NP-MRD: Showing NP-Card for Myrocin C (NP0017378)

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Record Information

Version

2.0

Created at

2021-01-06 02:06:37 UTC

Updated at

2021-07-15 17:25:20 UTC

NP-MRD ID

NP0017378

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Myrocin C

Provided By

NPAtlas

Description

Myrocin C is found in Albifimbria verrucaria, Myrothecium and Myrothecium verrucaria No. 55 (FERM P-8880). Myrocin C was first documented in 1989 (PMID: 2925513). Based on a literature review very few articles have been published on (1S,2S,5R,9S,12S,15S,17R)-5-ethenyl-2,9-dihydroxy-5,12-dimethyl-10-oxapentacyclo[7.7.1.0¹,¹⁵.0²,⁷.0¹²,¹⁷]Heptadec-6-ene-8,11-dione (PMID: 32615040) (PMID: 30415540) (PMID: 15493929).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242104233D          

 49 53  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306242104233D          

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  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  6  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 20 19  1  6  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25  3  1  0  0  0  0
 22  6  1  0  0  0  0
 21  9  1  0  0  0  0
 21 14  1  0  0  0  0
 20 18  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
  2 28  1  0  0  0  0
  4 29  1  0  0  0  0
  4 30  1  0  0  0  0
  4 31  1  0  0  0  0
  5 32  1  0  0  0  0
 10 33  1  0  0  0  0
 15 34  1  0  0  0  0
 15 35  1  0  0  0  0
 15 36  1  0  0  0  0
 16 37  1  0  0  0  0
 16 38  1  0  0  0  0
 17 39  1  0  0  0  0
 17 40  1  0  0  0  0
 18 41  1  1  0  0  0
 19 42  1  0  0  0  0
 19 43  1  0  0  0  0
 21 44  1  1  0  0  0
 23 45  1  0  0  0  0
 24 46  1  0  0  0  0
 24 47  1  0  0  0  0
 25 48  1  0  0  0  0
 25 49  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0017378

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]12OC(=O)[C@@]3(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]4([H])C([H])([H])[C@]4([C@@]13[H])[C@]1(O[H])C(=C([H])[C@](C([H])=C([H])[H])(C([H])([H])[H])C([H])([H])C1([H])[H])C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C20H24O5/c1-4-16(2)7-8-19(23)12(10-16)13(21)20(24)14-17(3,15(22)25-20)6-5-11-9-18(11,14)19/h4,10-11,14,23-24H,1,5-9H2,2-3H3/t11-,14-,16-,17-,18-,19+,20+/m0/s1

> <INCHI_KEY>
XMHQAXCZBRHGFM-AAORQCPHSA-N

> <FORMULA>
C20H24O5

> <MOLECULAR_WEIGHT>
344.407

> <EXACT_MASS>
344.162373873

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
35.930422132000615

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,2S,5R,9S,12S,15S,17R)-5-ethenyl-2,9-dihydroxy-5,12-dimethyl-10-oxapentacyclo[7.7.1.0^{1,15}.0^{2,7}.0^{12,17}]heptadec-6-ene-8,11-dione

