NP-MRD: Showing NP-Card for (7ar,8ar,8bs,8cr)-1,6,8c-trihydroxy-7ah,8ah,8bh,9h,10h-peryleno[1,2-b]oxirene-7,11-dione (NP0323056)

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Record Information

Version

2.0

Created at

2022-09-12 02:13:39 UTC

Updated at

2022-09-12 02:13:40 UTC

NP-MRD ID

NP0323056

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(7ar,8ar,8bs,8cr)-1,6,8c-trihydroxy-7ah,8ah,8bh,9h,10h-peryleno[1,2-b]oxirene-7,11-dione

Description

Stemphyltoxin II belongs to the class of organic compounds known as perylenequinones. These are heterocyclic compounds characterized by two 8-hydroxy-1,4-dihydronaphthalen-1-one moieties joined together one or two CC-bonds. (7ar,8ar,8bs,8cr)-1,6,8c-trihydroxy-7ah,8ah,8bh,9h,10h-peryleno[1,2-b]oxirene-7,11-dione is found in Alternaria cassiae and Stemphylium botryosum. (7ar,8ar,8bs,8cr)-1,6,8c-trihydroxy-7ah,8ah,8bh,9h,10h-peryleno[1,2-b]oxirene-7,11-dione was first documented in 2014 (PMID: 25056998). Based on a literature review a significant number of articles have been published on Stemphyltoxin II (PMID: 24428710) (PMID: 32623606) (PMID: 31641809) (PMID: 30321595) (PMID: 29766221) (PMID: 27682608).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122204132D          

 26 31  0  0  1  0            999 V2000
   -0.9126   -1.7612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3182   -1.1892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4745   -1.4180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0690   -0.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8708   -0.0451    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6634   -0.2739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0782    0.1837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1200    0.9845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9126    1.2133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5071    0.6413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3089   -0.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9034   -0.7316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5163   -0.3883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4745    1.5566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2763    2.3574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8708    2.9295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6634    2.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2579    3.2727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8616    1.8998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2671    1.3278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4653    0.5269    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2579    0.2981    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0505    0.0693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8524    0.8701    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6542    1.6710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2487    2.2430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  7 13  1  0  0  0  0
  2 13  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 14 20  1  0  0  0  0
 21 20  1  1  0  0  0
  5 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 24 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 19 25  1  0  0  0  0
 25 26  2  0  0  0  0
M  END

     RDKit          3D

 40 45  0  0  0  0  0  0  0  0999 V2000
   -4.5203   -1.2338    0.2456 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3808   -1.0514   -0.2475 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7550   -2.1181   -1.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2822   -1.8942   -1.2742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6547   -1.0867   -0.1577 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9708   -1.8197    1.0177 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3084    0.2115   -0.0026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6396    1.4243    0.1948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3053    2.6007    0.3611 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7089    2.5738    0.3292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3825    1.3975    0.1362 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7653    1.3570    0.1032 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6869    0.2014   -0.0326 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8173    1.4048    0.1958 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5662    2.5519    0.3905 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9459    2.5406    0.3979 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5754    1.3396    0.2043 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9776    1.2294    0.1935 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8557    0.1830    0.0093 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4706    0.1969    0.0005 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8173   -1.0881   -0.2693 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4700   -2.1870    0.5298 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1413   -3.1950   -0.1940 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9204   -2.2927    0.4568 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5475   -1.1120   -0.1759 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5972   -1.1355   -0.8383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8415   -3.1200   -0.5396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2718   -2.1924   -2.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1685   -1.2984   -2.2036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7247   -2.8418   -1.4086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7016   -1.4236    1.5177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7891    3.5164    0.5109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2278    3.5021    0.4608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2685    2.2235    0.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0755    3.4915    0.5431 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5295    3.4420    0.5503 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4963    2.0850    0.3376 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0846   -1.3094   -1.3576 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9894   -2.4733    1.4876 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4767   -2.5995    1.3855 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  0
 17 16  2  0
 16 15  1  0
 15 14  2  0
 14  8  1  0
  8  7  2  0
  7 13  1  0
 13  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  1
  5 21  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  2  0
 25 19  1  0
 19 20  2  0
 13 11  2  0
 11 12  1  0
 11 10  1  0
 10  9  2  0
 19 17  1  0
 20 14  1  0
  9  8  1  0
  5  7  1  0
 20 21  1  0
 24 22  1  0
 18 37  1  0
 16 36  1  0
 15 35  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  6 31  1  0
 21 38  1  6
 22 39  1  1
 24 40  1  1
 12 34  1  0
 10 33  1  0
  9 32  1  0
M  END


