NP-MRD: Showing NP-Card for Epothilone C5 (NP0003747)

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Record Information

Version

1.0

Created at

2020-12-09 00:54:39 UTC

Updated at

2021-07-15 16:47:16 UTC

NP-MRD ID

NP0003747

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Epothilone C5

Provided By

NPAtlas

Description

(4S,7R,8R,9Z,13Z,16S)-4,8-dihydroxy-5,5,7,9-tetramethyl-16-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-9,13-diene-2,6-dione belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members. Epothilone C5 is found in Sorangium cellulosum. It was first documented in 2001 (PMID: 11473410). Based on a literature review a significant number of articles have been published on (4S,7R,8R,9Z,13Z,16S)-4,8-dihydroxy-5,5,7,9-tetramethyl-16-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-9,13-diene-2,6-dione (PMID: 34600448) (PMID: 34600447) (PMID: 34600453) (PMID: 34600452) (PMID: 34600451) (PMID: 34600450).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117493D          

 70 71  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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 26 59  1  0
 26 60  1  0
 26 61  1  0
 27 62  1  0
 27 63  1  0
 27 64  1  0
 30 65  1  1
 31 66  1  0
 31 67  1  0
 31 68  1  0
 32 69  1  1
 33 70  1  0
M  END


  Mrv1652306242117493D          

 70 71  0  0  0  0            999 V2000
   -4.9716    2.4796   -0.3108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5887    1.9003   -0.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6232    2.7609    0.1048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2300    2.2112    0.2183 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1506    3.2353    0.2435 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7220    3.2867    1.3993 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3834    2.2214    1.8333 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3706    0.8985    1.2862 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7530    0.6167   -0.1121 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2291    0.9411   -0.2995 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6887    2.3267   -0.1349 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0637   -0.0111   -0.5635 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5275    0.1264   -0.7807 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0264    1.0211   -1.6993 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7138    0.8009   -1.5279 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.6910   -0.3989   -0.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8548   -1.0930    0.3538 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4007   -0.5684   -0.1060 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5858   -0.6984   -0.4673 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9855   -1.8138   -0.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6122   -2.7526    0.4766 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4610   -2.0566   -0.2986 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2676   -2.2436    0.9348 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7968   -3.2515    1.7819 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6782   -2.6427    0.5909 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6323   -4.0608    0.0581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4817   -2.7143    1.8841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3991   -1.8238   -0.3522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4058   -2.1322   -1.5424 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1888   -0.5663   -0.0396 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4613   -0.6317   -0.7974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2444    0.5188   -0.4167 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9532    0.3497   -1.7890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0455    3.3637    0.3572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1918    2.8275   -1.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7436    1.7656    0.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7628    3.8004    0.2772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2539    1.7030    1.1973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0846    1.5901   -0.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3678    3.3845   -0.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7529    4.2061    0.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8533    4.2177    1.9398 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0010    2.4441    2.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2118    0.3320    1.8371 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5270    0.2366    1.6255 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2565    1.2298   -0.8876 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1747    3.0383   -0.8232 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7703    2.4493   -0.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5412    2.6207    0.9337 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6537   -1.0334   -0.6354 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4689    1.6967   -2.3792 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1702   -1.9794   -0.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6828   -0.3860    0.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5578   -1.4114    1.3640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6221   -2.9971   -0.9154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9328   -1.2711   -0.9160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2576   -1.3302    1.6039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1875   -3.8840    1.3923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8304   -4.6675    0.5169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3909   -4.0051   -1.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6232   -4.5532    0.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3248   -1.7397    2.4215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5344   -2.9080    1.6865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0037   -3.4779    2.5333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3252   -0.5922    1.0721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6227   -1.6517   -1.2571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3057   -0.5574   -0.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5752    0.0822   -1.6153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3357    0.2910    0.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6040    0.9306   -2.2903 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  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
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  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
 10 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
  9 19  1  0  0  0  0
 19 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
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32  2  1  0  0  0  0
 18 13  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  3 37  1  0  0  0  0
  4 38  1  0  0  0  0
  4 39  1  0  0  0  0
  5 40  1  0  0  0  0
  5 41  1  0  0  0  0
  6 42  1  0  0  0  0
  7 43  1  0  0  0  0
  8 44  1  0  0  0  0
  8 45  1  0  0  0  0
  9 46  1  6  0  0  0
 11 47  1  0  0  0  0
 11 48  1  0  0  0  0
 11 49  1  0  0  0  0
 12 50  1  0  0  0  0
 14 51  1  0  0  0  0
 17 52  1  0  0  0  0
 17 53  1  0  0  0  0
 17 54  1  0  0  0  0
 22 55  1  0  0  0  0
 22 56  1  0  0  0  0
 23 57  1  1  0  0  0
 24 58  1  0  0  0  0
 26 59  1  0  0  0  0
 26 60  1  0  0  0  0
 26 61  1  0  0  0  0
 27 62  1  0  0  0  0
 27 63  1  0  0  0  0
 27 64  1  0  0  0  0
 30 65  1  1  0  0  0
 31 66  1  0  0  0  0
 31 67  1  0  0  0  0
 31 68  1  0  0  0  0
 32 69  1  1  0  0  0
 33 70  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003747

