NP-MRD: Showing NP-Card for (4s,8r)-18-hydroxy-2,16-dimethoxy-7,9-dioxapentacyclo[10.8.0.0³,¹⁰.0⁴,⁸.0¹⁴,¹⁹]icosa-1,3(10),11,14,16,18-hexaene-13,20-dione (NP0200534)

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Record Information

Version

2.0

Created at

2022-09-04 19:23:52 UTC

Updated at

2022-09-04 19:23:52 UTC

NP-MRD ID

NP0200534

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4s,8r)-18-hydroxy-2,16-dimethoxy-7,9-dioxapentacyclo[10.8.0.0³,¹⁰.0⁴,⁸.0¹⁴,¹⁹]icosa-1,3(10),11,14,16,18-hexaene-13,20-dione

Description

Aversin belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone. (4s,8r)-18-hydroxy-2,16-dimethoxy-7,9-dioxapentacyclo[10.8.0.0³,¹⁰.0⁴,⁸.0¹⁴,¹⁹]icosa-1,3(10),11,14,16,18-hexaene-13,20-dione was first documented in 2007 (PMID: 17372958). Based on a literature review a small amount of articles have been published on Aversin (PMID: 22363226) (PMID: 25103412) (PMID: 35566201) (PMID: 24458562).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042221232D          

 27 31  0  0  1  0            999 V2000
    7.4736    2.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8192    2.0212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0569    2.3367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9490    3.1546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1867    3.4701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0788    4.2881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5324    2.9677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6403    2.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4026    1.8343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9859    1.6474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0938    0.8295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2236    1.9629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5692    1.4605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8069    1.7760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6990    2.5939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3534    3.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2455    3.9142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8999    4.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1157    2.7808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7701    3.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6622    4.1011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8878    2.7440    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3197    3.3423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4248    2.9869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3169    2.1690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4944    2.0189    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0624    1.4206    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  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
  3  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  2  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  2  0  0  0  0
 22 15  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 26 25  1  1  0  0  0
 22 26  1  0  0  0  0
 26 27  1  0  0  0  0
 14 27  1  0  0  0  0
M  END

     RDKit          3D

 43 47  0  0  0  0  0  0  0  0999 V2000
    6.5820    1.0382    0.8325 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1298   -0.2451    1.1475 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7780   -0.5502    1.0350 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3171   -1.7964    1.3377 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9503   -2.1228    1.2292 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5472   -3.3913    1.5473 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0970   -1.1240    0.8025 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5493    0.1561    0.4884 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9018    0.4163    0.6144 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6548    1.2245    0.0346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0842    2.3745   -0.2441 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2308    0.9902   -0.1099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6396    1.9867   -0.5385 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0036    1.6875   -0.6546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4654    0.4335   -0.3499 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5694   -0.5426    0.0766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1111   -1.7864    0.3663 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5777   -2.1337    1.6491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2273   -0.2654    0.1960 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6659   -1.3400    0.6514 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1853   -2.4707    0.9166 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9265    0.4250   -0.5695 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2050   -0.0064   -1.9831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6181    1.2929   -2.6404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2095    1.9931   -1.5898 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2728    1.8769   -0.5858 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0726    2.5118   -1.0614 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5102    1.2583   -0.2705 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6560    1.1459    1.1582 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0028    1.8245    1.3585 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9923   -2.5955    1.6780 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6750   -3.7933    1.5359 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2360    1.4343    0.3608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2622    2.9570   -0.7714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6242   -1.7703    1.8229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5493   -3.2583    1.7238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9662   -1.7482    2.4702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4778   -0.1625    0.1821 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2773   -0.4243   -2.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0096   -0.7550   -2.0613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3395    1.1226   -3.4697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7517    1.8479   -3.0545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5896    2.2847    0.3848 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 20  1  0
 20 21  2  0
 20 19  1  0
 19 16  2  0
 16 17  1  0
 17 18  1  0
 16 15  1  0
 15 14  2  0
 14 27  1  0
 27 26  1  0
 26 25  1  0
 25 24  1  0
 24 23  1  0
 23 22  1  0
 14 13  1  0
 13 12  2  0
 12 10  1  0
 10 11  2  0
 10  8  1  0
  8  9  2  0
  9  3  1  0
  8  7  1  0
 12 19  1  0
 22 15  1  0
 22 26  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  4 31  1  0
  6 32  1  0
 18 35  1  0
 18 36  1  0
 18 37  1  0
 26 43  1  1
 24 41  1  0
 24 42  1  0
 23 39  1  0
 23 40  1  0
 22 38  1  1
 13 34  1  0
  9 33  1  0
M  END


