NP-MRD: Showing NP-Card for RP-1551-5 (NP0001653)

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Record Information

Version

1.0

Created at

2020-09-23 02:00:16 UTC

Updated at

2021-08-10 02:56:02 UTC

NP-MRD ID

NP0001653

Secondary Accession Numbers

None

Natural Product Identification

Common Name

RP-1551-5

Provided By

NPAtlas

Description

(6AS,9aS)-5-chloro-3-[(1E,3E)-3,5-dimethylhepta-1,3-dien-1-yl]-8-(2-hydroxypropyl)-8-methoxy-6a-methyl-6H,6aH,8H,9H,9aH-furo[2,3-h]isochromen-6-one belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals. RP-1551-5 is found in Penicillium and Penicillium sp. SPC-21609. It was first documented in 1999 (PMID: 10348038). Based on a literature review very few articles have been published on (6aS,9aS)-5-chloro-3-[(1E,3E)-3,5-dimethylhepta-1,3-dien-1-yl]-8-(2-hydroxypropyl)-8-methoxy-6a-methyl-6H,6aH,8H,9H,9aH-furo[2,3-h]isochromen-6-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117443D          

 64 66  0  0  0  0            999 V2000
    7.6047    0.6224   -2.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1069   -0.6346   -1.4295 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.5320   -0.5716   -0.0056 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.0411   -1.8303    0.6770 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0621   -0.6706   -0.0417 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2200    0.1819    0.5235 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7772    1.3377    1.2589 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7745   -0.0195    0.4179 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
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  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
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M  END

     RDKit          3D

 64 66  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306242117443D          

 64 66  0  0  0  0            999 V2000
    7.6047    0.6224   -2.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1069   -0.6346   -1.4295 C   0  0  2  0  0  0  0  0  0  0  0  0
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    6.0621   -0.6706   -0.0417 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2200    0.1819    0.5235 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7772    1.3377    1.2589 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3766   -0.8892   -0.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.1515   -1.6098    2.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
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  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
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 10 11  2  0  0  0  0
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 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
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 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
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 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
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 25 26  1  0  0  0  0
 20 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
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 31 10  1  0  0  0  0
 29 12  1  0  0  0  0
 28 17  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  2 35  1  0  0  0  0
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 27 62  1  0  0  0  0
 28 63  1  6  0  0  0
 30 64  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001653

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]([H])(C([H])([H])[H])C([H])([H])[C@@]1(OC([H])([H])[H])O[C@@]2(C(=O)C(Cl)=C3C([H])=C(OC([H])=C3[C@]2([H])C1([H])[H])C(\[H])=C(/[H])\C(=C(/[H])[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[H])\C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H33ClO5/c1-7-15(2)10-16(3)8-9-18-11-19-20(14-30-18)21-13-25(29-6,12-17(4)27)31-24(21,5)23(28)22(19)26/h8-11,14-15,17,21,27H,7,12-13H2,1-6H3/b9-8+,16-10+/t15-,17+,21-,24-,25+/m0/s1

> <INCHI_KEY>
BSWQHKGZQYRASI-DHJLSQDHSA-N

> <FORMULA>
C25H33ClO5

> <MOLECULAR_WEIGHT>
448.98

> <EXACT_MASS>
448.2016519

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
50.58303395688989

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6aS,8S,9aS)-5-chloro-3-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dien-1-yl]-8-[(2R)-2-hydroxypropyl]-8-methoxy-6a-methyl-6H,6aH,8H,9H,9aH-furo[2,3-h]isochromen-6-one

