NP-MRD: Showing NP-Card for Purpuromycin (NP0021482)

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Record Information

Version

1.0

Created at

2021-01-06 06:45:53 UTC

Updated at

2021-07-15 17:36:28 UTC

NP-MRD ID

NP0021482

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Purpuromycin

Provided By

NPAtlas

Description

Methyl (2R,4'S)-4',5,8,10'-tetrahydroxy-7-methoxy-4,9,9'-trioxo-4,4',9,9'-tetrahydro-3H,3'H-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-7'-carboxylate belongs to the class of organic compounds known as pyranochromenes. These are organic heterocyclic compounds containing a pyran ring fused to a chromene (1-benzopyran) moiety. Purpuromycin is found in Actinoplanes, Actinoplanes ianthinogenes and Actinoplanes ianthinogenes n. sp. A/1668. It was first documented in 1974 (PMID: 4836652). Based on a literature review very few articles have been published on methyl (2R,4'S)-4',5,8,10'-tetrahydroxy-7-methoxy-4,9,9'-trioxo-4,4',9,9'-tetrahydro-3H,3'H-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-7'-carboxylate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105163D          

 57 62  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306242105163D          

 57 62  0  0  0  0            999 V2000
  -10.9119    0.3607    0.2068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5856    0.4337    0.6979 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.6312    1.3228   -0.0210 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8288    0.6542   -0.2727 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4433   -0.7595   -0.2083 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2101   -1.4321   -0.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2438   -2.7639   -0.3818 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0439   -0.7573    0.0833 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7395   -1.3911    0.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6542   -2.6526   -0.0499 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1480    0.3482   -0.9912 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2173   -0.6658   -1.3225 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5667   -0.6200   -2.6718 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9383    0.6878   -0.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3201   -0.6562    0.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5136    1.0950    0.7760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2756   -0.4244   -1.4827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8979   -0.6880   -1.8945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0298    0.8031    3.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9579   -1.7199   -0.4062 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9434   -1.6852    1.4309 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0874    3.2367    0.4710 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6575    1.3951   -0.1893 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9475   -0.2020    0.4127 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8726    0.2627   -1.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3707   -1.2788   -0.4035 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6295   -3.4997   -0.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7013    0.2732   -1.7023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6306    1.3505   -1.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9472   -1.7064   -1.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5315   -1.5132   -3.0985 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
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 10 17  1  0  0  0  0
 18 17  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 21 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
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 18 37  1  0  0  0  0
 37 38  1  0  0  0  0
 38 39  1  0  0  0  0
 16  5  1  0  0  0  0
 22 18  1  0  0  0  0
 34 25  1  0  0  0  0
 13  7  1  0  0  0  0
 35 20  1  0  0  0  0
 38  9  1  0  0  0  0
  1 40  1  0  0  0  0
  1 41  1  0  0  0  0
  1 42  1  0  0  0  0
  6 43  1  0  0  0  0
  8 44  1  0  0  0  0
 12 45  1  0  0  0  0
 19 46  1  0  0  0  0
 19 47  1  0  0  0  0
 27 48  1  0  0  0  0
 30 49  1  0  0  0  0
 30 50  1  0  0  0  0
 30 51  1  0  0  0  0
 31 52  1  0  0  0  0
 33 53  1  0  0  0  0
 37 54  1  0  0  0  0
 37 55  1  0  0  0  0
 38 56  1  1  0  0  0
 39 57  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0021482

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(=O)C3=C(O[C@]4(OC5=C(C([H])=C6C([H])=C(OC(=O)C6=C5O[H])C(=O)OC([H])([H])[H])[C@@]([H])(O[H])C4([H])[H])C3([H])[H])C(=O)C2=C(O[H])C(OC([H])([H])[H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C26H18O13/c1-35-13-5-11(27)16-17(19(13)30)21(32)23-10(18(16)29)6-26(39-23)7-12(28)9-3-8-4-14(24(33)36-2)37-25(34)15(8)20(31)22(9)38-26/h3-5,12,27-28,30-31H,6-7H2,1-2H3/t12-,26+/m0/s1