  Mrv1652309042221232D          

 27 31  0  0  1  0            999 V2000
    7.4736    2.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8192    2.0212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0569    2.3367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9490    3.1546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1867    3.4701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0788    4.2881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5324    2.9677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6403    2.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4026    1.8343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9859    1.6474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0938    0.8295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2236    1.9629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5692    1.4605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8069    1.7760    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6990    2.5939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3534    3.0963    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2455    3.9142    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8999    4.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1157    2.7808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7701    3.2832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6622    4.1011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8878    2.7440    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3197    3.3423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4248    2.9869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3169    2.1690    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4944    2.0189    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0624    1.4206    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  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
  3  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  2  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  0  0  0  0
  7 20  1  0  0  0  0
 20 21  2  0  0  0  0
 22 15  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 26 25  1  1  0  0  0
 22 26  1  0  0  0  0
 26 27  1  0  0  0  0
 14 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0200534

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=C2C(=O)C3=C(OC)C4=C(O[C@H]5OCC[C@@H]45)C=C3C(=O)C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C20H16O7/c1-24-8-5-10-14(12(21)6-8)18(23)16-11(17(10)22)7-13-15(19(16)25-2)9-3-4-26-20(9)27-13/h5-7,9,20-21H,3-4H2,1-2H3/t9-,20+/m0/s1

> <INCHI_KEY>
RJMVOYLRGJZYAO-GWNMQOMSSA-N

> <FORMULA>
C20H16O7

> <MOLECULAR_WEIGHT>
368.341

> <EXACT_MASS>
368.089602855

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
43

> <JCHEM_AVERAGE_POLARIZABILITY>
36.72453945599635

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S,8R)-18-hydroxy-2,16-dimethoxy-7,9-dioxapentacyclo[10.8.0.0^{3,10}.0^{4,8}.0^{14,19}]icosa-1,3(10),11,14,16,18-hexaene-13,20-dione

> <JCHEM_LOGP>
2.8880072346666656

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.11067638434694

> <JCHEM_PKA_STRONGEST_BASIC>
-4.0792664364488225

> <JCHEM_POLAR_SURFACE_AREA>
91.29000000000002

> <JCHEM_REFRACTIVITY>
94.4074

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4S,8R)-18-hydroxy-2,16-dimethoxy-7,9-dioxapentacyclo[10.8.0.0^{3,10}.0^{4,8}.0^{14,19}]icosa-1,3(10),11,14,16,18-hexaene-13,20-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  C   UNK     0      13.951   4.711   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      12.729   3.773   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      11.306   4.362   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.105   5.889   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.682   6.478   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       9.480   8.004   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       8.460   5.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.662   4.013   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.085   3.424   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.440   3.075   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       7.642   1.548   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.017   3.664   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.796   2.726   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.373   3.315   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.172   4.842   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.393   5.780   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.192   7.307   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       5.413   8.244   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.816   5.191   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.037   6.129   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.836   7.655   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       1.657   5.122   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.597   6.239   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.793   5.576   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.591   4.049   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       0.923   3.769   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.983   2.652   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8   20                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    3                                                       
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   27                                                  
CONECT   15   14   16   22                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   12   20                                                  
CONECT   20   19    7   21                                                  
CONECT   21   20                                                            
CONECT   22   15   23   26                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   22   27                                                  
CONECT   27   26   14                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₁₆O₇

Average Mass

368.3410 Da

Monoisotopic Mass

368.08960 Da

IUPAC Name

(4S,8R)-18-hydroxy-2,16-dimethoxy-7,9-dioxapentacyclo[10.8.0.0^{3,10}.0^{4,8}.0^{14,19}]icosa-1,3(10),11,14,16,18-hexaene-13,20-dione

Traditional Name

(4S,8R)-18-hydroxy-2,16-dimethoxy-7,9-dioxapentacyclo[10.8.0.0^{3,10}.0^{4,8}.0^{14,19}]icosa-1,3(10),11,14,16,18-hexaene-13,20-dione

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=C2C(=O)C3=C(OC)C4=C(O[C@H]5OCC[C@@H]45)C=C3C(=O)C2=C1

InChI Identifier

InChI=1S/C20H16O7/c1-24-8-5-10-14(12(21)6-8)18(23)16-11(17(10)22)7-13-15(19(16)25-2)9-3-4-26-20(9)27-13/h5-7,9,20-21H,3-4H2,1-2H3/t9-,20+/m0/s1

InChI Key

RJMVOYLRGJZYAO-GWNMQOMSSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as anthraquinones. These are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

9,10-anthraquinone
Anthraquinone
Naphthofuran
Coumaran
Anisole
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Oxolane
Vinylogous acid
Ketone
Organoheterocyclic compound
Ether
Oxacycle
Acetal
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aldehyde
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	2.89	ChemAxon
pKa (Strongest Acidic)	8.11	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	91.29 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	94.41 m³·mol⁻¹	ChemAxon
Polarizability	36.72 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00023630