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]1([H])\C(=C([H])/C([H])([H])C([H])([H])\C([H])=C([H])/C([H])([H])[C@]([H])(OC(=O)C([H])([H])[C@]([H])(O[H])C(C(=O)[C@]1([H])C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C(=C(/[H])C1=C([H])SC(=N1)C([H])([H])[H])\C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C26H37NO5S/c1-16-11-9-7-8-10-12-21(17(2)13-20-15-33-19(4)27-20)32-23(29)14-22(28)26(5,6)25(31)18(3)24(16)30/h8,10-11,13,15,18,21-22,24,28,30H,7,9,12,14H2,1-6H3/b10-8-,16-11-,17-13+/t18-,21+,22+,24+/m1/s1

> <INCHI_KEY>
MVIPGYRWGVEDHK-KOXCDYQNSA-N

> <FORMULA>
C26H37NO5S

> <MOLECULAR_WEIGHT>
475.64

> <EXACT_MASS>
475.239244469

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
53.466831329626395

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S,7R,8R,9Z,13Z,16S)-4,8-dihydroxy-5,5,7,9-tetramethyl-16-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-9,13-diene-2,6-dione

> <ALOGPS_LOGP>
4.45

> <JCHEM_LOGP>
4.525322249666667

> <ALOGPS_LOGS>
-5.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.544075357283319