> <ALOGPS_LOGP>
4.64

> <JCHEM_LOGP>
4.276265931666666

> <ALOGPS_LOGS>
-5.29

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.489347998678376

> <JCHEM_PKA_STRONGEST_BASIC>
-2.5847591853780774

> <JCHEM_POLAR_SURFACE_AREA>
64.99000000000001

> <JCHEM_REFRACTIVITY>
126.94710000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.32e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6aS,8S,9aS)-5-chloro-3-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dien-1-yl]-8-[(2R)-2-hydroxypropyl]-8-methoxy-6a-methyl-9H,9aH-furo[2,3-h]isochromen-6-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 64 66  0  0  0  0  0  0  0  0999 V2000
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  1  2  1  0
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 22 24  1  0
 20 25  1  6
 25 26  1  0
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 28 29  1  0
 29 30  2  0
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 31 10  1  0
 29 12  1  0
 28 17  1  0
  1 32  1  0
  1 33  1  0
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  2 35  1  0
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  3 37  1  1
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  4 40  1  0
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 26 60  1  0
 27 61  1  0
 27 62  1  0
 28 63  1  6
 30 64  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       7.605   0.622  -2.128  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.107  -0.635  -1.430  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.532  -0.572  -0.006  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.041  -1.830   0.677  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.062  -0.671  -0.042  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.220   0.182   0.524  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.777   1.338   1.259  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.775  -0.020   0.418  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.858   0.762   0.935  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.417   0.480   0.778  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.542   1.301   1.320  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.908   1.066   1.193  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.793   1.880   1.731  0.00  0.00           C+0
HETATM   14 Cl   UNK     0      -1.270   3.286   2.623  0.00  0.00          Cl+0
HETATM   15  C   UNK     0      -3.239   1.586   1.586  0.00  0.00           C+0
HETATM   16  O   UNK     0      -4.076   2.498   1.725  0.00  0.00           O+0
HETATM   17  C   UNK     0      -3.694   0.218   1.278  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.705  -0.615   2.555  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.886   0.097   0.668  0.00  0.00           O+0
HETATM   20  C   UNK     0      -4.808   0.287  -0.714  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.168  -0.991  -1.383  0.00  0.00           C+0
HETATM   22  C   UNK     0      -6.453  -1.653  -1.135  0.00  0.00           C+0
HETATM   23  C   UNK     0      -7.665  -0.878  -1.517  0.00  0.00           C+0
HETATM   24  O   UNK     0      -6.496  -2.895  -1.827  0.00  0.00           O+0
HETATM   25  O   UNK     0      -5.251   1.458  -1.061  0.00  0.00           O+0
HETATM   26  C   UNK     0      -6.351   2.126  -0.967  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.221   0.317  -0.971  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.757  -0.411   0.258  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.341  -0.089   0.459  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.421  -0.881  -0.066  0.00  0.00           C+0
HETATM   31  O   UNK     0       0.943  -0.616   0.082  0.00  0.00           O+0
HETATM   32  H   UNK     0       6.593   0.385  -2.507  0.00  0.00           H+0
HETATM   33  H   UNK     0       8.299   0.899  -2.928  0.00  0.00           H+0
HETATM   34  H   UNK     0       7.486   1.427  -1.373  0.00  0.00           H+0
HETATM   35  H   UNK     0       9.211  -0.544  -1.350  0.00  0.00           H+0
HETATM   36  H   UNK     0       7.821  -1.554  -1.942  0.00  0.00           H+0
HETATM   37  H   UNK     0       7.934   0.353   0.418  0.00  0.00           H+0
HETATM   38  H   UNK     0       8.132  -2.653  -0.086  0.00  0.00           H+0
HETATM   39  H   UNK     0       9.025  -1.710   1.129  0.00  0.00           H+0
HETATM   40  H   UNK     0       7.294  -2.152   1.412  0.00  0.00           H+0
HETATM   41  H   UNK     0       5.639  -1.509  -0.574  0.00  0.00           H+0
HETATM   42  H   UNK     0       5.918   2.172   0.543  0.00  0.00           H+0
HETATM   43  H   UNK     0       6.709   1.099   1.814  0.00  0.00           H+0
HETATM   44  H   UNK     0       5.079   1.713   2.035  0.00  0.00           H+0
HETATM   45  H   UNK     0       3.377  -0.889  -0.134  0.00  0.00           H+0
HETATM   46  H   UNK     0       3.174   1.632   1.486  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.853   2.168   1.872  0.00  0.00           H+0
HETATM   48  H   UNK     0      -4.152  -1.610   2.314  0.00  0.00           H+0
HETATM   49  H   UNK     0      -4.380  -0.128   3.272  0.00  0.00           H+0
HETATM   50  H   UNK     0      -2.693  -0.739   2.971  0.00  0.00           H+0
HETATM   51  H   UNK     0      -5.019  -0.795  -2.513  0.00  0.00           H+0
HETATM   52  H   UNK     0      -4.352  -1.777  -1.224  0.00  0.00           H+0
HETATM   53  H   UNK     0      -6.517  -1.972  -0.038  0.00  0.00           H+0
HETATM   54  H   UNK     0      -7.982  -0.213  -0.697  0.00  0.00           H+0
HETATM   55  H   UNK     0      -7.480  -0.327  -2.457  0.00  0.00           H+0
HETATM   56  H   UNK     0      -8.514  -1.613  -1.666  0.00  0.00           H+0
HETATM   57  H   UNK     0      -6.041  -3.596  -1.291  0.00  0.00           H+0
HETATM   58  H   UNK     0      -6.169   3.197  -1.381  0.00  0.00           H+0
HETATM   59  H   UNK     0      -6.779   2.289   0.051  0.00  0.00           H+0
HETATM   60  H   UNK     0      -7.223   1.815  -1.616  0.00  0.00           H+0
HETATM   61  H   UNK     0      -2.996  -0.222  -1.876  0.00  0.00           H+0
HETATM   62  H   UNK     0      -2.911   1.375  -0.946  0.00  0.00           H+0
HETATM   63  H   UNK     0      -2.943  -1.506   0.195  0.00  0.00           H+0
HETATM   64  H   UNK     0      -0.764  -1.763  -0.626  0.00  0.00           H+0
CONECT    1    2   32   33   34                                             
CONECT    2    1    3   35   36                                             
CONECT    3    2    4    5   37                                             
CONECT    4    3   38   39   40                                             
CONECT    5    3    6   41                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6   42   43   44                                             
CONECT    8    6    9   45                                                  
CONECT    9    8   10   46                                                  
CONECT   10    9   11   31                                                  
CONECT   11   10   12   47                                                  
CONECT   12   11   13   29                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19   28                                             
CONECT   18   17   48   49   50                                             
CONECT   19   17   20                                                       
CONECT   20   19   21   25   27                                             
CONECT   21   20   22   51   52                                             
CONECT   22   21   23   24   53                                             
CONECT   23   22   54   55   56                                             
CONECT   24   22   57                                                       
CONECT   25   20   26                                                       
CONECT   26   25   58   59   60                                             
CONECT   27   20   28   61   62                                             
CONECT   28   27   29   17   63                                             
CONECT   29   28   30   12                                                  
CONECT   30   29   31   64                                                  
CONECT   31   30   10                                                       
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    2                                                            
CONECT   36    2                                                            
CONECT   37    3                                                            
CONECT   38    4                                                            
CONECT   39    4                                                            
CONECT   40    4                                                            
CONECT   41    5                                                            
CONECT   42    7                                                            
CONECT   43    7                                                            
CONECT   44    7                                                            
CONECT   45    8                                                            
CONECT   46    9                                                            
CONECT   47   11                                                            
CONECT   48   18                                                            
CONECT   49   18                                                            
CONECT   50   18                                                            
CONECT   51   21                                                            
CONECT   52   21                                                            
CONECT   53   22                                                            
CONECT   54   23                                                            
CONECT   55   23                                                            
CONECT   56   23                                                            
CONECT   57   24                                                            
CONECT   58   26                                                            
CONECT   59   26                                                            
CONECT   60   26                                                            
CONECT   61   27                                                            
CONECT   62   27                                                            
CONECT   63   28                                                            
CONECT   64   30                                                            
MASTER        0    0    0    0    0    0    0    0   64    0  132    0
END

