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5662    3.1960    0.0416 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3404    1.7140   -0.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0160    2.6196   -1.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8396    1.6880    1.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2987    1.2058    1.1843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3814   -0.2004    0.6568 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4094   -0.5754   -0.3802 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0181   -0.7806   -1.7732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1612   -1.7077   -1.6651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0066   -1.5406   -0.6722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1280   -2.4595   -0.5767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0522   -2.4054    0.3651 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9749   -1.3417    1.4234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5661   -0.8667    1.5542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0286   -0.8111    2.6601 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8443   -0.4678    0.3126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5402    0.7789   -0.1840 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3834   -0.9224    0.9141 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0018   -2.9479    1.3061 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2781   -3.3496    1.3961 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0998   -3.4497   -0.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7859   -2.1980   -1.0287 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5340   -0.5370   -1.0375 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4945   -1.5332    0.4535 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9772   -0.1877   -1.0055 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1289    1.5876    1.9819 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8667    0.5590    2.6775 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5215    2.2945    2.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9523   -0.5398   -2.2163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3772    0.5285   -2.6379 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3358    1.4163   -2.0574 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8191    2.4103   -2.3105 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0400    3.7153   -0.6565 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0037    3.0421   -0.6998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2035    2.2930   -2.0781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3941    3.5630   -1.1552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8330    2.6264    1.8021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3526    0.8353    1.8136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6274    1.2267    2.2703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9569    1.9282    0.6933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1905   -0.8585    1.5612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0108   -1.6220   -0.1658 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2246   -1.2990   -2.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3533    0.1484   -2.2261 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2783   -2.4890   -2.3902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2655   -3.2717   -1.3092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8758   -3.0918    0.4226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2735   -1.8299    2.3741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6667   -0.5429    1.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9172    1.3855    0.6682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4825    0.4067   -0.6881 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0006    1.3303   -0.9459 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4507   -0.6130    1.9578 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5888   -1.7055    0.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 29 31  1  0
 31 32  1  0
  8 33  1  0
 33  2  1  0
 15  9  1  0
 31 21  1  0
 17 12  1  0
 31 25  1  0
 22 12  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  4 37  1  0
  4 38  1  0
  4 39  1  0
  8 40  1  0
 10 41  1  0
 10 42  1  0
 10 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 16 48  1  0
 18 49  1  0
 18 50  1  0
 18 51  1  0
 19 52  1  0
 19 53  1  0
 20 54  1  0
 20 55  1  0
 21 56  1  0
 22 57  1  0
 23 58  1  0
 23 59  1  0
 24 60  1  0
 26 61  1  0
 27 62  1  0
 28 63  1  0
 28 64  1  0
 32 65  1  0
 32 66  1  0
 32 67  1  0
 33 68  1  0
 33 69  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(14a,17b,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide	Generator
(14Α,17β,20S,22R)-14,20-epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide	Generator

Chemical Formula

C₂₈H₃₆O₅

Average Molecular Weight

452.5824

Monoisotopic Molecular Weight

452.256274262

IUPAC Name

16-(4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)-15-hydroxy-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]nonadeca-4,6-dien-9-one

Traditional Name

16-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)-15-hydroxy-10,14,16-trimethyl-17-oxapentacyclo[13.2.2.0¹,¹⁴.0²,¹¹.0⁵,¹⁰]nonadeca-4,6-dien-9-one

CAS Registry Number

Not Available

SMILES

CC1=C(C)C(=O)OC(C1)C1(C)OC23CCC1(O)C2(C)CCC1C3CC=C2C=CCC(=O)C12C

InChI Identifier

InChI=1S/C28H36O5/c1-16-15-22(32-23(30)17(16)2)26(5)28(31)14-13-27(33-26)20-10-9-18-7-6-8-21(29)25(18,4)19(20)11-12-24(27,28)3/h6-7,9,19-20,22,31H,8,10-15H2,1-5H3

