NP-MRD: Showing NP-Card for Quinquangulone (NP0025854)

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Record Information

Version

2.0

Created at

2021-06-19 17:52:17 UTC

Updated at

2021-06-29 23:51:03 UTC

NP-MRD ID

NP0025854

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Quinquangulone

Provided By

JEOL Database JEOL Logo

Description

Quinquangulone is found in Cassia quinquangulata. Quinquangulone was first documented in 2001 (Li, X.-C., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119523D          

 36 38  0  0  0  0            999 V2000
   -4.3713   -4.0104    3.9796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3632   -3.0035    3.9682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9946   -2.4657    2.7434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5112   -2.8169    1.5563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0653   -2.1788    0.2976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3299   -2.7442   -0.7549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3231   -0.8888    0.3974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7810   -0.5114    1.6431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0800    0.7087    1.7424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9214    1.5367    0.6345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2233    2.7021    0.8285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0503    3.5574   -0.2471 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7227    4.7946    0.0884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5236    3.3162   -1.4773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2744    2.0774   -1.7273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7236    1.8170   -2.8377 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4627    1.1641   -0.5902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1686   -0.0431   -0.7178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7326   -0.3929   -1.9174 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9112   -1.4055    2.8644 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5649   -2.0746    3.1786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2503   -0.5652    3.9750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0466   -4.8942    3.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3166   -3.6217    3.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5346   -4.3095    5.0192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2538   -3.5924    1.4219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6607    1.0163    2.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2079    5.3607    0.8713 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8444    5.4526   -0.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7204    4.5293    0.4526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3858    3.9883   -2.3145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5206    0.2838   -2.5977 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2162   -1.3301    3.3734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6280   -2.6874    4.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2257   -2.7136    2.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6790   -1.1514    4.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  2  0  0  0  0
  3  4  2  0  0  0  0
  3 20  1  0  0  0  0
 10 11  1  0  0  0  0
 17 15  1  0  0  0  0
 15 14  1  0  0  0  0
 14 12  2  0  0  0  0
 12 11  1  0  0  0  0
  4  5  1  0  0  0  0
 15 16  2  0  0  0  0
  8  9  1  0  0  0  0
 18 19  1  0  0  0  0
  7 18  1  0  0  0  0
  5  6  2  0  0  0  0
 18 17  2  0  0  0  0
 20 22  1  0  0  0  0
 10  9  2  0  0  0  0
 12 13  1  0  0  0  0
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  3  2  1  0  0  0  0
  5  7  1  0  0  0  0
  2  1  1  0  0  0  0
  8 20  1  0  0  0  0
 20 21  1  0  0  0  0
  4 26  1  0  0  0  0
  9 27  1  0  0  0  0
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 19 32  1  0  0  0  0
 22 36  1  0  0  0  0
 13 28  1  0  0  0  0
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 13 30  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
 21 33  1  0  0  0  0
 21 34  1  0  0  0  0
 21 35  1  0  0  0  0
M  END

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
   -4.3713   -4.0104    3.9796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3632   -3.0035    3.9682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9946   -2.4657    2.7434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5112   -2.8169    1.5563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0653   -2.1788    0.2976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3299   -2.7442   -0.7549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3231   -0.8888    0.3974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7810   -0.5114    1.6431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0800    0.7087    1.7424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9214    1.5367    0.6345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2233    2.7021    0.8285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0503    3.5574   -0.2471 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7227    4.7946    0.0884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5236    3.3162   -1.4773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2744    2.0774   -1.7273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7236    1.8170   -2.8377 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4627    1.1641   -0.5902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1686   -0.0431   -0.7178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7326   -0.3929   -1.9174 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9112   -1.4055    2.8644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5649   -2.0746    3.1786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2503   -0.5652    3.9750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0466   -4.8942    3.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3166   -3.6217    3.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5346   -4.3095    5.0192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2538   -3.5924    1.4219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6607    1.0163    2.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2079    5.3607    0.8713 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8444    5.4526   -0.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7204    4.5293    0.4526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3858    3.9883   -2.3145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5206    0.2838   -2.5977 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2162   -1.3301    3.3734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6280   -2.6874    4.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2257   -2.7136    2.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6790   -1.1514    4.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  2  0
  3  4  2  0
  3 20  1  0
 10 11  1  0
 17 15  1  0
 15 14  1  0
 14 12  2  0
 12 11  1  0
  4  5  1  0
 15 16  2  0
  8  9  1  0
 18 19  1  0
  7 18  1  0
  5  6  2  0
 18 17  2  0
 20 22  1  0
 10  9  2  0
 12 13  1  0
 10 17  1  0
  3  2  1  0
  5  7  1  0
  2  1  1  0
  8 20  1  0
 20 21  1  0
  4 26  1  0
  9 27  1  0
 14 31  1  0
 19 32  1  0
 22 36  1  0
 13 28  1  0
 13 29  1  0
 13 30  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
 21 33  1  0
 21 34  1  0
 21 35  1  0
M  END