RDKit          3D

64 66  0  0  0  0  0  0  0  0999 V2000
    7.6047    0.6224   -2.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1069   -0.6346   -1.4295 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5320   -0.5716   -0.0056 C   0  0  2  0  0  0  0  0  0  0  0  0
    8.0411   -1.8303    0.6770 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0621   -0.6706   -0.0417 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2200    0.1819    0.5235 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7772    1.3377    1.2589 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7745   -0.0195    0.4179 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.7623    0.9354 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4168    0.4802    0.7784 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5418    1.3006    1.3199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9079    1.0657    1.1934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7933    1.8800    1.7314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2704    3.2859    2.6234 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.2388    1.5861    1.5862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0758    2.4983    1.7246 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6943    0.2177    1.2782 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.7053   -0.6145    2.5552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8865    0.0968    0.6683 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8083    0.2872   -0.7141 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.1685   -0.9909   -1.3835 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4528   -1.6534   -1.1351 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.6654   -0.8780   -1.5168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4964   -2.8948   -1.8271 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2514    1.4579   -1.0608 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3511    2.1255   -0.9672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2213    0.3172   -0.9705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7569   -0.4110    0.2576 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3407   -0.0887    0.4586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4214   -0.8814   -0.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9426   -0.6161    0.0822 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5934    0.3852   -2.5068 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2986    0.8988   -2.9284 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4859    1.4271   -1.3727 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2110   -0.5444   -1.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8212   -1.5541   -1.9419 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9339    0.3529    0.4184 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1320   -2.6534   -0.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0252   -1.7100    1.1291 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2943   -2.1521    1.4123 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6391   -1.5091   -0.5740 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9175    2.1723    0.5433 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7091    1.0985    1.8141 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0790    1.7134    2.0352 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3766   -0.8892   -0.1343 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1744    1.6320    1.4856 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8528    2.1684    1.8721 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1515   -1.6098    2.3140 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3804   -0.1276    3.2719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6934   -0.7390    2.9713 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0193   -0.7950   -2.5127 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3522   -1.7770   -1.2243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5173   -1.9723   -0.0380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9821   -0.2128   -0.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4801   -0.3274   -2.4572 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5136   -1.6131   -1.6655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0409   -3.5957   -1.2909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1686    3.1970   -1.3805 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7795    2.2890    0.0510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2225    1.8151   -1.6159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9959   -0.2215   -1.8763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9114    1.3746   -0.9462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9426   -1.5061    0.1950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7638   -1.7629   -0.6260 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 13 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  1
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  1  0
 20 25  1  6
 25 26  1  0
 20 27  1  0
 27 28  1  0
 28 29  1  0
 29 30  2  0
 30 31  1  0
 31 10  1  0
 29 12  1  0
 28 17  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  2 35  1  0
  2 36  1  0
  3 37  1  1
  4 38  1  0
  4 39  1  0
  4 40  1  0
  5 41  1  0
  7 42  1  0
  7 43  1  0
  7 44  1  0
  8 45  1  0
  9 46  1  0
 11 47  1  0
 18 48  1  0
 18 49  1  0
 18 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  1
 23 54  1  0
 23 55  1  0
 23 56  1  0
 24 57  1  0
 26 58  1  0
 26 59  1  0
 26 60  1  0
 27 61  1  0
 27 62  1  0
 28 63  1  6
 30 64  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₅H₃₃ClO₅

Average Mass

448.9800 Da

Monoisotopic Mass

448.20165 Da

IUPAC Name

(6aS,8S,9aS)-5-chloro-3-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dien-1-yl]-8-[(2R)-2-hydroxypropyl]-8-methoxy-6a-methyl-6H,6aH,8H,9H,9aH-furo[2,3-h]isochromen-6-one

Traditional Name

(6aS,8S,9aS)-5-chloro-3-[(1E,3E,5S)-3,5-dimethylhepta-1,3-dien-1-yl]-8-[(2R)-2-hydroxypropyl]-8-methoxy-6a-methyl-9H,9aH-furo[2,3-h]isochromen-6-one

CAS Registry Number

Not Available

SMILES

[H]O[C@]([H])(C([H])([H])[H])C([H])([H])[C@@]1(OC([H])([H])[H])O[C@@]2(C(=O)C(Cl)=C3C([H])=C(OC([H])=C3[C@]2([H])C1([H])[H])C(\[H])=C(/[H])\C(=C(/[H])[C@@]([H])(C([H])([H])[H])C([H])([H])C([H])([H])[H])\C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C25H33ClO5/c1-7-15(2)10-16(3)8-9-18-11-19-20(14-30-18)21-13-25(29-6,12-17(4)27)31-24(21,5)23(28)22(19)26/h8-11,14-15,17,21,27H,7,12-13H2,1-6H3/b9-8+,16-10+/t15-,17+,21-,24-,25+/m0/s1

InChI Key

BSWQHKGZQYRASI-DHJLSQDHSA-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
Penicillium	NPAtlas	10348038
Penicillium sp. SPC-21609	Fungi	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ketals. These are acetals derived from ketones by replacement of the oxo group by two hydrocarbyloxy groups R2C(OR)2 ( R not Hydrogen ). This term, once abandoned, has been reinstated as a subclass of acetals.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Ethers

Direct Parent

Ketals

Alternative Parents

Substituents

Ketal
Cyclohexenone
Pyran
Alpha-haloketone
Alpha-chloroketone
Oxolane
Ketone
Secondary alcohol
Oxacycle
Chloroalkene
Haloalkene
Organoheterocyclic compound
Vinyl halide
Vinyl chloride
Alcohol
Hydrocarbon derivative
Organochloride
Organohalogen compound
Organic oxide
Carbonyl group
Aldehyde
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	4.64	ALOGPS
logP	4.28	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	15.49	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	64.99 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	126.95 m³·mol⁻¹	ChemAxon
Polarizability	50.58 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

NPAtlas ID

NPA020570

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

8702885

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10527489

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Toki S, Tanaka T, Uosaki Y, Yoshida M, Suzuki Y, Kita K, Mihara A, Ando K, Lokker NA, Giese NA, Matsuda Y: RP-1551s, a family of azaphilones produced by Penicillium sp., inhibit the binding of PDGF to the extracellular domain of its receptor. J Antibiot (Tokyo). 1999 Mar;52(3):235-44. doi: 10.7164/antibiotics.52.235. [PubMed:10348038 ]

Showing NP-Card for RP-1551-5 (NP0001653)

MOL for NP0001653 (RP-1551-5)

3D MOL for NP0001653 (RP-1551-5)

3D SDF for NP0001653 (RP-1551-5)

3D-SDF for NP0001653 (RP-1551-5)

PDB for NP0001653 (RP-1551-5)

3D PDB for NP0001653 (RP-1551-5)

SMILES for NP0001653 (RP-1551-5)

INCHI for NP0001653 (RP-1551-5)

Structure for NP0001653 (RP-1551-5)

3D Structure for NP0001653 (RP-1551-5)