> <INCHI_KEY>
DJICBKSAAXLOMR-GWQKEKGPSA-N

> <FORMULA>
C26H18O13

> <MOLECULAR_WEIGHT>
538.417

> <EXACT_MASS>
538.07474064

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
52.37837758308538

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2R,4'S)-4',5,8,10'-tetrahydroxy-7-methoxy-4,9,9'-trioxo-4,4',9,9'-tetrahydro-3H,3'H-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-7'-carboxylate

> <ALOGPS_LOGP>
2.88

> <JCHEM_LOGP>
3.345865099666667

> <ALOGPS_LOGS>
-3.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.578667494543884

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.912904508917891

> <JCHEM_PKA_STRONGEST_BASIC>
-3.306766405266549

> <JCHEM_POLAR_SURFACE_AREA>
195.34999999999997

> <JCHEM_REFRACTIVITY>
129.9123

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.30e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2R,4'S)-4',5,8,10'-tetrahydroxy-7-methoxy-4,9,9'-trioxo-3',4'-dihydro-3H-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-7'-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 57 62  0  0  0  0  0  0  0  0999 V2000
  -10.9119    0.3607    0.2068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5856    0.4337    0.6979 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.7869   -0.2222   -1.2977 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.0715   -0.1262   -0.4677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7620   -0.0779   -0.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6969   -0.3897   -0.8794 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1490    0.0521    0.8616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2088    0.3692    1.6984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9675    0.7548    3.0069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5189    0.3056    1.2411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6031    0.6095    2.0302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3747    0.9597    3.2202 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8538    0.5466    1.5866 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8358    0.0984    1.2642 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2785    0.1444    0.4375 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1234   -1.1065    0.5022 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5239   -0.6227    0.4102 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5288    0.6764    0.6164 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2216    1.1254    0.8464 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8158    1.3557    0.5685 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8914    2.5934    0.7563 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0607    0.6245    0.3012 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2724    1.2874    0.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2657    2.6664    0.4800 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4392    0.5935    0.0076 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6312    1.3228   -0.0210 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8288    0.6542   -0.2727 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4433   -0.7595   -0.2083 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2101   -1.4321   -0.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2438   -2.7639   -0.3818 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0439   -0.7573    0.0833 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7395   -1.3911    0.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6542   -2.6526   -0.0499 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1480    0.3482   -0.9912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2173   -0.6658   -1.3225 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5667   -0.6200   -2.6718 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9383    0.6878   -0.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3201   -0.6562    0.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5136    1.0950    0.7760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2756   -0.4244   -1.4827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8979   -0.6880   -1.8945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0298    0.8031    3.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9579   -1.7199   -0.4062 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9434   -1.6852    1.4309 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0874    3.2367    0.4710 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6575    1.3951   -0.1893 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9475   -0.2020    0.4127 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8726    0.2627   -1.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3707   -1.2788   -0.4035 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6295   -3.4997   -0.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7013    0.2732   -1.7023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6306    1.3505   -1.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9472   -1.7064   -1.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5315   -1.5132   -3.0985 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 10 17  1  0
 18 17  1  1
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 28 31  2  0
 31 32  1  0
 32 33  1  0
 32 34  2  0
 34 35  1  0
 35 36  2  0
 18 37  1  0
 37 38  1  0
 38 39  1  0
 16  5  1  0
 22 18  1  0
 34 25  1  0
 13  7  1  0
 35 20  1  0
 38  9  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  6 43  1  0
  8 44  1  0
 12 45  1  0
 19 46  1  0
 19 47  1  0
 27 48  1  0
 30 49  1  0
 30 50  1  0
 30 51  1  0
 31 52  1  0
 33 53  1  0
 37 54  1  0
 37 55  1  0
 38 56  1  1
 39 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     -10.912   0.361   0.207  0.00  0.00           C+0
HETATM    2  O   UNK     0      -9.586   0.434   0.698  0.00  0.00           O+0
HETATM    3  C   UNK     0      -8.520   0.123  -0.117  0.00  0.00           C+0
HETATM    4  O   UNK     0      -8.787  -0.222  -1.298  0.00  0.00           O+0
HETATM    5  C   UNK     0      -7.129   0.187   0.358  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.072  -0.126  -0.468  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.762  -0.078  -0.061  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.697  -0.390  -0.879  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.391  -0.336  -0.455  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.149   0.052   0.862  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.209   0.369   1.698  0.00  0.00           C+0
HETATM   12  O   UNK     0      -2.967   0.755   3.007  0.00  0.00           O+0
HETATM   13  C   UNK     0      -4.519   0.306   1.241  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.603   0.610   2.030  0.00  0.00           C+0