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.936959484149362

> <JCHEM_PKA_STRONGEST_BASIC>
2.726300048022551

> <JCHEM_POLAR_SURFACE_AREA>
96.72000000000001

> <JCHEM_REFRACTIVITY>
132.5341

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.76e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4S,7R,8R,9Z,13Z,16S)-4,8-dihydroxy-5,5,7,9-tetramethyl-16-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-9,13-diene-2,6-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 70 71  0  0  0  0  0  0  0  0999 V2000
   -4.9716    2.4796   -0.3108 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5887    1.9003   -0.2053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6232    2.7609    0.1048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2300    2.2112    0.2183 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1506    3.2353    0.2435 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7220    3.2867    1.3993 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3834    2.2214    1.8333 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3706    0.8985    1.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7530    0.6167   -0.1121 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2291    0.9411   -0.2995 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6887    2.3267   -0.1349 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0637   -0.0111   -0.5635 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5275    0.1264   -0.7807 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0264    1.0211   -1.6993 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7138    0.8009   -1.5279 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.6910   -0.3989   -0.3161 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8548   -1.0930    0.3538 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4007   -0.5684   -0.1060 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5858   -0.6984   -0.4673 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9855   -1.8138   -0.0895 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6122   -2.7526    0.4766 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4610   -2.0566   -0.2986 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2676   -2.2436    0.9348 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7968   -3.2515    1.7819 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6782   -2.6427    0.5909 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6323   -4.0608    0.0581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4817   -2.7143    1.8841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3991   -1.8238   -0.3522 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4058   -2.1322   -1.5424 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1888   -0.5663   -0.0396 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4613   -0.6317   -0.7974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2444    0.5188   -0.4167 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9532    0.3497   -1.7890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0455    3.3637    0.3572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1918    2.8275   -1.3258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7436    1.7656    0.0846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7628    3.8004    0.2772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2539    1.7030    1.1973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0846    1.5901   -0.6616 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3678    3.3845   -0.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7529    4.2061    0.2704 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8533    4.2177    1.9398 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0010    2.4441    2.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2118    0.3320    1.8371 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5270    0.2366    1.6255 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2565    1.2298   -0.8876 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1747    3.0383   -0.8232 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7703    2.4493   -0.2985 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5412    2.6207    0.9337 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6537   -1.0334   -0.6354 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4689    1.6967   -2.3792 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1702   -1.9794   -0.2251 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.6828   -0.3860    0.4494 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5578   -1.4114    1.3640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6221   -2.9971   -0.9154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9328   -1.2711   -0.9160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2576   -1.3302    1.6039 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1875   -3.8840    1.3923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8304   -4.6675    0.5169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3909   -4.0051   -1.0334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6232   -4.5532    0.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3248   -1.7397    2.4215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5344   -2.9080    1.6865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0037   -3.4779    2.5333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3252   -0.5922    1.0721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6227   -1.6517   -1.2571 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3057   -0.5574   -0.0492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5752    0.0822   -1.6153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3357    0.2910    0.2181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6040    0.9306   -2.2903 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
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
  9 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 23 25  1  0
 25 26  1  6
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 25 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  1  0
 30 32  1  0
 32 33  1  0
 32  2  1  0
 18 13  1  0
  1 34  1  0
  1 35  1  0
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  3 37  1  0
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  7 43  1  0
  8 44  1  0
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  9 46  1  6
 11 47  1  0
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 30 65  1  1
 31 66  1  0
 31 67  1  0
 31 68  1  0
 32 69  1  1
 33 70  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0      -4.972   2.480  -0.311  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.589   1.900  -0.205  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.623   2.761   0.105  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.230   2.211   0.218  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.151   3.235   0.244  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.722   3.287   1.399  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.383   2.221   1.833  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.371   0.899   1.286  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.753   0.617  -0.112  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.229   0.941  -0.300  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.689   2.327  -0.135  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.064  -0.011  -0.564  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.527   0.126  -0.781  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.026   1.021  -1.699  0.00  0.00           C+0
HETATM   15  S   UNK     0       7.714   0.801  -1.528  0.00  0.00           S+0
HETATM   16  C   UNK     0       7.691  -0.399  -0.316  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.855  -1.093   0.354  0.00  0.00           C+0
HETATM   18  N   UNK     0       6.401  -0.568  -0.106  0.00  0.00           N+0
HETATM   19  O   UNK     0       1.586  -0.698  -0.467  0.00  0.00           O+0
HETATM   20  C   UNK     0       0.986  -1.814  -0.090  0.00  0.00           C+0
HETATM   21  O   UNK     0       1.612  -2.753   0.477  0.00  0.00           O+0
HETATM   22  C   UNK     0      -0.461  -2.057  -0.299  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.268  -2.244   0.935  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.797  -3.252   1.782  0.00  0.00           O+0
