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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 09:30:52 UTC

Update Date

2021-09-26 23:04:09 UTC

HMDB ID

HMDB0251873

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Epothilone A

Description

HMS3654L13 belongs to the class of organic compounds known as epothilones and analogues. These are macrolides consisting of a 16-member lactone ring conjugated at the carbon 16 with a 1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl group. Some epothilone analogues containing a lactam ring instead of the lactone ring. HMS3654L13 is a moderately basic compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Epothilone a is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Epothilone A is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

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

  Mrv1533004161508282D          

 34 36  0  0  0  0            999 V2000
    3.3048   -1.1701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8425   -0.4868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0196   -0.5455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5573    0.1378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7344    0.0791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2721    0.7624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1902    1.4457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6327    1.5044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4556    1.5631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8162    2.3052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6391    2.3639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9997    3.1059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5374    3.7892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8226    3.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2849    2.4813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1078    2.5400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9243    1.7393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6775    2.0759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7177    1.5130    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3866    1.0560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2095    1.1147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0260    0.3140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4883   -0.3693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2031    0.2553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6654   -0.4280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3539    2.9885    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7145    3.7305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2522    4.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4276    4.4414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1991    5.2341    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.8824    5.6964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9100    6.5209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5332    5.1894    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5310    2.9297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  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
  7  8  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
  2 24  1  0  0  0  0
 24 25  1  0  0  0  0
 10 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  4  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 28 33  1  0  0  0  0
 26 34  1  0  0  0  0
M  END

HMDB0251873
     RDKit          3D
Epothilone A
 73 75  0  0  0  0  0  0  0  0999 V2000
    4.5097    1.3190   -1.5286 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7317    0.3098   -0.7801 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3810   -0.6745   -0.2102 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8693   -0.7523   -0.3266 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4967   -1.9694   -0.4994 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1392   -1.4903   -0.5559 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.9290    0.1967   -0.3595 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9581    1.2972   -0.3043 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6169    0.2950   -0.2623 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2563    0.3777   -0.6643 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7585   -0.7493    0.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6683   -2.0483   -0.5247 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8373   -3.2657    0.0785 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5376   -2.8303    0.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4192   -3.3121   -1.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3946   -2.2260   -1.4358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7663   -2.7664   -1.4001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7166   -2.1020   -0.4668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0684   -2.7672   -0.6347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8746   -0.6383   -0.6221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0326   -0.0525   -1.5484 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6647    0.0739    0.6989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8722   -0.0600    1.6003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4452    1.5030    0.4452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8073    1.9646   -0.6233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8100    2.4487    1.3951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7145    3.6605    1.5304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5823    1.8858    2.7536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4801    2.9801    0.8771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9911    3.8246    1.8674 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5244    1.8390    0.5944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6442    2.2705   -0.2176 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4272    3.3110   -0.8986 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7718    1.5540   -0.1600 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0056    2.0325   -0.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8418    1.8773   -2.2387 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3182    0.9080   -2.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8855   -1.4690    0.3602 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0149   -2.9609   -0.5753 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5239    2.1548    0.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8414    0.9163    0.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2267    1.5290   -1.3496 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8888    0.1036   -1.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2339   -0.7955    1.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6797   -0.4638    0.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8646   -1.9980   -1.6176 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1245   -2.5212    1.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9899   -4.1950   -0.6456 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1272   -3.6746   -1.9338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1074   -1.9327   -2.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2195   -1.3751   -0.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7438   -3.8426   -1.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2026   -2.7298   -2.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3742   -2.3234    0.5764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8554   -2.0319   -0.9691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3858   -3.3073    0.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0636   -3.5520   -1.4324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9193   -0.3836   -0.9673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4459    0.0339   -2.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8006   -0.4293    1.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8184   -0.0533    1.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7944   -0.9248    2.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8943    0.8423    2.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3078    4.3571    2.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8084    4.2122    0.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7370    3.3569    1.8334 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
  2  3  2  3
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  2 10  1  0
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 11 12  1  0
 12 13  1  0
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 18 20  1  0
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 29 30  1  0
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 31 32  1  0
 32 33  2  0
 32 34  1  0
  9  4  1  0
 34 10  1  0
 14 12  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  3 38  1  0
  5 39  1  0
  8 40  1  0
  8 41  1  0
  8 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  0
 14 47  1  0
 15 48  1  0
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 27 66  1  0
 28 67  1  0
 28 68  1  0
 28 69  1  0
 29 70  1  0
 30 71  1  0
 31 72  1  0
 31 73  1  0
M  END

