NP-MRD: Showing NP-Card for 5-methoxy-3,4-dehydroxanthomegnin (NP0027192)

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Record Information

Version

2.0

Created at

2021-06-19 18:52:55 UTC

Updated at

2021-06-29 23:53:10 UTC

NP-MRD ID

NP0027192

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-methoxy-3,4-dehydroxanthomegnin

Provided By

JEOL Database JEOL Logo

Description

5-methoxy-3,4-dehydroxanthomegnin is found in Paepalanthus latipes. 5-methoxy-3,4-dehydroxanthomegnin was first documented in 2004 (Kitagawa, R. R., et al.). Based on a literature review very few articles have been published on 10-hydroxy-5,7-dimethoxy-3-methyl-1H,6H,9H-cyclohexa[g]isochromene-1,6,9-trione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192120523D          

 35 37  0  0  0  0            999 V2000
   -6.3503   -2.4810   -0.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3781   -1.0559   -0.2431 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1518   -0.4361   -0.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1384    0.6951    0.6608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9113    1.4495    0.9187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9614    2.5221    1.5108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6211    0.8849    0.4798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6004   -0.2882   -0.2777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3521   -0.8152   -0.6657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2786   -1.9940   -1.3711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2749   -1.7477   -2.7825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1403   -0.2096   -0.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1475   -0.8288   -0.5669 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2766   -0.2242   -0.1920 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6440   -0.7721   -0.4458 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2698    1.0037    0.4927 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1185    1.6527    0.8492 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1828    2.7250    1.4341 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    0.9851    0.4739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4166    1.5287    0.8404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4410    2.6870    1.5745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8839   -0.9497   -0.6560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9157   -1.8696   -1.4639 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3521   -2.8350    0.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1255   -2.8486   -1.2641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6485   -2.8866    0.4776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0519    1.1085    1.0745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2849   -1.4121   -3.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4965   -2.6926   -3.2872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0296   -1.0125   -3.0828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1716   -1.7854   -1.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6108   -1.7284   -0.9778 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2260   -0.0696   -1.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1691   -0.9309    0.5014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3635    2.9793    1.7480 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 20  2  0  0  0  0
 20  7  1  0  0  0  0
 19 12  1  0  0  0  0
  8 22  1  0  0  0  0
  7  5  1  0  0  0  0
  5  4  1  0  0  0  0
  4  3  2  0  0  0  0
  3 22  1  0  0  0  0
 19 17  1  0  0  0  0
 17 18  2  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 13 14  2  0  0  0  0
 20 21  1  0  0  0  0
 14 16  1  0  0  0  0
  9 10  1  0  0  0  0
 16 17  1  0  0  0  0
  5  6  2  0  0  0  0
  8  7  2  0  0  0  0
 22 23  2  0  0  0  0
  8  9  1  0  0  0  0
  3  2  1  0  0  0  0
  9 12  2  0  0  0  0
 10 11  1  0  0  0  0
  2  1  1  0  0  0  0
 13 31  1  0  0  0  0
  4 27  1  0  0  0  0
 15 32  1  0  0  0  0
 15 33  1  0  0  0  0
 15 34  1  0  0  0  0
 21 35  1  0  0  0  0
 11 28  1  0  0  0  0
 11 29  1  0  0  0  0
 11 30  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
M  END