HETATM   25  C   UNK     0      -2.678  -2.643   0.591  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.632  -4.061   0.058  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.482  -2.714   1.884  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.399  -1.824  -0.352  0.00  0.00           C+0
HETATM   29  O   UNK     0      -3.406  -2.132  -1.542  0.00  0.00           O+0
HETATM   30  C   UNK     0      -4.189  -0.566  -0.040  0.00  0.00           C+0
HETATM   31  C   UNK     0      -5.461  -0.632  -0.797  0.00  0.00           C+0
HETATM   32  C   UNK     0      -3.244   0.519  -0.417  0.00  0.00           C+0
HETATM   33  O   UNK     0      -2.953   0.350  -1.789  0.00  0.00           O+0
HETATM   34  H   UNK     0      -5.045   3.364   0.357  0.00  0.00           H+0
HETATM   35  H   UNK     0      -5.192   2.828  -1.326  0.00  0.00           H+0
HETATM   36  H   UNK     0      -5.744   1.766   0.085  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.763   3.800   0.277  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.254   1.703   1.197  0.00  0.00           H+0
HETATM   39  H   UNK     0      -1.085   1.590  -0.662  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.368   3.385  -0.753  0.00  0.00           H+0
HETATM   41  H   UNK     0      -0.753   4.206   0.270  0.00  0.00           H+0
HETATM   42  H   UNK     0       0.853   4.218   1.940  0.00  0.00           H+0
HETATM   43  H   UNK     0       2.001   2.444   2.738  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.212   0.332   1.837  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.527   0.237   1.626  0.00  0.00           H+0
HETATM   46  H   UNK     0       1.256   1.230  -0.888  0.00  0.00           H+0
HETATM   47  H   UNK     0       3.175   3.038  -0.823  0.00  0.00           H+0
HETATM   48  H   UNK     0       4.770   2.449  -0.299  0.00  0.00           H+0
HETATM   49  H   UNK     0       3.541   2.621   0.934  0.00  0.00           H+0
HETATM   50  H   UNK     0       3.654  -1.033  -0.635  0.00  0.00           H+0
HETATM   51  H   UNK     0       5.469   1.697  -2.379  0.00  0.00           H+0
HETATM   52  H   UNK     0       9.170  -1.979  -0.225  0.00  0.00           H+0
HETATM   53  H   UNK     0       9.683  -0.386   0.449  0.00  0.00           H+0
HETATM   54  H   UNK     0       8.558  -1.411   1.364  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.622  -2.997  -0.915  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.933  -1.271  -0.916  0.00  0.00           H+0
HETATM   57  H   UNK     0      -1.258  -1.330   1.604  0.00  0.00           H+0
HETATM   58  H   UNK     0      -0.188  -3.884   1.392  0.00  0.00           H+0
HETATM   59  H   UNK     0      -1.830  -4.668   0.517  0.00  0.00           H+0
HETATM   60  H   UNK     0      -2.391  -4.005  -1.033  0.00  0.00           H+0
HETATM   61  H   UNK     0      -3.623  -4.553   0.164  0.00  0.00           H+0
HETATM   62  H   UNK     0      -3.325  -1.740   2.422  0.00  0.00           H+0
HETATM   63  H   UNK     0      -4.534  -2.908   1.687  0.00  0.00           H+0
HETATM   64  H   UNK     0      -3.004  -3.478   2.533  0.00  0.00           H+0
HETATM   65  H   UNK     0      -4.325  -0.592   1.072  0.00  0.00           H+0
HETATM   66  H   UNK     0      -5.623  -1.652  -1.257  0.00  0.00           H+0
HETATM   67  H   UNK     0      -6.306  -0.557  -0.049  0.00  0.00           H+0
HETATM   68  H   UNK     0      -5.575   0.082  -1.615  0.00  0.00           H+0
HETATM   69  H   UNK     0      -2.336   0.291   0.218  0.00  0.00           H+0
HETATM   70  H   UNK     0      -3.604   0.931  -2.290  0.00  0.00           H+0
CONECT    1    2   34   35   36                                             
CONECT    2    1    3   32                                                  
CONECT    3    2    4   37                                                  
CONECT    4    3    5   38   39                                             
CONECT    5    4    6   40   41                                             
CONECT    6    5    7   42                                                  
CONECT    7    6    8   43                                                  
CONECT    8    7    9   44   45                                             
CONECT    9    8   10   19   46                                             
CONECT   10    9   11   12                                                  
CONECT   11   10   47   48   49                                             
CONECT   12   10   13   50                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13   15   51                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16   52   53   54                                             
CONECT   18   16   13                                                       
CONECT   19    9   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   55   56                                             
CONECT   23   22   24   25   57                                             
CONECT   24   23   58                                                       
CONECT   25   23   26   27   28                                             
CONECT   26   25   59   60   61                                             
CONECT   27   25   62   63   64                                             
CONECT   28   25   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32   65                                             
CONECT   31   30   66   67   68                                             
CONECT   32   30   33    2   69                                             
CONECT   33   32   70                                                       
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    3                                                            
CONECT   38    4                                                            
CONECT   39    4                                                            
CONECT   40    5                                                            
CONECT   41    5                                                            
CONECT   42    6                                                            
CONECT   43    7                                                            
CONECT   44    8                                                            
CONECT   45    8                                                            
CONECT   46    9                                                            
CONECT   47   11                                                            
CONECT   48   11                                                            
CONECT   49   11                                                            
CONECT   50   12                                                            
CONECT   51   14                                                            
CONECT   52   17                                                            
CONECT   53   17                                                            
CONECT   54   17                                                            
CONECT   55   22                                                            
CONECT   56   22                                                            
CONECT   57   23                                                            
CONECT   58   24                                                            
CONECT   59   26                                                            
CONECT   60   26                                                            
CONECT   61   26                                                            
CONECT   62   27                                                            
CONECT   63   27                                                            
CONECT   64   27                                                            
CONECT   65   30                                                            
CONECT   66   31                                                            
CONECT   67   31                                                            
CONECT   68   31                                                            
CONECT   69   32                                                            
CONECT   70   33                                                            
MASTER        0    0    0    0    0    0    0    0   70    0  142    0
END