  Mrv1533004161508282D          

 34 36  0  0  0  0            999 V2000
    3.3048   -1.1701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8425   -0.4868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0196   -0.5455    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5573    0.1378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7344    0.0791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2721    0.7624    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1902    1.4457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6327    1.5044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4556    1.5631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8162    2.3052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6391    2.3639    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9997    3.1059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5374    3.7892    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8226    3.1646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2849    2.4813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1078    2.5400    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9243    1.7393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.2031    0.2553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6654   -0.4280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2522    4.4138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1991    5.2341    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.8824    5.6964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9100    6.5209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5332    5.1894    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5310    2.9297    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  5  6  1  0  0  0  0
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  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
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 15 16  1  0  0  0  0
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 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
  2 24  1  0  0  0  0
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 10 26  1  0  0  0  0
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 27 28  1  4  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  2  0  0  0  0
 28 33  1  0  0  0  0
 26 34  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0251873

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CCCC2OC2CC(OC(=O)CC(O)C(C)(C)C(=O)C(C)C1O)C(C)=CC1=CSC(C)=N1

> <INCHI_IDENTIFIER>
InChI=1S/C26H39NO6S/c1-14-8-7-9-19-21(32-19)11-20(15(2)10-18-13-34-17(4)27-18)33-23(29)12-22(28)26(5,6)25(31)16(3)24(14)30/h10,13-14,16,19-22,24,28,30H,7-9,11-12H2,1-6H3

> <INCHI_KEY>
HESCAJZNRMSMJG-UHFFFAOYSA-N

> <FORMULA>
C26H39NO6S

> <MOLECULAR_WEIGHT>
493.66

> <EXACT_MASS>
493.249809154

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
53.628257572152485

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
7,11-dihydroxy-8,8,10,12-tetramethyl-3-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione

> <ALOGPS_LOGP>
3.28

> <JCHEM_LOGP>
3.8421570899999993

> <ALOGPS_LOGS>
-5.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.727575467617832

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.086928945208811

> <JCHEM_PKA_STRONGEST_BASIC>
2.7263327178808083

> <JCHEM_POLAR_SURFACE_AREA>
109.25

> <JCHEM_REFRACTIVITY>
130.1218

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.37e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7,11-dihydroxy-8,8,10,12-tetramethyl-3-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0251873
     RDKit          3D
Epothilone A
 73 75  0  0  0  0  0  0  0  0999 V2000
    4.5097    1.3190   -1.5286 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7317    0.3098   -0.7801 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3810   -0.6745   -0.2102 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8693   -0.7523   -0.3266 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4967   -1.9694   -0.4994 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1392   -1.4903   -0.5559 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.9290    0.1967   -0.3595 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9581    1.2972   -0.3043 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6169    0.2950   -0.2623 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2563    0.3777   -0.6643 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7585   -0.7493    0.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6683   -2.0483   -0.5247 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8373   -3.2657    0.0785 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5376   -2.8303    0.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4192   -3.3121   -1.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3946   -2.2260   -1.4358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7663   -2.7664   -1.4001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7166   -2.1020   -0.4668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0684   -2.7672   -0.6347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8746   -0.6383   -0.6221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0326   -0.0525   -1.5484 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6647    0.0739    0.6989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8722   -0.0600    1.6003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4452    1.5030    0.4452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8073    1.9646   -0.6233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8100    2.4487    1.3951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7145    3.6605    1.5304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5823    1.8858    2.7536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4801    2.9801    0.8771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9911    3.8246    1.8674 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5244    1.8390    0.5944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6442    2.2705   -0.2176 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4272    3.3110   -0.8986 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7718    1.5540   -0.1600 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0056    2.0325   -0.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8418    1.8773   -2.2387 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3182    0.9080   -2.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8855   -1.4690    0.3602 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0149   -2.9609   -0.5753 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5239    2.1548    0.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8414    0.9163    0.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2267    1.5290   -1.3496 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8888    0.1036   -1.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2339   -0.7955    1.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6797   -0.4638    0.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8646   -1.9980   -1.6176 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1245   -2.5212    1.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9899   -4.1950   -0.6456 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1272   -3.6746   -1.9338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1074   -1.9327   -2.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2195   -1.3751   -0.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7438   -3.8426   -1.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2026   -2.7298   -2.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3742   -2.3234    0.5764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8554   -2.0319   -0.9691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3858   -3.3073    0.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0636   -3.5520   -1.4324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9193   -0.3836   -0.9673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4459    0.0339   -2.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8006   -0.4293    1.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8184   -0.0533    1.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7944   -0.9248    2.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8943    0.8423    2.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3078    4.3571    2.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8084    4.2122    0.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7370    3.3569    1.8334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5899    2.2190    3.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3710    2.2380    3.4485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5538    0.7854    2.7938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6203    3.5793   -0.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0053    3.9110    1.7983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2495    1.4178    1.5752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0872    1.0831    0.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  2 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 32 33  2  0
 32 34  1  0
  9  4  1  0
 34 10  1  0
 14 12  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  3 38  1  0
  5 39  1  0
  8 40  1  0
  8 41  1  0
  8 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 16 50  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 18 54  1  0
 19 55  1  0
 19 56  1  0
 19 57  1  0
 20 58  1  0
 21 59  1  0
 22 60  1  0
 23 61  1  0
 23 62  1  0
 23 63  1  0
 27 64  1  0
 27 65  1  0
 27 66  1  0
 28 67  1  0
 28 68  1  0
 28 69  1  0
 29 70  1  0
 30 71  1  0
 31 72  1  0
 31 73  1  0
M  END