> <ALOGPS_LOGP>
1.29

> <JCHEM_LOGP>
2.494746818333333

> <ALOGPS_LOGS>
-3.20

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.584851138527508

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.94424182681816

> <JCHEM_PKA_STRONGEST_BASIC>
-3.426676342886708

> <JCHEM_POLAR_SURFACE_AREA>
83.83000000000001

> <JCHEM_REFRACTIVITY>
90.06809999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.16e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,5R,9S,12S,15S,17R)-5-ethenyl-2,9-dihydroxy-5,12-dimethyl-10-oxapentacyclo[7.7.1.0^{1,15}.0^{2,7}.0^{12,17}]heptadec-6-ene-8,11-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 49 53  0  0  0  0  0  0  0  0999 V2000
    4.4116    1.4020    1.1686 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8664    0.2018    1.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3367   -0.4595    0.0523 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5568   -0.7866   -0.8204 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4898    0.4575   -0.7575 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1672    0.4627   -0.7009 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3355    1.3478   -1.4818 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8636    2.1167   -2.3256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1012    1.3633   -1.3074 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6200    2.6386   -1.5089 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7972    0.5129   -2.2265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0926    0.4590   -1.7214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1453    0.2218   -2.3958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0574    0.7234   -0.2609 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6179    2.1371   -0.0530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8380   -0.2293    0.5549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9762   -0.7064    1.6941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6895   -1.3020    1.2672 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6332   -1.8126   -0.1458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9379   -0.5591    0.2103 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5861    0.7692    0.0083 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5405   -0.5013    0.2213 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9404   -0.1005    1.5168 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2238   -1.8185   -0.0409 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6727   -1.7451    0.3783 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4655    1.8820    0.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8183    1.9418    2.0217 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7955   -0.3147    2.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3225   -0.0070   -0.7456 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1664   -0.8722   -1.8605 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9245   -1.7978   -0.5352 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9496    1.1671   -1.4358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7231    2.8001   -2.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8922    2.7647    0.5042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9324    2.5964   -1.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5289    2.0898    0.5805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7213    0.2833    1.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2916   -1.0662   -0.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5523   -1.4608    2.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8557    0.1661    2.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1399   -1.8413    2.0652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5328   -1.7508   -0.7908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0993   -2.7540   -0.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3395    1.5115    0.7933 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0633   -0.8734    2.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7842   -2.6650    0.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1203   -2.0439   -1.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7074   -1.9076    1.4793 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1793   -2.6413   -0.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  3  2  1  1
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  1
  9 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  6
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 20 19  1  6
 20 21  1  0
 20 22  1  0
 22 23  1  1
 22 24  1  0
 24 25  1  0
 25  3  1  0
 22  6  1  0
 21  9  1  0
 21 14  1  0
 20 18  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  4 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
 10 33  1  0
 15 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  1
 19 42  1  0
 19 43  1  0
 21 44  1  1
 23 45  1  0
 24 46  1  0
 24 47  1  0
 25 48  1  0
 25 49  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       4.412   1.402   1.169  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.866   0.202   1.272  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.337  -0.460   0.052  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.557  -0.787  -0.820  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.490   0.458  -0.758  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.167   0.463  -0.701  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.336   1.348  -1.482  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.864   2.117  -2.326  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.101   1.363  -1.307  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.620   2.639  -1.509  0.00  0.00           O+0
HETATM   11  O   UNK     0      -1.797   0.513  -2.227  0.00  0.00           O+0
HETATM   12  C   UNK     0      -3.093   0.459  -1.721  0.00  0.00           C+0
HETATM   13  O   UNK     0      -4.145   0.222  -2.396  0.00  0.00           O+0
HETATM   14  C   UNK     0      -3.057   0.723  -0.261  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.618   2.137  -0.053  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.838  -0.229   0.555  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.976  -0.706   1.694  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.690  -1.302   1.267  0.00  0.00           C+0
HETATM   19  C   UNK     0      -1.633  -1.813  -0.146  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.938  -0.559   0.210  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.586   0.769   0.008  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.541  -0.501   0.221  0.00  0.00           C+0
HETATM   23  O   UNK     0       0.940  -0.101   1.517  0.00  0.00           O+0
HETATM   24  C   UNK     0       1.224  -1.819  -0.041  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.673  -1.745   0.378  0.00  0.00           C+0
HETATM   26  H   UNK     0       4.465   1.882   0.213  0.00  0.00           H+0
HETATM   27  H   UNK     0       4.818   1.942   2.022  0.00  0.00           H+0
HETATM   28  H   UNK     0       3.796  -0.315   2.228  0.00  0.00           H+0
HETATM   29  H   UNK     0       5.322  -0.007  -0.746  0.00  0.00           H+0
HETATM   30  H   UNK     0       4.166  -0.872  -1.861  0.00  0.00           H+0
HETATM   31  H   UNK     0       4.925  -1.798  -0.535  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.950   1.167  -1.436  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.723   2.800  -2.483  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.892   2.765   0.504  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.932   2.596  -1.009  0.00  0.00           H+0
HETATM   36  H   UNK     0      -4.529   2.090   0.581  0.00  0.00           H+0
HETATM   37  H   UNK     0      -4.721   0.283   1.037  0.00  0.00           H+0
HETATM   38  H   UNK     0      -4.292  -1.066  -0.018  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.552  -1.461   2.255  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.856   0.166   2.390  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.140  -1.841   2.065  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.533  -1.751  -0.791  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.099  -2.754  -0.247  0.00  0.00           H+0
HETATM   44  H   UNK     0      -1.339   1.512   0.793  0.00  0.00           H+0
HETATM   45  H   UNK     0       1.063  -0.873   2.109  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.784  -2.665   0.514  0.00  0.00           H+0
HETATM   47  H   UNK     0       1.120  -2.044  -1.121  0.00  0.00           H+0
HETATM   48  H   UNK     0       2.707  -1.908   1.479  0.00  0.00           H+0
HETATM   49  H   UNK     0       3.179  -2.641  -0.064  0.00  0.00           H+0
CONECT    1    2   26   27                                                  
CONECT    2    1    3   28                                                  
CONECT    3    2    4    5   25                                             
CONECT    4    3   29   30   31                                             
CONECT    5    3    6   32                                                  
CONECT    6    5    7   22                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11   21                                             
CONECT   10    9   33                                                       
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16   21                                             
CONECT   15   14   34   35   36                                             
CONECT   16   14   17   37   38                                             
CONECT   17   16   18   39   40                                             
CONECT   18   17   19   20   41                                             
CONECT   19   18   20   42   43                                             
CONECT   20   19   21   22   18                                             
CONECT   21   20    9   14   44                                             
CONECT   22   20   23   24    6                                             
CONECT   23   22   45                                                       
CONECT   24   22   25   46   47                                             
CONECT   25   24    3   48   49                                             
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    2                                                            
CONECT   29    4                                                            
CONECT   30    4                                                            
CONECT   31    4                                                            
CONECT   32    5                                                            
CONECT   33   10                                                            
CONECT   34   15                                                            
CONECT   35   15                                                            
CONECT   36   15                                                            
CONECT   37   16                                                            
CONECT   38   16                                                            
CONECT   39   17                                                            
CONECT   40   17                                                            
CONECT   41   18                                                            
CONECT   42   19                                                            
CONECT   43   19                                                            
CONECT   44   21                                                            
CONECT   45   23                                                            
CONECT   46   24                                                            
CONECT   47   24                                                            
CONECT   48   25                                                            
CONECT   49   25                                                            
MASTER        0    0    0    0    0    0    0    0   49    0  106    0
END

