NP-MRD: Showing NP-Card for Pleuromutilin (NP0052042)

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Record Information

Version

2.0

Created at

2022-04-27 23:13:33 UTC

Updated at

2022-04-27 23:13:34 UTC

NP-MRD ID

NP0052042

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Pleuromutilin

Description

Pleuromutilin, also known as drosophilin b, belongs to the class of organic compounds known as pleuromutilin and derivatives. These are mutilins with a hydroxyacetate derivative attached to the C8 carbon atom of the cyclopenta[8]annulene moiety. Pleuromutilin is found in Pleurotus mutilus. Pleuromutilin was first documented in 2022 (PMID: 35472849). Based on a literature review a significant number of articles have been published on Pleuromutilin (PMID: 35468515) (PMID: 35430480) (PMID: 35398097) (PMID: 35393429) (PMID: 35220163) (PMID: 35164203).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282201132D          

 27 29  0  0  1  0            999 V2000
    4.6139    1.0453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9036    1.5225    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0357    1.4272    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9156    0.6783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6442   -0.1008    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3850   -0.5335    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2367   -0.4503    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7515    0.2152    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5575    0.3916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8077    1.1777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3774   -0.3223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6358   -1.1723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2084   -1.3394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8365    0.2117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5765    1.0161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1869    1.6009    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9581    2.3935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8194   -0.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5810    0.7063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2585    1.1771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7877    1.8546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0738    2.2513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1005    2.3237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8928    2.5537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0898    3.3548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4881    1.9825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2804    2.2125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  1  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  2  0  0  0  0
  8 11  1  6  0  0  0
  7 12  1  1  0  0  0
  6 13  1  6  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  3 16  1  0  0  0  0
 16 17  1  1  0  0  0
  5 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  4 20  1  6  0  0  0
 20 21  2  0  0  0  0
  3 22  1  6  0  0  0
  2 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END

     RDKit          3D

 61 63  0  0  0  0  0  0  0  0999 V2000
    3.6201   -1.8408    1.0434 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7015   -0.9711    0.6481 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7416   -1.3032   -0.4434 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5854   -2.1597   -1.4197 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3448   -0.1168   -1.2262 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6270    0.9850   -0.4947 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0831    2.2363   -1.0515 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8520    3.1374   -0.3706 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1967    2.8912    0.8059 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2820    4.3988   -1.0048 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0417    5.1202   -0.1053 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8458    0.9724   -0.6599 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1700    1.6288   -2.0032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5758    1.7324    0.3911 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2189    3.1737    0.4836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4617    1.1045    1.7625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1063   -0.2617    1.6531 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5025   -1.1106    0.5826 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4884   -2.2363    0.2908 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2154   -1.8696   -0.9595 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8127   -0.4551   -1.2062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4770    0.4539   -1.6710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3787   -0.4367   -0.7354 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2057   -1.6766    1.1118 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.6214   -2.8333    2.0369 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6925   -2.2214    0.0575 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3995   -3.2949    0.6635 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3050   -1.5794    1.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6844   -2.8165    0.5706 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6691   -0.0118    1.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5773   -3.2061   -1.1031 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6212   -1.8098   -1.4387 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0957   -2.1119   -2.4214 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3380    0.3414   -1.5441 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8947   -0.3815   -2.2052 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0100    0.9826    0.5375 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8373    4.2154   -1.9477 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3937    5.0476   -1.2532 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9036    4.8536    0.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4360    0.8701   -2.7717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0570    2.3015   -1.9149 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3254    2.2547   -2.3637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6669    1.6822    0.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9717    3.6653   -0.4611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1351    3.7284    0.8584 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4764    3.3085    1.2997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0939    1.7056    2.4479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4484    1.0835    2.1589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9774   -0.7538    2.6318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1972   -0.0924    1.4668 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9351   -3.1904    0.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2300   -2.3485    1.1088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7897   -2.4936   -1.7924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3137   -1.9858   -0.8860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8482   -1.0629   -1.4464 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3371   -0.9730    1.7537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6627   -2.7496    2.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0089   -2.8597    2.9476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4746   -3.7878    1.5176 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1356   -2.7078   -0.7806 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1403   -4.1647    0.3307 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 16  1  0
 16 17  1  0
 18 17  1  1
 18 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 12  1  0
 12 13  1  6
 12  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  1  6
  3  2  1  0
  2  1  2  3
  3 26  1  0
 26 27  1  0
 26 24  1  0
 24 25  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 12 14  1  0
 23 18  1  0
 24 18  1  0
 15 44  1  0
 15 45  1  0
 15 46  1  0
 14 43  1  6
 16 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 19 51  1  0
 19 52  1  0
 20 53  1  0
 20 54  1  0
 23 55  1  6
 13 40  1  0
 13 41  1  0
 13 42  1  0
  6 36  1  1
  5 34  1  0
  5 35  1  0
  4 31  1  0
  4 32  1  0
  4 33  1  0
  2 30  1  0
  1 28  1  0
  1 29  1  0
 26 60  1  6
 27 61  1  0
 24 56  1  1
 25 57  1  0
 25 58  1  0
 25 59  1  0
 10 37  1  0
 10 38  1  0
 11 39  1  0
M  END