  Mrv1652309122204132D          

 26 31  0  0  1  0            999 V2000
   -0.9126   -1.7612    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3182   -1.1892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4745   -1.4180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0690   -0.8460    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8708   -0.0451    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6634   -0.2739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0782    0.1837    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1200    0.9845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9126    1.2133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5071    0.6413    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3089   -0.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9034   -0.7316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5163   -0.3883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4745    1.5566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2763    2.3574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8708    2.9295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6634    2.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2579    3.2727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8616    1.8998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2671    1.3278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4653    0.5269    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2579    0.2981    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0505    0.0693    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8524    0.8701    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6542    1.6710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2487    2.2430    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  7 13  1  0  0  0  0
  2 13  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 14 20  1  0  0  0  0
 21 20  1  1  0  0  0
  5 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  6  0  0  0
 24 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 19 25  1  0  0  0  0
 25 26  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0323056

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC=C2C3=C4C(C(=O)CC[C@@]4(O)[C@@H]4[C@H]5O[C@H]5C(=O)C1=C24)=C(O)C=C3

> <INCHI_IDENTIFIER>
InChI=1S/C20H14O6/c21-9-4-2-8-7-1-3-10(22)14-12(7)16(18-19(26-18)17(14)24)20(25)6-5-11(23)13(9)15(8)20/h1-4,16,18-19,21-22,25H,5-6H2/t16-,18+,19-,20-/m0/s1

> <INCHI_KEY>
UBVHBTLDPUYTDO-RNQOJCNYSA-N

> <FORMULA>
C20H14O6

> <MOLECULAR_WEIGHT>
350.326

> <EXACT_MASS>
350.079038171

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
34.57803606431298

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(10R,11S,12R,14R)-5,10,17-trihydroxy-13-oxahexacyclo[9.8.1.1^{2,6}.0^{12,14}.0^{16,20}.0^{10,21}]henicosa-1(20),2(21),3,5,16,18-hexaene-7,15-dione

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.864676276900207

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.17703298037955

> <JCHEM_PKA_STRONGEST_BASIC>
-3.473160111963516

> <JCHEM_POLAR_SURFACE_AREA>
107.36

> <JCHEM_REFRACTIVITY>
90.4823

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(10R,11S,12R,14R)-5,10,17-trihydroxy-13-oxahexacyclo[9.8.1.1^{2,6}.0^{12,14}.0^{16,20}.0^{10,21}]henicosa-1(20),2(21),3,5,16,18-hexaene-7,15-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  O   UNK     0      -1.704  -3.288   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.594  -2.220   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.886  -2.647   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.995  -1.579   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.625  -0.084   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.105  -0.511   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       0.146   0.343   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.224   1.838   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.704   2.265   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.813   1.197   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.443  -0.298   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -3.553  -1.366   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.964  -0.725   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.886   2.906   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.516   4.401   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.625   5.468   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.105   5.041   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       4.215   6.109   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.475   3.546   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.365   2.478   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.735   0.984   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.215   0.556   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.694   0.129   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.324   1.624   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.955   3.119   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.064   4.187   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7   21                                             
CONECT    6    5                                                            
CONECT    7    5    8   13                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    7    2                                                  
CONECT   14    8   15   20                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   25                                                  
CONECT   20   19   14   21                                                  
CONECT   21   20    5   22                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22   24                                                       
CONECT   24   23   22   25                                                  
CONECT   25   24   19   26                                                  
CONECT   26   25                                                            
MASTER        0    0    0    0    0    0    0    0   26    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₁₄O₆

