NP-MRD: Showing NP-Card for Tirandamycin A (NP0021547)

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Record Information

Version

1.0

Created at

2021-01-06 06:50:22 UTC

Updated at

2021-07-15 17:36:38 UTC

NP-MRD ID

NP0021547

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Tirandamycin A

Provided By

NPAtlas

Description

Tirandamycin A is found in Streptomyces flaveolus and Streptomyces tirandamycinicus. It was first documented in 1971 (PMID: 5118218). Based on a literature review very few articles have been published on Tirandamycin A (PMID: 26593927) (PMID: 33569241) (PMID: 22763704) (PMID: 21778983).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105163D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306242105163D          

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    3.8643   -0.2648    1.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0719    2.0730   -1.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4659    3.1901    1.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0567    3.5962    2.3063 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2715    1.0566    2.5312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2340    0.0212   -1.3810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0821   -1.9074   -1.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5621   -3.1065    1.1298 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2563   -3.5683   -0.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5186   -3.7023   -0.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8070   -0.5031    0.8579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1108   -0.6797   -3.5826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5103    0.9925   -3.4187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3124    0.6827   -3.5272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3310   -2.0553   -0.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7355    2.0263    0.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1496    3.4460   -1.8058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6018    2.6247   -2.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0022    3.1889   -0.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1655   -2.8258   -0.5510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3731   -2.6100    1.8212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8013   -1.7366    2.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8188   -3.4261    1.7324 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  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 22 29  1  0  0  0  0
 29 30  1  0  0  0  0
 12  7  1  0  0  0  0
 29 17  1  0  0  0  0
 27 19  1  0  0  0  0
 27 25  1  0  0  0  0
  1 31  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  3 34  1  0  0  0  0
  4 35  1  0  0  0  0
  6 36  1  0  0  0  0
 10 37  1  0  0  0  0
 10 38  1  0  0  0  0
 11 39  1  0  0  0  0
 14 40  1  0  0  0  0
 15 41  1  6  0  0  0
 16 42  1  0  0  0  0
 16 43  1  0  0  0  0
 16 44  1  0  0  0  0
 17 45  1  1  0  0  0
 20 46  1  0  0  0  0
 20 47  1  0  0  0  0
 20 48  1  0  0  0  0
 22 49  1  6  0  0  0
 25 50  1  1  0  0  0
 28 51  1  0  0  0  0
 28 52  1  0  0  0  0
 28 53  1  0  0  0  0
 29 54  1  6  0  0  0
 30 55  1  0  0  0  0
 30 56  1  0  0  0  0
 30 57  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0021547

> <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@]3([H])O[C@]23C([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/C22H27NO7/c1-10(6-7-13(24)15-14(25)9-23-20(15)27)8-11(2)17-12(3)18-16(26)19-21(4,30-19)22(5,28-17)29-18/h6-8,11-12,17-19,24H,9H2,1-5H3,(H,23,27)/b7-6+,10-8+,15-13+/t11-,12-,17-,18+,19+,21+,22+/m1/s1

> <INCHI_KEY>
URGUBECARCAPRI-UYWODMNRSA-N

> <FORMULA>
C22H27NO7

> <MOLECULAR_WEIGHT>
417.458

> <EXACT_MASS>
417.178752213

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
43.347639922634905

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3E)-3-[(2E,4E,6R)-1-hydroxy-4-methyl-6-[(1S,2S,4R,6S,7R,8R)-1,2,7-trimethyl-5-oxo-3,9,10-trioxatricyclo[4.3.1.0^{2,4}]decan-8-yl]hepta-2,4-dien-1-ylidene]pyrrolidine-2,4-dione

> <ALOGPS_LOGP>
1.91

> <JCHEM_LOGP>
1.6066328989999996

> <ALOGPS_LOGS>
-3.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.720067722269503

