NP-MRD: Showing NP-Card for Tirandamycin D (NP0008842)

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Record Information

Version

2.0

Created at

2020-12-09 06:20:13 UTC

Updated at

2021-07-15 17:01:34 UTC

NP-MRD ID

NP0008842

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tirandamycin D

Provided By

NPAtlas

Description

Tirandamycin D belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond. Tirandamycin D is found in Streptomyces sp. 307-9. Tirandamycin D was first documented in 2009 (PMID: 19883065). Based on a literature review very few articles have been published on tirandamycin D.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242106303D          

 56 58  0  0  0  0            999 V2000
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    1.3085    0.5166   -0.2610 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0742   -0.3847    0.2299 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1063   -0.9390    1.5823 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1666   -1.4934    2.1852 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4946   -0.7057    2.0935 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -3.8104   -0.7903   -1.3965 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652306242106303D          

 56 58  0  0  0  0            999 V2000
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    7.6342    0.3455    2.3603 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1746   -1.4507    0.8707 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9148    1.3124   -2.0824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1149    2.3537   -1.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6003   -0.1643   -2.8054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4943    1.3797   -2.6610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8459    1.4255   -3.2838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7726    1.2971    0.8060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1552    2.1423   -1.7435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7937    0.7715   -2.8139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1884    0.6087   -1.7289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6904   -2.4253   -0.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9249   -1.4120    1.5235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2526    0.9265    2.0084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8120    1.9080    1.6781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1715    1.9691    0.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0541   -1.2165   -0.1973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9742    0.0496    2.1797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2575   -1.6063    1.9979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0026   -1.3674    2.0068 H   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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 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
  2 14  2  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
 18 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 22 28  1  0  0  0  0
 28 29  1  0  0  0  0
 12  7  1  0  0  0  0
 28 17  1  0  0  0  0
 26 19  1  0  0  0  0
  1 30  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  3 33  1  0  0  0  0
  4 34  1  0  0  0  0
  6 35  1  0  0  0  0
 10 36  1  0  0  0  0
 10 37  1  0  0  0  0
 11 38  1  0  0  0  0
 14 39  1  0  0  0  0
 15 40  1  6  0  0  0
 16 41  1  0  0  0  0
 16 42  1  0  0  0  0
 16 43  1  0  0  0  0
 17 44  1  1  0  0  0
 20 45  1  0  0  0  0
 20 46  1  0  0  0  0
 20 47  1  0  0  0  0
 22 48  1  6  0  0  0
 25 49  1  0  0  0  0
 27 50  1  0  0  0  0
 27 51  1  0  0  0  0
 27 52  1  0  0  0  0
 28 53  1  6  0  0  0
 29 54  1  0  0  0  0
 29 55  1  0  0  0  0
 29 56  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0008842

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O\C(\C(\[H])=C(/[H])\C(=C(/[H])[C@@]([H])(C([H])([H])[H])[C@@]1([H])O[C@]2(O[C@]([H])(C(=O)C([H])=C2C([H])([H])[H])[C@]1([H])C([H])([H])[H])C([H])([H])[H])\C([H])([H])[H])=C1/C(=O)N([H])C([H])([H])C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H27NO6/c1-11(6-7-15(24)18-17(26)10-23-21(18)27)8-12(2)19-14(4)20-16(25)9-13(3)22(5,28-19)29-20/h6-9,12,14,19-20,24H,10H2,1-5H3,(H,23,27)/b7-6+,11-8+,18-15-/t12-,14-,19-,20+,22+/m1/s1

> <INCHI_KEY>
WORJTWSOUPGODS-QFBRIWFWSA-N

> <FORMULA>
C22H27NO6

> <MOLECULAR_WEIGHT>
401.459

> <EXACT_MASS>
401.183837593

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
42.82378227622378

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3Z)-3-[(2E,4E,6R)-1-hydroxy-4-methyl-6-[(1S,3R,4R,5S)-1,4,8-trimethyl-6-oxo-2,9-dioxabicyclo[3.3.1]non-7-en-3-yl]hepta-2,4-dien-1-ylidene]pyrrolidine-2,4-dione

> <ALOGPS_LOGP>
1.95

> <JCHEM_LOGP>
2.1955994873333324

> <ALOGPS_LOGS>
-4.33

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.720133956664577

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.336725245106886

> <JCHEM_PKA_STRONGEST_BASIC>
-1.692702585342059

> <JCHEM_POLAR_SURFACE_AREA>
101.93

> <JCHEM_REFRACTIVITY>
110.5976

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.89e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3Z)-3-[(2E,4E,6R)-1-hydroxy-4-methyl-6-[(1S,3R,4R,5S)-1,4,8-trimethyl-6-oxo-2,9-dioxabicyclo[3.3.1]non-7-en-3-yl]hepta-2,4-dien-1-ylidene]pyrrolidine-2,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 56 58  0  0  0  0  0  0  0  0999 V2000
    1.0767    0.0088    1.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3085    0.5166   -0.2610 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7167    0.4961   -0.7248 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7038    0.0530    0.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0812    0.0537   -0.4899 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3037    0.5382   -1.7645 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0742   -0.3847    0.2299 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1063   -0.9390    1.5823 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1666   -1.4934    2.1852 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4946   -0.7057    2.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2565   -0.9599    0.8790 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5005   -0.4195   -0.1859 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9601   -0.0393   -1.2839 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4126    0.9684   -1.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9915    1.1905   -1.1688 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5225    0.8862   -2.5866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9822    0.7531   -0.1429 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2053    1.2621   -0.6005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2263    0.4088   -0.7940 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1817    1.0503   -1.8168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8104   -0.7903   -1.3965 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1031   -1.5218   -0.4664 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0854   -2.0618    0.5381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0463   -3.2015    1.0140 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1268   -1.0730    0.9089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9922    0.1594    0.4537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6048    1.2766    1.1865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0190   -0.7080    0.1310 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0647   -0.9290    1.6513 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2783    0.6173    1.6290 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9601    0.1752    1.7928 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9017   -1.0736    1.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9635    0.8625   -1.7222 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5876   -0.3416    1.0088 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7274   -0.0915   -2.4352 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7632   -1.3904    2.9008 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6342    0.3455    2.3603 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1746   -1.4507    0.8707 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9148    1.3124   -2.0824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1149    2.3537   -1.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6003   -0.1643   -2.8054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4943    1.3797   -2.6610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8459    1.4255   -3.2838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7726    1.2971    0.8060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1552    2.1423   -1.7435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7937    0.7715   -2.8139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1884    0.6087   -1.7289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6904   -2.4253   -0.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9249   -1.4120    1.5235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2526    0.9265    2.0084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8120    1.9080    1.6781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1715    1.9691    0.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0541   -1.2165   -0.1973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9742    0.0496    2.1797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2575   -1.6063    1.9979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0026   -1.3674    2.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
  2 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 22 28  1  0
 28 29  1  0
 12  7  1  0
 28 17  1  0
 26 19  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  4 34  1  0
  6 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 14 39  1  0
 15 40  1  6
 16 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  1
 20 45  1  0
 20 46  1  0
 20 47  1  0
 22 48  1  6
 25 49  1  0
 27 50  1  0
 27 51  1  0
 27 52  1  0
 28 53  1  6
 29 54  1  0
 29 55  1  0
 29 56  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       1.077   0.009   1.095  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.309   0.517  -0.261  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.717   0.496  -0.725  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.704   0.053   0.012  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.081   0.054  -0.490  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.304   0.538  -1.765  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.074  -0.385   0.230  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.106  -0.939   1.582  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.167  -1.493   2.185  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.495  -0.706   2.094  0.00  0.00           C+0
HETATM   11  N   UNK     0       8.257  -0.960   0.879  0.00  0.00           N+0
HETATM   12  C   UNK     0       7.500  -0.420  -0.186  0.00  0.00           C+0
HETATM   13  O   UNK     0       7.960  -0.039  -1.284  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.413   0.968  -1.083  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.992   1.190  -1.169  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.523   0.886  -2.587  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.982   0.753  -0.143  0.00  0.00           C+0
HETATM   18  O   UNK     0      -3.205   1.262  -0.601  0.00  0.00           O+0
HETATM   19  C   UNK     0      -4.226   0.409  -0.794  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.182   1.050  -1.817  0.00  0.00           C+0
HETATM   21  O   UNK     0      -3.810  -0.790  -1.397  0.00  0.00           O+0
HETATM   22  C   UNK     0      -3.103  -1.522  -0.466  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.085  -2.062   0.538  0.00  0.00           C+0
HETATM   24  O   UNK     0      -4.046  -3.201   1.014  0.00  0.00           O+0
HETATM   25  C   UNK     0      -5.127  -1.073   0.909  0.00  0.00           C+0
HETATM   26  C   UNK     0      -4.992   0.159   0.454  0.00  0.00           C+0
HETATM   27  C   UNK     0      -5.605   1.277   1.187  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.019  -0.708   0.131  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.065  -0.929   1.651  0.00  0.00           C+0
HETATM   30  H   UNK     0       0.278   0.617   1.629  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.960   0.175   1.793  0.00  0.00           H+0
HETATM   32  H   UNK     0       0.902  -1.074   1.147  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.963   0.863  -1.722  0.00  0.00           H+0
HETATM   34  H   UNK     0       3.588  -0.342   1.009  0.00  0.00           H+0
HETATM   35  H   UNK     0       5.727  -0.092  -2.435  0.00  0.00           H+0
HETATM   36  H   UNK     0       7.763  -1.390   2.901  0.00  0.00           H+0
HETATM   37  H   UNK     0       7.634   0.346   2.360  0.00  0.00           H+0
HETATM   38  H   UNK     0       9.175  -1.451   0.871  0.00  0.00           H+0
HETATM   39  H   UNK     0       0.915   1.312  -2.082  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.115   2.354  -1.158  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.600  -0.164  -2.805  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.494   1.380  -2.661  0.00  0.00           H+0
HETATM   43  H   UNK     0      -0.846   1.426  -3.284  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.773   1.297   0.806  0.00  0.00           H+0
HETATM   45  H   UNK     0      -5.155   2.142  -1.744  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.794   0.772  -2.814  0.00  0.00           H+0
HETATM   47  H   UNK     0      -6.188   0.609  -1.729  0.00  0.00           H+0
HETATM   48  H   UNK     0      -2.690  -2.425  -0.989  0.00  0.00           H+0
HETATM   49  H   UNK     0      -5.925  -1.412   1.524  0.00  0.00           H+0
HETATM   50  H   UNK     0      -6.253   0.927   2.008  0.00  0.00           H+0
HETATM   51  H   UNK     0      -4.812   1.908   1.678  0.00  0.00           H+0
HETATM   52  H   UNK     0      -6.172   1.969   0.515  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.054  -1.216  -0.197  0.00  0.00           H+0
HETATM   54  H   UNK     0      -1.974   0.050   2.180  0.00  0.00           H+0
HETATM   55  H   UNK     0      -1.258  -1.606   1.998  0.00  0.00           H+0
HETATM   56  H   UNK     0      -3.003  -1.367   2.007  0.00  0.00           H+0
CONECT    1    2   30   31   32                                             
CONECT    2    1    3   14                                                  
CONECT    3    2    4   33                                                  
CONECT    4    3    5   34                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5   35                                                       
CONECT    7    5    8   12                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   36   37                                             
CONECT   11   10   12   38                                                  
CONECT   12   11   13    7                                                  
CONECT   13   12                                                            
CONECT   14    2   15   39                                                  
CONECT   15   14   16   17   40                                             
CONECT   16   15   41   42   43                                             
CONECT   17   15   18   28   44                                             
CONECT   18   17   19                                                       
CONECT   19   18   20   21   26                                             
CONECT   20   19   45   46   47                                             
CONECT   21   19   22                                                       
CONECT   22   21   23   28   48                                             
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   49                                                  
CONECT   26   25   27   19                                                  
CONECT   27   26   50   51   52                                             
CONECT   28   22   29   17   53                                             
CONECT   29   28   54   55   56                                             
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    3                                                            
CONECT   34    4                                                            
CONECT   35    6                                                            
CONECT   36   10                                                            
CONECT   37   10                                                            
CONECT   38   11                                                            
CONECT   39   14                                                            
CONECT   40   15                                                            
CONECT   41   16                                                            
CONECT   42   16                                                            
CONECT   43   16                                                            
CONECT   44   17                                                            
CONECT   45   20                                                            
CONECT   46   20                                                            
CONECT   47   20                                                            
CONECT   48   22                                                            
CONECT   49   25                                                            
CONECT   50   27                                                            
CONECT   51   27                                                            
CONECT   52   27                                                            
CONECT   53   28                                                            
CONECT   54   29                                                            
CONECT   55   29                                                            
CONECT   56   29                                                            
MASTER        0    0    0    0    0    0    0    0   56    0  116    0
END

RDKit          3D

56 58  0  0  0  0  0  0  0  0999 V2000
    1.0767    0.0088    1.0955 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3085    0.5166   -0.2610 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7167    0.4961   -0.7248 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7038    0.0530    0.0116 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0812    0.0537   -0.4899 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3037    0.5382   -1.7645 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0742   -0.3847    0.2299 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1063   -0.9390    1.5823 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1666   -1.4934    2.1852 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4946   -0.7057    2.0935 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2565   -0.9599    0.8790 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5005   -0.4195   -0.1859 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9601   -0.0393   -1.2839 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4126    0.9684   -1.0827 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9915    1.1905   -1.1688 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5225    0.8862   -2.5866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9822    0.7531   -0.1429 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2053    1.2621   -0.6005 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2263    0.4088   -0.7940 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1817    1.0503   -1.8168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8104   -0.7903   -1.3965 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1031   -1.5218   -0.4664 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.0854   -2.0618    0.5381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0463   -3.2015    1.0140 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1268   -1.0730    0.9089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9922    0.1594    0.4537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6048    1.2766    1.1865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0190   -0.7080    0.1310 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0647   -0.9290    1.6513 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2783    0.6173    1.6290 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9601    0.1752    1.7928 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9017   -1.0736    1.1471 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9635    0.8625   -1.7222 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5876   -0.3416    1.0088 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7274   -0.0915   -2.4352 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7632   -1.3904    2.9008 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6342    0.3455    2.3603 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1746   -1.4507    0.8707 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9148    1.3124   -2.0824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1149    2.3537   -1.1580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6003   -0.1643   -2.8054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4943    1.3797   -2.6610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8459    1.4255   -3.2838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7726    1.2971    0.8060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1552    2.1423   -1.7435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7937    0.7715   -2.8139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1884    0.6087   -1.7289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6904   -2.4253   -0.9887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9249   -1.4120    1.5235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2526    0.9265    2.0084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8120    1.9080    1.6781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1715    1.9691    0.5149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0541   -1.2165   -0.1973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9742    0.0496    2.1797 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2575   -1.6063    1.9979 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0026   -1.3674    2.0068 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
  2 14  2  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 22 28  1  0
 28 29  1  0
 12  7  1  0
 28 17  1  0
 26 19  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  4 34  1  0
  6 35  1  0
 10 36  1  0
 10 37  1  0
 11 38  1  0
 14 39  1  0
 15 40  1  6
 16 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  1
 20 45  1  0
 20 46  1  0
 20 47  1  0
 22 48  1  6
 25 49  1  0
 27 50  1  0
 27 51  1  0
 27 52  1  0
 28 53  1  6
 29 54  1  0
 29 55  1  0
 29 56  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₂H₂₇NO₆

Average Mass

401.4590 Da

Monoisotopic Mass

401.18384 Da

IUPAC Name

(3Z)-3-[(2E,4E,6R)-1-hydroxy-4-methyl-6-[(1S,3R,4R,5S)-1,4,8-trimethyl-6-oxo-2,9-dioxabicyclo[3.3.1]non-7-en-3-yl]hepta-2,4-dien-1-ylidene]pyrrolidine-2,4-dione

Traditional Name

(3Z)-3-[(2E,4E,6R)-1-hydroxy-4-methyl-6-[(1S,3R,4R,5S)-1,4,8-trimethyl-6-oxo-2,9-dioxabicyclo[3.3.1]non-7-en-3-yl]hepta-2,4-dien-1-ylidene]pyrrolidine-2,4-dione

CAS Registry Number

Not Available

SMILES

C[C@H](C=C(C)C=CC(O)=C1C(=O)CNC1=O)[C@H]1O[C@@]2(C)O[C@@H]([C@@H]1C)C(=O)C=C2C

InChI Identifier

InChI=1S/C22H27NO6/c1-11(6-7-15(24)18-17(26)10-23-21(18)27)8-12(2)19-14(4)20-16(25)9-13(3)22(5,28-19)29-20/h6-9,12,14,19-20,24H,10H2,1-5H3,(H,23,27)/t12-,14-,19-,20+,22+/m1/s1

InChI Key

WORJTWSOUPGODS-QFBRIWFWSA-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
Streptomyces sp. 307-9	NPAtlas	19883065

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as dihydropyranones. Dihydropyranones are compounds containing a hydrogenated pyran ring which bears a ketone, and contains one double bond.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Pyranones and derivatives

Direct Parent

Dihydropyranones

Alternative Parents

Substituents

Dihydropyranone
Ketal
Meta-dioxane
Pyrroline
Cyclic carboximidic acid
Vinylogous acid
Ketone
Lactim
Cyclic ketone
Acetal
Enol
Oxacycle
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Azacycle
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	1.95	ALOGPS
logP	2.2	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	5.34	ChemAxon
pKa (Strongest Basic)	-1.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	101.93 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	110.6 m³·mol⁻¹	ChemAxon
Polarizability	42.82 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA005085

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00048209

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

139584509

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Carlson JC, Li S, Burr DA, Sherman DH: Isolation and characterization of tirandamycins from a marine-derived Streptomyces sp. J Nat Prod. 2009 Nov;72(11):2076-9. doi: 10.1021/np9005597. [PubMed:19883065 ]

Showing NP-Card for Tirandamycin D (NP0008842)

MOL for NP0008842 (Tirandamycin D)

3D MOL for NP0008842 (Tirandamycin D)

3D SDF for NP0008842 (Tirandamycin D)

3D-SDF for NP0008842 (Tirandamycin D)

PDB for NP0008842 (Tirandamycin D)

3D PDB for NP0008842 (Tirandamycin D)

SMILES for NP0008842 (Tirandamycin D)

INCHI for NP0008842 (Tirandamycin D)

Structure for NP0008842 (Tirandamycin D)

3D Structure for NP0008842 (Tirandamycin D)