  Mrv1652306192119523D          

 36 38  0  0  0  0            999 V2000
   -4.3713   -4.0104    3.9796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3632   -3.0035    3.9682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9946   -2.4657    2.7434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5112   -2.8169    1.5563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0653   -2.1788    0.2976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3299   -2.7442   -0.7549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3231   -0.8888    0.3974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7810   -0.5114    1.6431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0800    0.7087    1.7424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9214    1.5367    0.6345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2233    2.7021    0.8285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0503    3.5574   -0.2471 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7227    4.7946    0.0884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5236    3.3162   -1.4773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2744    2.0774   -1.7273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7236    1.8170   -2.8377 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4627    1.1641   -0.5902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1686   -0.0431   -0.7178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7326   -0.3929   -1.9174 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9112   -1.4055    2.8644 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5649   -2.0746    3.1786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2503   -0.5652    3.9750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0466   -4.8942    3.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3166   -3.6217    3.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5346   -4.3095    5.0192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2538   -3.5924    1.4219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6607    1.0163    2.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2079    5.3607    0.8713 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8444    5.4526   -0.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7204    4.5293    0.4526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3858    3.9883   -2.3145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5206    0.2838   -2.5977 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2162   -1.3301    3.3734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6280   -2.6874    4.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2257   -2.7136    2.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6790   -1.1514    4.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  2  0  0  0  0
  3  4  2  0  0  0  0
  3 20  1  0  0  0  0
 10 11  1  0  0  0  0
 17 15  1  0  0  0  0
 15 14  1  0  0  0  0
 14 12  2  0  0  0  0
 12 11  1  0  0  0  0
  4  5  1  0  0  0  0
 15 16  2  0  0  0  0
  8  9  1  0  0  0  0
 18 19  1  0  0  0  0
  7 18  1  0  0  0  0
  5  6  2  0  0  0  0
 18 17  2  0  0  0  0
 20 22  1  0  0  0  0
 10  9  2  0  0  0  0
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 10 17  1  0  0  0  0
  3  2  1  0  0  0  0
  5  7  1  0  0  0  0
  2  1  1  0  0  0  0
  8 20  1  0  0  0  0
 20 21  1  0  0  0  0
  4 26  1  0  0  0  0
  9 27  1  0  0  0  0
 14 31  1  0  0  0  0
 19 32  1  0  0  0  0
 22 36  1  0  0  0  0
 13 28  1  0  0  0  0
 13 29  1  0  0  0  0
 13 30  1  0  0  0  0
  1 23  1  0  0  0  0
  1 24  1  0  0  0  0
  1 25  1  0  0  0  0
 21 33  1  0  0  0  0
 21 34  1  0  0  0  0
 21 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0025854

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2C(=O)C([H])=C(OC2=C([H])C2=C1C(=O)C([H])=C(OC([H])([H])[H])[C@@]2(O[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C16H14O6/c1-7-4-9(17)14-11(22-7)5-8-13(15(14)19)10(18)6-12(21-3)16(8,2)20/h4-6,19-20H,1-3H3/t16-/m1/s1

> <INCHI_KEY>
BBYBQQJQBBMKBQ-MRXNPFEDSA-N

> <FORMULA>
C16H14O6

> <MOLECULAR_WEIGHT>
302.282

> <EXACT_MASS>
302.079038171

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
30.423066419045274

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9R)-5,9-dihydroxy-8-methoxy-2,9-dimethyl-4H,6H,9H-cyclohexa[g]chromene-4,6-dione