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0       6.169  -2.184   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.306  -0.909   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.770  -1.018   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.907   0.257   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.371   0.148   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.508   1.423   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.355   2.699   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.181   2.808   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.717   2.918   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.390   4.303   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.926   4.413   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.599   5.798   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.736   7.073   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       7.135   5.907   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.998   4.632   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.535   4.741   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.325   3.247   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.731   3.875   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.806   2.824   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.188   1.971   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.724   2.081   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       7.515   0.586   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.378  -0.689   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.979   0.476   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.842  -0.799   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.527   5.578   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.200   6.964   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.337   8.239   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.798   8.291   0.000  0.00  0.00           C+0
HETATM   30  S   UNK     0       0.372   9.770   0.000  0.00  0.00           S+0
HETATM   31  C   UNK     0       1.647  10.633   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.699  12.172   0.000  0.00  0.00           C+0
HETATM   33  N   UNK     0       2.862   9.687   0.000  0.00  0.00           N+0
HETATM   34  C   UNK     0       0.991   5.469   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   24                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6    8                                                       
CONECT    8    7    6    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   26                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22    2   25                                                  
CONECT   25   24                                                            
CONECT   26   10   27   34                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   28                                                       
CONECT   34   26                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   72    0
END

COMPND    HMDB0251873
HETATM    1  C1  UNL     1       4.510   1.319  -1.529  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.732   0.310  -0.780  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.381  -0.674  -0.210  1.00  0.00           C  
HETATM    4  C4  UNL     1       5.869  -0.752  -0.327  1.00  0.00           C  
HETATM    5  C5  UNL     1       6.497  -1.969  -0.499  1.00  0.00           C  
HETATM    6  S1  UNL     1       8.139  -1.490  -0.556  1.00  0.00           S  
HETATM    7  C6  UNL     1       7.929   0.197  -0.359  1.00  0.00           C  
HETATM    8  C7  UNL     1       8.958   1.297  -0.304  1.00  0.00           C  
HETATM    9  N1  UNL     1       6.617   0.295  -0.262  1.00  0.00           N  
HETATM   10  C8  UNL     1       2.256   0.378  -0.664  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.759  -0.749   0.221  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.668  -2.048  -0.525  1.00  0.00           C  
HETATM   13  O1  UNL     1       1.837  -3.266   0.078  1.00  0.00           O  
HETATM   14  C11 UNL     1       0.538  -2.830   0.027  1.00  0.00           C  
HETATM   15  C12 UNL     1      -0.419  -3.312  -1.043  1.00  0.00           C  
HETATM   16  C13 UNL     1      -1.395  -2.226  -1.436  1.00  0.00           C  
HETATM   17  C14 UNL     1      -2.766  -2.766  -1.400  1.00  0.00           C  
HETATM   18  C15 UNL     1      -3.717  -2.102  -0.467  1.00  0.00           C  
HETATM   19  C16 UNL     1      -5.068  -2.767  -0.635  1.00  0.00           C  
HETATM   20  C17 UNL     1      -3.875  -0.638  -0.622  1.00  0.00           C  
HETATM   21  O2  UNL     1      -3.033  -0.053  -1.548  1.00  0.00           O  
HETATM   22  C18 UNL     1      -3.665   0.074   0.699  1.00  0.00           C  
