NP-MRD: Showing NP-Card for L-783277 (NP0003173)

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Record Information

Version

1.0

Created at

2020-12-09 00:31:30 UTC

Updated at

2021-07-15 16:45:42 UTC

NP-MRD ID

NP0003173

Secondary Accession Numbers

None

Natural Product Identification

Common Name

L-783277

Provided By

NPAtlas

Description

L-783277 belongs to the class of organic compounds known as zearalenones. These are macrolides which contains a fourteen-member lactone fused to 1,3-dihydroxybenzene. L-783277 is found in Phoma sp. and Phoma sp. (ATCC 74403). It was first documented in 1999 (PMID: 10695671). Based on a literature review a significant number of articles have been published on L-783277 (PMID: 33494352) (PMID: 32162636) (PMID: 31513411) (PMID: 28103025).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117453D          

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     RDKit          3D

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  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  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
  9  3  1  0  0  0  0
 25  7  1  0  0  0  0
  1 27  1  0  0  0  0
  1 28  1  0  0  0  0
  1 29  1  0  0  0  0
  4 30  1  0  0  0  0
  6 31  1  0  0  0  0
  9 32  1  0  0  0  0
 10 33  1  0  0  0  0
 10 34  1  0  0  0  0
 11 35  1  0  0  0  0
 11 36  1  0  0  0  0
 12 37  1  0  0  0  0
 12 38  1  0  0  0  0
 13 39  1  6  0  0  0
 14 40  1  0  0  0  0
 15 41  1  1  0  0  0
 16 42  1  0  0  0  0
 19 43  1  0  0  0  0
 20 44  1  0  0  0  0
 21 45  1  0  0  0  0
 21 46  1  0  0  0  0
 22 47  1  1  0  0  0
 23 48  1  0  0  0  0
 23 49  1  0  0  0  0
 23 50  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003173

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])C([H])([H])C([H])([H])[C@]([H])(O[H])[C@]([H])(O[H])C(=O)\C([H])=C([H])/C([H])([H])[C@@]([H])(OC2=O)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C19H24O7/c1-11-5-3-7-14(20)18(23)15(21)8-4-6-12-9-13(25-2)10-16(22)17(12)19(24)26-11/h3,7,9-11,15,18,21-23H,4-6,8H2,1-2H3/b7-3-/t11-,15-,18+/m0/s1

> <INCHI_KEY>
QXPNJMHRUZCEAP-MKICMPBKSA-N

> <FORMULA>
C19H24O7

> <MOLECULAR_WEIGHT>
364.394

> <EXACT_MASS>
364.152203113

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
50

> <JCHEM_AVERAGE_POLARIZABILITY>
37.578484413037415

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(8S,9S)-8,9,16-trihydroxy-14-methoxy-3-methyl-3,4,7,8,9,10,11,12-octahydro-1H-2-benzoxacyclotetradecine-1,7-dione

> <ALOGPS_LOGP>
1.63

> <JCHEM_LOGP>
2.8511352803333327

> <ALOGPS_LOGS>
-2.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.43314411137861