Average Mass

350.3260 Da

Monoisotopic Mass

350.07904 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

OC1=CC=C2C3=C4C(C(=O)CC[C@@]4(O)[C@@H]4[C@H]5O[C@H]5C(=O)C1=C24)=C(O)C=C3

InChI Identifier

InChI=1S/C20H14O6/c21-9-4-2-8-7-1-3-10(22)14-12(7)16(18-19(26-18)17(14)24)20(25)6-5-11(23)13(9)15(8)20/h1-4,16,18-19,21-22,25H,5-6H2/t16-,18+,19-,20-/m0/s1

InChI Key

UBVHBTLDPUYTDO-RNQOJCNYSA-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
Alternaria cassiae	LOTUS Database	35616633
Stemphylium botryosum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as perylenequinones. These are heterocyclic compounds characterized by two 8-hydroxy-1,4-dihydronaphthalen-1-one moieties joined together one or two CC-bonds.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Perylenequinones

Sub Class

Not Available

Direct Parent

Perylenequinones

Alternative Parents

Substituents

Perylenequinone
Phenanthrene
Naphthalene
Tetralin
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Phenol
Tertiary alcohol
Vinylogous acid
Ketone
Polyol
Oxacycle
Ether
Oxirane
Dialkyl ether
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen 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

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

8060435

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9884761

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Podlech J, Fleck SC, Metzler M, Burck J, Ulrich AS: Determination of the absolute configuration of perylene quinone-derived mycotoxins by measurement and calculation of electronic circular dichroism spectra and specific rotations. Chemistry. 2014 Sep 1;20(36):11463-70. doi: 10.1002/chem.201402567. Epub 2014 Jul 23. [PubMed:25056998 ]
Fleck SC, Pfeiffer E, Podlech J, Metzler M: Epoxide reduction to an alcohol: a novel metabolic pathway for perylene quinone-type alternaria mycotoxins in mammalian cells. Chem Res Toxicol. 2014 Feb 17;27(2):247-53. doi: 10.1021/tx400366w. Epub 2014 Jan 27. [PubMed:24428710 ]
Crudo F, Aichinger G, Mihajlovic J, Dellafiora L, Varga E, Puntscher H, Warth B, Dall'Asta C, Berry D, Marko D: Gut microbiota and undigested food constituents modify toxin composition and suppress the genotoxicity of a naturally occurring mixture of Alternaria toxins in vitro. Arch Toxicol. 2020 Oct;94(10):3541-3552. doi: 10.1007/s00204-020-02831-1. Epub 2020 Jul 4. [PubMed:32623606 ]
Puntscher H, Aichinger G, Grabher S, Attakpah E, Kruger F, Tillmann K, Motschnig T, Hohenbichler J, Braun D, Plasenzotti R, Pahlke G, Hoger H, Marko D, Warth B: Bioavailability, metabolism, and excretion of a complex Alternaria culture extract versus altertoxin II: a comparative study in rats. Arch Toxicol. 2019 Nov;93(11):3153-3167. doi: 10.1007/s00204-019-02575-7. Epub 2019 Oct 22. [PubMed:31641809 ]
Puntscher H, Hankele S, Tillmann K, Attakpah E, Braun D, Kutt ML, Del Favero G, Aichinger G, Pahlke G, Hoger H, Marko D, Warth B: First insights into Alternaria multi-toxin in vivo metabolism. Toxicol Lett. 2019 Feb;301:168-178. doi: 10.1016/j.toxlet.2018.10.006. Epub 2018 Oct 12. [PubMed:30321595 ]
Puntscher H, Kutt ML, Skrinjar P, Mikula H, Podlech J, Frohlich J, Marko D, Warth B: Tracking emerging mycotoxins in food: development of an LC-MS/MS method for free and modified Alternaria toxins. Anal Bioanal Chem. 2018 Jul;410(18):4481-4494. doi: 10.1007/s00216-018-1105-8. Epub 2018 May 16. [PubMed:29766221 ]
Jarolim K, Del Favero G, Ellmer D, Stark TD, Hofmann T, Sulyok M, Humpf HU, Marko D: Dual effectiveness of Alternaria but not Fusarium mycotoxins against human topoisomerase II and bacterial gyrase. Arch Toxicol. 2017 Apr;91(4):2007-2016. doi: 10.1007/s00204-016-1855-z. Epub 2016 Sep 28. [PubMed:27682608 ]
Zwickel T, Klaffke H, Richards K, Rychlik M: Development of a high performance liquid chromatography tandem mass spectrometry based analysis for the simultaneous quantification of various Alternaria toxins in wine, vegetable juices and fruit juices. J Chromatogr A. 2016 Jul 15;1455:74-85. doi: 10.1016/j.chroma.2016.04.066. Epub 2016 May 6. [PubMed:27283097 ]
Fleck SC, Sauter F, Pfeiffer E, Metzler M, Hartwig A, Koberle B: DNA damage and repair kinetics of the Alternaria mycotoxins alternariol, altertoxin II and stemphyltoxin III in cultured cells. Mutat Res Genet Toxicol Environ Mutagen. 2016 Mar;798-799:27-34. doi: 10.1016/j.mrgentox.2016.02.001. Epub 2016 Feb 8. [PubMed:26994491 ]
Liu Y, Rychlik M: Biosynthesis of seven carbon-13 labeled Alternaria toxins including altertoxins, alternariol, and alternariol methyl ether, and their application to a multiple stable isotope dilution assay. Anal Bioanal Chem. 2015 Feb;407(5):1357-69. doi: 10.1007/s00216-014-8307-5. Epub 2015 Jan 11. [PubMed:25577349 ]
LOTUS database [Link]