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.312747662292604

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6924477295739018

> <JCHEM_POLAR_SURFACE_AREA>
114.46000000000001

> <JCHEM_REFRACTIVITY>
109.05010000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.74e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3E)-3-[(2E,4E,6R)-1-hydroxy-4-methyl-6-[(1S,2S,4R,6S,7R,8R)-1,2,7-trimethyl-5-oxo-3,9,10-trioxatricyclo[4.3.1.0^{2,4}]decan-8-yl]hepta-2,4-dien-1-ylidene]pyrrolidine-2,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 57 60  0  0  0  0  0  0  0  0999 V2000
    1.7088   -1.7988    1.1784 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4174   -0.8270    0.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4078    0.2352   -0.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5582    0.3928    0.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4588    1.5072    0.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0742    2.3872   -0.9118 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6015    1.6791    0.7030 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5483    2.7671    0.3801 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5353    3.4313   -0.7056 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4588    2.8956    1.5400 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4868    1.5356    2.0456 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2291    0.9082    1.7723 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7585   -0.1005    2.3363 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3377   -0.7976   -0.6056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7790   -1.7064   -0.5577 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6267   -3.0301    0.0607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0647   -1.0129   -0.1144 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2863   -0.0145   -1.0252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4659    0.1259   -1.6361 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3255    0.3286   -3.1539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4112   -0.8759   -1.4998 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5344   -1.2987   -0.1821 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7769   -0.1649    0.7476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9945   -0.3307    1.9223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7499    1.2100    0.2081 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4898    1.3991   -0.9479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1126    1.4026   -1.0534 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4418    2.7242   -1.3423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1674   -1.9463    0.1239 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2897   -2.4492    1.5405 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9349   -1.6507    1.9844 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7684   -2.8448    0.9357 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6945   -1.5682    1.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1989    0.9749   -0.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8643   -0.2648    1.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0719    2.0730   -1.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4659    3.1901    1.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0567    3.5962    2.3063 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2715    1.0566    2.5312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2340    0.0212   -1.3810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0821   -1.9074   -1.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5621   -3.1065    1.1298 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2563   -3.5683   -0.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5186   -3.7023   -0.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8070   -0.5031    0.8579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1108   -0.6797   -3.5826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5103    0.9925   -3.4187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3124    0.6827   -3.5272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3310   -2.0553   -0.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7355    2.0263    0.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1496    3.4460   -1.8058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6018    2.6247   -2.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0022    3.1889   -0.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1655   -2.8258   -0.5510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3731   -2.6100    1.8212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8013   -1.7366    2.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8188   -3.4261    1.7324 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  1  0
 26 27  1  0
 27 28  1  1
 22 29  1  0
 29 30  1  0
 12  7  1  0
 29 17  1  0
 27 19  1  0
 27 25  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  4 35  1  0
  6 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 14 40  1  0
 15 41  1  6
 16 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  1
 20 46  1  0
 20 47  1  0
 20 48  1  0
 22 49  1  6
 25 50  1  1
 28 51  1  0
 28 52  1  0
 28 53  1  0
 29 54  1  6
 30 55  1  0
 30 56  1  0
 30 57  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       1.709  -1.799   1.178  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.417  -0.827   0.134  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.408   0.235  -0.139  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.558   0.393   0.481  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.459   1.507   0.104  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.074   2.387  -0.912  0.00  0.00           O+0
HETATM    7  C   UNK     0       5.601   1.679   0.703  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.548   2.767   0.380  0.00  0.00           C+0
HETATM    9  O   UNK     0       6.535   3.431  -0.706  0.00  0.00           O+0
HETATM   10  C   UNK     0       7.459   2.896   1.540  0.00  0.00           C+0
HETATM   11  N   UNK     0       7.487   1.536   2.046  0.00  0.00           N+0
HETATM   12  C   UNK     0       6.229   0.908   1.772  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.758  -0.101   2.336  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.338  -0.798  -0.606  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.779  -1.706  -0.558  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.627  -3.030   0.061  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.065  -1.013  -0.114  0.00  0.00           C+0
HETATM   18  O   UNK     0      -2.286  -0.015  -1.025  0.00  0.00           O+0