InChI Key

KOYNICXFSFFIPU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as withanolides and derivatives. These are c28 steroids structurally characterized by an ergostane skeleton usually functionalized at carbons 1, 22 and 26 to form a lactone ring.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Withanolides and derivatives

Alternative Parents

Substituents

Withanolide-skeleton
1-oxosteroid
Oxosteroid
Naphthofuran
Dihydropyranone
Cyclohexenone
Monosaccharide
Oxane
Pyran
Tetrahydrofuran
Tertiary alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Cyclic alcohol
Carboxylic acid ester
Ketone
Lactone
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Oxacycle
Ether
Dialkyl ether
Carboxylic acid derivative
Alcohol
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0032685)

Tissue

Nervous tissue

Hepatic tissue (HMDB: HMDB0032685)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032685)

Source

Endogenous

Endogenous (HMDB: HMDB0032685)

Plant

Plant (HMDB: HMDB0032685)

Animal

Animal (HMDB: HMDB0032685)

Exogenous

Food

Food (HMDB: HMDB0032685)

Fruit

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0032685)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0032685)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0032685)

Lipid metabolism pathway (HMDB: HMDB0032685)

Cellular process

Cell signaling (HMDB: HMDB0032685)

Biochemical process

Lipid transport (HMDB: HMDB0032685)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0032685)