> <ALOGPS_LOGP>
1.73

> <JCHEM_LOGP>
1.8213438413333327

> <ALOGPS_LOGS>
-3.03

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.805414285694933

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.560146319011021

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8050219583287275

> <JCHEM_POLAR_SURFACE_AREA>
93.06

> <JCHEM_REFRACTIVITY>
81.09330000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.83e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9R)-5,9-dihydroxy-8-methoxy-2,9-dimethylcyclohexa[g]chromene-4,6-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 36 38  0  0  0  0  0  0  0  0999 V2000
   -4.3713   -4.0104    3.9796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3632   -3.0035    3.9682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9946   -2.4657    2.7434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5112   -2.8169    1.5563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0653   -2.1788    0.2976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3299   -2.7442   -0.7549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3231   -0.8888    0.3974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7810   -0.5114    1.6431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0800    0.7087    1.7424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9214    1.5367    0.6345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2233    2.7021    0.8285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0503    3.5574   -0.2471 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7227    4.7946    0.0884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5236    3.3162   -1.4773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2744    2.0774   -1.7273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7236    1.8170   -2.8377 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4627    1.1641   -0.5902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1686   -0.0431   -0.7178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7326   -0.3929   -1.9174 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9112   -1.4055    2.8644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5649   -2.0746    3.1786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2503   -0.5652    3.9750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0466   -4.8942    3.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3166   -3.6217    3.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5346   -4.3095    5.0192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2538   -3.5924    1.4219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6607    1.0163    2.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2079    5.3607    0.8713 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8444    5.4526   -0.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7204    4.5293    0.4526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3858    3.9883   -2.3145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5206    0.2838   -2.5977 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2162   -1.3301    3.3734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6280   -2.6874    4.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2257   -2.7136    2.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6790   -1.1514    4.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  2  0
  3  4  2  0
  3 20  1  0
 10 11  1  0
 17 15  1  0
 15 14  1  0
 14 12  2  0
 12 11  1  0
  4  5  1  0
 15 16  2  0
  8  9  1  0
 18 19  1  0
  7 18  1  0
  5  6  2  0
 18 17  2  0
 20 22  1  0
 10  9  2  0
 12 13  1  0
 10 17  1  0
  3  2  1  0
  5  7  1  0
  2  1  1  0
  8 20  1  0
 20 21  1  0
  4 26  1  0
  9 27  1  0
 14 31  1  0
 19 32  1  0
 22 36  1  0
 13 28  1  0
 13 29  1  0
 13 30  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
 21 33  1  0
 21 34  1  0
 21 35  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      -4.371  -4.010   3.980  0.00  0.00           C+0
HETATM    2  O   UNK     0      -3.363  -3.003   3.968  0.00  0.00           O+0
HETATM    3  C   UNK     0      -2.995  -2.466   2.743  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.511  -2.817   1.556  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.065  -2.179   0.298  0.00  0.00           C+0
HETATM    6  O   UNK     0      -3.330  -2.744  -0.755  0.00  0.00           O+0
HETATM    7  C   UNK     0      -2.323  -0.889   0.397  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.781  -0.511   1.643  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.080   0.709   1.742  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.921   1.537   0.635  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.223   2.702   0.829  0.00  0.00           O+0
HETATM   12  C   UNK     0      -0.050   3.557  -0.247  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.723   4.795   0.088  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.524   3.316  -1.477  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.274   2.077  -1.727  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.724   1.817  -2.838  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.463   1.164  -0.590  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.169  -0.043  -0.718  0.00  0.00           C+0
HETATM   19  O   UNK     0      -2.733  -0.393  -1.917  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.911  -1.406   2.864  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.565  -2.075   3.179  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.250  -0.565   3.975  0.00  0.00           O+0
HETATM   23  H   UNK     0      -4.047  -4.894   3.421  0.00  0.00           H+0
HETATM   24  H   UNK     0      -5.317  -3.622   3.588  0.00  0.00           H+0
HETATM   25  H   UNK     0      -4.535  -4.309   5.019  0.00  0.00           H+0
HETATM   26  H   UNK     0      -4.254  -3.592   1.422  0.00  0.00           H+0
HETATM   27  H   UNK     0      -0.661   1.016   2.700  0.00  0.00           H+0
HETATM   28  H   UNK     0       0.208   5.361   0.871  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.844   5.453  -0.778  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.720   4.529   0.453  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.386   3.988  -2.314  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.521   0.284  -2.598  0.00  0.00           H+0
HETATM   33  H   UNK     0       0.216  -1.330   3.373  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.628  -2.687   4.086  0.00  0.00           H+0
HETATM   35  H   UNK     0      -0.226  -2.714   2.355  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.679  -1.151   4.627  0.00  0.00           H+0
CONECT    1    2   23   24   25                                             
CONECT    2    3    1                                                       
CONECT    3    4   20    2                                                  
CONECT    4    3    5   26                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    8   18    5                                                  
CONECT    8    7    9   20                                                  
CONECT    9    8   10   27                                                  
CONECT   10   11    9   17                                                  
CONECT   11   10   12                                                       
CONECT   12   14   11   13                                                  
CONECT   13   12   28   29   30                                             
CONECT   14   15   12   31                                                  
CONECT   15   17   14   16                                                  
CONECT   16   15                                                            
CONECT   17   15   18   10                                                  
CONECT   18   19    7   17                                                  
CONECT   19   18   32                                                       
CONECT   20    3   22    8   21                                             
CONECT   21   20   33   34   35                                             
CONECT   22   20   36                                                       
CONECT   23    1                                                            
CONECT   24    1                                                            
CONECT   25    1                                                            
CONECT   26    4                                                            
CONECT   27    9                                                            
CONECT   28   13                                                            
CONECT   29   13                                                            
CONECT   30   13                                                            
CONECT   31   14                                                            
CONECT   32   19                                                            
CONECT   33   21                                                            
CONECT   34   21                                                            
CONECT   35   21                                                            
CONECT   36   22                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