HETATM   15  O   UNK     0      -5.375   0.960   3.220  0.00  0.00           O+0
HETATM   16  O   UNK     0      -6.854   0.547   1.587  0.00  0.00           O+0
HETATM   17  O   UNK     0      -0.836   0.098   1.264  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.279   0.144   0.438  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.123  -1.107   0.502  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.524  -0.623   0.410  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.529   0.676   0.616  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.222   1.125   0.846  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.816   1.356   0.569  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.891   2.593   0.756  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.061   0.625   0.301  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.272   1.287   0.260  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.266   2.666   0.480  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.439   0.594   0.008  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.631   1.323  -0.021  0.00  0.00           O+0
HETATM   30  C   UNK     0       9.829   0.654  -0.273  0.00  0.00           C+0
HETATM   31  C   UNK     0       7.443  -0.760  -0.208  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.210  -1.432  -0.166  0.00  0.00           C+0
HETATM   33  O   UNK     0       6.244  -2.764  -0.382  0.00  0.00           O+0
HETATM   34  C   UNK     0       5.044  -0.757   0.083  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.740  -1.391   0.141  0.00  0.00           C+0
HETATM   36  O   UNK     0       3.654  -2.653  -0.050  0.00  0.00           O+0
HETATM   37  C   UNK     0      -0.148   0.348  -0.991  0.00  0.00           C+0
HETATM   38  C   UNK     0      -1.217  -0.666  -1.323  0.00  0.00           C+0
HETATM   39  O   UNK     0      -1.567  -0.620  -2.672  0.00  0.00           O+0
HETATM   40  H   UNK     0     -10.938   0.688  -0.874  0.00  0.00           H+0
HETATM   41  H   UNK     0     -11.320  -0.656   0.221  0.00  0.00           H+0
HETATM   42  H   UNK     0     -11.514   1.095   0.776  0.00  0.00           H+0
HETATM   43  H   UNK     0      -6.276  -0.424  -1.483  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.898  -0.688  -1.895  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.030   0.803   3.343  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.958  -1.720  -0.406  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.943  -1.685   1.431  0.00  0.00           H+0
HETATM   48  H   UNK     0       7.087   3.237   0.471  0.00  0.00           H+0
HETATM   49  H   UNK     0      10.658   1.395  -0.189  0.00  0.00           H+0
HETATM   50  H   UNK     0       9.947  -0.202   0.413  0.00  0.00           H+0
HETATM   51  H   UNK     0       9.873   0.263  -1.323  0.00  0.00           H+0
HETATM   52  H   UNK     0       8.371  -1.279  -0.404  0.00  0.00           H+0
HETATM   53  H   UNK     0       5.630  -3.500  -0.424  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.701   0.273  -1.702  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.631   1.351  -1.050  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.947  -1.706  -1.088  0.00  0.00           H+0
HETATM   57  H   UNK     0      -1.532  -1.513  -3.099  0.00  0.00           H+0
CONECT    1    2   40   41   42                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   16                                                  
CONECT    6    5    7   43                                                  
CONECT    7    6    8   13                                                  
CONECT    8    7    9   44                                                  
CONECT    9    8   10   38                                                  
CONECT   10    9   11   17                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11   45                                                       
CONECT   13   11   14    7                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    5                                                       
CONECT   17   10   18                                                       
CONECT   18   17   19   37   22                                             
CONECT   19   18   20   46   47                                             
CONECT   20   19   21   35                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21   18                                                       
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   34                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26   48                                                       
CONECT   28   26   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29   49   50   51                                             
CONECT   31   28   32   52                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32   53                                                       
CONECT   34   32   35   25                                                  
CONECT   35   34   36   20                                                  
CONECT   36   35                                                            
CONECT   37   18   38   54   55                                             
CONECT   38   37   39    9   56                                             
CONECT   39   38   57                                                       
CONECT   40    1                                                            
CONECT   41    1                                                            
CONECT   42    1                                                            
CONECT   43    6                                                            
CONECT   44    8                                                            
CONECT   45   12                                                            
CONECT   46   19                                                            
CONECT   47   19                                                            
CONECT   48   27                                                            
CONECT   49   30                                                            
CONECT   50   30                                                            
CONECT   51   30                                                            
CONECT   52   31                                                            
CONECT   53   33                                                            
CONECT   54   37                                                            
CONECT   55   37                                                            
CONECT   56   38                                                            
CONECT   57   39                                                            
MASTER        0    0    0    0    0    0    0    0   57    0  124    0
END