HETATM   23  C19 UNL     1      -4.872  -0.060   1.600  1.00  0.00           C  
HETATM   24  C20 UNL     1      -3.445   1.503   0.445  1.00  0.00           C  
HETATM   25  O3  UNL     1      -3.807   1.965  -0.623  1.00  0.00           O  
HETATM   26  C21 UNL     1      -2.810   2.449   1.395  1.00  0.00           C  
HETATM   27  C22 UNL     1      -3.714   3.661   1.530  1.00  0.00           C  
HETATM   28  C23 UNL     1      -2.582   1.886   2.754  1.00  0.00           C  
HETATM   29  C24 UNL     1      -1.480   2.980   0.877  1.00  0.00           C  
HETATM   30  O4  UNL     1      -0.991   3.825   1.867  1.00  0.00           O  
HETATM   31  C25 UNL     1      -0.524   1.839   0.594  1.00  0.00           C  
HETATM   32  C26 UNL     1       0.644   2.271  -0.218  1.00  0.00           C  
HETATM   33  O5  UNL     1       0.427   3.311  -0.899  1.00  0.00           O  
HETATM   34  O6  UNL     1       1.772   1.554  -0.160  1.00  0.00           O  
HETATM   35  H1  UNL     1       5.006   2.032  -0.807  1.00  0.00           H  
HETATM   36  H2  UNL     1       3.842   1.877  -2.239  1.00  0.00           H  
HETATM   37  H3  UNL     1       5.318   0.908  -2.151  1.00  0.00           H  
HETATM   38  H4  UNL     1       3.886  -1.469   0.360  1.00  0.00           H  
HETATM   39  H5  UNL     1       6.015  -2.961  -0.575  1.00  0.00           H  
HETATM   40  H6  UNL     1       8.524   2.155   0.238  1.00  0.00           H  
HETATM   41  H7  UNL     1       9.841   0.916   0.282  1.00  0.00           H  
HETATM   42  H8  UNL     1       9.227   1.529  -1.350  1.00  0.00           H  
HETATM   43  H9  UNL     1       1.889   0.104  -1.686  1.00  0.00           H  
HETATM   44  H10 UNL     1       2.234  -0.796   1.205  1.00  0.00           H  
HETATM   45  H11 UNL     1       0.680  -0.464   0.443  1.00  0.00           H  
HETATM   46  H12 UNL     1       1.865  -1.998  -1.618  1.00  0.00           H  
HETATM   47  H13 UNL     1       0.124  -2.521   1.005  1.00  0.00           H  
HETATM   48  H14 UNL     1      -0.990  -4.195  -0.646  1.00  0.00           H  
HETATM   49  H15 UNL     1       0.127  -3.675  -1.934  1.00  0.00           H  
HETATM   50  H16 UNL     1      -1.107  -1.933  -2.489  1.00  0.00           H  
HETATM   51  H17 UNL     1      -1.220  -1.375  -0.739  1.00  0.00           H  
HETATM   52  H18 UNL     1      -2.744  -3.843  -1.132  1.00  0.00           H  
HETATM   53  H19 UNL     1      -3.203  -2.730  -2.433  1.00  0.00           H  
HETATM   54  H20 UNL     1      -3.374  -2.323   0.576  1.00  0.00           H  
HETATM   55  H21 UNL     1      -5.855  -2.032  -0.969  1.00  0.00           H  
HETATM   56  H22 UNL     1      -5.386  -3.307   0.287  1.00  0.00           H  
HETATM   57  H23 UNL     1      -5.064  -3.552  -1.432  1.00  0.00           H  
HETATM   58  H24 UNL     1      -4.919  -0.384  -0.967  1.00  0.00           H  
HETATM   59  H25 UNL     1      -3.446   0.034  -2.443  1.00  0.00           H  
HETATM   60  H26 UNL     1      -2.801  -0.429   1.177  1.00  0.00           H  
HETATM   61  H27 UNL     1      -5.818  -0.053   1.035  1.00  0.00           H  
HETATM   62  H28 UNL     1      -4.794  -0.925   2.308  1.00  0.00           H  
HETATM   63  H29 UNL     1      -4.894   0.842   2.244  1.00  0.00           H  
HETATM   64  H30 UNL     1      -3.308   4.357   2.270  1.00  0.00           H  
HETATM   65  H31 UNL     1      -3.808   4.212   0.559  1.00  0.00           H  
HETATM   66  H32 UNL     1      -4.737   3.357   1.833  1.00  0.00           H  
HETATM   67  H33 UNL     1      -1.590   2.219   3.169  1.00  0.00           H  
HETATM   68  H34 UNL     1      -3.371   2.238   3.449  1.00  0.00           H  
HETATM   69  H35 UNL     1      -2.554   0.785   2.794  1.00  0.00           H  
HETATM   70  H36 UNL     1      -1.620   3.579  -0.047  1.00  0.00           H  
HETATM   71  H37 UNL     1      -0.005   3.911   1.798  1.00  0.00           H  
HETATM   72  H38 UNL     1      -0.250   1.418   1.575  1.00  0.00           H  
HETATM   73  H39 UNL     1      -1.087   1.083   0.025  1.00  0.00           H  
CONECT    1    2   35   36   37
CONECT    2    3    3   10
CONECT    3    4   38
CONECT    4    5    5    9
CONECT    5    6   39
CONECT    6    7
CONECT    7    8    9    9
CONECT    8   40   41   42
CONECT   10   11   34   43
CONECT   11   12   44   45
CONECT   12   13   14   46
CONECT   13   14
CONECT   14   15   47
CONECT   15   16   48   49
CONECT   16   17   50   51
CONECT   17   18   52   53
CONECT   18   19   20   54
CONECT   19   55   56   57
CONECT   20   21   22   58
CONECT   21   59
CONECT   22   23   24   60
CONECT   23   61   62   63
CONECT   24   25   25   26
CONECT   26   27   28   29
CONECT   27   64   65   66
CONECT   28   67   68   69
CONECT   29   30   31   70
CONECT   30   71
CONECT   31   32   72   73
CONECT   32   33   33   34
END