Showing NP-Card for (7ar,8ar,8bs,8cr)-1,6,8c-trihydroxy-7ah,8ah,8bh,9h,10h-peryleno[1,2-b]oxirene-7,11-dione (NP0323056)

MOL for NP0323056 ((7ar,8ar,8bs,8cr)-1,6,8c-trihydroxy-7ah,8ah,8bh,9h,10h-peryleno[1,2-b]oxirene-7,11-dione)

3D MOL for NP0323056 ((7ar,8ar,8bs,8cr)-1,6,8c-trihydroxy-7ah,8ah,8bh,9h,10h-peryleno[1,2-b]oxirene-7,11-dione)

3D SDF for NP0323056 ((7ar,8ar,8bs,8cr)-1,6,8c-trihydroxy-7ah,8ah,8bh,9h,10h-peryleno[1,2-b]oxirene-7,11-dione)

3D-SDF for NP0323056 ((7ar,8ar,8bs,8cr)-1,6,8c-trihydroxy-7ah,8ah,8bh,9h,10h-peryleno[1,2-b]oxirene-7,11-dione)

PDB for NP0323056 ((7ar,8ar,8bs,8cr)-1,6,8c-trihydroxy-7ah,8ah,8bh,9h,10h-peryleno[1,2-b]oxirene-7,11-dione)

3D PDB for NP0323056 ((7ar,8ar,8bs,8cr)-1,6,8c-trihydroxy-7ah,8ah,8bh,9h,10h-peryleno[1,2-b]oxirene-7,11-dione)

SMILES for NP0323056 ((7ar,8ar,8bs,8cr)-1,6,8c-trihydroxy-7ah,8ah,8bh,9h,10h-peryleno[1,2-b]oxirene-7,11-dione)

INCHI for NP0323056 ((7ar,8ar,8bs,8cr)-1,6,8c-trihydroxy-7ah,8ah,8bh,9h,10h-peryleno[1,2-b]oxirene-7,11-dione)

Structure for NP0323056 ((7ar,8ar,8bs,8cr)-1,6,8c-trihydroxy-7ah,8ah,8bh,9h,10h-peryleno[1,2-b]oxirene-7,11-dione)

3D Structure for NP0323056 ((7ar,8ar,8bs,8cr)-1,6,8c-trihydroxy-7ah,8ah,8bh,9h,10h-peryleno[1,2-b]oxirene-7,11-dione)