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
   -6.3503   -2.4810   -0.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3781   -1.0559   -0.2431 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1518   -0.4361   -0.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1384    0.6951    0.6608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9113    1.4495    0.9187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9614    2.5221    1.5108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6211    0.8849    0.4798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6004   -0.2882   -0.2777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3521   -0.8152   -0.6657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2786   -1.9940   -1.3711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2749   -1.7477   -2.7825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1403   -0.2096   -0.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1475   -0.8288   -0.5669 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2766   -0.2242   -0.1920 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6440   -0.7721   -0.4458 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2698    1.0037    0.4927 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1185    1.6527    0.8492 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1828    2.7250    1.4341 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    0.9851    0.4739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4166    1.5287    0.8404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4410    2.6870    1.5745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8839   -0.9497   -0.6560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9157   -1.8696   -1.4639 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3521   -2.8350    0.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1255   -2.8486   -1.2641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6485   -2.8866    0.4776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0519    1.1085    1.0745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2849   -1.4121   -3.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4965   -2.6926   -3.2872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0296   -1.0125   -3.0828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1716   -1.7854   -1.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6108   -1.7284   -0.9778 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2260   -0.0696   -1.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1691   -0.9309    0.5014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3635    2.9793    1.7480 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 20  2  0
 20  7  1  0
 19 12  1  0
  8 22  1  0
  7  5  1  0
  5  4  1  0
  4  3  2  0
  3 22  1  0
 19 17  1  0
 17 18  2  0
 12 13  1  0
 14 15  1  0
 13 14  2  0
 20 21  1  0
 14 16  1  0
  9 10  1  0
 16 17  1  0
  5  6  2  0
  8  7  2  0
 22 23  2  0
  8  9  1  0
  3  2  1  0
  9 12  2  0
 10 11  1  0
  2  1  1  0
 13 31  1  0
  4 27  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
 21 35  1  0
 11 28  1  0
 11 29  1  0
 11 30  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
M  END


  Mrv1652306192120523D          

 35 37  0  0  0  0            999 V2000
   -6.3503   -2.4810   -0.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3781   -1.0559   -0.2431 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1518   -0.4361   -0.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1384    0.6951    0.6608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9113    1.4495    0.9187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9614    2.5221    1.5108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6211    0.8849    0.4798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6004   -0.2882   -0.2777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3521   -0.8152   -0.6657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2786   -1.9940   -1.3711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2749   -1.7477   -2.7825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1403   -0.2096   -0.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1475   -0.8288   -0.5669 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2766   -0.2242   -0.1920 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6440   -0.7721   -0.4458 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2698    1.0037    0.4927 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1185    1.6527    0.8492 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1828    2.7250    1.4341 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    0.9851    0.4739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4166    1.5287    0.8404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4410    2.6870    1.5745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8839   -0.9497   -0.6560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9157   -1.8696   -1.4639 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3521   -2.8350    0.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1255   -2.8486   -1.2641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6485   -2.8866    0.4776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0519    1.1085    1.0745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2849   -1.4121   -3.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4965   -2.6926   -3.2872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0296   -1.0125   -3.0828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1716   -1.7854   -1.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6108   -1.7284   -0.9778 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2260   -0.0696   -1.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1691   -0.9309    0.5014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3635    2.9793    1.7480 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 20  2  0  0  0  0
 20  7  1  0  0  0  0
 19 12  1  0  0  0  0
  8 22  1  0  0  0  0
  7  5  1  0  0  0  0
  5  4  1  0  0  0  0
  4  3  2  0  0  0  0
  3 22  1  0  0  0  0
 19 17  1  0  0  0  0
 17 18  2  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 13 14  2  0  0  0  0
 20 21  1  0  0  0  0
 14 16  1  0  0  0  0
  9 10  1  0  0  0  0
 16 17  1  0  0  0  0
  5  6  2  0  0  0  0
  8  7  2  0  0  0  0
 22 23  2  0  0  0  0
  8  9  1  0  0  0  0
  3  2  1  0  0  0  0
  9 12  2  0  0  0  0
 10 11  1  0  0  0  0
  2  1  1  0  0  0  0
 13 31  1  0  0  0  0
  4 27  1  0  0  0  0
 15 32  1  0  0  0  0
 15 33  1  0  0  0  0
 15 34  1  0  0  0  0
 21 35  1  0  0  0  0
 11 28  1  0  0  0  0
 11 29  1  0  0  0  0
 11 30  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0027192

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(=O)OC(=C([H])C2=C(OC([H])([H])[H])C2=C1C(=O)C([H])=C(OC([H])([H])[H])C2=O)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H12O7/c1-6-4-7-10(16(20)23-6)14(19)11-8(17)5-9(21-2)13(18)12(11)15(7)22-3/h4-5,19H,1-3H3