  Mrv1652304282201132D          

 27 29  0  0  1  0            999 V2000
    4.6139    1.0453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9036    1.5225    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0357    1.4272    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9156    0.6783    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6442   -0.1008    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3850   -0.5335    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2367   -0.4503    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.7515    0.2152    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.5575    0.3916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8077    1.1777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3774   -0.3223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6358   -1.1723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2084   -1.3394    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8365    0.2117    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5765    1.0161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1869    1.6009    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9581    2.3935    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8194   -0.0835    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5810    0.7063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2585    1.1771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7877    1.8546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0738    2.2513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1005    2.3237    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8928    2.5537    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0898    3.3548    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4881    1.9825    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2804    2.2125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  1  8  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  2  0  0  0  0
  8 11  1  6  0  0  0
  7 12  1  1  0  0  0
  6 13  1  6  0  0  0
  5 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  3 16  1  0  0  0  0
 16 17  1  1  0  0  0
  5 18  1  6  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  4 20  1  6  0  0  0
 20 21  2  0  0  0  0
  3 22  1  6  0  0  0
  2 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0052042

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC[C@@]23CCC(=O)[C@H]2[C@]1(C)[C@@H](C[C@@](C)(C=C)[C@@H](O)[C@@H]3C)OC(=O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C22H34O5/c1-6-20(4)11-16(27-17(25)12-23)21(5)13(2)7-9-22(14(3)19(20)26)10-8-15(24)18(21)22/h6,13-14,16,18-19,23,26H,1,7-12H2,2-5H3/t13-,14+,16-,18+,19+,20-,21+,22+/m1/s1

> <INCHI_KEY>
ZRZNJUXESFHSIO-BKUNHTPHSA-N

> <FORMULA>
C22H34O5

> <MOLECULAR_WEIGHT>
378.509

> <EXACT_MASS>
378.240624195

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
41.37721467227676

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2R,3S,4S,6R,7R,8R,14R)-4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0^{1,8}]tetradecan-6-yl 2-hydroxyacetate

> <ALOGPS_LOGP>
2.60

> <JCHEM_LOGP>
2.5980298783333327

> <ALOGPS_LOGS>
-4.02

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.44683189862533

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.105548226794394

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0500695982334696

> <JCHEM_POLAR_SURFACE_AREA>
83.83

> <JCHEM_REFRACTIVITY>
102.24259999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.66e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,3S,4S,6R,7R,8R,14R)-4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0^{1,8}]tetradecan-6-yl hydroxyacetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       8.613   1.951   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.287   2.842   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.667   2.664   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.442   1.266   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.936  -0.188   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.319  -0.996   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.909  -0.840   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.870   0.402   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.374   0.731   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.841   2.198   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.038  -0.602   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       8.653  -2.188   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.989  -2.500   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.428   0.395   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.943   1.897   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.082   2.988   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.655   4.468   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.396  -0.156   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.951   1.318   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.216   2.197   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       3.337   3.462   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       5.738   4.202   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       7.654   4.338   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       9.133   4.767   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       9.501   6.262   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      10.245   3.701   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      11.723   4.130   0.000  0.00  0.00           O+0
CONECT    1    2    8                                                       
CONECT    2    1    3   23                                                  
CONECT    3    2    4   16   22                                             
CONECT    4    3    5   20                                                  
CONECT    5    4    6   14   18                                             
CONECT    6    5    7   13                                                  
CONECT    7    6    8   12                                                  
CONECT    8    7    1    9   11                                             
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8                                                            
CONECT   12    7                                                            
CONECT   13    6                                                            
CONECT   14    5   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    3   17                                                  
CONECT   17   16                                                            
CONECT   18    5   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19    4   21                                                  
CONECT   21   20                                                            
CONECT   22    3                                                            
CONECT   23    2   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Value	Source
Drosophilin b	MeSH
Octahydro-5,8-dihydroxy-4,6,9,10- tetramethyl-6-vinyl-3a,9-propano-3ah-cyclopenta- cycloocten-1(4H)-one 8-glycolate	MeSH

Chemical Formula

C₂₂H₃₄O₅

Average Mass

378.5090 Da

Monoisotopic Mass

378.24062 Da

IUPAC Name

(1S,2R,3S,4S,6R,7R,8R,14R)-4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0^{1,8}]tetradecan-6-yl 2-hydroxyacetate

Traditional Name

(1S,2R,3S,4S,6R,7R,8R,14R)-4-ethenyl-3-hydroxy-2,4,7,14-tetramethyl-9-oxotricyclo[5.4.3.0^{1,8}]tetradecan-6-yl hydroxyacetate

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC[C@@]23CCC(=O)[C@H]2[C@]1(C)[C@@H](C[C@@](C)(C=C)[C@@H](O)[C@@H]3C)OC(=O)CO