RDKit          3D

57 62  0  0  0  0  0  0  0  0999 V2000
  -10.9119    0.3607    0.2068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5856    0.4337    0.6979 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5201    0.1229   -0.1173 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7869   -0.2222   -1.2977 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1290    0.1873    0.3579 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0715   -0.1262   -0.4677 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7620   -0.0779   -0.0606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6969   -0.3897   -0.8794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3914   -0.3357   -0.4548 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1490    0.0521    0.8616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2088    0.3692    1.6984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9675    0.7548    3.0069 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5189    0.3056    1.2411 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6031    0.6095    2.0302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3747    0.9597    3.2202 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8538    0.5466    1.5866 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8358    0.0984    1.2642 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2785    0.1444    0.4375 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1234   -1.1065    0.5022 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5239   -0.6227    0.4102 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5288    0.6764    0.6164 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2216    1.1254    0.8464 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8158    1.3557    0.5685 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8914    2.5934    0.7563 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0607    0.6245    0.3012 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2724    1.2874    0.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2657    2.6664    0.4800 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4392    0.5935    0.0076 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6312    1.3228   -0.0210 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.8288    0.6542   -0.2727 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4433   -0.7595   -0.2083 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2101   -1.4321   -0.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2438   -2.7639   -0.3818 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0439   -0.7573    0.0833 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7395   -1.3911    0.1405 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6542   -2.6526   -0.0499 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1480    0.3482   -0.9912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2173   -0.6658   -1.3225 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5667   -0.6200   -2.6718 O   0  0  0  0  0  0  0  0  0  0  0  0
  -10.9383    0.6878   -0.8737 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3201   -0.6562    0.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5136    1.0950    0.7760 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2756   -0.4244   -1.4827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8979   -0.6880   -1.8945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0298    0.8031    3.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9579   -1.7199   -0.4062 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9434   -1.6852    1.4309 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0874    3.2367    0.4710 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.6575    1.3951   -0.1893 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.9475   -0.2020    0.4127 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8726    0.2627   -1.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3707   -1.2788   -0.4035 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6295   -3.4997   -0.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7013    0.2732   -1.7023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6306    1.3505   -1.0496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9472   -1.7064   -1.0877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5315   -1.5132   -3.0985 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 11 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 10 17  1  0
 18 17  1  1
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 21 23  1  0
 23 24  2  0
 23 25  1  0
 25 26  2  0
 26 27  1  0
 26 28  1  0
 28 29  1  0
 29 30  1  0
 28 31  2  0
 31 32  1  0
 32 33  1  0
 32 34  2  0
 34 35  1  0
 35 36  2  0
 18 37  1  0
 37 38  1  0
 38 39  1  0
 16  5  1  0
 22 18  1  0
 34 25  1  0
 13  7  1  0
 35 20  1  0
 38  9  1  0
  1 40  1  0
  1 41  1  0
  1 42  1  0
  6 43  1  0
  8 44  1  0
 12 45  1  0
 19 46  1  0
 19 47  1  0
 27 48  1  0
 30 49  1  0
 30 50  1  0
 30 51  1  0
 31 52  1  0
 33 53  1  0
 37 54  1  0
 37 55  1  0
 38 56  1  1
 39 57  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
Methyl (2R,4's)-4',5,8,10'-tetrahydroxy-7-methoxy-4,9,9'-trioxo-4,4',9,9'-tetrahydro-3H,3'H-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-7'-carboxylic acid	Generator