HMDB0251873
     RDKit          3D
Epothilone A
 73 75  0  0  0  0  0  0  0  0999 V2000
    4.5097    1.3190   -1.5286 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7317    0.3098   -0.7801 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3810   -0.6745   -0.2102 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8693   -0.7523   -0.3266 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4967   -1.9694   -0.4994 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1392   -1.4903   -0.5559 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.9290    0.1967   -0.3595 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9581    1.2972   -0.3043 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6169    0.2950   -0.2623 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2563    0.3777   -0.6643 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7585   -0.7493    0.2208 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6683   -2.0483   -0.5247 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8373   -3.2657    0.0785 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5376   -2.8303    0.0273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4192   -3.3121   -1.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3946   -2.2260   -1.4358 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7663   -2.7664   -1.4001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7166   -2.1020   -0.4668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0684   -2.7672   -0.6347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8746   -0.6383   -0.6221 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0326   -0.0525   -1.5484 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6647    0.0739    0.6989 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8722   -0.0600    1.6003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4452    1.5030    0.4452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8073    1.9646   -0.6233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8100    2.4487    1.3951 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7145    3.6605    1.5304 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5823    1.8858    2.7536 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4801    2.9801    0.8771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9911    3.8246    1.8674 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5244    1.8390    0.5944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6442    2.2705   -0.2176 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4272    3.3110   -0.8986 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7718    1.5540   -0.1600 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0056    2.0325   -0.8068 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8418    1.8773   -2.2387 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3182    0.9080   -2.1511 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8855   -1.4690    0.3602 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0149   -2.9609   -0.5753 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5239    2.1548    0.2378 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8414    0.9163    0.2824 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2267    1.5290   -1.3496 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8888    0.1036   -1.6862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2339   -0.7955    1.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6797   -0.4638    0.4432 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8646   -1.9980   -1.6176 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1245   -2.5212    1.0052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9899   -4.1950   -0.6456 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1272   -3.6746   -1.9338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1074   -1.9327   -2.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2195   -1.3751   -0.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7438   -3.8426   -1.1318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2026   -2.7298   -2.4327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3742   -2.3234    0.5764 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8554   -2.0319   -0.9691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3858   -3.3073    0.2869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0636   -3.5520   -1.4324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9193   -0.3836   -0.9673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4459    0.0339   -2.4428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8006   -0.4293    1.1770 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8184   -0.0533    1.0348 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7944   -0.9248    2.3076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8943    0.8423    2.2443 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3078    4.3571    2.2702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8084    4.2122    0.5590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7370    3.3569    1.8334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5899    2.2190    3.1694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3710    2.2380    3.4485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5538    0.7854    2.7938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6203    3.5793   -0.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0053    3.9110    1.7983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2495    1.4178    1.5752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0872    1.0831    0.0250 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  3
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  2 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  2  0
 24 26  1  0
 26 27  1  0
 26 28  1  0
 26 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  1  0
 32 33  2  0
 32 34  1  0
  9  4  1  0
 34 10  1  0
 14 12  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  3 38  1  0
  5 39  1  0
  8 40  1  0
  8 41  1  0
  8 42  1  0
 10 43  1  0
 11 44  1  0
 11 45  1  0
 12 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 16 50  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 18 54  1  0
 19 55  1  0
 19 56  1  0
 19 57  1  0
 20 58  1  0
 21 59  1  0
 22 60  1  0
 23 61  1  0
 23 62  1  0
 23 63  1  0
 27 64  1  0
 27 65  1  0
 27 66  1  0
 28 67  1  0
 28 68  1  0
 28 69  1  0
 29 70  1  0
 30 71  1  0
 31 72  1  0
 31 73  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₂₆H₃₉NO₆S