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.739927583756696

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2271629421171006

> <JCHEM_POLAR_SURFACE_AREA>
113.29000000000002

> <JCHEM_REFRACTIVITY>
95.65219999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.13e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(8S,9S)-8,9,16-trihydroxy-14-methoxy-3-methyl-4,8,9,10,11,12-hexahydro-3H-2-benzoxacyclotetradecine-1,7-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 50 51  0  0  0  0  0  0  0  0999 V2000
    6.4141   -0.0197   -0.2809 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2052   -0.7032   -0.5053 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0066   -0.1482   -0.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9931    1.0288    0.6669 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7637    1.5320    1.1313 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8505    2.7427    1.8146 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5680    0.8808    0.9247 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6273   -0.3233    0.2194 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8284   -0.8234   -0.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4360   -1.1455   -0.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3833   -2.4778    0.5631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9586   -2.7064    1.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1068   -2.4122    0.3395 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7567   -2.2150   -0.9714 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0015   -1.3304    0.8421 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7812   -1.9633    1.8700 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0218   -0.8514   -0.1131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5011   -1.7568   -0.8889 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5267    0.4889   -0.2576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8301    1.5271   -0.6583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4139    1.4767   -1.0281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4888    2.2586   -0.1277 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6083    3.1040   -1.0169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8658    1.5472    0.8409 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3263    1.4398    1.4529 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4484    1.8709    2.6755 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3322    0.9833   -0.7833 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2239   -0.6146   -0.7386 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6237    0.1092    0.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9131    1.5778    0.8543 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0556    3.2068    2.1589 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8926   -1.7533   -0.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3693   -1.2988   -1.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5028   -0.6243    0.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5376   -3.2862   -0.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1552   -2.6275    1.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9974   -1.9178    2.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9995   -3.6762    1.7586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7210   -3.3714    0.3389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4846   -3.0253   -1.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5030   -0.5063    1.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1547   -2.7815    1.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6232    0.6739   -0.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3350    2.5016   -0.7184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3609    1.9081   -2.0933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0287    0.4708   -1.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1652    3.0132    0.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2715    3.8343   -1.5251 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0576    3.6878   -0.3493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0029    2.4956   -1.7116 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  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  2  0
  9  3  1  0
 25  7  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  6 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  6
 14 40  1  0
 15 41  1  1
 16 42  1  0
 19 43  1  0
 20 44  1  0
 21 45  1  0
 21 46  1  0
 22 47  1  1
 23 48  1  0
 23 49  1  0
 23 50  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       6.414  -0.020  -0.281  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.205  -0.703  -0.505  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.007  -0.148  -0.015  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.993   1.029   0.667  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.764   1.532   1.131  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.850   2.743   1.815  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.568   0.881   0.925  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.627  -0.323   0.219  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.828  -0.823  -0.240  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.436  -1.145  -0.104  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.383  -2.478   0.563  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.959  -2.706   1.265  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.107  -2.412   0.340  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.757  -2.215  -0.971  0.00  0.00           O+0
HETATM   15  C   UNK     0      -3.002  -1.330   0.842  0.00  0.00           C+0
HETATM   16  O   UNK     0      -3.781  -1.963   1.870  0.00  0.00           O+0
HETATM   17  C   UNK     0      -4.022  -0.851  -0.113  0.00  0.00           C+0
HETATM   18  O   UNK     0      -4.501  -1.757  -0.889  0.00  0.00           O+0
HETATM   19  C   UNK     0      -4.527   0.489  -0.258  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.830   1.527  -0.658  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.414   1.477  -1.028  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.489   2.259  -0.128  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.608   3.104  -1.017  0.00  0.00           C+0
HETATM   24  O   UNK     0      -0.866   1.547   0.841  0.00  0.00           O+0
HETATM   25  C   UNK     0       0.326   1.440   1.453  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.448   1.871   2.676  0.00  0.00           O+0
HETATM   27  H   UNK     0       6.332   0.983  -0.783  0.00  0.00           H+0
HETATM   28  H   UNK     0       7.224  -0.615  -0.739  0.00  0.00           H+0
HETATM   29  H   UNK     0       6.624   0.109   0.787  0.00  0.00           H+0
HETATM   30  H   UNK     0       4.913   1.578   0.854  0.00  0.00           H+0
HETATM   31  H   UNK     0       2.056   3.207   2.159  0.00  0.00           H+0
HETATM   32  H   UNK     0       2.893  -1.753  -0.787  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.369  -1.299  -1.223  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.503  -0.624   0.161  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.538  -3.286  -0.181  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.155  -2.628   1.344  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.997  -1.918   2.071  0.00  0.00           H+0
HETATM   38  H   UNK     0      -1.000  -3.676   1.759  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.721  -3.371   0.339  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.485  -3.025  -1.453  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.503  -0.506   1.382  0.00  0.00           H+0
HETATM   42  H   UNK     0      -4.155  -2.781   1.423  0.00  0.00           H+0
HETATM   43  H   UNK     0      -5.623   0.674  -0.021  0.00  0.00           H+0
HETATM   44  H   UNK     0      -4.335   2.502  -0.718  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.361   1.908  -2.093  0.00  0.00           H+0
HETATM   46  H   UNK     0      -2.029   0.471  -1.152  0.00  0.00           H+0
HETATM   47  H   UNK     0      -2.165   3.013   0.384  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.272   3.834  -1.525  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.058   3.688  -0.349  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.003   2.496  -1.712  0.00  0.00           H+0
CONECT    1    2   27   28   29                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5   30                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5   31                                                       
CONECT    7    5    8   25                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    3   32                                                  
CONECT   10    8   11   33   34                                             
CONECT   11   10   12   35   36                                             
CONECT   12   11   13   37   38                                             
CONECT   13   12   14   15   39                                             
CONECT   14   13   40                                                       
CONECT   15   13   16   17   41                                             
CONECT   16   15   42                                                       
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   43                                                  
CONECT   20   19   21   44                                                  
CONECT   21   20   22   45   46                                             
CONECT   22   21   23   24   47                                             
CONECT   23   22   48   49   50                                             
CONECT   24   22   25                                                       
CONECT   25   24   26    7                                                  
CONECT   26   25                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    4                                                            
CONECT   31    6                                                            
CONECT   32    9                                                            
CONECT   33   10                                                            
CONECT   34   10                                                            
CONECT   35   11                                                            
CONECT   36   11                                                            
CONECT   37   12                                                            
CONECT   38   12                                                            
CONECT   39   13                                                            
CONECT   40   14                                                            
CONECT   41   15                                                            
CONECT   42   16                                                            
CONECT   43   19                                                            
CONECT   44   20                                                            
CONECT   45   21                                                            
CONECT   46   21                                                            
CONECT   47   22                                                            
CONECT   48   23                                                            
CONECT   49   23                                                            
CONECT   50   23                                                            
MASTER        0    0    0    0    0    0    0    0   50    0  102    0
END

RDKit          3D

50 51  0  0  0  0  0  0  0  0999 V2000
    6.4141   -0.0197   -0.2809 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2052   -0.7032   -0.5053 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0066   -0.1482   -0.0154 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9931    1.0288    0.6669 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7637    1.5320    1.1313 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8505    2.7427    1.8146 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5680    0.8808    0.9247 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6273   -0.3233    0.2194 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8284   -0.8234   -0.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4360   -1.1455   -0.1037 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3833   -2.4778    0.5631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9586   -2.7064    1.2647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1068   -2.4122    0.3395 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7567   -2.2150   -0.9714 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0015   -1.3304    0.8421 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.7812   -1.9633    1.8700 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0218   -0.8514   -0.1131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5011   -1.7568   -0.8889 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5267    0.4889   -0.2576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8301    1.5271   -0.6583 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4139    1.4767   -1.0281 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4888    2.2586   -0.1277 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6083    3.1040   -1.0169 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8658    1.5472    0.8409 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3263    1.4398    1.4529 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4484    1.8709    2.6755 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3322    0.9833   -0.7833 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2239   -0.6146   -0.7386 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6237    0.1092    0.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9131    1.5778    0.8543 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0556    3.2068    2.1589 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8926   -1.7533   -0.7866 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3693   -1.2988   -1.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5028   -0.6243    0.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5376   -3.2862   -0.1806 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1552   -2.6275    1.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9974   -1.9178    2.0708 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9995   -3.6762    1.7586 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7210   -3.3714    0.3389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4846   -3.0253   -1.4528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5030   -0.5063    1.3819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1547   -2.7815    1.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6232    0.6739   -0.0206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3350    2.5016   -0.7184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3609    1.9081   -2.0933 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0287    0.4708   -1.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1652    3.0132    0.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2715    3.8343   -1.5251 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0576    3.6878   -0.3493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0029    2.4956   -1.7116 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  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 25 26  2  0
  9  3  1  0
 25  7  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
  4 30  1  0
  6 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 12 37  1  0
 12 38  1  0
 13 39  1  6
 14 40  1  0
 15 41  1  1
 16 42  1  0
 19 43  1  0
 20 44  1  0
 21 45  1  0
 21 46  1  0
 22 47  1  1
 23 48  1  0
 23 49  1  0
 23 50  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₁₉H₂₄O₇

Average Mass

364.3940 Da

Monoisotopic Mass

364.15220 Da

IUPAC Name

(8S,9S)-8,9,16-trihydroxy-14-methoxy-3-methyl-3,4,7,8,9,10,11,12-octahydro-1H-2-benzoxacyclotetradecine-1,7-dione

Traditional Name

(8S,9S)-8,9,16-trihydroxy-14-methoxy-3-methyl-4,8,9,10,11,12-hexahydro-3H-2-benzoxacyclotetradecine-1,7-dione

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(CCC[C@H](O)[C@H](O)C(=O)\C=C/CC(C)OC2=O)=C1

InChI Identifier

InChI=1S/C19H24O7/c1-11-5-3-7-14(20)18(23)15(21)8-4-6-12-9-13(25-2)10-16(22)17(12)19(24)26-11/h3,7,9-11,15,18,21-23H,4-6,8H2,1-2H3/b7-3-/t11?,15-,18+/m0/s1

InChI Key

QXPNJMHRUZCEAP-MKICMPBKSA-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
Phoma sp.	NPAtlas	10695671
Phoma sp. (ATCC 74403)	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as zearalenones. These are macrolides which contains a fourteen-member lactone fused to 1,3-dihydroxybenzene.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Macrolides and analogues

Sub Class

Zearalenones

Direct Parent

Zearalenones

Alternative Parents

Substituents

Zearalenone-skeleton
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Vinylogous acid
Cyclic ketone
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
1,2-diol
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	1.63	ALOGPS
logP	2.85	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	9.74	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	95.65 m³·mol⁻¹	ChemAxon
Polarizability	37.58 Å³	ChemAxon
Number of Rings	2	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

NPA012221

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78437725

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139586502

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhao A, Lee SH, Mojena M, Jenkins RG, Patrick DR, Huber HE, Goetz MA, Hensens OD, Zink DL, Vilella D, Dombrowski AW, Lingham RB, Huang L: Resorcylic acid lactones: naturally occurring potent and selective inhibitors of MEK. J Antibiot (Tokyo). 1999 Dec;52(12):1086-94. doi: 10.7164/antibiotics.52.1086. [PubMed:10695671 ]
Kim Y, Sengupta S, Sim T: Natural and Synthetic Lactones Possessing Antitumor Activities. Int J Mol Sci. 2021 Jan 21;22(3). pii: ijms22031052. doi: 10.3390/ijms22031052. [PubMed:33494352 ]
Chakraborty J, Ghosh A, Nanda S: Asymmetric total syntheses of naturally occurring alpha,beta-enone-containing RALs, L-783290 and L-783277 through intramolecular base-mediated macrolactonization reaction. Org Biomol Chem. 2020 Mar 25;18(12):2331-2345. doi: 10.1039/d0ob00237b. [PubMed:32162636 ]
Han Y, Sengupta S, Lee BJ, Cho H, Kim J, Choi HG, Dash U, Kim JH, Kim ND, Kim JH, Sim T: Identification of a Unique Resorcylic Acid Lactone Derivative That Targets Both Lymphangiogenesis and Angiogenesis. J Med Chem. 2019 Oct 24;62(20):9141-9160. doi: 10.1021/acs.jmedchem.9b01025. Epub 2019 Oct 7. [PubMed:31513411 ]
Cho H, Sengupta S, Jeon SS, Hur W, Choi HG, Seo HS, Lee BJ, Kim JH, Chung M, Jeon NL, Kim ND, Sim T: Identification of the First Selective Activin Receptor-Like Kinase 1 Inhibitor, a Reversible Version of L-783277. J Med Chem. 2017 Feb 23;60(4):1495-1508. doi: 10.1021/acs.jmedchem.6b01679. Epub 2017 Feb 6. [PubMed:28103025 ]

Showing NP-Card for L-783277 (NP0003173)

MOL for NP0003173 (L-783277)

3D MOL for NP0003173 (L-783277)

3D SDF for NP0003173 (L-783277)

3D-SDF for NP0003173 (L-783277)

PDB for NP0003173 (L-783277)

3D PDB for NP0003173 (L-783277)

SMILES for NP0003173 (L-783277)

INCHI for NP0003173 (L-783277)

Structure for NP0003173 (L-783277)

3D Structure for NP0003173 (L-783277)