RDKit          3D

70 71  0  0  0  0  0  0  0  0999 V2000
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    5.5275    0.1264   -0.7807 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.7138    0.8009   -1.5279 S   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0
  2  3  2  0
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  9 19  1  0
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 33 70  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₆H₃₇NO₅S

Average Mass

475.6400 Da

Monoisotopic Mass

475.23924 Da

IUPAC Name

(4S,7R,8R,9Z,13Z,16S)-4,8-dihydroxy-5,5,7,9-tetramethyl-16-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-9,13-diene-2,6-dione

Traditional Name

(4S,7R,8R,9Z,13Z,16S)-4,8-dihydroxy-5,5,7,9-tetramethyl-16-[(1E)-1-(2-methyl-1,3-thiazol-4-yl)prop-1-en-2-yl]-1-oxacyclohexadeca-9,13-diene-2,6-dione

CAS Registry Number

Not Available

SMILES

C[C@@H]1[C@@H](O)\C(C)=C/CC\C=C/C[C@H](OC(=O)C[C@H](O)C(C)(C)C1=O)C(\C)=C\C1=CSC(C)=N1

InChI Identifier

InChI=1S/C26H37NO5S/c1-16-11-9-7-8-10-12-21(17(2)13-20-15-33-19(4)27-20)32-23(29)14-22(28)26(5,6)25(31)18(3)24(16)30/h8,10-11,13,15,18,21-22,24,28,30H,7,9,12,14H2,1-6H3/b10-8-,16-11-,17-13+/t18-,21+,22+,24+/m1/s1

InChI Key

MVIPGYRWGVEDHK-KOXCDYQNSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Sorangium cellulosum	NPAtlas	11473410

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as macrolides and analogues. These are organic compounds containing a lactone ring of at least twelve members.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Not Available

