NP-MRD: Showing NP-Card for 3,9-dihydroxy-7-methoxy-17-methyl-16,21-dioxapentacyclo[15.3.1.0²,¹⁵.0⁴,¹³.0⁶,¹¹]henicosa-2,4(13),6(11),7,9,14-hexaene-5,12-dione (NP0326172)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-12 07:30:11 UTC

Updated at

2022-09-12 07:30:11 UTC

NP-MRD ID

NP0326172

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,9-dihydroxy-7-methoxy-17-methyl-16,21-dioxapentacyclo[15.3.1.0²,¹⁵.0⁴,¹³.0⁶,¹¹]henicosa-2,4(13),6(11),7,9,14-hexaene-5,12-dione

Description

8-O-methyl averufin belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group. Thus, 8-O-methyl averufin is considered to be an aromatic polyketide. 3,9-dihydroxy-7-methoxy-17-methyl-16,21-dioxapentacyclo[15.3.1.0²,¹⁵.0⁴,¹³.0⁶,¹¹]henicosa-2,4(13),6(11),7,9,14-hexaene-5,12-dione is found in Penicillium chrysogenum. 3,9-dihydroxy-7-methoxy-17-methyl-16,21-dioxapentacyclo[15.3.1.0²,¹⁵.0⁴,¹³.0⁶,¹¹]henicosa-2,4(13),6(11),7,9,14-hexaene-5,12-dione was first documented in 2014 (PMID: 25022791). Based on a literature review very few articles have been published on 8-o-methyl averufin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122209302D          

 28 32  0  0  0  0            999 V2000
    6.9366    2.6444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2349    2.2105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2598    1.3859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9864    0.9952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0113    0.1705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7379   -0.2202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3096   -0.2633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5831    0.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5582    0.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8316    1.3428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8067    2.1674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1299    0.9089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1548    0.0843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4531   -0.3496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7265    0.0412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7016    0.8658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4033    1.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3784    2.1243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1009    1.4313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2762    1.4064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7108    0.8057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7357   -0.0190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3364   -0.5845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0438   -1.3558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1610   -0.5595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9706    0.3278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8814   -0.3065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9063   -1.1311    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
  9 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  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 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
 23 25  1  0  0  0  0
 15 25  1  0  0  0  0
 23 26  1  0  0  0  0
 19 26  1  0  0  0  0
 13 27  1  0  0  0  0
  8 27  1  0  0  0  0
 27 28  2  0  0  0  0
M  END

     RDKit          3D

 46 50  0  0  0  0  0  0  0  0999 V2000
    5.6349   -2.9324   -0.1851 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3846   -2.2857   -0.0971 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3453   -0.9005   -0.1554 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5147   -0.1823   -0.2968 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4924    1.1833   -0.3557 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7031    1.8586   -0.4991 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2794    1.8529   -0.2723 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1052    1.1614   -0.1317 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1498   -0.2180   -0.0742 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9212   -0.9823    0.0748 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0185   -2.2293    0.1215 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6330   -0.2767    0.1637 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5675    1.0988    0.1083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6454    1.7388    0.1929 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8155    1.0137    0.3348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7374   -0.3709    0.3897 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5321   -1.0401    0.3067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3932   -2.4124    0.3544 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0369   -1.0712    0.5458 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8046   -0.9926   -0.7587 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2635   -0.6561   -0.4641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3385    0.7144    0.1724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1495    0.8823    1.0568 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.4873    1.7296    2.2915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0731    1.5927    0.4258 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7495   -0.3415    1.5282 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8033    1.8493   -0.0407 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8036    3.1049   -0.0969 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2662   -2.6571    0.6829 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1618   -2.7157   -1.1341 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5090   -4.0378   -0.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4356   -0.7525   -0.3574 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7525    2.8719   -0.5490 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3010    2.9216   -0.3221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7292    2.8186    0.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1969   -2.9968    0.4506 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8775   -2.0888    0.8866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7559   -1.9867   -1.2239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3971   -0.2269   -1.4475 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6539   -1.4266    0.2322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8546   -0.7079   -1.3921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2571    0.7762    0.7852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3513    1.5264   -0.5624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6183    2.3353    2.6141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3162    2.4003    2.0766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7485    1.0577    3.1554 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
 10 11  2  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 25  1  0
 25 23  1  0
 23 24  1  1
 23 22  1  0
 22 21  1  0
 21 20  1  0
 20 19  1  0
 19 26  1  0
 19 16  1  0
 16 17  2  0
 17 18  1  0
 13 27  1  0
 27 28  2  0
  9  3  1  0
 17 12  1  0
 27  8  1  0
 16 15  1  0
 26 23  1  0
  1 29  1  0
  1 30  1  0
  1 31  1  0
  4 32  1  0
  6 33  1  0
  7 34  1  0
 14 35  1  0
 24 44  1  0
 24 45  1  0
 24 46  1  0
 22 42  1  0
 22 43  1  0
 21 40  1  0
 21 41  1  0
 20 38  1  0
 20 39  1  0
 19 37  1  1
 18 36  1  0
M  END