HETATM   19  C   UNK     0      -3.466   0.126  -1.636  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.325   0.329  -3.154  0.00  0.00           C+0
HETATM   21  O   UNK     0      -4.411  -0.876  -1.500  0.00  0.00           O+0
HETATM   22  C   UNK     0      -4.534  -1.299  -0.182  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.777  -0.165   0.748  0.00  0.00           C+0
HETATM   24  O   UNK     0      -4.995  -0.331   1.922  0.00  0.00           O+0
HETATM   25  C   UNK     0      -4.750   1.210   0.208  0.00  0.00           C+0
HETATM   26  O   UNK     0      -5.490   1.399  -0.948  0.00  0.00           O+0
HETATM   27  C   UNK     0      -4.113   1.403  -1.053  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.442   2.724  -1.342  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.167  -1.946   0.124  0.00  0.00           C+0
HETATM   30  C   UNK     0      -3.290  -2.449   1.541  0.00  0.00           C+0
HETATM   31  H   UNK     0       0.935  -1.651   1.984  0.00  0.00           H+0
HETATM   32  H   UNK     0       1.768  -2.845   0.936  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.695  -1.568   1.663  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.199   0.975  -0.920  0.00  0.00           H+0
HETATM   35  H   UNK     0       3.864  -0.265   1.257  0.00  0.00           H+0
HETATM   36  H   UNK     0       4.072   2.073  -1.881  0.00  0.00           H+0
HETATM   37  H   UNK     0       8.466   3.190   1.196  0.00  0.00           H+0
HETATM   38  H   UNK     0       7.057   3.596   2.306  0.00  0.00           H+0
HETATM   39  H   UNK     0       8.271   1.057   2.531  0.00  0.00           H+0
HETATM   40  H   UNK     0       0.234   0.021  -1.381  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.082  -1.907  -1.704  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.562  -3.107   1.130  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.256  -3.568  -0.414  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.519  -3.702  -0.220  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.807  -0.503   0.858  0.00  0.00           H+0
HETATM   46  H   UNK     0      -3.111  -0.680  -3.583  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.510   0.993  -3.419  0.00  0.00           H+0
HETATM   48  H   UNK     0      -4.312   0.683  -3.527  0.00  0.00           H+0
HETATM   49  H   UNK     0      -5.331  -2.055  -0.147  0.00  0.00           H+0
HETATM   50  H   UNK     0      -4.736   2.026   0.969  0.00  0.00           H+0
HETATM   51  H   UNK     0      -4.150   3.446  -1.806  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.602   2.625  -2.060  0.00  0.00           H+0
HETATM   53  H   UNK     0      -3.002   3.189  -0.436  0.00  0.00           H+0
HETATM   54  H   UNK     0      -3.166  -2.826  -0.551  0.00  0.00           H+0
HETATM   55  H   UNK     0      -4.373  -2.610   1.821  0.00  0.00           H+0
HETATM   56  H   UNK     0      -2.801  -1.737   2.261  0.00  0.00           H+0
HETATM   57  H   UNK     0      -2.819  -3.426   1.732  0.00  0.00           H+0
CONECT    1    2   31   32   33                                             
CONECT    2    1    3   14                                                  
CONECT    3    2    4   34                                                  
CONECT    4    3    5   35                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5   36                                                       
CONECT    7    5    8   12                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   37   38                                             
CONECT   11   10   12   39                                                  
CONECT   12   11   13    7                                                  
CONECT   13   12                                                            
CONECT   14    2   15   40                                                  
CONECT   15   14   16   17   41                                             
CONECT   16   15   42   43   44                                             
CONECT   17   15   18   29   45                                             
CONECT   18   17   19                                                       
CONECT   19   18   20   21   27                                             
CONECT   20   19   46   47   48                                             
CONECT   21   19   22                                                       
CONECT   22   21   23   29   49                                             
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27   50                                             
CONECT   26   25   27                                                       
CONECT   27   26   28   19   25                                             
CONECT   28   27   51   52   53                                             
CONECT   29   22   30   17   54                                             
CONECT   30   29   55   56   57                                             
CONECT   31    1                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    3                                                            
CONECT   35    4                                                            
CONECT   36    6                                                            
CONECT   37   10                                                            
CONECT   38   10                                                            
CONECT   39   11                                                            
CONECT   40   14                                                            
CONECT   41   15                                                            
CONECT   42   16                                                            
CONECT   43   16                                                            
CONECT   44   16                                                            
CONECT   45   17                                                            
CONECT   46   20                                                            
CONECT   47   20                                                            
CONECT   48   20                                                            
CONECT   49   22                                                            
CONECT   50   25                                                            
CONECT   51   28                                                            
CONECT   52   28                                                            
CONECT   53   28                                                            
CONECT   54   29                                                            
CONECT   55   30                                                            
CONECT   56   30                                                            
CONECT   57   30                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  120    0
END