> <INCHI_KEY>
WLLOBDXUIMMLIA-UHFFFAOYSA-N

> <FORMULA>
C16H12O7

> <MOLECULAR_WEIGHT>
316.265

> <EXACT_MASS>
316.058302726

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
30.340668416267963

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
10-hydroxy-5,7-dimethoxy-3-methyl-1H,6H,9H-cyclohexa[g]isochromene-1,6,9-trione

> <ALOGPS_LOGP>
1.74

> <JCHEM_LOGP>
2.2094682966666666

> <ALOGPS_LOGS>
-3.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.02814335761257

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.939949768231012

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9240109086847577

> <JCHEM_POLAR_SURFACE_AREA>
99.13

> <JCHEM_REFRACTIVITY>
82.59299999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.85e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
10-hydroxy-5,7-dimethoxy-3-methylcyclohexa[g]isochromene-1,6,9-trione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 35 37  0  0  0  0  0  0  0  0999 V2000
   -6.3503   -2.4810   -0.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3781   -1.0559   -0.2431 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1518   -0.4361   -0.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1384    0.6951    0.6608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9113    1.4495    0.9187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9614    2.5221    1.5108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6211    0.8849    0.4798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6004   -0.2882   -0.2777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3521   -0.8152   -0.6657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2786   -1.9940   -1.3711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2749   -1.7477   -2.7825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1403   -0.2096   -0.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1475   -0.8288   -0.5669 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2766   -0.2242   -0.1920 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6440   -0.7721   -0.4458 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2698    1.0037    0.4927 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1185    1.6527    0.8492 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1828    2.7250    1.4341 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    0.9851    0.4739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4166    1.5287    0.8404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4410    2.6870    1.5745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8839   -0.9497   -0.6560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9157   -1.8696   -1.4639 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3521   -2.8350    0.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1255   -2.8486   -1.2641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6485   -2.8866    0.4776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0519    1.1085    1.0745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2849   -1.4121   -3.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4965   -2.6926   -3.2872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0296   -1.0125   -3.0828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1716   -1.7854   -1.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6108   -1.7284   -0.9778 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2260   -0.0696   -1.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1691   -0.9309    0.5014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3635    2.9793    1.7480 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 20  2  0
 20  7  1  0
 19 12  1  0
  8 22  1  0
  7  5  1  0
  5  4  1  0
  4  3  2  0
  3 22  1  0
 19 17  1  0
 17 18  2  0
 12 13  1  0
 14 15  1  0
 13 14  2  0
 20 21  1  0
 14 16  1  0
  9 10  1  0
 16 17  1  0
  5  6  2  0
  8  7  2  0
 22 23  2  0
  8  9  1  0
  3  2  1  0
  9 12  2  0
 10 11  1  0
  2  1  1  0
 13 31  1  0
  4 27  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
 21 35  1  0
 11 28  1  0
 11 29  1  0
 11 30  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -6.350  -2.481  -0.259  0.00  0.00           C+0
HETATM    2  O   UNK     0      -6.378  -1.056  -0.243  0.00  0.00           O+0
HETATM    3  C   UNK     0      -5.152  -0.436  -0.044  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.138   0.695   0.661  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.911   1.450   0.919  0.00  0.00           C+0
HETATM    6  O   UNK     0      -3.961   2.522   1.511  0.00  0.00           O+0
HETATM    7  C   UNK     0      -2.621   0.885   0.480  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.600  -0.288  -0.278  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.352  -0.815  -0.666  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.279  -1.994  -1.371  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.275  -1.748  -2.783  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.140  -0.210  -0.259  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.147  -0.829  -0.567  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.277  -0.224  -0.192  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.644  -0.772  -0.446  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.270   1.004   0.493  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.119   1.653   0.849  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.183   2.725   1.434  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.171   0.985   0.474  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.417   1.529   0.840  0.00  0.00           C+0
HETATM   21  O   UNK     0      -1.441   2.687   1.575  0.00  0.00           O+0
HETATM   22  C   UNK     0      -3.884  -0.950  -0.656  0.00  0.00           C+0
HETATM   23  O   UNK     0      -3.916  -1.870  -1.464  0.00  0.00           O+0
HETATM   24  H   UNK     0      -7.352  -2.835   0.003  0.00  0.00           H+0
HETATM   25  H   UNK     0      -6.125  -2.849  -1.264  0.00  0.00           H+0
HETATM   26  H   UNK     0      -5.649  -2.887   0.478  0.00  0.00           H+0
HETATM   27  H   UNK     0      -6.052   1.109   1.075  0.00  0.00           H+0
HETATM   28  H   UNK     0      -0.285  -1.412  -3.107  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.496  -2.693  -3.287  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.030  -1.012  -3.083  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.172  -1.785  -1.079  0.00  0.00           H+0
HETATM   32  H   UNK     0       3.611  -1.728  -0.978  0.00  0.00           H+0
HETATM   33  H   UNK     0       4.226  -0.070  -1.051  0.00  0.00           H+0
HETATM   34  H   UNK     0       4.169  -0.931   0.501  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.364   2.979   1.748  0.00  0.00           H+0
CONECT    1    2   24   25   26                                             
CONECT    2    3    1                                                       
CONECT    3    4   22    2                                                  
CONECT    4    5    3   27                                                  
CONECT    5    7    4    6                                                  
CONECT    6    5                                                            
CONECT    7   20    5    8                                                  
CONECT    8   22    7    9                                                  
CONECT    9   10    8   12                                                  
CONECT   10    9   11                                                       
CONECT   11   10   28   29   30                                             
CONECT   12   19   13    9                                                  
CONECT   13   12   14   31                                                  
CONECT   14   15   13   16                                                  
CONECT   15   14   32   33   34                                             
CONECT   16   14   17                                                       
CONECT   17   19   18   16                                                  
CONECT   18   17                                                            
CONECT   19   20   12   17                                                  
CONECT   20   19    7   21                                                  
CONECT   21   20   35                                                       
CONECT   22    8    3   23                                                  
CONECT   23   22                                                            
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    4                                                            
CONECT   28   11                                                            
CONECT   29   11                                                            
CONECT   30   11                                                            
CONECT   31   13                                                            
CONECT   32   15                                                            
CONECT   33   15                                                            
CONECT   34   15                                                            
CONECT   35   21                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

