NP-MRD: Showing NP-Card for WS-5995 A (NP0022180)

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Record Information

Version

2.0

Created at

2021-01-06 07:24:24 UTC

Updated at

2021-07-15 17:38:21 UTC

NP-MRD ID

NP0022180

Secondary Accession Numbers

None

Natural Product Identification

Common Name

WS-5995 A

Provided By

NPAtlas

Description

WS-5995 A is found in Streptomyces and Streptomyces acidiscabies. WS-5995 A was first documented in 1980 (PMID: 7451360). Based on a literature review a small amount of articles have been published on WS-5995 A (PMID: 26389922) (PMID: 16238342).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105213D          

 37 40  0  0  0  0            999 V2000
    1.7180    2.8322    1.7289 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0096    1.7578    1.0716 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6777    0.7270    0.4981 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0857    0.7747    0.5855 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8483   -0.2199    0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3367   -0.1550    0.1381 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2745   -1.2751   -0.6032 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9078   -1.3360   -0.6966 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3029   -2.3845   -1.3344 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0152   -3.3274   -1.8547 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0182   -2.4710   -1.4393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7645   -1.5458   -0.9323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2696   -0.4273   -0.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1141   -0.3236   -0.1392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1417    0.5702    0.2871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8167    1.5645    0.8814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6039    0.3957    0.1233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4807    1.3355    0.6348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8515    1.2055    0.5008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3669    0.1317   -0.1479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4891   -0.8323   -0.6736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0827   -1.8755   -1.3077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1051   -0.7012   -0.5383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2118   -1.6957   -1.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6307   -2.7297   -1.7026 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0057    3.6348    2.0133 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4610    3.2886    1.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2253    2.3859    2.6065 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5916    1.5907    1.0834 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7666   -1.1375    0.3326 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7362    0.2630   -0.8123 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6366    0.5515    0.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8517   -2.0807   -1.0490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0773    2.1832    1.1468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4870    1.9705    0.9205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4337    0.0110   -0.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7705   -2.6560   -1.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
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 17 18  2  0  0  0  0
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  7 33  1  0  0  0  0
 18 34  1  0  0  0  0
 19 35  1  0  0  0  0
 20 36  1  0  0  0  0
 22 37  1  0  0  0  0
M  END

     RDKit          3D

 37 40  0  0  0  0  0  0  0  0999 V2000
    1.7180    2.8322    1.7289 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0096    1.7578    1.0716 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6777    0.7270    0.4981 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0857    0.7747    0.5855 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8483   -0.2199    0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3367   -0.1550    0.1381 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2745   -1.2751   -0.6032 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9078   -1.3360   -0.6966 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3029   -2.3845   -1.3344 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0152   -3.3274   -1.8547 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0182   -2.4710   -1.4393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7645   -1.5458   -0.9323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2696   -0.4273   -0.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1141   -0.3236   -0.1392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1417    0.5702    0.2871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8167    1.5645    0.8814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6039    0.3957    0.1233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4807    1.3355    0.6348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8515    1.2055    0.5008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3669    0.1317   -0.1479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4891   -0.8323   -0.6736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0827   -1.8755   -1.3077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1051   -0.7012   -0.5383 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.6307   -2.7297   -1.7026 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4610    3.2886    1.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.6366    0.5515    0.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8517   -2.0807   -1.0490 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.4337    0.0110   -0.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7705   -2.6560   -1.7502 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  1  0
  9 10  2  0
  9 11  1  0
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 17 18  2  0
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 14  3  1  0
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 14  8  2  0
 24 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  6 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
 22 37  1  0
M  END


  Mrv1652306242105213D          

 37 40  0  0  0  0            999 V2000
    1.7180    2.8322    1.7289 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0096    1.7578    1.0716 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6777    0.7270    0.4981 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0857    0.7747    0.5855 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8483   -0.2199    0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3367   -0.1550    0.1381 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2745   -1.2751   -0.6032 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9078   -1.3360   -0.6966 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3029   -2.3845   -1.3344 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0152   -3.3274   -1.8547 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0182   -2.4710   -1.4393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7645   -1.5458   -0.9323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2696   -0.4273   -0.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1141   -0.3236   -0.1392 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.8515    1.2055    0.5008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3669    0.1317   -0.1479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4891   -0.8323   -0.6736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0827   -1.8755   -1.3077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1051   -0.7012   -0.5383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2118   -1.6957   -1.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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 14  3  1  0  0  0  0
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 14  8  2  0  0  0  0
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  1 26  1  0  0  0  0
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  1 28  1  0  0  0  0
  4 29  1  0  0  0  0
  6 30  1  0  0  0  0
  6 31  1  0  0  0  0
  6 32  1  0  0  0  0
  7 33  1  0  0  0  0
 18 34  1  0  0  0  0
 19 35  1  0  0  0  0
 20 36  1  0  0  0  0
 22 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0022180

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(=O)C3=C(C(=O)C2=C([H])C([H])=C1[H])C1=C(C([H])=C(C([H])=C1OC([H])([H])[H])C([H])([H])[H])C(=O)O3

> <INCHI_IDENTIFIER>
InChI=1S/C19H12O6/c1-8-6-10-14(12(7-8)24-2)15-16(21)9-4-3-5-11(20)13(9)17(22)18(15)25-19(10)23/h3-7,20H,1-2H3

> <INCHI_KEY>
LUXDHHSVJLVLPS-UHFFFAOYSA-N

> <FORMULA>
C19H12O6

> <MOLECULAR_WEIGHT>
336.299

> <EXACT_MASS>
336.063388106

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
33.78267674513431

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
8-hydroxy-1-methoxy-3-methyl-7,12-dihydro-5H-6-oxatetraphene-5,7,12-trione

> <ALOGPS_LOGP>
2.73

> <JCHEM_LOGP>
3.409521118333333

> <ALOGPS_LOGS>
-3.92

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.041268517539002

> <JCHEM_PKA_STRONGEST_BASIC>
-4.861804318514478

> <JCHEM_POLAR_SURFACE_AREA>
89.9

> <JCHEM_REFRACTIVITY>
89.85199999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.06e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-hydroxy-1-methoxy-3-methyl-6-oxatetraphene-5,7,12-trione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 37 40  0  0  0  0  0  0  0  0999 V2000
    1.7180    2.8322    1.7289 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0096    1.7578    1.0716 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6777    0.7270    0.4981 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0857    0.7747    0.5855 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8483   -0.2199    0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3367   -0.1550    0.1381 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2745   -1.2751   -0.6032 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9078   -1.3360   -0.6966 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3029   -2.3845   -1.3344 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0152   -3.3274   -1.8547 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0182   -2.4710   -1.4393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7645   -1.5458   -0.9323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2696   -0.4273   -0.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1141   -0.3236   -0.1392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1417    0.5702    0.2871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8167    1.5645    0.8814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6039    0.3957    0.1233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4807    1.3355    0.6348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8515    1.2055    0.5008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3669    0.1317   -0.1479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4891   -0.8323   -0.6736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0827   -1.8755   -1.3077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1051   -0.7012   -0.5383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2118   -1.6957   -1.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6307   -2.7297   -1.7026 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0057    3.6348    2.0133 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4610    3.2886    1.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2253    2.3859    2.6065 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5916    1.5907    1.0834 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7666   -1.1375    0.3326 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7362    0.2630   -0.8123 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6366    0.5515    0.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8517   -2.0807   -1.0490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0773    2.1832    1.1468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4870    1.9705    0.9205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4337    0.0110   -0.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7705   -2.6560   -1.7502 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
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 14  3  1  0
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  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  6 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
 22 37  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       1.718   2.832   1.729  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.010   1.758   1.072  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.678   0.727   0.498  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.086   0.775   0.586  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.848  -0.220   0.037  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.337  -0.155   0.138  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.275  -1.275  -0.603  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.908  -1.336  -0.697  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.303  -2.385  -1.334  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.015  -3.327  -1.855  0.00  0.00           O+0
HETATM   11  O   UNK     0       0.018  -2.471  -1.439  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.765  -1.546  -0.932  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.270  -0.427  -0.258  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.114  -0.324  -0.139  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.142   0.570   0.287  0.00  0.00           C+0
HETATM   16  O   UNK     0      -0.817   1.565   0.881  0.00  0.00           O+0
HETATM   17  C   UNK     0      -2.604   0.396   0.123  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.481   1.335   0.635  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.851   1.206   0.501  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.367   0.132  -0.148  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.489  -0.832  -0.674  0.00  0.00           C+0
HETATM   22  O   UNK     0      -5.083  -1.876  -1.308  0.00  0.00           O+0
HETATM   23  C   UNK     0      -3.105  -0.701  -0.538  0.00  0.00           C+0
HETATM   24  C   UNK     0      -2.212  -1.696  -1.081  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.631  -2.730  -1.703  0.00  0.00           O+0
HETATM   26  H   UNK     0       1.006   3.635   2.013  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.461   3.289   1.059  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.225   2.386   2.607  0.00  0.00           H+0
HETATM   29  H   UNK     0       3.592   1.591   1.083  0.00  0.00           H+0
HETATM   30  H   UNK     0       5.767  -1.137   0.333  0.00  0.00           H+0
HETATM   31  H   UNK     0       5.736   0.263  -0.812  0.00  0.00           H+0
HETATM   32  H   UNK     0       5.637   0.552   0.935  0.00  0.00           H+0
HETATM   33  H   UNK     0       3.852  -2.081  -1.049  0.00  0.00           H+0
HETATM   34  H   UNK     0      -3.077   2.183   1.147  0.00  0.00           H+0
HETATM   35  H   UNK     0      -5.487   1.970   0.921  0.00  0.00           H+0
HETATM   36  H   UNK     0      -6.434   0.011  -0.264  0.00  0.00           H+0
HETATM   37  H   UNK     0      -4.771  -2.656  -1.750  0.00  0.00           H+0
CONECT    1    2   26   27   28                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5   29                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5   30   31   32                                             
CONECT    7    5    8   33                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   24                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13    3    8                                                  
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   23                                                  
CONECT   18   17   19   34                                                  
CONECT   19   18   20   35                                                  
CONECT   20   19   21   36                                                  
CONECT   21   20   22   23                                                  
CONECT   22   21   37                                                       
CONECT   23   21   24   17                                                  
CONECT   24   23   25   12                                                  
CONECT   25   24                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    4                                                            
CONECT   30    6                                                            
CONECT   31    6                                                            
CONECT   32    6                                                            
CONECT   33    7                                                            
CONECT   34   18                                                            
CONECT   35   19                                                            
CONECT   36   20                                                            
CONECT   37   22                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

RDKit          3D

37 40  0  0  0  0  0  0  0  0999 V2000
    1.7180    2.8322    1.7289 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0096    1.7578    1.0716 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6777    0.7270    0.4981 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0857    0.7747    0.5855 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8483   -0.2199    0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3367   -0.1550    0.1381 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2745   -1.2751   -0.6032 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9078   -1.3360   -0.6966 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3029   -2.3845   -1.3344 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0152   -3.3274   -1.8547 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0182   -2.4710   -1.4393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7645   -1.5458   -0.9323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2696   -0.4273   -0.2583 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1141   -0.3236   -0.1392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1417    0.5702    0.2871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8167    1.5645    0.8814 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6039    0.3957    0.1233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4807    1.3355    0.6348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8515    1.2055    0.5008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3669    0.1317   -0.1479 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4891   -0.8323   -0.6736 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0827   -1.8755   -1.3077 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1051   -0.7012   -0.5383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2118   -1.6957   -1.0811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6307   -2.7297   -1.7026 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0057    3.6348    2.0133 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4610    3.2886    1.0593 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2253    2.3859    2.6065 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5916    1.5907    1.0834 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7666   -1.1375    0.3326 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7362    0.2630   -0.8123 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6366    0.5515    0.9350 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8517   -2.0807   -1.0490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0773    2.1832    1.1468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4870    1.9705    0.9205 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4337    0.0110   -0.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7705   -2.6560   -1.7502 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  1  0
  9 10  2  0
  9 11  1  0
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 23 24  1  0
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 14  3  1  0
 23 17  1  0
 14  8  2  0
 24 12  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  4 29  1  0
  6 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
 18 34  1  0
 19 35  1  0
 20 36  1  0
 22 37  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
WS-5995 a	MeSH

Chemical Formula

C₁₉H₁₂O₆

Average Mass

336.2990 Da

Monoisotopic Mass

336.06339 Da

IUPAC Name

8-hydroxy-1-methoxy-3-methyl-7,12-dihydro-5H-6-oxatetraphene-5,7,12-trione

Traditional Name

8-hydroxy-1-methoxy-3-methyl-6-oxatetraphene-5,7,12-trione

CAS Registry Number

Not Available

SMILES

COC1=C2C(=CC(C)=C1)C(=O)OC1=C2C(=O)C2=C(C(O)=CC=C2)C1=O

InChI Identifier

InChI=1S/C19H12O6/c1-8-6-10-14(12(7-8)24-2)15-16(21)9-4-3-5-11(20)13(9)17(22)18(15)25-19(10)23/h3-7,20H,1-2H3

InChI Key

LUXDHHSVJLVLPS-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Streptomyces	NPAtlas	7451360
Streptomyces acidiscabies	LOTUS Database	35616633

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as naphthopyranones. These are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Naphthopyranones

Direct Parent

Naphthopyranones

Alternative Parents

Substituents

Naphthopyranone
Isocoumarin
Benzopyran
Naphthalene
2-benzopyran
Anisole
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Lactone
Ketone
Oxacycle
Ether
Organic oxygen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
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	2.73	ALOGPS
logP	3.41	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	8.04	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.9 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	89.85 m³·mol⁻¹	ChemAxon
Polarizability	33.78 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA002308

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

137716

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

156387

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Mullowney MW, O hAinmhire E, Tanouye U, Burdette JE, Pham VC, Murphy BT: A Pimarane Diterpene and Cytotoxic Angucyclines from a Marine-Derived Micromonospora sp. in Vietnam's East Sea. Mar Drugs. 2015 Sep 15;13(9):5815-27. doi: 10.3390/md13095815. [PubMed:26389922 ]
Ikushima H, Okamoto M, Tanaka H, Ohe O, Kohsaka M, Aoki H, Imanaka H: New anticoccidial antibiotics, WS-5995 A and B. I. Isolation and characterization. J Antibiot (Tokyo). 1980 Oct;33(10):1107-13. doi: 10.7164/antibiotics.33.1107. [PubMed:7451360 ]
Patra A, Pahari P, Ray S, Mal D: A brief and convergent synthetic route to defucogilvocarcin M chromophore: the formal synthesis of WS-5995 A and C. J Org Chem. 2005 Oct 28;70(22):9017-20. doi: 10.1021/jo0512960. [PubMed:16238342 ]

Showing NP-Card for WS-5995 A (NP0022180)

MOL for NP0022180 (WS-5995 A)

3D MOL for NP0022180 (WS-5995 A)

3D SDF for NP0022180 (WS-5995 A)

3D-SDF for NP0022180 (WS-5995 A)

PDB for NP0022180 (WS-5995 A)

3D PDB for NP0022180 (WS-5995 A)

SMILES for NP0022180 (WS-5995 A)

INCHI for NP0022180 (WS-5995 A)

Structure for NP0022180 (WS-5995 A)

3D Structure for NP0022180 (WS-5995 A)