RDKit          3D

57 60  0  0  0  0  0  0  0  0999 V2000
    1.7088   -1.7988    1.1784 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4174   -0.8270    0.1342 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4078    0.2352   -0.1391 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5582    0.3928    0.4814 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4588    1.5072    0.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0742    2.3872   -0.9118 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6015    1.6791    0.7030 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5483    2.7671    0.3801 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5353    3.4313   -0.7056 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4588    2.8956    1.5400 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4868    1.5356    2.0456 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2291    0.9082    1.7723 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7585   -0.1005    2.3363 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3377   -0.7976   -0.6056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7790   -1.7064   -0.5577 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6267   -3.0301    0.0607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0647   -1.0129   -0.1144 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2863   -0.0145   -1.0252 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4659    0.1259   -1.6361 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3255    0.3286   -3.1539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4112   -0.8759   -1.4998 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5344   -1.2987   -0.1821 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7769   -0.1649    0.7476 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9945   -0.3307    1.9223 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7499    1.2100    0.2081 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.4898    1.3991   -0.9479 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1126    1.4026   -1.0534 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4418    2.7242   -1.3423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1674   -1.9463    0.1239 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2897   -2.4492    1.5405 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9349   -1.6507    1.9844 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7684   -2.8448    0.9357 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6945   -1.5682    1.6633 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1989    0.9749   -0.9200 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8643   -0.2648    1.2567 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0719    2.0730   -1.8808 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4659    3.1901    1.1956 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0567    3.5962    2.3063 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2715    1.0566    2.5312 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2340    0.0212   -1.3810 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0821   -1.9074   -1.7042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5621   -3.1065    1.1298 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2563   -3.5683   -0.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5186   -3.7023   -0.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8070   -0.5031    0.8579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1108   -0.6797   -3.5826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5103    0.9925   -3.4187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3124    0.6827   -3.5272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3310   -2.0553   -0.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7355    2.0263    0.9694 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1496    3.4460   -1.8058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6018    2.6247   -2.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0022    3.1889   -0.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1655   -2.8258   -0.5510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3731   -2.6100    1.8212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8013   -1.7366    2.2611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8188   -3.4261    1.7324 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  1  0
 26 27  1  0
 27 28  1  1
 22 29  1  0
 29 30  1  0
 12  7  1  0
 29 17  1  0
 27 19  1  0
 27 25  1  0
  1 31  1  0
  1 32  1  0
  1 33  1  0
  3 34  1  0
  4 35  1  0
  6 36  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
 14 40  1  0
 15 41  1  6
 16 42  1  0
 16 43  1  0
 16 44  1  0
 17 45  1  1
 20 46  1  0
 20 47  1  0
 20 48  1  0
 22 49  1  6
 25 50  1  1
 28 51  1  0
 28 52  1  0
 28 53  1  0
 29 54  1  6
 30 55  1  0
 30 56  1  0
 30 57  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₂H₂₇NO₇

Average Mass

417.4580 Da

Monoisotopic Mass

417.17875 Da

IUPAC Name

(3E)-3-[(2E,4E,6R)-1-hydroxy-4-methyl-6-[(1S,2S,4R,6S,7R,8R)-1,2,7-trimethyl-5-oxo-3,9,10-trioxatricyclo[4.3.1.0^{2,4}]decan-8-yl]hepta-2,4-dien-1-ylidene]pyrrolidine-2,4-dione

