NP-MRD: Showing NP-Card for 5,7-dihydroxy-3', 4'-dimethoxyspiro{2H-1- (NP0030677)

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Record Information

Version

2.0

Created at

2021-06-19 21:58:06 UTC

Updated at

2021-06-29 23:58:48 UTC

NP-MRD ID

NP0030677

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,7-dihydroxy-3', 4'-dimethoxyspiro{2H-1-

Provided By

JEOL Database JEOL Logo

Description

5,7-dihydroxy-3', 4'-dimethoxyspiro{2H-1- is found in Ledebouria graminifolia. 5,7-dihydroxy-3', 4'-dimethoxyspiro{2H-1- was first documented in 2003 (Mutanyatta, J., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192123583D          

 40 43  0  0  0  0            999 V2000
    4.0636   -2.0331    1.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0007   -1.7011    2.1492 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7715   -1.4387    1.5919 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5245   -1.4109    0.2122 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2429   -1.1303   -0.2003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7729   -0.8859    0.6877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743   -0.8984    2.0504 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7174   -1.1793    2.5154 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0644   -1.2237    3.8449 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0365   -1.0026    4.7997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8069   -0.6689   -0.3957 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3649    0.7418   -0.4586 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2688    0.9927    0.6273 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2780    0.0740    0.7482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4263    0.5190    1.4048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5024   -0.3459    1.5825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6059    0.1381    2.2203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4495   -1.6579    1.1244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2950   -2.1083    0.4882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2978   -3.4147    0.0775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2033   -1.2490    0.3020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9505   -1.7180   -0.3265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9081   -2.8806   -0.7383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6308   -0.9550   -1.4091 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8347   -2.9365    0.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3052   -1.1935    0.6079 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9491   -2.2423    1.8758 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2911   -1.5981   -0.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4058   -0.6895    2.7111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4809   -1.0899    5.7959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3767    0.0072    4.7081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7488   -1.7614    4.7189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5703    1.4949   -0.3975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8940    0.9176   -1.4045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4870    1.5404    1.7714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2709   -0.5689    2.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2826   -2.3406    1.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4227   -3.6080   -0.3311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3760   -0.1176   -2.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7645   -1.8439   -2.0360 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
  5  4  1  0  0  0  0
 16 18  2  0  0  0  0
  4  3  2  0  0  0  0
 14 15  2  0  0  0  0
  3  8  1  0  0  0  0
 15 16  1  0  0  0  0
  8  7  2  0  0  0  0
  7  6  1  0  0  0  0
 14 13  1  0  0  0  0
  8  9  1  0  0  0  0
  5  6  2  0  0  0  0
 21 22  1  0  0  0  0
 22 11  1  0  0  0  0
 11 12  1  0  0  0  0
 24  5  1  0  0  0  0
 12 13  1  0  0  0  0
  9 10  1  0  0  0  0
 14 21  1  0  0  0  0
  3  2  1  0  0  0  0
 22 23  2  0  0  0  0
  2  1  1  0  0  0  0
 11  6  1  0  0  0  0
 11 24  1  0  0  0  0
 18 37  1  0  0  0  0
 15 35  1  0  0  0  0
 12 33  1  0  0  0  0
 12 34  1  0  0  0  0
 17 36  1  0  0  0  0
 20 38  1  0  0  0  0
  4 28  1  0  0  0  0
  7 29  1  0  0  0  0
 24 39  1  0  0  0  0
 24 40  1  0  0  0  0
 10 30  1  0  0  0  0
 10 31  1  0  0  0  0
 10 32  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
M  END