Direct Parent

Macrolides and analogues

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	4.45	ALOGPS
logP	4.53	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Acidic)	13.94	ChemAxon
pKa (Strongest Basic)	2.73	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	96.72 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	132.53 m³·mol⁻¹	ChemAxon
Polarizability	53.47 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA019973

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB 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

101129996

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hardt IH, Steinmetz H, Gerth K, Sasse F, Reichenbach H, Hofle G: New natural epothilones from Sorangium cellulosum, strains So ce90/B2 and So ce90/D13: isolation, structure elucidation, and SAR studies. J Nat Prod. 2001 Jul;64(7):847-56. doi: 10.1021/np000629f. [PubMed:11473410 ]
Leow XYJ, Tan JTC, Yeo TH, Wong KPL, Mahadev A, Ang B, Vasanwala RF, Ng ZM: Evaluation of risk factors associated with fragility fractures and recommendations to optimise bone health in children with long-term neurological condition. Singapore Med J. 2021 Oct 3. doi: 10.11622/smedj.2021124. [PubMed:34600448 ]
Goktas SY, Oral AY, Yilmaz E, Akalin EH, Guvenc F, Ozkaya G, Kocaeli H, Dogan S, Yilmazlar S, Oral HB: Diagnostic value of the CSF levels of D-Lactate and pro-inflammatory cytokines (TNF-alpha, IL-6, IL-8 and IL-17) in the patients with suspected nosocomial meningitis. Singapore Med J. 2021 Oct 3. doi: 10.11622/smedj.2021123. [PubMed:34600447 ]
Chew NW, Wong RC, Djohan AH, Ngiam JN, Chai P, Yeo TC, Tan HC, Sia CH: The association of face mask use with self-reported cardiovascular symptoms during the COVID-19 pandemic. Singapore Med J. 2021 Oct 3. doi: 10.11622/smedj.2021140. [PubMed:34600453 ]
Mohamad Nizam M, Othman A, Mohamad Ikram I: Increased internalising and externalising behavioural problems associated with corticosteroid usage in children with nephrotic syndrome: a South East Asian perspective. Singapore Med J. 2021 Oct 3. doi: 10.11622/smedj.2021128. [PubMed:34600452 ]
Li JW, Ngu JC, Lim KR, Tay SW, Jiang B, Wijaya R, Yusof S, Ong CJ, Kwek ABE, Ang TL: Colonic stenting in acute malignant large bowel obstruction - an audit of efficacy and safety in a tertiary referral centre in Singapore. Singapore Med J. 2021 Oct 3. doi: 10.11622/smedj.2021127. [PubMed:34600451 ]
Lim SH, Guek TY, Woon FP, Tay DDY, Ho SS, Ng SC, De Silva DA: National Institutes of Health Stroke Scale: comparison of the original versus a modified version for Singapore culture. Singapore Med J. 2021 Oct 3. doi: 10.11622/smedj.2021126. [PubMed:34600450 ]
Md Hussin NS, Karuppannan M, Gopalan Y, Tan KM, Gnanasan S: Exploration of non-pharmacological interventions in the management of behavioural and psychological symptoms of dementia. Singapore Med J. 2021 Oct 3. doi: 10.11622/smedj.2021125. [PubMed:34600449 ]
Tam WJ, Fisher D: COVID-19: a missed opportunity for medical education. Singapore Med J. 2021 Oct 3. doi: 10.11622/smedj.2021133. [PubMed:34600446 ]

Showing NP-Card for Epothilone C5 (NP0003747)

MOL for NP0003747 (Epothilone C5)

3D MOL for NP0003747 (Epothilone C5)

3D SDF for NP0003747 (Epothilone C5)

3D-SDF for NP0003747 (Epothilone C5)

PDB for NP0003747 (Epothilone C5)

3D PDB for NP0003747 (Epothilone C5)

SMILES for NP0003747 (Epothilone C5)

INCHI for NP0003747 (Epothilone C5)

Structure for NP0003747 (Epothilone C5)

3D Structure for NP0003747 (Epothilone C5)