Traditional Name

(3E)-3-[(2E,4E,6R)-1-hydroxy-4-methyl-6-[(1S,2S,4R,6S,7R,8R)-1,2,7-trimethyl-5-oxo-3,9,10-trioxatricyclo[4.3.1.0^{2,4}]decan-8-yl]hepta-2,4-dien-1-ylidene]pyrrolidine-2,4-dione

CAS Registry Number

Not Available

SMILES

C[C@H](\C=C(/C)\C=C\C(\O)=C1\C(=O)CNC1=O)[C@H]1O[C@@]2(C)O[C@@H]([C@@H]1C)C(=O)[C@@H]1O[C@]21C

InChI Identifier

InChI=1S/C22H27NO7/c1-10(6-7-13(24)15-14(25)9-23-20(15)27)8-11(2)17-12(3)18-16(26)19-21(4,30-19)22(5,28-17)29-18/h6-8,11-12,17-19,24H,9H2,1-5H3,(H,23,27)/b7-6+,10-8+,15-13+/t11-,12-,17-,18+,19+,21+,22+/m1/s1

InChI Key

URGUBECARCAPRI-UYWODMNRSA-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 flaveolus	NPAtlas	5118218
Streptomyces tirandamycinicus	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Streptomyces sp. 307-9	KNApSAcK Database	22123792

Chemical Taxonomy

Classification

Not classified

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	1.91	ALOGPS
logP	1.61	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	5.31	ChemAxon
pKa (Strongest Basic)	-1.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	114.46 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	109.05 m³·mol⁻¹	ChemAxon
Polarizability	43.35 Å³	ChemAxon
Number of Rings	4	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

NPA017695

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00048206

Chemspider ID

26231493

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

54717225

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhen X, Gong T, Liu F, Zhang PC, Zhou WQ, Li Y, Zhu P: A New Analogue of Echinomycin and a New Cyclic Dipeptide from a Marine-Derived Streptomyces sp. LS298. Mar Drugs. 2015 Nov 18;13(11):6947-61. doi: 10.3390/md13116947. [PubMed:26593927 ]
MacKellar FA, Grostic MF, Olson EC, Wnuk RJ: Tirandamycin. I. Structure assignment. J Am Chem Soc. 1971 Sep;93(19):4943-5. doi: 10.1021/ja00748a067. [PubMed:5118218 ]
Newmister SA, Srivastava KR, Espinoza RV, Haatveit KC, Khatri Y, Martini RM, Garcia-Borras M, Podust LM, Houk KN, Sherman DH: Molecular Basis of Iterative C horizontal line H Oxidation by TamI, a Multifunctional P450 monooxygenase from the Tirandamycin Biosynthetic Pathway. ACS Catal. 2020 Nov 20;10(22):13445-13454. doi: 10.1021/acscatal.0c03248. Epub 2020 Nov 4. [PubMed:33569241 ]
Espinosa A, Socha AM, Ryke E, Rowley DC: Antiamoebic properties of the actinomycete metabolites echinomycin A and tirandamycin A. Parasitol Res. 2012 Dec;111(6):2473-7. doi: 10.1007/s00436-012-3019-2. Epub 2012 Jul 5. [PubMed:22763704 ]
Carlson JC, Li S, Gunatilleke SS, Anzai Y, Burr DA, Podust LM, Sherman DH: Tirandamycin biosynthesis is mediated by co-dependent oxidative enzymes. Nat Chem. 2011 Jul 17;3(8):628-33. doi: 10.1038/nchem.1087. [PubMed:21778983 ]

Showing NP-Card for Tirandamycin A (NP0021547)

MOL for NP0021547 (Tirandamycin A)

3D MOL for NP0021547 (Tirandamycin A)

3D SDF for NP0021547 (Tirandamycin A)

3D-SDF for NP0021547 (Tirandamycin A)

PDB for NP0021547 (Tirandamycin A)

3D PDB for NP0021547 (Tirandamycin A)

SMILES for NP0021547 (Tirandamycin A)

INCHI for NP0021547 (Tirandamycin A)

Structure for NP0021547 (Tirandamycin A)

3D Structure for NP0021547 (Tirandamycin A)