Chemspider ID

20055393

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

22296216

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Miao FP, Li XD, Liu XH, Cichewicz RH, Ji NY: Secondary metabolites from an algicolous Aspergillus versicolor strain. Mar Drugs. 2012 Jan;10(1):131-9. doi: 10.3390/md10010131. Epub 2012 Jan 16. [PubMed:22363226 ]
Li H, Wei J, Pan SY, Gao JM, Tian JM: Antifungal, phytotoxic and toxic metabolites produced by Penicillium purpurogenum. Nat Prod Res. 2014;28(24):2358-61. doi: 10.1080/14786419.2014.940586. Epub 2014 Aug 7. [PubMed:25103412 ]
Cao TQ, Liu Z, Dong L, Lee H, Ko W, Vinh LB, Tuan NQ, Kim YC, Sohn JH, Yim JH, Lee DS, Oh H: Identification of Potential Anti-Neuroinflammatory Inhibitors from Antarctic Fungal Strain Aspergillus sp. SF-7402 via Regulating the NF-kappaB Signaling Pathway in Microglia. Molecules. 2022 Apr 29;27(9):2851. doi: 10.3390/molecules27092851. [PubMed:35566201 ]
Song F, Ren B, Chen C, Yu K, Liu X, Zhang Y, Yang N, He H, Liu X, Dai H, Zhang L: Three new sterigmatocystin analogues from marine-derived fungus Aspergillus versicolor MF359. Appl Microbiol Biotechnol. 2014 Apr;98(8):3753-8. doi: 10.1007/s00253-013-5409-5. Epub 2014 Jan 24. [PubMed:24458562 ]
Shao C, She Z, Guo Z, Peng H, Cai X, Zhou S, Gu Y, Lin Y: 1H and 13C NMR assignments for two anthraquinones and two xanthones from the mangrove fungus (ZSUH-36). Magn Reson Chem. 2007 May;45(5):434-8. doi: 10.1002/mrc.1974. [PubMed:17372958 ]
LOTUS database [Link]

Showing NP-Card for (4s,8r)-18-hydroxy-2,16-dimethoxy-7,9-dioxapentacyclo[10.8.0.0³,¹⁰.0⁴,⁸.0¹⁴,¹⁹]icosa-1,3(10),11,14,16,18-hexaene-13,20-dione (NP0200534)

MOL for NP0200534 ((4s,8r)-18-hydroxy-2,16-dimethoxy-7,9-dioxapentacyclo[10.8.0.0³,¹⁰.0⁴,⁸.0¹⁴,¹⁹]icosa-1,3(10),11,14,16,18-hexaene-13,20-dione)

3D MOL for NP0200534 ((4s,8r)-18-hydroxy-2,16-dimethoxy-7,9-dioxapentacyclo[10.8.0.0³,¹⁰.0⁴,⁸.0¹⁴,¹⁹]icosa-1,3(10),11,14,16,18-hexaene-13,20-dione)

3D SDF for NP0200534 ((4s,8r)-18-hydroxy-2,16-dimethoxy-7,9-dioxapentacyclo[10.8.0.0³,¹⁰.0⁴,⁸.0¹⁴,¹⁹]icosa-1,3(10),11,14,16,18-hexaene-13,20-dione)

3D-SDF for NP0200534 ((4s,8r)-18-hydroxy-2,16-dimethoxy-7,9-dioxapentacyclo[10.8.0.0³,¹⁰.0⁴,⁸.0¹⁴,¹⁹]icosa-1,3(10),11,14,16,18-hexaene-13,20-dione)

PDB for NP0200534 ((4s,8r)-18-hydroxy-2,16-dimethoxy-7,9-dioxapentacyclo[10.8.0.0³,¹⁰.0⁴,⁸.0¹⁴,¹⁹]icosa-1,3(10),11,14,16,18-hexaene-13,20-dione)

3D PDB for NP0200534 ((4s,8r)-18-hydroxy-2,16-dimethoxy-7,9-dioxapentacyclo[10.8.0.0³,¹⁰.0⁴,⁸.0¹⁴,¹⁹]icosa-1,3(10),11,14,16,18-hexaene-13,20-dione)

SMILES for NP0200534 ((4s,8r)-18-hydroxy-2,16-dimethoxy-7,9-dioxapentacyclo[10.8.0.0³,¹⁰.0⁴,⁸.0¹⁴,¹⁹]icosa-1,3(10),11,14,16,18-hexaene-13,20-dione)

INCHI for NP0200534 ((4s,8r)-18-hydroxy-2,16-dimethoxy-7,9-dioxapentacyclo[10.8.0.0³,¹⁰.0⁴,⁸.0¹⁴,¹⁹]icosa-1,3(10),11,14,16,18-hexaene-13,20-dione)

Structure for NP0200534 ((4s,8r)-18-hydroxy-2,16-dimethoxy-7,9-dioxapentacyclo[10.8.0.0³,¹⁰.0⁴,⁸.0¹⁴,¹⁹]icosa-1,3(10),11,14,16,18-hexaene-13,20-dione)

3D Structure for NP0200534 ((4s,8r)-18-hydroxy-2,16-dimethoxy-7,9-dioxapentacyclo[10.8.0.0³,¹⁰.0⁴,⁸.0¹⁴,¹⁹]icosa-1,3(10),11,14,16,18-hexaene-13,20-dione)