     RDKit          3D

 40 43  0  0  0  0  0  0  0  0999 V2000
    4.0636   -2.0331    1.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0007   -1.7011    2.1492 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7715   -1.4387    1.5919 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5245   -1.4109    0.2122 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2429   -1.1303   -0.2003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7729   -0.8859    0.6877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743   -0.8984    2.0504 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7174   -1.1793    2.5154 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0644   -1.2237    3.8449 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0365   -1.0026    4.7997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8069   -0.6689   -0.3957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3649    0.7418   -0.4586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2688    0.9927    0.6273 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2780    0.0740    0.7482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4263    0.5190    1.4048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5024   -0.3459    1.5825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6059    0.1381    2.2203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4495   -1.6579    1.1244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2950   -2.1083    0.4882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2978   -3.4147    0.0775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2033   -1.2490    0.3020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9505   -1.7180   -0.3265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9081   -2.8806   -0.7383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6308   -0.9550   -1.4091 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8347   -2.9365    0.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3052   -1.1935    0.6079 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9491   -2.2423    1.8758 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2911   -1.5981   -0.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4058   -0.6895    2.7111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4809   -1.0899    5.7959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3767    0.0072    4.7081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7488   -1.7614    4.7189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5703    1.4949   -0.3975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8940    0.9176   -1.4045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4870    1.5404    1.7714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2709   -0.5689    2.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2826   -2.3406    1.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4227   -3.6080   -0.3311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3760   -0.1176   -2.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7645   -1.8439   -2.0360 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0
 18 19  1  0
 19 20  1  0
 19 21  2  0
  5  4  1  0
 16 18  2  0
  4  3  2  0
 14 15  2  0
  3  8  1  0
 15 16  1  0
  8  7  2  0
  7  6  1  0
 14 13  1  0
  8  9  1  0
  5  6  2  0
 21 22  1  0
 22 11  1  0
 11 12  1  0
 24  5  1  0
 12 13  1  0
  9 10  1  0
 14 21  1  0
  3  2  1  0
 22 23  2  0
  2  1  1  0
 11  6  1  0
 11 24  1  0
 18 37  1  0
 15 35  1  0
 12 33  1  0
 12 34  1  0
 17 36  1  0
 20 38  1  0
  4 28  1  0
  7 29  1  0
 24 39  1  0
 24 40  1  0
 10 30  1  0
 10 31  1  0
 10 32  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
M  END


  Mrv1652306192123583D          

 40 43  0  0  0  0            999 V2000
    4.0636   -2.0331    1.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0007   -1.7011    2.1492 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7715   -1.4387    1.5919 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5245   -1.4109    0.2122 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2429   -1.1303   -0.2003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7729   -0.8859    0.6877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743   -0.8984    2.0504 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7174   -1.1793    2.5154 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0644   -1.2237    3.8449 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0365   -1.0026    4.7997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8069   -0.6689   -0.3957 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3649    0.7418   -0.4586 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.2688    0.9927    0.6273 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2780    0.0740    0.7482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4263    0.5190    1.4048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5024   -0.3459    1.5825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6059    0.1381    2.2203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4495   -1.6579    1.1244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2950   -2.1083    0.4882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2978   -3.4147    0.0775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2033   -1.2490    0.3020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9505   -1.7180   -0.3265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9081   -2.8806   -0.7383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6308   -0.9550   -1.4091 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8347   -2.9365    0.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3052   -1.1935    0.6079 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9491   -2.2423    1.8758 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2911   -1.5981   -0.5280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4058   -0.6895    2.7111 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4809   -1.0899    5.7959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3767    0.0072    4.7081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7488   -1.7614    4.7189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5703    1.4949   -0.3975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8940    0.9176   -1.4045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4870    1.5404    1.7714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2709   -0.5689    2.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2826   -2.3406    1.2589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4227   -3.6080   -0.3311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3760   -0.1176   -2.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7645   -1.8439   -2.0360 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
  5  4  1  0  0  0  0
 16 18  2  0  0  0  0
  4  3  2  0  0  0  0
 14 15  2  0  0  0  0
  3  8  1  0  0  0  0
 15 16  1  0  0  0  0
  8  7  2  0  0  0  0
  7  6  1  0  0  0  0
 14 13  1  0  0  0  0
  8  9  1  0  0  0  0
  5  6  2  0  0  0  0
 21 22  1  0  0  0  0
 22 11  1  0  0  0  0
 11 12  1  0  0  0  0
 24  5  1  0  0  0  0
 12 13  1  0  0  0  0
  9 10  1  0  0  0  0
 14 21  1  0  0  0  0
  3  2  1  0  0  0  0
 22 23  2  0  0  0  0
  2  1  1  0  0  0  0
 11  6  1  0  0  0  0
 11 24  1  0  0  0  0
 18 37  1  0  0  0  0
 15 35  1  0  0  0  0
 12 33  1  0  0  0  0
 12 34  1  0  0  0  0
 17 36  1  0  0  0  0
 20 38  1  0  0  0  0
  4 28  1  0  0  0  0
  7 29  1  0  0  0  0
 24 39  1  0  0  0  0
 24 40  1  0  0  0  0
 10 30  1  0  0  0  0
 10 31  1  0  0  0  0
 10 32  1  0  0  0  0
  1 25  1  0  0  0  0
  1 26  1  0  0  0  0
  1 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0030677

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(O[H])=C2C(OC([H])([H])[C@@]3(C4=C(C([H])=C(OC([H])([H])[H])C(OC([H])([H])[H])=C4[H])C3([H])[H])C2=O)=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C18H16O6/c1-22-13-3-9-7-18(11(9)6-14(13)23-2)8-24-15-5-10(19)4-12(20)16(15)17(18)21/h3-6,19-20H,7-8H2,1-2H3/t18-/m0/s1