RDKit          3D

36 38  0  0  0  0  0  0  0  0999 V2000
   -4.3713   -4.0104    3.9796 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3632   -3.0035    3.9682 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9946   -2.4657    2.7434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5112   -2.8169    1.5563 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0653   -2.1788    0.2976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3299   -2.7442   -0.7549 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3231   -0.8888    0.3974 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7810   -0.5114    1.6431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0800    0.7087    1.7424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9214    1.5367    0.6345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2233    2.7021    0.8285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0503    3.5574   -0.2471 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7227    4.7946    0.0884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5236    3.3162   -1.4773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2744    2.0774   -1.7273 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7236    1.8170   -2.8377 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4627    1.1641   -0.5902 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1686   -0.0431   -0.7178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7326   -0.3929   -1.9174 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9112   -1.4055    2.8644 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5649   -2.0746    3.1786 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2503   -0.5652    3.9750 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0466   -4.8942    3.4212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3166   -3.6217    3.5877 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5346   -4.3095    5.0192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2538   -3.5924    1.4219 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6607    1.0163    2.7002 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2079    5.3607    0.8713 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8444    5.4526   -0.7783 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7204    4.5293    0.4526 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3858    3.9883   -2.3145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5206    0.2838   -2.5977 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2162   -1.3301    3.3734 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6280   -2.6874    4.0860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2257   -2.7136    2.3552 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6790   -1.1514    4.6266 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  2  0
  3  4  2  0
  3 20  1  0
 10 11  1  0
 17 15  1  0
 15 14  1  0
 14 12  2  0
 12 11  1  0
  4  5  1  0
 15 16  2  0
  8  9  1  0
 18 19  1  0
  7 18  1  0
  5  6  2  0
 18 17  2  0
 20 22  1  0
 10  9  2  0
 12 13  1  0
 10 17  1  0
  3  2  1  0
  5  7  1  0
  2  1  1  0
  8 20  1  0
 20 21  1  0
  4 26  1  0
  9 27  1  0
 14 31  1  0
 19 32  1  0
 22 36  1  0
 13 28  1  0
 13 29  1  0
 13 30  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
 21 33  1  0
 21 34  1  0
 21 35  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₆H₁₄O₆

Average Mass

302.2820 Da

Monoisotopic Mass

302.07904 Da

IUPAC Name

(9R)-5,9-dihydroxy-8-methoxy-2,9-dimethyl-4H,6H,9H-cyclohexa[g]chromene-4,6-dione

Traditional Name

(9R)-5,9-dihydroxy-8-methoxy-2,9-dimethylcyclohexa[g]chromene-4,6-dione

CAS Registry Number

Not Available

SMILES

[H]OC1=C2C(=O)C([H])=C(OC2=C([H])C2=C1C(=O)C([H])=C(OC([H])([H])[H])[C@@]2(O[H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C16H14O6/c1-7-4-9(17)14-11(22-7)5-8-13(15(14)19)10(18)6-12(21-3)16(8,2)20/h4-6,19-20H,1-3H3/t16-/m1/s1

InChI Key

BBYBQQJQBBMKBQ-MRXNPFEDSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, DMSO-d6, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cassia quinquangulata	JEOL database	Li, X.-C., et al, J. Nat. Prod. 64, 1153 (2001)

Chemical Taxonomy

Classification

Not classified

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	1.73	ALOGPS
logP	1.82	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	6.56	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	81.09 m³·mol⁻¹	ChemAxon
Polarizability	30.42 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

Not Available

References

General References

Li, X.-C., et al. (2001). Li, X.-C., et al, J. Nat. Prod. 64, 1153 (2001). J. Nat. Prod..

Showing NP-Card for Quinquangulone (NP0025854)

MOL for NP0025854 (Quinquangulone)

3D MOL for NP0025854 (Quinquangulone)

3D SDF for NP0025854 (Quinquangulone)

3D-SDF for NP0025854 (Quinquangulone)

PDB for NP0025854 (Quinquangulone)

3D PDB for NP0025854 (Quinquangulone)

SMILES for NP0025854 (Quinquangulone)

INCHI for NP0025854 (Quinquangulone)

Structure for NP0025854 (Quinquangulone)

3D Structure for NP0025854 (Quinquangulone)