Average Molecular Weight

493.66

Monoisotopic Molecular Weight

493.249809154

IUPAC Name

7,11-dihydroxy-8,8,10,12-tetramethyl-3-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione

Traditional Name

7,11-dihydroxy-8,8,10,12-tetramethyl-3-[1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione

CAS Registry Number

Not Available

SMILES

CC1CCCC2OC2CC(OC(=O)CC(O)C(C)(C)C(=O)C(C)C1O)C(C)=CC1=CSC(C)=N1

InChI Identifier

InChI=1S/C26H39NO6S/c1-14-8-7-9-19-21(32-19)11-20(15(2)10-18-13-34-17(4)27-18)33-23(29)12-22(28)26(5,6)25(31)16(3)24(14)30/h10,13-14,16,19-22,24,28,30H,7-9,11-12H2,1-6H3

InChI Key

HESCAJZNRMSMJG-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as epothilones and analogues. These are macrolides consisting of a 16-member lactone ring conjugated at the carbon 16 with a 1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl group. Some epothilone analogues containing a lactam ring instead of the lactone ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Epothilones and analogues

Direct Parent

Epothilones and analogues

Alternative Parents

Substituents

Epothilone
2,4-disubstituted 1,3-thiazole
Azole
Heteroaromatic compound
Thiazole
Carboxylic acid ester
Ketone
Lactone
Secondary alcohol
Cyclic ketone
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Azacycle
Monocarboxylic acid or derivatives
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Organic oxide
Organonitrogen compound
Organooxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	3.28	ALOGPS
logP	3.84	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Acidic)	14.09	ChemAxon
pKa (Strongest Basic)	2.73	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	109.25 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	130.12 m³·mol⁻¹	ChemAxon
Polarizability	53.63 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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]+	215.694	30932474
DeepCCS	[M-H]-	213.336	30932474
DeepCCS	[M-2H]-	246.462	30932474
DeepCCS	[M+Na]+	221.788	30932474
AllCCS	[M+H]+	219.9	32859911
AllCCS	[M+H-H2O]+	218.0	32859911
AllCCS	[M+NH4]+	221.7	32859911
AllCCS	[M+Na]+	222.2	32859911
AllCCS	[M-H]-	222.5	32859911
AllCCS	[M+Na-2H]-	225.0	32859911
AllCCS	[M+HCOO]-	227.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Epothilone A	CC1CCCC2OC2CC(OC(=O)CC(O)C(C)(C)C(=O)C(C)C1O)C(C)=CC1=CSC(C)=N1	4098.6	Standard polar	33892256
Epothilone A	CC1CCCC2OC2CC(OC(=O)CC(O)C(C)(C)C(=O)C(C)C1O)C(C)=CC1=CSC(C)=N1	3346.2	Standard non polar	33892256
Epothilone A	CC1CCCC2OC2CC(OC(=O)CC(O)C(C)(C)C(=O)C(C)C1O)C(C)=CC1=CSC(C)=N1	3790.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Epothilone A,3TMS,isomer #1	CC(=CC1=CSC(C)=N1)C1CC2OC2CCCC(C)C(O[Si](C)(C)C)C(C)=C(O[Si](C)(C)C)C(C)(C)C(O[Si](C)(C)C)CC(=O)O1	3778.4	Semi standard non polar	33892256
Epothilone A,3TMS,isomer #1	CC(=CC1=CSC(C)=N1)C1CC2OC2CCCC(C)C(O[Si](C)(C)C)C(C)=C(O[Si](C)(C)C)C(C)(C)C(O[Si](C)(C)C)CC(=O)O1	3679.7	Standard non polar	33892256
Epothilone A,3TMS,isomer #1	CC(=CC1=CSC(C)=N1)C1CC2OC2CCCC(C)C(O[Si](C)(C)C)C(C)=C(O[Si](C)(C)C)C(C)(C)C(O[Si](C)(C)C)CC(=O)O1	4162.4	Standard polar	33892256
