NP-MRD: Showing NP-Card for FCRC-57-G (NP0003501)

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Record Information

Version

2.0

Created at

2020-12-09 00:43:54 UTC

Updated at

2021-07-15 16:46:34 UTC

NP-MRD ID

NP0003501

Secondary Accession Numbers

None

Natural Product Identification

Common Name

FCRC-57-G

Provided By

NPAtlas

Description

3,3',5,8,10'-Pentahydroxy-7-methoxy-7'-methyl-4,4',9,9'-tetrahydro-3H,3'H-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-4,9,9'-trione belongs to the class of organic compounds known as pyranochromenes. These are organic heterocyclic compounds containing a pyran ring fused to a chromene (1-benzopyran) moiety. FCRC-57-G is found in Streptomyces and Streptomyces griseus. FCRC-57-G was first documented in 1979 (PMID: 110759). Based on a literature review very few articles have been published on 3,3',5,8,10'-pentahydroxy-7-methoxy-7'-methyl-4,4',9,9'-tetrahydro-3H,3'H-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-4,9,9'-trione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117483D          

 55 60  0  0  0  0            999 V2000
    8.8312   -0.2687    1.4753 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.2504   -1.2065    1.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9201   -1.6785    1.1636 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6637   -2.8709    1.7782 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9863   -0.9500    0.4743 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.6493    0.7288   -0.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9763    1.9244   -0.6125 O   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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  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
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  9  3  1  0  0  0  0
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 15  7  1  0  0  0  0
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M  END

     RDKit          3D

 55 60  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306242117483D          

 55 60  0  0  0  0            999 V2000
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   -3.7634    0.0177   -2.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5313   -0.1608   -3.3549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7439    0.9758    1.0533 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4588    1.2541    0.3530 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2241    2.6271    0.1976 O   0  0  0  0  0  0  0  0  0  0  0  0
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    8.9479   -1.2624    0.9891 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7959    0.2803    1.5153 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9934   -1.7769    1.8172 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8898   -3.4300    1.8783 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0009   -1.5577   -1.4949 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0633   -1.7182    1.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2910    0.5532    1.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5549    0.0379    1.5295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2885    0.3784    0.4022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7219   -1.0362    1.3288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4899   -1.3134   -0.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0950   -0.4047   -4.0787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0262    1.9071    1.6151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6830    0.1815    1.8259 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3695    0.8974    1.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9022    3.0424   -0.3657 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  2  0  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 14 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
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 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 23 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
  9  3  1  0  0  0  0
 20 13  1  0  0  0  0
 33 22  1  0  0  0  0
 15  7  1  0  0  0  0
 36 19  1  0  0  0  0
 32 25  1  0  0  0  0
  1 38  1  0  0  0  0
  1 39  1  0  0  0  0
  1 40  1  0  0  0  0
  4 41  1  0  0  0  0
  6 42  1  0  0  0  0
 10 43  1  0  0  0  0
 17 44  1  6  0  0  0
 18 45  1  0  0  0  0
 24 46  1  0  0  0  0
 26 47  1  0  0  0  0
 28 48  1  0  0  0  0
 28 49  1  0  0  0  0
 28 50  1  0  0  0  0
 34 51  1  0  0  0  0
 35 52  1  0  0  0  0
 35 53  1  0  0  0  0
 36 54  1  1  0  0  0
 37 55  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003501

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(=O)C3=C(O[C@@]4(OC5=C(C([H])=C6C([H])=C(OC(=O)C6=C5O[H])C([H])([H])[H])C([H])([H])[C@]4([H])O[H])[C@]3([H])O[H])C(=O)C2=C(O[H])C(OC([H])([H])[H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H18O12/c1-7-3-8-4-9-5-12(27)25(36-21(9)19(30)13(8)24(33)35-7)23(32)16-18(29)14-10(26)6-11(34-2)17(28)15(14)20(31)22(16)37-25/h3-4,6,12,23,26-28,30,32H,5H2,1-2H3/t12-,23+,25+/m0/s1

> <INCHI_KEY>
FMTLKIJHTZJTFK-UHFFFAOYSA-N

> <FORMULA>
C25H18O12

> <MOLECULAR_WEIGHT>
510.407

> <EXACT_MASS>
510.07982602

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
49.76218230576383

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R,3'S)-3,3',5,8,10'-pentahydroxy-7-methoxy-7'-methyl-4,4',9,9'-tetrahydro-3H,3'H-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-4,9,9'-trione

> <ALOGPS_LOGP>
1.90

> <JCHEM_LOGP>
2.8691473243333334

> <ALOGPS_LOGS>
-2.72

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.864626892609133

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.497197671429307

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4699666980589248

> <JCHEM_POLAR_SURFACE_AREA>
189.27999999999997

> <JCHEM_REFRACTIVITY>
125.05729999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.64e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R,3'S)-3,3',5,8,10'-pentahydroxy-7-methoxy-7'-methyl-3',4'-dihydro-3H-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-4,9,9'-trione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 55 60  0  0  0  0  0  0  0  0999 V2000
    8.8312   -0.2687    1.4753 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8717    0.4744    0.7702 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.3672    1.0094   -0.8357 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7094    2.0874   -1.3598 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9727    0.5238   -0.9568 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6166   -0.6131   -0.4017 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6152   -1.3895    0.3338 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1795   -0.8815   -0.6476 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4951   -1.3119    0.4760 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2857    0.5429   -0.9466 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8630    1.0515   -1.5834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4192    0.5589   -1.7720 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6651    0.3909   -1.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8390    0.5832    0.1196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0877    0.4122    0.6645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1797    0.0488   -0.1031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4315   -0.1207    0.4545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5136   -0.4818   -0.3123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8748   -0.6640    0.3066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3110   -0.6577   -1.5848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1303   -0.5108   -2.1862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0368   -0.7033   -3.4213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0071   -0.1511   -1.4789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7634    0.0177   -2.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5313   -0.1608   -3.3549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7439    0.9758    1.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4588    1.2541    0.3530 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2241    2.6271    0.1976 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4473   -0.4254    2.5040 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9479   -1.2624    0.9891 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7959    0.2803    1.5153 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9934   -1.7769    1.8172 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8898   -3.4300    1.8783 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8770    2.3473   -0.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0009   -1.5577   -1.4949 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0633   -1.7182    1.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2910    0.5532    1.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5549    0.0379    1.5295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2885    0.3784    0.4022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7219   -1.0362    1.3288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4899   -1.3134   -0.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0950   -0.4047   -4.0787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0262    1.9071    1.6151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6830    0.1815    1.8259 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3695    0.8974    1.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9022    3.0424   -0.3657 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
  9 10  1  0
  8 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 32 33  2  0
 33 34  1  0
 23 35  1  0
 35 36  1  0
 36 37  1  0
  9  3  1  0
 20 13  1  0
 33 22  1  0
 15  7  1  0
 36 19  1  0
 32 25  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  4 41  1  0
  6 42  1  0
 10 43  1  0
 17 44  1  6
 18 45  1  0
 24 46  1  0
 26 47  1  0
 28 48  1  0
 28 49  1  0
 28 50  1  0
 34 51  1  0
 35 52  1  0
 35 53  1  0
 36 54  1  1
 37 55  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       8.831  -0.269   1.475  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.872   0.474   0.770  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.572  -0.023   0.683  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.250  -1.206   1.274  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.920  -1.679   1.164  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.664  -2.871   1.778  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.986  -0.950   0.474  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.359   0.236  -0.104  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.649   0.729  -0.016  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.976   1.924  -0.613  0.00  0.00           O+0
HETATM   11  C   UNK     0       3.367   1.009  -0.836  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.709   2.087  -1.360  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.973   0.524  -0.957  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.617  -0.613  -0.402  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.615  -1.389   0.334  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.262  -2.467   0.854  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.180  -0.882  -0.648  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.495  -1.312   0.476  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.286   0.543  -0.947  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.863   1.052  -1.583  0.00  0.00           O+0
HETATM   21  O   UNK     0      -1.419   0.559  -1.772  0.00  0.00           O+0
HETATM   22  C   UNK     0      -2.665   0.391  -1.214  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.839   0.583   0.120  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.088   0.412   0.665  0.00  0.00           C+0
HETATM   25  C   UNK     0      -5.180   0.049  -0.103  0.00  0.00           C+0
HETATM   26  C   UNK     0      -6.431  -0.121   0.455  0.00  0.00           C+0
HETATM   27  C   UNK     0      -7.514  -0.482  -0.312  0.00  0.00           C+0
HETATM   28  C   UNK     0      -8.875  -0.664   0.307  0.00  0.00           C+0
HETATM   29  O   UNK     0      -7.311  -0.658  -1.585  0.00  0.00           O+0
HETATM   30  C   UNK     0      -6.130  -0.511  -2.186  0.00  0.00           C+0
HETATM   31  O   UNK     0      -6.037  -0.703  -3.421  0.00  0.00           O+0
HETATM   32  C   UNK     0      -5.007  -0.151  -1.479  0.00  0.00           C+0
HETATM   33  C   UNK     0      -3.763   0.018  -2.030  0.00  0.00           C+0
HETATM   34  O   UNK     0      -3.531  -0.161  -3.355  0.00  0.00           O+0
HETATM   35  C   UNK     0      -1.744   0.976   1.053  0.00  0.00           C+0
HETATM   36  C   UNK     0      -0.459   1.254   0.353  0.00  0.00           C+0
HETATM   37  O   UNK     0      -0.224   2.627   0.198  0.00  0.00           O+0
HETATM   38  H   UNK     0       8.447  -0.425   2.504  0.00  0.00           H+0
HETATM   39  H   UNK     0       8.948  -1.262   0.989  0.00  0.00           H+0
HETATM   40  H   UNK     0       9.796   0.280   1.515  0.00  0.00           H+0
HETATM   41  H   UNK     0       6.993  -1.777   1.817  0.00  0.00           H+0
HETATM   42  H   UNK     0       3.890  -3.430   1.878  0.00  0.00           H+0
HETATM   43  H   UNK     0       6.877   2.347  -0.598  0.00  0.00           H+0
HETATM   44  H   UNK     0       0.001  -1.558  -1.495  0.00  0.00           H+0
HETATM   45  H   UNK     0       0.063  -1.718   1.165  0.00  0.00           H+0
HETATM   46  H   UNK     0      -4.291   0.553   1.736  0.00  0.00           H+0
HETATM   47  H   UNK     0      -6.555   0.038   1.530  0.00  0.00           H+0
HETATM   48  H   UNK     0      -9.289   0.378   0.402  0.00  0.00           H+0
HETATM   49  H   UNK     0      -8.722  -1.036   1.329  0.00  0.00           H+0
HETATM   50  H   UNK     0      -9.490  -1.313  -0.314  0.00  0.00           H+0
HETATM   51  H   UNK     0      -4.095  -0.405  -4.079  0.00  0.00           H+0
HETATM   52  H   UNK     0      -2.026   1.907   1.615  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.683   0.182   1.826  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.370   0.897   1.034  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.902   3.042  -0.366  0.00  0.00           H+0
CONECT    1    2   38   39   40                                             
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5   41                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5   42                                                       
CONECT    7    5    8   15                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10    3                                                  
CONECT   10    9   43                                                       
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   20                                                  
CONECT   14   13   15   17                                                  
CONECT   15   14   16    7                                                  
CONECT   16   15                                                            
CONECT   17   14   18   19   44                                             
CONECT   18   17   45                                                       
CONECT   19   17   20   21   36                                             
CONECT   20   19   13                                                       
CONECT   21   19   22                                                       
CONECT   22   21   23   33                                                  
CONECT   23   22   24   35                                                  
CONECT   24   23   25   46                                                  
CONECT   25   24   26   32                                                  
CONECT   26   25   27   47                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27   48   49   50                                             
CONECT   29   27   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   25                                                  
CONECT   33   32   34   22                                                  
CONECT   34   33   51                                                       
CONECT   35   23   36   52   53                                             
CONECT   36   35   37   19   54                                             
CONECT   37   36   55                                                       
CONECT   38    1                                                            
CONECT   39    1                                                            
CONECT   40    1                                                            
CONECT   41    4                                                            
CONECT   42    6                                                            
CONECT   43   10                                                            
CONECT   44   17                                                            
CONECT   45   18                                                            
CONECT   46   24                                                            
CONECT   47   26                                                            
CONECT   48   28                                                            
CONECT   49   28                                                            
CONECT   50   28                                                            
CONECT   51   34                                                            
CONECT   52   35                                                            
CONECT   53   35                                                            
CONECT   54   36                                                            
CONECT   55   37                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  120    0
END

RDKit          3D

55 60  0  0  0  0  0  0  0  0999 V2000
    8.8312   -0.2687    1.4753 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8717    0.4744    0.7702 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5724   -0.0226    0.6831 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2504   -1.2065    1.2740 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9201   -1.6785    1.1636 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6637   -2.8709    1.7782 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9863   -0.9500    0.4743 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3588    0.2363   -0.1035 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6493    0.7288   -0.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9763    1.9244   -0.6125 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3672    1.0094   -0.8357 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7094    2.0874   -1.3598 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9727    0.5238   -0.9568 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6166   -0.6131   -0.4017 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6152   -1.3895    0.3338 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2618   -2.4669    0.8544 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1795   -0.8815   -0.6476 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4951   -1.3119    0.4760 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2857    0.5429   -0.9466 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8630    1.0515   -1.5834 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4192    0.5589   -1.7720 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6651    0.3909   -1.2135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8390    0.5832    0.1196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0877    0.4122    0.6645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1797    0.0488   -0.1031 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4315   -0.1207    0.4545 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5136   -0.4818   -0.3123 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8748   -0.6640    0.3066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3110   -0.6577   -1.5848 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1303   -0.5108   -2.1862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0368   -0.7033   -3.4213 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0071   -0.1511   -1.4789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7634    0.0177   -2.0303 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5313   -0.1608   -3.3549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7439    0.9758    1.0533 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4588    1.2541    0.3530 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2241    2.6271    0.1976 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4473   -0.4254    2.5040 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9479   -1.2624    0.9891 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.7959    0.2803    1.5153 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9934   -1.7769    1.8172 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8898   -3.4300    1.8783 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8770    2.3473   -0.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0009   -1.5577   -1.4949 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0633   -1.7182    1.1652 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2910    0.5532    1.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5549    0.0379    1.5295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2885    0.3784    0.4022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7219   -1.0362    1.3288 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4899   -1.3134   -0.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0950   -0.4047   -4.0787 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0262    1.9071    1.6151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6830    0.1815    1.8259 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3695    0.8974    1.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9022    3.0424   -0.3657 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
  9 10  1  0
  8 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 14 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  6
 19 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 32 33  2  0
 33 34  1  0
 23 35  1  0
 35 36  1  0
 36 37  1  0
  9  3  1  0
 20 13  1  0
 33 22  1  0
 15  7  1  0
 36 19  1  0
 32 25  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
  4 41  1  0
  6 42  1  0
 10 43  1  0
 17 44  1  6
 18 45  1  0
 24 46  1  0
 26 47  1  0
 28 48  1  0
 28 49  1  0
 28 50  1  0
 34 51  1  0
 35 52  1  0
 35 53  1  0
 36 54  1  1
 37 55  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₅H₁₈O₁₂

Average Mass

510.4070 Da

Monoisotopic Mass

510.07983 Da

IUPAC Name

(2R,3R,3'S)-3,3',5,8,10'-pentahydroxy-7-methoxy-7'-methyl-4,4',9,9'-tetrahydro-3H,3'H-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-4,9,9'-trione

Traditional Name

(2R,3R,3'S)-3,3',5,8,10'-pentahydroxy-7-methoxy-7'-methyl-3',4'-dihydro-3H-spiro[naphtho[2,3-b]furan-2,2'-pyrano[3,2-g]isochromene]-4,9,9'-trione

CAS Registry Number

Not Available

SMILES

COC1=C(O)C2=C(C(O)=C1)C(=O)C1=C(OC3(OC4=C(CC3O)C=C3C=C(C)OC(=O)C3=C4O)C1O)C2=O

InChI Identifier

InChI=1S/C25H18O12/c1-7-3-8-4-9-5-12(27)25(36-21(9)19(30)13(8)24(33)35-7)23(32)16-18(29)14-10(26)6-11(34-2)17(28)15(14)20(31)22(16)37-25/h3-4,6,12,23,26-28,30,32H,5H2,1-2H3

InChI Key

FMTLKIJHTZJTFK-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	110759
Streptomyces griseus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranochromenes. These are organic heterocyclic compounds containing a pyran ring fused to a chromene (1-benzopyran) moiety.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

Pyranochromenes

Alternative Parents

Substituents

Pyranochromene
Naphthofuran
Naphthoquinone
Isocoumarin
2-benzopyran
Naphthalene
Aryl ketone
Quinone
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Ketal
Pyranone
Alkyl aryl ether
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous ester
Vinylogous acid
Dihydrofuran
Secondary alcohol
Lactone
Ketone
Oxacycle
Polyol
Ether
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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	1.9	ALOGPS
logP	2.87	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	8.5	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	189.28 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	125.06 m³·mol⁻¹	ChemAxon
Polarizability	49.76 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA002821

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78444483

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Stroshane RM, Chan JA, Rubalcaba EA, Garretson AL, Aszalos AA, Roller PP: Isolation and structure elucidation of a novel griseorhodin. J Antibiot (Tokyo). 1979 Mar;32(3):197-204. doi: 10.7164/antibiotics.32.197. [PubMed:110759 ]

Showing NP-Card for FCRC-57-G (NP0003501)

MOL for NP0003501 (FCRC-57-G)

3D MOL for NP0003501 (FCRC-57-G)

3D SDF for NP0003501 (FCRC-57-G)

3D-SDF for NP0003501 (FCRC-57-G)

PDB for NP0003501 (FCRC-57-G)

3D PDB for NP0003501 (FCRC-57-G)

SMILES for NP0003501 (FCRC-57-G)

INCHI for NP0003501 (FCRC-57-G)

Structure for NP0003501 (FCRC-57-G)

3D Structure for NP0003501 (FCRC-57-G)