> <INCHI_KEY>
MKPGLCWEMPNQKG-SFHVURJKSA-N

> <FORMULA>
C18H16O6

> <MOLECULAR_WEIGHT>
328.32

> <EXACT_MASS>
328.094688235

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
33.81090104005372

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3R)-5,7-dihydroxy-3',4'-dimethoxy-2,4-dihydrospiro[1-benzopyran-3,7'-bicyclo[4.2.0]octane]-1'(6'),2',4'-trien-4-one

> <ALOGPS_LOGP>
2.70

> <JCHEM_LOGP>
2.877022028

> <ALOGPS_LOGS>
-3.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.475688325541475

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.837948665261201

> <JCHEM_PKA_STRONGEST_BASIC>
-4.425348081389533

> <JCHEM_POLAR_SURFACE_AREA>
85.22

> <JCHEM_REFRACTIVITY>
85.76099999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.52e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-5,7-dihydroxy-3',4'-dimethoxy-2H-spiro[1-benzopyran-3,7'-bicyclo[4.2.0]octane]-1'(6'),2',4'-trien-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 40 43  0  0  0  0  0  0  0  0999 V2000
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    3.0007   -1.7011    2.1492 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7715   -1.4387    1.5919 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5245   -1.4109    0.2122 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0365   -1.0026    4.7997 C   0  0  0  0  0  0  0  0  0  0  0  0
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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       4.064  -2.033   1.268  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.001  -1.701   2.149  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.772  -1.439   1.592  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.525  -1.411   0.212  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.243  -1.130  -0.200  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.773  -0.886   0.688  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.574  -0.898   2.050  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.717  -1.179   2.515  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.064  -1.224   3.845  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.037  -1.003   4.800  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.807  -0.669  -0.396  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.365   0.742  -0.459  0.00  0.00           C+0
HETATM   13  O   UNK     0      -3.269   0.993   0.627  0.00  0.00           O+0
HETATM   14  C   UNK     0      -4.278   0.074   0.748  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.426   0.519   1.405  0.00  0.00           C+0
HETATM   16  C   UNK     0      -6.502  -0.346   1.583  0.00  0.00           C+0
HETATM   17  O   UNK     0      -7.606   0.138   2.220  0.00  0.00           O+0
HETATM   18  C   UNK     0      -6.449  -1.658   1.124  0.00  0.00           C+0
HETATM   19  C   UNK     0      -5.295  -2.108   0.488  0.00  0.00           C+0
HETATM   20  O   UNK     0      -5.298  -3.415   0.078  0.00  0.00           O+0
HETATM   21  C   UNK     0      -4.203  -1.249   0.302  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.950  -1.718  -0.327  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.908  -2.881  -0.738  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.631  -0.955  -1.409  0.00  0.00           C+0
HETATM   25  H   UNK     0       3.835  -2.937   0.693  0.00  0.00           H+0
HETATM   26  H   UNK     0       4.305  -1.194   0.608  0.00  0.00           H+0
HETATM   27  H   UNK     0       4.949  -2.242   1.876  0.00  0.00           H+0
HETATM   28  H   UNK     0       2.291  -1.598  -0.528  0.00  0.00           H+0
HETATM   29  H   UNK     0      -1.406  -0.690   2.711  0.00  0.00           H+0
HETATM   30  H   UNK     0       0.481  -1.090   5.796  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.377   0.007   4.708  0.00  0.00           H+0
HETATM   32  H   UNK     0      -0.749  -1.761   4.719  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.570   1.495  -0.398  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.894   0.918  -1.405  0.00  0.00           H+0
HETATM   35  H   UNK     0      -5.487   1.540   1.771  0.00  0.00           H+0
HETATM   36  H   UNK     0      -8.271  -0.569   2.278  0.00  0.00           H+0
HETATM   37  H   UNK     0      -7.283  -2.341   1.259  0.00  0.00           H+0
HETATM   38  H   UNK     0      -4.423  -3.608  -0.331  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.376  -0.118  -2.069  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.765  -1.844  -2.036  0.00  0.00           H+0
CONECT    1    2   25   26   27                                             
CONECT    2    3    1                                                       
CONECT    3    4    8    2                                                  
CONECT    4    5    3   28                                                  
CONECT    5    4    6   24                                                  
CONECT    6    7    5   11                                                  
CONECT    7    8    6   29                                                  
CONECT    8    3    7    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   30   31   32                                             
CONECT   11   22   12    6   24                                             
CONECT   12   11   13   33   34                                             
CONECT   13   14   12                                                       
CONECT   14   15   13   21                                                  
CONECT   15   14   16   35                                                  
CONECT   16   17   18   15                                                  
CONECT   17   16   36                                                       
CONECT   18   19   16   37                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19   38                                                       
CONECT   21   19   22   14                                                  
CONECT   22   21   11   23                                                  
CONECT   23   22                                                            
CONECT   24    5   11   39   40                                             
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    4                                                            
CONECT   29    7                                                            
CONECT   30   10                                                            
CONECT   31   10                                                            
CONECT   32   10                                                            
CONECT   33   12                                                            
CONECT   34   12                                                            
CONECT   35   15                                                            
CONECT   36   17                                                            
CONECT   37   18                                                            
CONECT   38   20                                                            
CONECT   39   24                                                            
CONECT   40   24                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   86    0
END