Chemical Formula

C₂₆H₁₈O₁₃

Average Mass

538.4170 Da

Monoisotopic Mass

538.07474 Da

IUPAC Name

methyl (2R,4'S)-4',5,8,10'-tetrahydroxy-7-methoxy-4,9,9'-trioxo-4,4',9,9'-tetrahydro-3H,3'H-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-7'-carboxylate

Traditional Name

methyl (2R,4'S)-4',5,8,10'-tetrahydroxy-7-methoxy-4,9,9'-trioxo-3',4'-dihydro-3H-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-7'-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CC2=CC3=C(O[C@@]4(CC5=C(O4)C(=O)C4=C(C(O)=CC(OC)=C4O)C5=O)C[C@@H]3O)C(O)=C2C(=O)O1

InChI Identifier

InChI=1S/C26H18O13/c1-35-13-5-11(27)16-17(19(13)30)21(32)23-10(18(16)29)6-26(39-23)7-12(28)9-3-8-4-14(24(33)36-2)37-25(34)15(8)20(31)22(9)38-26/h3-5,12,27-28,30-31H,6-7H2,1-2H3/t12-,26+/m0/s1

InChI Key

DJICBKSAAXLOMR-GWQKEKGPSA-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
Actinoplanes	NPAtlas	4836652
Actinoplanes ianthinogenes	LOTUS Database	35616633
Actinoplanes ianthinogenes n. sp. A/1668	Bacteria	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranochromenes. These are organic heterocyclic compounds containing a pyran ring fused to a chromene (1-benzopyran) moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Pyranochromenes

Alternative Parents

Substituents

Pyranochromene
Naphthofuran
Naphthoquinone
Isocoumarin
2-benzopyran
Naphthalene
Aryl ketone
Quinone
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Ketal
Pyranone
Alkyl aryl ether
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous ester
Vinylogous acid
Methyl ester
Dihydrofuran
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Polyol
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	2.88	ALOGPS
logP	3.35	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	2.91	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	195.35 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	129.91 m³·mol⁻¹	ChemAxon
Polarizability	52.38 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA021172

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78443163

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Coronelli C, Pagani H, Bardone MR, Lancini GC: Purpuromycin, a new antibiotic isolated from Actinoplanes ianthinogenes N. sp. J Antibiot (Tokyo). 1974 Mar;27(3):161-8. doi: 10.7164/antibiotics.27.161. [PubMed:4836652 ]

Showing NP-Card for Purpuromycin (NP0021482)

MOL for NP0021482 (Purpuromycin)

3D MOL for NP0021482 (Purpuromycin)

3D SDF for NP0021482 (Purpuromycin)

3D-SDF for NP0021482 (Purpuromycin)

PDB for NP0021482 (Purpuromycin)

3D PDB for NP0021482 (Purpuromycin)

SMILES for NP0021482 (Purpuromycin)

INCHI for NP0021482 (Purpuromycin)

Structure for NP0021482 (Purpuromycin)

3D Structure for NP0021482 (Purpuromycin)