  Mrv1652309122209302D          

 28 32  0  0  0  0            999 V2000
    6.9366    2.6444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2349    2.2105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2598    1.3859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9864    0.9952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0113    0.1705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7379   -0.2202    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3096   -0.2633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5831    0.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5582    0.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8316    1.3428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8067    2.1674    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1299    0.9089    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1548    0.0843    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4531   -0.3496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7265    0.0412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7016    0.8658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4033    1.2997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3784    2.1243    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1009    1.4313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2762    1.4064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7108    0.8057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7357   -0.0190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3364   -0.5845    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0438   -1.3558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1610   -0.5595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9706    0.3278    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8814   -0.3065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9063   -1.1311    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
  9 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  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 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
 23 25  1  0  0  0  0
 15 25  1  0  0  0  0
 23 26  1  0  0  0  0
 19 26  1  0  0  0  0
 13 27  1  0  0  0  0
  8 27  1  0  0  0  0
 27 28  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0326172

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(O)=CC2=C1C(=O)C1=C(C=C3OC4(C)CCCC(O4)C3=C1O)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C21H18O7/c1-21-5-3-4-12(27-21)17-14(28-21)8-11-16(20(17)25)19(24)15-10(18(11)23)6-9(22)7-13(15)26-2/h6-8,12,22,25H,3-5H2,1-2H3

> <INCHI_KEY>
QZGXXZPRJHSVTD-UHFFFAOYSA-N

> <FORMULA>
C21H18O7

> <MOLECULAR_WEIGHT>
382.368

> <EXACT_MASS>
382.10525292

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
46

> <JCHEM_AVERAGE_POLARIZABILITY>
38.83596103070295

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,9-dihydroxy-7-methoxy-17-methyl-16,21-dioxapentacyclo[15.3.1.0^{2,15}.0^{4,13}.0^{6,11}]henicosa-2,4(13),6(11),7,9,14-hexaene-5,12-dione

> <JCHEM_LOGP>
3.605857224666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.863977222495055

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.156739737072676

> <JCHEM_PKA_STRONGEST_BASIC>
-4.204922091537611

> <JCHEM_POLAR_SURFACE_AREA>
102.29000000000002

> <JCHEM_REFRACTIVITY>
99.3193

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3,9-dihydroxy-7-methoxy-17-methyl-16,21-dioxapentacyclo[15.3.1.0^{2,15}.0^{4,13}.0^{6,11}]henicosa-2,4(13),6(11),7,9,14-hexaene-5,12-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  C   UNK     0      12.948   4.936   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      11.639   4.126   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      11.685   2.587   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.041   1.858   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.088   0.318   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      14.444  -0.411   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      11.778  -0.492   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.422   0.238   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.375   1.777   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.019   2.507   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.972   4.046   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.709   1.697   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.756   0.157   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.446  -0.653   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.089   0.077   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.043   1.616   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.353   2.426   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       6.306   3.965   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.922   2.672   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.382   2.625   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.327   1.504   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.373  -0.035   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.495  -1.091   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.948  -2.531   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.034  -1.044   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       3.678   0.612   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       9.112  -0.572   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       9.158  -2.111   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                                                       
CONECT    8    7    9   27                                                  
CONECT    9    8    3   10                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   17                                                  
CONECT   13   12   14   27                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   25                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16   12   18                                                  
CONECT   18   17                                                            
CONECT   19   16   20   26                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25   26                                             
CONECT   24   23                                                            
CONECT   25   23   15                                                       
CONECT   26   23   19                                                       
CONECT   27   13    8   28                                                  
CONECT   28   27                                                            
MASTER        0    0    0    0    0    0    0    0   28    0   64    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₁H₁₈O₇

Average Mass

382.3680 Da

Monoisotopic Mass

382.10525 Da

IUPAC Name

3,9-dihydroxy-7-methoxy-17-methyl-16,21-dioxapentacyclo[15.3.1.0^{2,15}.0^{4,13}.0^{6,11}]henicosa-2,4(13),6(11),7,9,14-hexaene-5,12-dione

Traditional Name

3,9-dihydroxy-7-methoxy-17-methyl-16,21-dioxapentacyclo[15.3.1.0^{2,15}.0^{4,13}.0^{6,11}]henicosa-2,4(13),6(11),7,9,14-hexaene-5,12-dione