InChI Identifier

InChI=1S/C22H34O5/c1-6-20(4)11-16(27-17(25)12-23)21(5)13(2)7-9-22(14(3)19(20)26)10-8-15(24)18(21)22/h6,13-14,16,18-19,23,26H,1,7-12H2,2-5H3/t13-,14+,16-,18+,19+,20-,21+,22+/m1/s1

InChI Key

ZRZNJUXESFHSIO-BKUNHTPHSA-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
Pleurotus mutilus	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pleuromutilin and derivatives. These are mutilins with a hydroxyacetate derivative attached to the C8 carbon atom of the cyclopenta[8]annulene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Pleuromutilin and derivatives

Alternative Parents

Substituents

Pleuromutilin
Secondary alcohol
Ketone
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic 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	2.6	ALOGPS
logP	2.6	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	13.11	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	83.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	102.24 m³·mol⁻¹	ChemAxon
Polarizability	41.38 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00003473

Chemspider ID

8061754

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Pleuromutilin

METLIN ID

Not Available

PubChem Compound

9886081

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhou Y, Yi Y, Wang J, Yang Z, Liu Q, Pu W, Shang R: Discovery of novel pleuromutilin derivatives as potent antibacterial agents. Eur J Med Chem. 2022 Apr 20;237:114403. doi: 10.1016/j.ejmech.2022.114403. [PubMed:35472849 ]
Ding R, Wang X, Fu J, Chang Y, Li Y, Liu Y, Liu Y, Ma J, Hu J: Design, synthesis and antibacterial activity of novel pleuromutilin derivatives with thieno[2,3-d]pyrimidine substitution. Eur J Med Chem. 2022 Apr 19;237:114398. doi: 10.1016/j.ejmech.2022.114398. [PubMed:35468515 ]
Wang X, Wang R, Zhang ZS, Zhang GY, Jin Z, Shen R, Du D, Tang YZ: Semisynthetic pleuromutilin antimicrobials with therapeutic potential against methicillin-resistant Staphylococcus aureus by targeting 50S ribosomal subunit. Eur J Med Chem. 2022 Apr 12;237:114341. doi: 10.1016/j.ejmech.2022.114341. [PubMed:35430480 ]
Hsu MH, Johnson EF: Structural characterization of the homotropic cooperative binding of azamulin to human cytochrome P450 3A5. J Biol Chem. 2022 Apr 6;298(5):101909. doi: 10.1016/j.jbc.2022.101909. [PubMed:35398097 ]
Li Q, Chen S, Zhu K, Huang X, Huang Y, Shen Z, Ding S, Gu D, Yang Q, Sun H, Hu F, Wang H, Cai J, Ma B, Zhang R, Shen J: Collateral sensitivity to pleuromutilins in vancomycin-resistant Enterococcus faecium. Nat Commun. 2022 Apr 7;13(1):1888. doi: 10.1038/s41467-022-29493-0. [PubMed:35393429 ]
Wu G, Zhu Z, Li J, Luo X, Zhu W, Liao G, Xia J, Zhang W, Pan W, Li T, Wu S: Design, synthesis and antibacterial evaluation of pleuromutilin derivatives. Bioorg Med Chem. 2022 Apr 1;59:116676. doi: 10.1016/j.bmc.2022.116676. Epub 2022 Feb 23. [PubMed:35220163 ]
Fang HQ, Zeng J, Wang SK, Wang X, Chen F, Li B, Liu J, Jin Z, Liu YH, Tang YZ: Discovery of Novel Pleuromutilin Derivatives as Potent Antibacterial Agents for the Treatment of MRSA Infection. Molecules. 2022 Jan 29;27(3). pii: molecules27030931. doi: 10.3390/molecules27030931. [PubMed:35164203 ]
Mohamad M, Nicholson D, Saha CK, Hauryliuk V, Edwards TA, Atkinson GC, Ranson NA, O'Neill AJ: Sal-type ABC-F proteins: intrinsic and common mediators of pleuromutilin resistance by target protection in staphylococci. Nucleic Acids Res. 2022 Feb 28;50(4):2128-2142. doi: 10.1093/nar/gkac058. [PubMed:35137182 ]
Fan Y, Fu Y, Zhou Y, Liu Y, Hao B, Shang R: Acute, subacute oral toxicity and Ames test of Py-mulin: an antibacterial drug candidate. BMC Pharmacol Toxicol. 2022 Jan 4;23(1):2. doi: 10.1186/s40360-021-00543-5. [PubMed:34983673 ]

Showing NP-Card for Pleuromutilin (NP0052042)

MOL for NP0052042 (Pleuromutilin)

3D MOL for NP0052042 (Pleuromutilin)

3D SDF for NP0052042 (Pleuromutilin)

3D-SDF for NP0052042 (Pleuromutilin)

PDB for NP0052042 (Pleuromutilin)

3D PDB for NP0052042 (Pleuromutilin)

SMILES for NP0052042 (Pleuromutilin)

INCHI for NP0052042 (Pleuromutilin)

Structure for NP0052042 (Pleuromutilin)

3D Structure for NP0052042 (Pleuromutilin)