RDKit          3D

35 37  0  0  0  0  0  0  0  0999 V2000
   -6.3503   -2.4810   -0.2592 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3781   -1.0559   -0.2431 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1518   -0.4361   -0.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1384    0.6951    0.6608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9113    1.4495    0.9187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9614    2.5221    1.5108 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6211    0.8849    0.4798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6004   -0.2882   -0.2777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3521   -0.8152   -0.6657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2786   -1.9940   -1.3711 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2749   -1.7477   -2.7825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1403   -0.2096   -0.2593 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1475   -0.8288   -0.5669 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2766   -0.2242   -0.1920 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6440   -0.7721   -0.4458 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2698    1.0037    0.4927 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1185    1.6527    0.8492 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1828    2.7250    1.4341 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1712    0.9851    0.4739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4166    1.5287    0.8404 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4410    2.6870    1.5745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8839   -0.9497   -0.6560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9157   -1.8696   -1.4639 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3521   -2.8350    0.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1255   -2.8486   -1.2641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6485   -2.8866    0.4776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0519    1.1085    1.0745 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2849   -1.4121   -3.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4965   -2.6926   -3.2872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0296   -1.0125   -3.0828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1716   -1.7854   -1.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6108   -1.7284   -0.9778 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2260   -0.0696   -1.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1691   -0.9309    0.5014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3635    2.9793    1.7480 H   0  0  0  0  0  0  0  0  0  0  0  0
 19 20  2  0
 20  7  1  0
 19 12  1  0
  8 22  1  0
  7  5  1  0
  5  4  1  0
  4  3  2  0
  3 22  1  0
 19 17  1  0
 17 18  2  0
 12 13  1  0
 14 15  1  0
 13 14  2  0
 20 21  1  0
 14 16  1  0
  9 10  1  0
 16 17  1  0
  5  6  2  0
  8  7  2  0
 22 23  2  0
  8  9  1  0
  3  2  1  0
  9 12  2  0
 10 11  1  0
  2  1  1  0
 13 31  1  0
  4 27  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
 21 35  1  0
 11 28  1  0
 11 29  1  0
 11 30  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
M  END