CAS Registry Number

Not Available

SMILES

COC1=CC(O)=CC2=C1C(=O)C1=C(C=C3OC4(C)CCCC(O4)C3=C1O)C2=O

InChI Identifier

InChI=1S/C21H18O7/c1-21-5-3-4-12(27-21)17-14(28-21)8-11-16(20(17)25)19(24)15-10(18(11)23)6-9(22)7-13(15)26-2/h6-8,12,22,25H,3-5H2,1-2H3

InChI Key

QZGXXZPRJHSVTD-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
Penicillium chrysogenum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxyanthraquinones. Hydroxyanthraquinones are compounds containing a hydroxyanthraquinone moiety, which consists of an anthracene bearing a quinone, and hydroxyl group.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Hydroxyanthraquinones

Alternative Parents

Substituents

Hydroxyanthraquinone
Anisole
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Ketal
Oxane
Vinylogous acid
Ketone
Acetal
Ether
Oxacycle
Organoheterocyclic compound
Aldehyde
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Organic oxide
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	3.61	ChemAxon
pKa (Strongest Acidic)	7.16	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	102.29 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	99.32 m³·mol⁻¹	ChemAxon
Polarizability	38.84 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

Not Available

Chemspider ID

113369001

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

85109402

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Liu K, Zheng Y, Miao C, Xiong Z, Xu L, Guan H, Yang Y, Zhao L: The antifungal metabolites obtained from the rhizospheric Aspergillus sp. YIM PH30001 against pathogenic fungi of Panax notoginseng. Nat Prod Res. 2014;28(24):2334-7. doi: 10.1080/14786419.2014.935941. Epub 2014 Jul 15. [PubMed:25022791 ]
LOTUS database [Link]

Showing NP-Card for 3,9-dihydroxy-7-methoxy-17-methyl-16,21-dioxapentacyclo[15.3.1.0²,¹⁵.0⁴,¹³.0⁶,¹¹]henicosa-2,4(13),6(11),7,9,14-hexaene-5,12-dione (NP0326172)

MOL for NP0326172 (3,9-dihydroxy-7-methoxy-17-methyl-16,21-dioxapentacyclo[15.3.1.0²,¹⁵.0⁴,¹³.0⁶,¹¹]henicosa-2,4(13),6(11),7,9,14-hexaene-5,12-dione)

3D MOL for NP0326172 (3,9-dihydroxy-7-methoxy-17-methyl-16,21-dioxapentacyclo[15.3.1.0²,¹⁵.0⁴,¹³.0⁶,¹¹]henicosa-2,4(13),6(11),7,9,14-hexaene-5,12-dione)

3D SDF for NP0326172 (3,9-dihydroxy-7-methoxy-17-methyl-16,21-dioxapentacyclo[15.3.1.0²,¹⁵.0⁴,¹³.0⁶,¹¹]henicosa-2,4(13),6(11),7,9,14-hexaene-5,12-dione)

3D-SDF for NP0326172 (3,9-dihydroxy-7-methoxy-17-methyl-16,21-dioxapentacyclo[15.3.1.0²,¹⁵.0⁴,¹³.0⁶,¹¹]henicosa-2,4(13),6(11),7,9,14-hexaene-5,12-dione)

PDB for NP0326172 (3,9-dihydroxy-7-methoxy-17-methyl-16,21-dioxapentacyclo[15.3.1.0²,¹⁵.0⁴,¹³.0⁶,¹¹]henicosa-2,4(13),6(11),7,9,14-hexaene-5,12-dione)

3D PDB for NP0326172 (3,9-dihydroxy-7-methoxy-17-methyl-16,21-dioxapentacyclo[15.3.1.0²,¹⁵.0⁴,¹³.0⁶,¹¹]henicosa-2,4(13),6(11),7,9,14-hexaene-5,12-dione)

SMILES for NP0326172 (3,9-dihydroxy-7-methoxy-17-methyl-16,21-dioxapentacyclo[15.3.1.0²,¹⁵.0⁴,¹³.0⁶,¹¹]henicosa-2,4(13),6(11),7,9,14-hexaene-5,12-dione)

INCHI for NP0326172 (3,9-dihydroxy-7-methoxy-17-methyl-16,21-dioxapentacyclo[15.3.1.0²,¹⁵.0⁴,¹³.0⁶,¹¹]henicosa-2,4(13),6(11),7,9,14-hexaene-5,12-dione)

Structure for NP0326172 (3,9-dihydroxy-7-methoxy-17-methyl-16,21-dioxapentacyclo[15.3.1.0²,¹⁵.0⁴,¹³.0⁶,¹¹]henicosa-2,4(13),6(11),7,9,14-hexaene-5,12-dione)

3D Structure for NP0326172 (3,9-dihydroxy-7-methoxy-17-methyl-16,21-dioxapentacyclo[15.3.1.0²,¹⁵.0⁴,¹³.0⁶,¹¹]henicosa-2,4(13),6(11),7,9,14-hexaene-5,12-dione)