Epothilone A,3TBDMS,isomer #1	CC(=CC1=CSC(C)=N1)C1CC2OC2CCCC(C)C(O[Si](C)(C)C(C)(C)C)C(C)=C(O[Si](C)(C)C(C)(C)C)C(C)(C)C(O[Si](C)(C)C(C)(C)C)CC(=O)O1	4417.5	Semi standard non polar	33892256
Epothilone A,3TBDMS,isomer #1	CC(=CC1=CSC(C)=N1)C1CC2OC2CCCC(C)C(O[Si](C)(C)C(C)(C)C)C(C)=C(O[Si](C)(C)C(C)(C)C)C(C)(C)C(O[Si](C)(C)C(C)(C)C)CC(=O)O1	4290.7	Standard non polar	33892256
Epothilone A,3TBDMS,isomer #1	CC(=CC1=CSC(C)=N1)C1CC2OC2CCCC(C)C(O[Si](C)(C)C(C)(C)C)C(C)=C(O[Si](C)(C)C(C)(C)C)C(C)(C)C(O[Si](C)(C)C(C)(C)C)CC(=O)O1	4337.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Epothilone A GC-MS (Non-derivatized) - 70eV, Positive	splash10-004r-1701900000-4cd67ce53d5a71871486	2021-09-24	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epothilone A GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epothilone A GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epothilone A GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epothilone A GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epothilone A GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epothilone A GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epothilone A GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epothilone A GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epothilone A GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epothilone A GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epothilone A GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epothilone A GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-11-04	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Epothilone A GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-11-04	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 - Epothilone A 10V, Positive-QTOF	splash10-002f-0000900000-9af3adade17b6972f0b2	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epothilone A 20V, Positive-QTOF	splash10-0a4i-0000900000-413894c25841499bf398	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epothilone A 40V, Positive-QTOF	splash10-0bvu-4807900000-7fac18aa303695fe7759	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epothilone A 10V, Negative-QTOF	splash10-0006-0000900000-01059924986a919e73a4	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epothilone A 20V, Negative-QTOF	splash10-0006-0000900000-a0d886fe0b99582422c0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Epothilone A 40V, Negative-QTOF	splash10-0079-9804500000-ac1229a19c61f53eb106	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

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

Not Available

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

73106690

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

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for Epothilone A (HMDB0251873)

MOL for HMDB0251873 (Epothilone A)

3D MOL for HMDB0251873 (Epothilone A)

3D SDF for HMDB0251873 (Epothilone A)

3D-SDF for HMDB0251873 (Epothilone A)

PDB for HMDB0251873 (Epothilone A)

3D PDB for HMDB0251873 (Epothilone A)

SMILES for HMDB0251873 (Epothilone A)

INCHI for HMDB0251873 (Epothilone A)

Structure for HMDB0251873 (Epothilone A)

3D Structure for HMDB0251873 (Epothilone A)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra