NP-MRD: Showing NP-Card for 15-hydroxy-11,18-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,9,11,14,16,18-hexaen-5-yl 4-(2,6-dihydroxy-6-methylheptan-2-yl)-3-hydroxybenzoate (NP0206569)

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Record Information

Version

2.0

Created at

2022-09-05 02:51:35 UTC

Updated at

2022-09-05 02:51:36 UTC

NP-MRD ID

NP0206569

Secondary Accession Numbers

None

Natural Product Identification

Common Name

15-hydroxy-11,18-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,9,11,14,16,18-hexaen-5-yl 4-(2,6-dihydroxy-6-methylheptan-2-yl)-3-hydroxybenzoate

Description

15-Hydroxy-11,18-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]Icosa-1(12),2(9),10,14,16,18-hexaen-5-yl 4-(2,6-dihydroxy-6-methylheptan-2-yl)-3-hydroxybenzoate belongs to the class of organic compounds known as sterigmatocystins. These are a group of closely related fungal metabolites chemically characterized by a xanthone moiety fused to a dihydrodifurano or a tetrahydrodifurano moiety. The chemical difference among the various sterigmagocystins are the presence or absence of unsaturation at positions 2 and 3 of the difurano ring system, the substitution pattern on positions 6, 7, and 10 of the xanthone system and/or the substituent on position 3 of the difurano system. They are produced by Aspergilus spp. And Bipolaris spp. 15-hydroxy-11,18-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,9,11,14,16,18-hexaen-5-yl 4-(2,6-dihydroxy-6-methylheptan-2-yl)-3-hydroxybenzoate is found in Aspergillus tennesseensis. Based on a literature review very few articles have been published on 15-hydroxy-11,18-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]Icosa-1(12),2(9),10,14,16,18-hexaen-5-yl 4-(2,6-dihydroxy-6-methylheptan-2-yl)-3-hydroxybenzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052204512D          

 46 51  0  0  0  0            999 V2000
    5.9043    4.0988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5365    3.3603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9922    2.6725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8157    2.7233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2713    2.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9036    1.2971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3593    0.6093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0802    1.2463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 21 45  1  0  0  0  0
 45 46  1  0  0  0  0
 16 46  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309052204512D          

 46 51  0  0  0  0            999 V2000
    5.9043    4.0988    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5365    3.3603    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.8157    2.7233    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2713    2.0356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9036    1.2971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3593    0.6093    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0802    1.2463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7124    0.5078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1681   -0.1799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8890    0.4570    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5212   -0.2815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9769   -0.9692    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6091   -1.7077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6978   -0.3322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2421    0.3555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6098    1.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4333    1.1448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8010    1.8833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6245    1.9340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0211    1.6720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8846    2.4856    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0686    2.6071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6873    3.3387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8630    3.3743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4201    2.6783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4818    4.1059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3425    4.1415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7238    4.8731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2808    5.5691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6621    6.3007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0695    6.6820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3937    5.9194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0434    7.0323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8677    7.0679    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2490    7.7995    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0732    7.8351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8974    7.8707    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0376    8.6593    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1088    7.0108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5434    5.5335    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9863    6.2295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9247    4.8019    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7008    1.8686    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2895    1.2907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4261    0.4770    0.0000 O   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  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  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  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
  3 20  2  0  0  0  0
  8 20  1  0  0  0  0
 17 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 31 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 37 40  1  0  0  0  0
 30 41  1  0  0  0  0
 41 42  1  0  0  0  0
 41 43  2  0  0  0  0
 27 43  1  0  0  0  0
 23 44  1  0  0  0  0
 44 45  1  0  0  0  0
 21 45  1  0  0  0  0
 45 46  1  0  0  0  0
 16 46  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0206569

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2OC3=C4C5CC(OC(=O)C6=CC=C(C(O)=C6)C(C)(O)CCCC(C)(C)O)OC5OC4=CC(OC)=C3C(=O)C2=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C34H36O12/c1-33(2,39)11-6-12-34(3,40)18-8-7-16(13-20(18)36)31(38)44-24-14-17-25-23(43-32(17)45-24)15-22(42-5)27-28(37)26-19(35)9-10-21(41-4)29(26)46-30(25)27/h7-10,13,15,17,24,32,35-36,39-40H,6,11-12,14H2,1-5H3

> <INCHI_KEY>
OMTAWALVOBKTKI-UHFFFAOYSA-N

> <FORMULA>
C34H36O12

> <MOLECULAR_WEIGHT>
636.65

> <EXACT_MASS>
636.220676599

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
65.53077008594684

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
15-hydroxy-11,18-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0^{2,9}.0^{3,7}.0^{14,19}]icosa-1,9,11,14,16,18-hexaen-5-yl 4-(2,6-dihydroxy-6-methylheptan-2-yl)-3-hydroxybenzoate

> <JCHEM_LOGP>
5.129685226666667

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.558894501326591

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.762458819766126

> <JCHEM_PKA_STRONGEST_BASIC>
-1.2528733248289279

> <JCHEM_POLAR_SURFACE_AREA>
170.44

> <JCHEM_REFRACTIVITY>
163.6005

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
15-hydroxy-11,18-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0^{2,9}.0^{3,7}.0^{14,19}]icosa-1,9,11,14,16,18-hexaen-5-yl 4-(2,6-dihydroxy-6-methylheptan-2-yl)-3-hydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      11.021   7.651   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      10.335   6.272   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      11.185   4.989   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.723   5.083   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.573   3.800   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.887   2.421   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      13.737   1.137   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      11.350   2.326   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.663   0.948   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      11.514  -0.336   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       9.126   0.853   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.440  -0.525   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.290  -1.809   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.604  -3.188   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.903  -0.620   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.052   0.664   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.738   2.042   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.275   2.137   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.962   3.515   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      10.499   3.610   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.639   3.121   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.385   4.640   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.861   4.867   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       3.150   6.232   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.611   6.299   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       0.784   5.000   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.899   7.664   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.639   7.731   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.351   9.096   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.524  10.396   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -1.236  11.761   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.130  12.473   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -2.602  11.050   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      -1.948  13.127   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -3.486  13.193   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -4.198  14.559   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -5.737  14.625   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -7.275  14.692   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      -5.670  16.164   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -5.803  13.087   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       1.014  10.329   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       1.841  11.628   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       1.726   8.964   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0       3.175   3.488   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0       4.274   2.409   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       4.529   0.890   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   20                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   18                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16                                                       
CONECT   16   15   17   46                                                  
CONECT   17   16   18   21                                                  
CONECT   18   17   11   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19    3    8                                                  
CONECT   21   17   22   45                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   44                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   43                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   41                                                  
CONECT   31   30   32   33   34                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   31   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   38   39   40                                             
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40   37                                                            
CONECT   41   30   42   43                                                  
CONECT   42   41                                                            
CONECT   43   41   27                                                       
CONECT   44   23   45                                                       
CONECT   45   44   21   46                                                  
CONECT   46   45   16                                                       
MASTER        0    0    0    0    0    0    0    0   46    0  102    0
END

View in JSmol

Synonyms

Value	Source
15-Hydroxy-11,18-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0,.0,.0,]icosa-1(12),2(9),10,14,16,18-hexaen-5-yl 4-(2,6-dihydroxy-6-methylheptan-2-yl)-3-hydroxybenzoic acid	Generator

Chemical Formula

C₃₄H₃₆O₁₂

Average Mass

636.6500 Da

Monoisotopic Mass

636.22068 Da

IUPAC Name

15-hydroxy-11,18-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0^{2,9}.0^{3,7}.0^{14,19}]icosa-1,9,11,14,16,18-hexaen-5-yl 4-(2,6-dihydroxy-6-methylheptan-2-yl)-3-hydroxybenzoate

Traditional Name

15-hydroxy-11,18-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0^{2,9}.0^{3,7}.0^{14,19}]icosa-1,9,11,14,16,18-hexaen-5-yl 4-(2,6-dihydroxy-6-methylheptan-2-yl)-3-hydroxybenzoate

CAS Registry Number

Not Available

SMILES

COC1=C2OC3=C4C5CC(OC(=O)C6=CC=C(C(O)=C6)C(C)(O)CCCC(C)(C)O)OC5OC4=CC(OC)=C3C(=O)C2=C(O)C=C1

InChI Identifier

InChI=1S/C34H36O12/c1-33(2,39)11-6-12-34(3,40)18-8-7-16(13-20(18)36)31(38)44-24-14-17-25-23(43-32(17)45-24)15-22(42-5)27-28(37)26-19(35)9-10-21(41-4)29(26)46-30(25)27/h7-10,13,15,17,24,32,35-36,39-40H,6,11-12,14H2,1-5H3

InChI Key

OMTAWALVOBKTKI-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Aspergillus tennesseensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sterigmatocystins. These are a group of closely related fungal metabolites chemically characterized by a xanthone moiety fused to a dihydrodifurano or a tetrahydrodifurano moiety. The chemical difference among the various sterigmagocystins are the presence or absence of unsaturation at positions 2 and 3 of the difurano ring system, the substitution pattern on positions 6, 7, and 10 of the xanthone system and/or the substituent on position 3 of the difurano system. They are produced by Aspergilus spp. And Bipolaris spp.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Sterigmatocystins

Sub Class

Not Available

Direct Parent

Sterigmatocystins

Alternative Parents

Substituents

Sterigmatocystin backbone
Xanthone
Bisabolane sesquiterpenoid
Sesquiterpenoid
Xanthene
Dibenzopyran
M-hydroxybenzoic acid ester
Chromone
1-benzopyran
Benzopyran
Benzoate ester
Coumaran
Benzoic acid or derivatives
Benzoyl
Anisole
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Pyranone
Phenol
Alkyl aryl ether
Benzenoid
Pyran
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous ester
Vinylogous acid
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic alcohol
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	5.13	ChemAxon
pKa (Strongest Acidic)	8.76	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	170.44 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	163.6 m³·mol⁻¹	ChemAxon
Polarizability	65.53 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	Yes	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162816216

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 15-hydroxy-11,18-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,9,11,14,16,18-hexaen-5-yl 4-(2,6-dihydroxy-6-methylheptan-2-yl)-3-hydroxybenzoate (NP0206569)

MOL for NP0206569 (15-hydroxy-11,18-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,9,11,14,16,18-hexaen-5-yl 4-(2,6-dihydroxy-6-methylheptan-2-yl)-3-hydroxybenzoate)

3D MOL for NP0206569 (15-hydroxy-11,18-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,9,11,14,16,18-hexaen-5-yl 4-(2,6-dihydroxy-6-methylheptan-2-yl)-3-hydroxybenzoate)

3D SDF for NP0206569 (15-hydroxy-11,18-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,9,11,14,16,18-hexaen-5-yl 4-(2,6-dihydroxy-6-methylheptan-2-yl)-3-hydroxybenzoate)

3D-SDF for NP0206569 (15-hydroxy-11,18-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,9,11,14,16,18-hexaen-5-yl 4-(2,6-dihydroxy-6-methylheptan-2-yl)-3-hydroxybenzoate)

PDB for NP0206569 (15-hydroxy-11,18-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,9,11,14,16,18-hexaen-5-yl 4-(2,6-dihydroxy-6-methylheptan-2-yl)-3-hydroxybenzoate)

3D PDB for NP0206569 (15-hydroxy-11,18-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,9,11,14,16,18-hexaen-5-yl 4-(2,6-dihydroxy-6-methylheptan-2-yl)-3-hydroxybenzoate)

SMILES for NP0206569 (15-hydroxy-11,18-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,9,11,14,16,18-hexaen-5-yl 4-(2,6-dihydroxy-6-methylheptan-2-yl)-3-hydroxybenzoate)

INCHI for NP0206569 (15-hydroxy-11,18-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,9,11,14,16,18-hexaen-5-yl 4-(2,6-dihydroxy-6-methylheptan-2-yl)-3-hydroxybenzoate)

Structure for NP0206569 (15-hydroxy-11,18-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,9,11,14,16,18-hexaen-5-yl 4-(2,6-dihydroxy-6-methylheptan-2-yl)-3-hydroxybenzoate)

3D Structure for NP0206569 (15-hydroxy-11,18-dimethoxy-13-oxo-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1,9,11,14,16,18-hexaen-5-yl 4-(2,6-dihydroxy-6-methylheptan-2-yl)-3-hydroxybenzoate)