View in JSmol View DFT Assignments 3D Conformers

Synonyms

Not Available

Chemical Formula

C₁₆H₁₂O₇

Average Mass

316.2650 Da

Monoisotopic Mass

316.05830 Da

IUPAC Name

10-hydroxy-5,7-dimethoxy-3-methyl-1H,6H,9H-cyclohexa[g]isochromene-1,6,9-trione

Traditional Name

10-hydroxy-5,7-dimethoxy-3-methylcyclohexa[g]isochromene-1,6,9-trione

CAS Registry Number

Not Available

SMILES

[H]OC1=C2C(=O)OC(=C([H])C2=C(OC([H])([H])[H])C2=C1C(=O)C([H])=C(OC([H])([H])[H])C2=O)C([H])([H])[H]

InChI Identifier

InChI=1S/C16H12O7/c1-6-4-7-10(16(20)23-6)14(19)11-8(17)5-9(21-2)13(18)12(11)15(7)22-3/h4-5,19H,1-3H3

InChI Key

WLLOBDXUIMMLIA-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, chcl3, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, chcl3, 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
Paepalanthus latipes	JEOL database	Kitagawa, R. R., et al, Chem. Pharm. Bull. 52, 1487 (2004)

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as isochromanequinones. These are polycyclic compounds containing an isochromanequinone, which is structurally characterized by a quinone fused to an isochromane, and forming a naphtho[2,3-c]pyran-6,9-dione skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isochromanequinones

Sub Class

Not Available

Direct Parent

Isochromanequinones

Alternative Parents

Substituents

Isochromanequinone
Naphthopyranone
Naphthopyran
Naphthoquinone
Isocoumarin
Benzopyran
Isochromane
Naphthalene
2-benzopyran
Anisole
Aryl ketone
Quinone
Alkyl aryl ether
Pyranone
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous ester
Vinylogous acid
Lactone
Ketone
Organoheterocyclic compound
Oxacycle
Ether
Aldehyde
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.74	ALOGPS
logP	2.21	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	8.94	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	99.13 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	82.59 m³·mol⁻¹	ChemAxon
Polarizability	30.34 Å³	ChemAxon
Number of Rings	3	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

9522561

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11347623

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kitagawa, R. R., et al. (2004). Kitagawa, R. R., et al, Chem. Pharm. Bull. 52, 1487 (2004). Chem. Pharm. Bull..

Showing NP-Card for 5-methoxy-3,4-dehydroxanthomegnin (NP0027192)

MOL for NP0027192 (5-methoxy-3,4-dehydroxanthomegnin)

3D MOL for NP0027192 (5-methoxy-3,4-dehydroxanthomegnin)

3D SDF for NP0027192 (5-methoxy-3,4-dehydroxanthomegnin)

3D-SDF for NP0027192 (5-methoxy-3,4-dehydroxanthomegnin)

PDB for NP0027192 (5-methoxy-3,4-dehydroxanthomegnin)

3D PDB for NP0027192 (5-methoxy-3,4-dehydroxanthomegnin)

SMILES for NP0027192 (5-methoxy-3,4-dehydroxanthomegnin)

INCHI for NP0027192 (5-methoxy-3,4-dehydroxanthomegnin)

Structure for NP0027192 (5-methoxy-3,4-dehydroxanthomegnin)

3D Structure for NP0027192 (5-methoxy-3,4-dehydroxanthomegnin)