RDKit          3D

49 53  0  0  0  0  0  0  0  0999 V2000
    4.4116    1.4020    1.1686 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8664    0.2018    1.2724 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3367   -0.4595    0.0523 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5568   -0.7866   -0.8204 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4898    0.4575   -0.7575 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1672    0.4627   -0.7009 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3355    1.3478   -1.4818 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8636    2.1167   -2.3256 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1012    1.3633   -1.3074 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6200    2.6386   -1.5089 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7972    0.5129   -2.2265 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0926    0.4590   -1.7214 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1453    0.2218   -2.3958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0574    0.7234   -0.2609 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6179    2.1371   -0.0530 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8380   -0.2293    0.5549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9762   -0.7064    1.6941 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6895   -1.3020    1.2672 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6332   -1.8126   -0.1458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9379   -0.5591    0.2103 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.5861    0.7692    0.0083 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5405   -0.5013    0.2213 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9404   -0.1005    1.5168 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2238   -1.8185   -0.0409 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6727   -1.7451    0.3783 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4655    1.8820    0.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8183    1.9418    2.0217 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7955   -0.3147    2.2285 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3225   -0.0070   -0.7456 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1664   -0.8722   -1.8605 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9245   -1.7978   -0.5352 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9496    1.1671   -1.4358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7231    2.8001   -2.4826 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8922    2.7647    0.5042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9324    2.5964   -1.0092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5289    2.0898    0.5805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7213    0.2833    1.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2916   -1.0662   -0.0181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5523   -1.4608    2.2553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8557    0.1661    2.3905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1399   -1.8413    2.0652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5328   -1.7508   -0.7908 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0993   -2.7540   -0.2465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3395    1.5115    0.7933 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0633   -0.8734    2.1092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7842   -2.6650    0.5142 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1203   -2.0439   -1.1214 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7074   -1.9076    1.4793 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1793   -2.6413   -0.0643 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  3  2  1  1
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  1
  9 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  6
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 20 19  1  6
 20 21  1  0
 20 22  1  0
 22 23  1  1
 22 24  1  0
 24 25  1  0
 25  3  1  0
 22  6  1  0
 21  9  1  0
 21 14  1  0
 20 18  1  0
  1 26  1  0
  1 27  1  0
  2 28  1  0
  4 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
 10 33  1  0
 15 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  1
 19 42  1  0
 19 43  1  0
 21 44  1  1
 23 45  1  0
 24 46  1  0
 24 47  1  0
 25 48  1  0
 25 49  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₀H₂₄O₅

Average Mass

344.4070 Da

Monoisotopic Mass

344.16237 Da

IUPAC Name

(1S,2S,5R,9S,12S,15S,17R)-5-ethenyl-2,9-dihydroxy-5,12-dimethyl-10-oxapentacyclo[7.7.1.0^{1,15}.0^{2,7}.0^{12,17}]heptadec-6-ene-8,11-dione

Traditional Name

(1S,2S,5R,9S,12S,15S,17R)-5-ethenyl-2,9-dihydroxy-5,12-dimethyl-10-oxapentacyclo[7.7.1.0^{1,15}.0^{2,7}.0^{12,17}]heptadec-6-ene-8,11-dione

CAS Registry Number

Not Available

SMILES

C[C@]12CC[C@H]3C[C@@]33[C@H]1[C@](O)(OC2=O)C(=O)C1=C[C@](C)(CC[C@]31O)C=C

InChI Identifier

InChI=1S/C20H24O5/c1-4-16(2)7-8-19(23)12(10-16)13(21)20(24)14-17(3,15(22)25-20)6-5-11-9-18(11,14)19/h4,10-11,14,23-24H,1,5-9H2,2-3H3/t11-,14-,16-,17-,18-,19+,20+/m0/s1

InChI Key

XMHQAXCZBRHGFM-AAORQCPHSA-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
Albifimbria verrucaria	LOTUS Database	35616633
Myrothecium	NPAtlas	2925513
Myrothecium verrucaria No. 55 (FERM P-8880)	Fungi	KNApSAcK

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	1.29	ALOGPS
logP	2.49	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	9.94	ChemAxon
pKa (Strongest Basic)	-3.4	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	1	ChemAxon
Refractivity	90.07 m³·mol⁻¹	ChemAxon
Polarizability	35.93 Å³	ChemAxon
Number of Rings	5	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

NPA003998

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

9243066

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11067914

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Hsu YH, Hirota A, Shima S, Nakagawa M, Adachi T, Nozaki H, Nakayama M: Myrocin C, a new diterpene antitumor antibiotic from Myrothecium verrucaria. II. Physico-chemical properties and structure determination. J Antibiot (Tokyo). 1989 Feb;42(2):223-9. doi: 10.7164/antibiotics.42.223. [PubMed:2925513 ]
Tomanik M, Economou C, Frischling MC, Xue M, Marks VA, Mercado BQ, Herzon SB: Development of a Convergent Enantioselective Synthetic Route to (-)-Myrocin G. J Org Chem. 2020 Jul 17;85(14):8952-8989. doi: 10.1021/acs.joc.0c00891. Epub 2020 Jul 2. [PubMed:32615040 ]
Economou C, Tomanik M, Herzon SB: Synthesis of Myrocin G, the Putative Active Form of the Myrocin Antitumor Antibiotics. J Am Chem Soc. 2018 Nov 28;140(47):16058-16061. doi: 10.1021/jacs.8b10891. Epub 2018 Nov 16. [PubMed:30415540 ]
Hu QY, Zhou G, Corey EJ: Application of chiral cationic catalysts to several classical syntheses of racemic natural products transforms them into highly enantioselective pathways. J Am Chem Soc. 2004 Oct 27;126(42):13708-13. doi: 10.1021/ja046154m. [PubMed:15493929 ]

Showing NP-Card for Myrocin C (NP0017378)

MOL for NP0017378 (Myrocin C)

3D MOL for NP0017378 (Myrocin C)

3D SDF for NP0017378 (Myrocin C)

3D-SDF for NP0017378 (Myrocin C)

PDB for NP0017378 (Myrocin C)

3D PDB for NP0017378 (Myrocin C)

SMILES for NP0017378 (Myrocin C)

INCHI for NP0017378 (Myrocin C)

Structure for NP0017378 (Myrocin C)

3D Structure for NP0017378 (Myrocin C)