RDKit          3D

40 43  0  0  0  0  0  0  0  0999 V2000
    4.0636   -2.0331    1.2679 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0007   -1.7011    2.1492 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7715   -1.4387    1.5919 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5245   -1.4109    0.2122 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2429   -1.1303   -0.2003 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7729   -0.8859    0.6877 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743   -0.8984    2.0504 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7174   -1.1793    2.5154 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0644   -1.2237    3.8449 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0365   -1.0026    4.7997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8069   -0.6689   -0.3957 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.5024   -0.3459    1.5825 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6059    0.1381    2.2203 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4495   -1.6579    1.1244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2950   -2.1083    0.4882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2978   -3.4147    0.0775 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2033   -1.2490    0.3020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9505   -1.7180   -0.3265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9081   -2.8806   -0.7383 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6308   -0.9550   -1.4091 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8347   -2.9365    0.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3052   -1.1935    0.6079 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4809   -1.0899    5.7959 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8940    0.9176   -1.4045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4870    1.5404    1.7714 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.4227   -3.6080   -0.3311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3760   -0.1176   -2.0692 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7645   -1.8439   -2.0360 H   0  0  0  0  0  0  0  0  0  0  0  0
 16 17  1  0
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 24  5  1  0
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  4 28  1  0
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  1 25  1  0
  1 26  1  0
  1 27  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₈H₁₆O₆

Average Mass

328.3200 Da

Monoisotopic Mass

328.09469 Da

IUPAC Name

(3R)-5,7-dihydroxy-3',4'-dimethoxy-2,4-dihydrospiro[1-benzopyran-3,7'-bicyclo[4.2.0]octane]-1'(6'),2',4'-trien-4-one

Traditional Name

(3R)-5,7-dihydroxy-3',4'-dimethoxy-2H-spiro[1-benzopyran-3,7'-bicyclo[4.2.0]octane]-1'(6'),2',4'-trien-4-one

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C(O[H])=C2C(OC([H])([H])[C@@]3(C4=C(C([H])=C(OC([H])([H])[H])C(OC([H])([H])[H])=C4[H])C3([H])[H])C2=O)=C1[H]

InChI Identifier

InChI=1S/C18H16O6/c1-22-13-3-9-7-18(11(9)6-14(13)23-2)8-24-15-5-10(19)4-12(20)16(15)17(18)21/h3-6,19-20H,7-8H2,1-2H3/t18-/m0/s1

InChI Key

MKPGLCWEMPNQKG-SFHVURJKSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, 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
Ledebouria graminifolia	JEOL database	Mutanyatta, J., et al., Phytochemistry 62, 797 (2003)

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	2.7	ALOGPS
logP	2.88	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	7.84	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	85.76 m³·mol⁻¹	ChemAxon
Polarizability	33.81 Å³	ChemAxon
Number of Rings	4	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

Mutanyatta, J., et al. (2003). Mutanyatta, J., et al., Phytochemistry 62, 797 (2003). Phytochem..

Showing NP-Card for 5,7-dihydroxy-3', 4'-dimethoxyspiro{2H-1- (NP0030677)

MOL for NP0030677 (5,7-dihydroxy-3', 4'-dimethoxyspiro{2H-1-)

3D MOL for NP0030677 (5,7-dihydroxy-3', 4'-dimethoxyspiro{2H-1-)

3D SDF for NP0030677 (5,7-dihydroxy-3', 4'-dimethoxyspiro{2H-1-)

3D-SDF for NP0030677 (5,7-dihydroxy-3', 4'-dimethoxyspiro{2H-1-)

PDB for NP0030677 (5,7-dihydroxy-3', 4'-dimethoxyspiro{2H-1-)

3D PDB for NP0030677 (5,7-dihydroxy-3', 4'-dimethoxyspiro{2H-1-)

SMILES for NP0030677 (5,7-dihydroxy-3', 4'-dimethoxyspiro{2H-1-)

INCHI for NP0030677 (5,7-dihydroxy-3', 4'-dimethoxyspiro{2H-1-)

Structure for NP0030677 (5,7-dihydroxy-3', 4'-dimethoxyspiro{2H-1-)

3D Structure for NP0030677 (5,7-dihydroxy-3', 4'-dimethoxyspiro{2H-1-)