Molecular messenger

Signaling molecule (HMDB: HMDB0032685)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0032685)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	192 - 193 °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	0.0038 g/L	ALOGPS
logP	4.32	ALOGPS
logP	4.16	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	13.19	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	126.4 m³·mol⁻¹	ChemAxon
Polarizability	50.6 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	206.168	31661259
DarkChem	[M-H]-	197.141	31661259
DeepCCS	[M-2H]-	235.883	30932474
DeepCCS	[M+Na]+	211.081	30932474
AllCCS	[M+H]+	209.6	32859911
AllCCS	[M+H-H2O]+	207.5	32859911
AllCCS	[M+NH4]+	211.5	32859911
AllCCS	[M+Na]+	212.1	32859911
AllCCS	[M-H]-	216.6	32859911
AllCCS	[M+Na-2H]-	218.0	32859911
AllCCS	[M+HCOO]-	219.7	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.	7.76 minutes	32390414
Predicted by Siyang on May 30, 2022	17.7416 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.46 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3280.1 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	256.7 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	230.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	169.0 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	160.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	958.2 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	961.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	84.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1537.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	560.7 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	1565.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	619.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	476.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	321.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	530.3 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
(14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide	CC1=C(C)C(=O)OC(C1)C1(C)OC23CCC1(O)C2(C)CCC1C3CC=C2C=CCC(=O)C12C	4585.5	Standard polar	33892256
(14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide	CC1=C(C)C(=O)OC(C1)C1(C)OC23CCC1(O)C2(C)CCC1C3CC=C2C=CCC(=O)C12C	3322.5	Standard non polar	33892256
(14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide	CC1=C(C)C(=O)OC(C1)C1(C)OC23CCC1(O)C2(C)CCC1C3CC=C2C=CCC(=O)C12C	4002.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide,1TMS,isomer #1	CC1=C(C)C(=O)OC(C2(C)OC34CCC2(O[Si](C)(C)C)C3(C)CCC2C4CC=C3C=CCC(=O)C32C)C1	3803.2	Semi standard non polar	33892256
(14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide,1TMS,isomer #2	CC1=C(C)C(=O)OC(C2(C)OC34CCC2(O)C3(C)CCC2C4CC=C3C=CC=C(O[Si](C)(C)C)C32C)C1	3750.3	Semi standard non polar	33892256
(14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide,2TMS,isomer #1	CC1=C(C)C(=O)OC(C2(C)OC34CCC2(O[Si](C)(C)C)C3(C)CCC2C4CC=C3C=CC=C(O[Si](C)(C)C)C32C)C1	3789.2	Semi standard non polar	33892256
(14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide,2TMS,isomer #1	CC1=C(C)C(=O)OC(C2(C)OC34CCC2(O[Si](C)(C)C)C3(C)CCC2C4CC=C3C=CC=C(O[Si](C)(C)C)C32C)C1	3623.2	Standard non polar	33892256
(14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide,1TBDMS,isomer #1	CC1=C(C)C(=O)OC(C2(C)OC34CCC2(O[Si](C)(C)C(C)(C)C)C3(C)CCC2C4CC=C3C=CCC(=O)C32C)C1	4037.7	Semi standard non polar	33892256
(14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide,1TBDMS,isomer #2	CC1=C(C)C(=O)OC(C2(C)OC34CCC2(O)C3(C)CCC2C4CC=C3C=CC=C(O[Si](C)(C)C(C)(C)C)C32C)C1	3976.0	Semi standard non polar	33892256
(14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide,2TBDMS,isomer #1	CC1=C(C)C(=O)OC(C2(C)OC34CCC2(O[Si](C)(C)C(C)(C)C)C3(C)CCC2C4CC=C3C=CC=C(O[Si](C)(C)C(C)(C)C)C32C)C1	4238.1	Semi standard non polar	33892256
(14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide,2TBDMS,isomer #1	CC1=C(C)C(=O)OC(C2(C)OC34CCC2(O[Si](C)(C)C(C)(C)C)C3(C)CCC2C4CC=C3C=CC=C(O[Si](C)(C)C(C)(C)C)C32C)C1	4076.7	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide GC-MS (Non-derivatized) - 70eV, Positive	splash10-003i-5893600000-e53d4ccf4fcc74d2a9ac	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide GC-MS (1 TMS) - 70eV, Positive	splash10-0a4i-5509350000-b3e360222f23f8242978	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide 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 - (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide 10V, Positive-QTOF	splash10-0udi-0102900000-ed52c032774b8d3cc85d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide 20V, Positive-QTOF	splash10-0udi-9107400000-84e673e3ace95618e03b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide 40V, Positive-QTOF	splash10-0uyr-9474200000-fbfc8ef57fcafd44cb0c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide 10V, Negative-QTOF	splash10-0udi-0002900000-a1a519533d32bcf115c6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide 20V, Negative-QTOF	splash10-0zfr-1003900000-1a7c20ce888212ac3d57	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide 40V, Negative-QTOF	splash10-02t9-9203000000-aff88b35db039e3664ca	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide 10V, Positive-QTOF	splash10-0udi-0000900000-159b2996bf6fe76614e4	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide 20V, Positive-QTOF	splash10-0udr-4338900000-d38aebf7f02d6fec872b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide 40V, Positive-QTOF	splash10-0j4r-4928100000-1bb4260ea21842302f3e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide 10V, Negative-QTOF	splash10-0udi-0000900000-169e1b4194a44a788bba	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide 20V, Negative-QTOF	splash10-0fb9-2109700000-4eae2bb02656d7cd3a69	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide 40V, Negative-QTOF	splash10-0fn9-9300100000-a8985d2a0afcf49ad95b	2021-09-24	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

FDB010642

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

73699089

PDB ID

Not Available

ChEBI ID

176145

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 (14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide (HMDB0032685)

MOL for HMDB0032685 ((14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide)

3D MOL for HMDB0032685 ((14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide)

3D SDF for HMDB0032685 ((14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide)

3D-SDF for HMDB0032685 ((14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide)

PDB for HMDB0032685 ((14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide)

3D PDB for HMDB0032685 ((14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide)

SMILES for HMDB0032685 ((14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide)

INCHI for HMDB0032685 ((14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide)

Structure for HMDB0032685 ((14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide)

3D Structure for HMDB0032685 ((14alpha,17beta,20S,22R)-14,20-Epoxy-17-hydroxy-1-oxowitha-3,5,24-trienolide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra