NP-MRD: Showing NP-Card for (6bS,7R,8S)-7-methoxy-4,8,9-trihydroxy-1,6b,7,8-tetrahydro-2H-benzo[j]flu+ (NP0025559)

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Record Information

Version

1.0

Created at

2021-06-19 17:39:03 UTC

Updated at

2021-06-29 23:50:35 UTC

NP-MRD ID

NP0025559

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6bS,7R,8S)-7-methoxy-4,8,9-trihydroxy-1,6b,7,8-tetrahydro-2H-benzo[j]flu+

Provided By

JEOL Database JEOL Logo

Description

(6bS,7R,8S)-7-methoxy-4,8,9-trihydroxy-1,6b,7,8-tetrahydro-2H-benzo[j]flu+ is found in Cladosporium cf. cladosporioides and Cladosporium cladosporioides. It was first documented in 2001 (Wrigley, S. K., et al.). Based on a literature review very few articles have been published on SCHEMBL6841952.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119393D          

 44 48  0  0  0  0            999 V2000
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   -1.1039   -0.8966    1.6522 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0422   -0.1341    1.2127 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2209   -1.1060    0.9414 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7300   -2.3812    0.4843 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2646   -0.6508   -0.0562 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3816   -1.4629   -0.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4831   -2.7133    0.2344 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4036   -1.0570   -1.1608 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9423    1.3767   -0.5494 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5422    3.8855   -1.0677 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0687    5.1946   -0.4203 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -1.2616    4.1715   -0.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.3047    5.3656    0.3617 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

 44 48  0  0  0  0  0  0  0  0999 V2000
   -1.1017   -1.1179    3.0599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1039   -0.8966    1.6522 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0422   -0.1341    1.2127 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2209   -1.1060    0.9414 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7300   -2.3812    0.4843 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2646   -0.6508   -0.0562 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3816   -1.4629   -0.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4831   -2.7133    0.2344 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4036   -1.0570   -1.1608 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2999    0.1637   -1.8175 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1736    0.9670   -1.6233 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.9423    1.3767   -0.5494 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.5422    3.8855   -1.0677 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306192119393D          

 44 48  0  0  0  0            999 V2000
   -1.1017   -1.1179    3.0599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1039   -0.8966    1.6522 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0025559

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C2C3=C1C(=O)C([H])([H])C([H])([H])C3=C1C3=C(C(O[H])=C([H])C([H])=C3[H])[C@]([H])(O[H])[C@]([H])(OC([H])([H])[H])[C@@]21[H]

> <INCHI_IDENTIFIER>
InChI=1S/C21H18O5/c1-26-21-18-11-6-8-14(24)19-13(23)7-5-10(16(11)19)15(18)9-3-2-4-12(22)17(9)20(21)25/h2-4,6,8,18,20-22,24-25H,5,7H2,1H3/t18-,20-,21+/m0/s1

> <INCHI_KEY>
XAABSYWNTKOZII-SESVDKBCSA-N

> <FORMULA>
C21H18O5

> <MOLECULAR_WEIGHT>
350.37

> <EXACT_MASS>
350.11542368

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
44

> <JCHEM_AVERAGE_POLARIZABILITY>
36.945883135269455

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9S,10R,11S)-7,9,15-trihydroxy-10-methoxypentacyclo[10.7.1.0^{2,11}.0^{3,8}.0^{16,20}]icosa-1,3(8),4,6,12,14,16(20)-heptaen-17-one

> <ALOGPS_LOGP>
2.02

> <JCHEM_LOGP>
2.661841180333334

> <ALOGPS_LOGS>
-3.85

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.238328323993608

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.071761721436996

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6084214766083154

> <JCHEM_POLAR_SURFACE_AREA>
86.99

> <JCHEM_REFRACTIVITY>
96.64189999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.90e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9S,10R,11S)-7,9,15-trihydroxy-10-methoxypentacyclo[10.7.1.0^{2,11}.0^{3,8}.0^{16,20}]icosa-1,3(8),4,6,12,14,16(20)-heptaen-17-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 44 48  0  0  0  0  0  0  0  0999 V2000
   -1.1017   -1.1179    3.0599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1039   -0.8966    1.6522 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0422   -0.1341    1.2127 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2209   -1.1060    0.9414 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7300   -2.3812    0.4843 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2646   -0.6508   -0.0562 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3816   -1.4629   -0.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4831   -2.7133    0.2344 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4036   -1.0570   -1.1608 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2999    0.1637   -1.8175 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1736    0.9670   -1.6233 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1549    0.5772   -0.7412 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9423    1.3767   -0.5494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7306    2.7025   -0.6633 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5422    3.8855   -1.0677 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0687    5.1946   -0.4203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4437    5.3708   -0.3962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9959    6.4665   -0.4702 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2616    4.1715   -0.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981    4.2001    0.2483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3047    5.3656    0.3617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2660    3.0066    0.5658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6015    1.7718    0.5014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2763    1.7581    0.0991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6371    2.9470   -0.2432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3054    0.6207   -0.0731 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9832   -1.7131    3.3128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2086   -1.6698    3.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1603   -0.1649    3.5941 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3318    0.5931    1.9858 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7166   -1.2995    1.9009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2118   -2.4064    0.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5621   -3.0283    0.3610 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2592   -1.7040   -1.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0821    0.4785   -2.5033 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0986    1.8882   -2.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5999    3.7390   -0.8253 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4675    3.9920   -2.1575 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4197    5.2516    0.6173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5048    6.0386   -0.9667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7183    6.1017    0.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3083    3.0445    0.8752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1205    0.8526    0.7580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6811   -0.0508   -0.8560 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0
  3 26  1  0
 26 13  1  0
 13 12  1  0
 14 13  2  0
 24 26  1  0
 15 14  1  0
 17 18  2  0
 19 20  1  0
 20 21  1  0
  6 12  2  0
 24 23  2  0
 23 22  1  0
 22 20  2  0
 24 25  1  0
 14 25  1  0
 19 17  1  0
  6  7  1  0
 12 11  1  0
 11 10  2  0
 10  9  1  0
  9  7  2  0
  6  4  1  0
  7  8  1  0
 19 25  2  0
 26 44  1  6
  3  2  1  0
 16 15  1  0
  4  5  1  0
 16 17  1  0
  2  1  1  0
 16 39  1  0
 16 40  1  0
 15 37  1  0
 15 38  1  0
 23 43  1  0
 22 42  1  0
  4 31  1  1
  3 30  1  1
 21 41  1  0
 11 36  1  0
 10 35  1  0
  9 34  1  0
  8 33  1  0
  5 32  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.102  -1.118   3.060  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.104  -0.897   1.652  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.042  -0.134   1.213  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.221  -1.106   0.941  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.730  -2.381   0.484  0.00  0.00           O+0
HETATM    6  C   UNK     0       2.265  -0.651  -0.056  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.382  -1.463  -0.312  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.483  -2.713   0.234  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.404  -1.057  -1.161  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.300   0.164  -1.817  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.174   0.967  -1.623  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.155   0.577  -0.741  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.942   1.377  -0.549  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.731   2.703  -0.663  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.542   3.886  -1.068  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.069   5.195  -0.420  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.444   5.371  -0.396  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.996   6.466  -0.470  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.262   4.172  -0.145  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.598   4.200   0.248  0.00  0.00           C+0
HETATM   21  O   UNK     0      -3.305   5.366   0.362  0.00  0.00           O+0
HETATM   22  C   UNK     0      -3.266   3.007   0.566  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.602   1.772   0.501  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.276   1.758   0.099  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.637   2.947  -0.243  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.305   0.621  -0.073  0.00  0.00           C+0
HETATM   27  H   UNK     0      -1.983  -1.713   3.313  0.00  0.00           H+0
HETATM   28  H   UNK     0      -0.209  -1.670   3.366  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.160  -0.165   3.594  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.332   0.593   1.986  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.717  -1.300   1.901  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.212  -2.406   0.754  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.562  -3.028   0.361  0.00  0.00           H+0
HETATM   34  H   UNK     0       5.259  -1.704  -1.331  0.00  0.00           H+0
HETATM   35  H   UNK     0       5.082   0.479  -2.503  0.00  0.00           H+0
HETATM   36  H   UNK     0       3.099   1.888  -2.193  0.00  0.00           H+0
HETATM   37  H   UNK     0       2.600   3.739  -0.825  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.468   3.992  -2.158  0.00  0.00           H+0
HETATM   39  H   UNK     0       1.420   5.252   0.617  0.00  0.00           H+0
HETATM   40  H   UNK     0       1.505   6.039  -0.967  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.718   6.102   0.075  0.00  0.00           H+0
HETATM   42  H   UNK     0      -4.308   3.045   0.875  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.120   0.853   0.758  0.00  0.00           H+0
HETATM   44  H   UNK     0      -0.681  -0.051  -0.856  0.00  0.00           H+0
CONECT    1    2   27   28   29                                             
CONECT    2    3    1                                                       
CONECT    3    4   26    2   30                                             
CONECT    4    3    6    5   31                                             
CONECT    5    4   32                                                       
CONECT    6   12    7    4                                                  
CONECT    7    6    9    8                                                  
CONECT    8    7   33                                                       
CONECT    9   10    7   34                                                  
CONECT   10   11    9   35                                                  
CONECT   11   12   10   36                                                  
CONECT   12   13    6   11                                                  
CONECT   13   26   12   14                                                  
CONECT   14   13   15   25                                                  
CONECT   15   14   16   37   38                                             
CONECT   16   15   17   39   40                                             
CONECT   17   18   19   16                                                  
CONECT   18   17                                                            
CONECT   19   20   17   25                                                  
CONECT   20   19   21   22                                                  
CONECT   21   20   41                                                       
CONECT   22   23   20   42                                                  
CONECT   23   24   22   43                                                  
CONECT   24   26   23   25                                                  
CONECT   25   24   14   19                                                  
CONECT   26    3   13   24   44                                             
CONECT   27    1                                                            
CONECT   28    1                                                            
CONECT   29    1                                                            
CONECT   30    3                                                            
CONECT   31    4                                                            
CONECT   32    5                                                            
CONECT   33    8                                                            
CONECT   34    9                                                            
CONECT   35   10                                                            
CONECT   36   11                                                            
CONECT   37   15                                                            
CONECT   38   15                                                            
CONECT   39   16                                                            
CONECT   40   16                                                            
CONECT   41   21                                                            
CONECT   42   22                                                            
CONECT   43   23                                                            
CONECT   44   26                                                            
MASTER        0    0    0    0    0    0    0    0   44    0   96    0
END

RDKit          3D

44 48  0  0  0  0  0  0  0  0999 V2000
   -1.1017   -1.1179    3.0599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1039   -0.8966    1.6522 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0422   -0.1341    1.2127 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2209   -1.1060    0.9414 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7300   -2.3812    0.4843 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2646   -0.6508   -0.0562 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3816   -1.4629   -0.3122 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4831   -2.7133    0.2344 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4036   -1.0570   -1.1608 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2999    0.1637   -1.8175 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1736    0.9670   -1.6233 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1549    0.5772   -0.7412 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9423    1.3767   -0.5494 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7306    2.7025   -0.6633 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5422    3.8855   -1.0677 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0687    5.1946   -0.4203 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4437    5.3708   -0.3962 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9959    6.4665   -0.4702 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2616    4.1715   -0.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5981    4.2001    0.2483 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3047    5.3656    0.3617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2660    3.0066    0.5658 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6015    1.7718    0.5014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2763    1.7581    0.0991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6371    2.9470   -0.2432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3054    0.6207   -0.0731 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9832   -1.7131    3.3128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2086   -1.6698    3.3657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1603   -0.1649    3.5941 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3318    0.5931    1.9858 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7166   -1.2995    1.9009 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2118   -2.4064    0.7543 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5621   -3.0283    0.3610 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2592   -1.7040   -1.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0821    0.4785   -2.5033 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0986    1.8882   -2.1935 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5999    3.7390   -0.8253 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4675    3.9920   -2.1575 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4197    5.2516    0.6173 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5048    6.0386   -0.9667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7183    6.1017    0.0746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3083    3.0445    0.8752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1205    0.8526    0.7580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6811   -0.0508   -0.8560 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0
  3 26  1  0
 26 13  1  0
 13 12  1  0
 14 13  2  0
 24 26  1  0
 15 14  1  0
 17 18  2  0
 19 20  1  0
 20 21  1  0
  6 12  2  0
 24 23  2  0
 23 22  1  0
 22 20  2  0
 24 25  1  0
 14 25  1  0
 19 17  1  0
  6  7  1  0
 12 11  1  0
 11 10  2  0
 10  9  1  0
  9  7  2  0
  6  4  1  0
  7  8  1  0
 19 25  2  0
 26 44  1  6
  3  2  1  0
 16 15  1  0
  4  5  1  0
 16 17  1  0
  2  1  1  0
 16 39  1  0
 16 40  1  0
 15 37  1  0
 15 38  1  0
 23 43  1  0
 22 42  1  0
  4 31  1  1
  3 30  1  1
 21 41  1  0
 11 36  1  0
 10 35  1  0
  9 34  1  0
  8 33  1  0
  5 32  1  0
  1 27  1  0
  1 28  1  0
  1 29  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₂₁H₁₈O₅

Average Mass

350.3700 Da

Monoisotopic Mass

350.11542 Da

IUPAC Name

(9S,10R,11S)-7,9,15-trihydroxy-10-methoxypentacyclo[10.7.1.0^{2,11}.0^{3,8}.0^{16,20}]icosa-1,3(8),4,6,12,14,16(20)-heptaen-17-one

Traditional Name

(9S,10R,11S)-7,9,15-trihydroxy-10-methoxypentacyclo[10.7.1.0^{2,11}.0^{3,8}.0^{16,20}]icosa-1,3(8),4,6,12,14,16(20)-heptaen-17-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C2C3=C1C(=O)C([H])([H])C([H])([H])C3=C1C3=C(C(O[H])=C([H])C([H])=C3[H])[C@]([H])(O[H])[C@]([H])(OC([H])([H])[H])[C@@]21[H]

InChI Identifier

InChI=1S/C21H18O5/c1-26-21-18-11-6-8-14(24)19-13(23)7-5-10(16(11)19)15(18)9-3-2-4-12(22)17(9)20(21)25/h2-4,6,8,18,20-22,24-25H,5,7H2,1H3/t18-,20-,21+/m0/s1

InChI Key

XAABSYWNTKOZII-SESVDKBCSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Cladosporium cf. cladosporioides	JEOL database	Wrigley, S. K., et al, J. Antibiotics 54, 479 (2001)
Cladosporium cladosporioides	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignans, neolignans and related compounds. These are plant products of low molecular weight formed primarily from oxidative coupling of two p-propylphenol moieties. They can also be described as micromolecules with two phenylpropanoid units coupled together. They can be attached in various manners, like C5-C5', C8-C8'. Most known natural lignans are oxidized at C9 and C9´ and, based upon the way in which oxygen is incorporated into the skeleton and on the cyclization patterns, a wide range of lignans of very different structural types can be formed.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Not Available

Sub Class

Not Available

Direct Parent

Lignans, neolignans and related compounds

Alternative Parents

Substituents

Neolignan skeleton
Tetralin
Indene
Aryl alkyl ketone
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Vinylogous acid
Ketone
Secondary alcohol
Ether
Dialkyl ether
Polyol
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Alcohol
Organic oxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic 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	2.02	ALOGPS
logP	2.66	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	8.07	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	96.64 m³·mol⁻¹	ChemAxon
Polarizability	36.95 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8017027

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9841312

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wrigley, S. K., et al. (2001). Wrigley, S. K., et al, J. Antibiotics 54, 479 (2001). J. Antibiotics.

Showing NP-Card for (6bS,7R,8S)-7-methoxy-4,8,9-trihydroxy-1,6b,7,8-tetrahydro-2H-benzo[j]flu+ (NP0025559)

MOL for NP0025559 ((6bS,7R,8S)-7-methoxy-4,8,9-trihydroxy-1,6b,7,8-tetrahydro-2H-benzo[j]flu+)

3D MOL for NP0025559 ((6bS,7R,8S)-7-methoxy-4,8,9-trihydroxy-1,6b,7,8-tetrahydro-2H-benzo[j]flu+)

3D SDF for NP0025559 ((6bS,7R,8S)-7-methoxy-4,8,9-trihydroxy-1,6b,7,8-tetrahydro-2H-benzo[j]flu+)

3D-SDF for NP0025559 ((6bS,7R,8S)-7-methoxy-4,8,9-trihydroxy-1,6b,7,8-tetrahydro-2H-benzo[j]flu+)

PDB for NP0025559 ((6bS,7R,8S)-7-methoxy-4,8,9-trihydroxy-1,6b,7,8-tetrahydro-2H-benzo[j]flu+)

3D PDB for NP0025559 ((6bS,7R,8S)-7-methoxy-4,8,9-trihydroxy-1,6b,7,8-tetrahydro-2H-benzo[j]flu+)

SMILES for NP0025559 ((6bS,7R,8S)-7-methoxy-4,8,9-trihydroxy-1,6b,7,8-tetrahydro-2H-benzo[j]flu+)

INCHI for NP0025559 ((6bS,7R,8S)-7-methoxy-4,8,9-trihydroxy-1,6b,7,8-tetrahydro-2H-benzo[j]flu+)

Structure for NP0025559 ((6bS,7R,8S)-7-methoxy-4,8,9-trihydroxy-1,6b,7,8-tetrahydro-2H-benzo[j]flu+)

3D Structure for NP0025559 ((6bS,7R,8S)-7-methoxy-4,8,9-trihydroxy-1,6b,7,8-tetrahydro-2H-benzo[j]flu+)