NP-MRD: Showing NP-Card for Betulinan A (NP0023323)

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Record Information

Version

2.0

Created at

2021-01-06 08:25:21 UTC

Updated at

2021-07-15 17:41:27 UTC

NP-MRD ID

NP0023323

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Betulinan A

Provided By

NPAtlas

Description

Betulinan A is found in Cylindropuntia versicolor, Lenzites and Lenzites betulinus. Based on a literature review very few articles have been published on 2,5-dimethoxy-3,6-diphenylcyclohexa-2,5-diene-1,4-dione.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI

  Mrv1652306242105413D          

 40 42  0  0  0  0            999 V2000
    1.6895   -3.1220   -1.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6654   -1.7264   -1.4277 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8676   -0.8609   -0.7037 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4585    0.0992   -0.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9108    0.2438   -0.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6285    0.1948   -1.1822 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0005    0.3073   -1.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7120    0.4758   -0.0339 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0153    0.5289    1.1643 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6191    0.4110    1.1496 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6012    1.0013    0.7372 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1424    1.9402    1.4134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8492    0.8573    0.7291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6621    1.7514    1.4596 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6431    3.1404    1.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4683   -0.0937    0.0497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9058   -0.2154    0.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5911   -0.5616   -1.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9447   -0.7101   -1.1874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6953   -0.5084   -0.0510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0914   -0.1652    1.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6954   -0.0233    1.1731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5713   -0.9971   -0.7035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270   -1.9195   -1.3666 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0336   -3.2564   -0.0766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6368   -3.5275   -1.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3402   -3.6661   -1.8688 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0422    0.0611   -2.1084 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5082    0.2691   -2.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8047    0.5700   -0.0186 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5668    0.6561    2.0616 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0962    0.4523    2.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9620    3.3365    0.0834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6014    3.4980    1.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3666    3.6515    1.8221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9800   -0.7089   -1.9878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4306   -0.9817   -2.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7898   -0.6393   -0.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6927   -0.0032    2.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2717    0.2405    2.1286 H   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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  4 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 16 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23  3  1  0  0  0  0
 10  5  1  0  0  0  0
 22 17  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
  6 28  1  0  0  0  0
  7 29  1  0  0  0  0
  8 30  1  0  0  0  0
  9 31  1  0  0  0  0
 10 32  1  0  0  0  0
 15 33  1  0  0  0  0
 15 34  1  0  0  0  0
 15 35  1  0  0  0  0
 18 36  1  0  0  0  0
 19 37  1  0  0  0  0
 20 38  1  0  0  0  0
 21 39  1  0  0  0  0
 22 40  1  0  0  0  0
M  END

     RDKit          3D

 40 42  0  0  0  0  0  0  0  0999 V2000
    1.6895   -3.1220   -1.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6654   -1.7264   -1.4277 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8676   -0.8609   -0.7037 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4585    0.0992   -0.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9108    0.2438   -0.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6285    0.1948   -1.1822 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0005    0.3073   -1.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7120    0.4758   -0.0339 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0153    0.5289    1.1643 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6191    0.4110    1.1496 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6012    1.0013    0.7372 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1424    1.9402    1.4134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8492    0.8573    0.7291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6621    1.7514    1.4596 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6431    3.1404    1.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4683   -0.0937    0.0497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9058   -0.2154    0.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5911   -0.5616   -1.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9447   -0.7101   -1.1874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6953   -0.5084   -0.0510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0914   -0.1652    1.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6954   -0.0233    1.1731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5713   -0.9971   -0.7035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270   -1.9195   -1.3666 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0336   -3.2564   -0.0766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6368   -3.5275   -1.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3402   -3.6661   -1.8688 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0422    0.0611   -2.1084 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5082    0.2691   -2.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8047    0.5700   -0.0186 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5668    0.6561    2.0616 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0962    0.4523    2.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9620    3.3365    0.0834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6014    3.4980    1.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3666    3.6515    1.8221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9800   -0.7089   -1.9878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4306   -0.9817   -2.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7898   -0.6393   -0.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6927   -0.0032    2.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2717    0.2405    2.1286 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  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  4 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 13 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 16 23  1  0
 23 24  2  0
 23  3  1  0
 10  5  1  0
 22 17  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 21 39  1  0
 22 40  1  0
M  END

  Mrv1652306242105413D          

 40 42  0  0  0  0            999 V2000
    1.6895   -3.1220   -1.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6654   -1.7264   -1.4277 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8676   -0.8609   -0.7037 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4585    0.0992   -0.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9108    0.2438   -0.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6285    0.1948   -1.1822 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0005    0.3073   -1.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7120    0.4758   -0.0339 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0153    0.5289    1.1643 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6191    0.4110    1.1496 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6012    1.0013    0.7372 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1424    1.9402    1.4134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8492    0.8573    0.7291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6621    1.7514    1.4596 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6431    3.1404    1.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4683   -0.0937    0.0497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9058   -0.2154    0.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5911   -0.5616   -1.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9447   -0.7101   -1.1874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6953   -0.5084   -0.0510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0914   -0.1652    1.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6954   -0.0233    1.1731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5713   -0.9971   -0.7035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270   -1.9195   -1.3666 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0336   -3.2564   -0.0766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6368   -3.5275   -1.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3402   -3.6661   -1.8688 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0422    0.0611   -2.1084 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5082    0.2691   -2.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8047    0.5700   -0.0186 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5668    0.6561    2.0616 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0962    0.4523    2.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9620    3.3365    0.0834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6014    3.4980    1.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3666    3.6515    1.8221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9800   -0.7089   -1.9878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4306   -0.9817   -2.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7898   -0.6393   -0.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6927   -0.0032    2.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2717    0.2405    2.1286 H   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  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  4 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 13 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 16 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23  3  1  0  0  0  0
 10  5  1  0  0  0  0
 22 17  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
  6 28  1  0  0  0  0
  7 29  1  0  0  0  0
  8 30  1  0  0  0  0
  9 31  1  0  0  0  0
 10 32  1  0  0  0  0
 15 33  1  0  0  0  0
 15 34  1  0  0  0  0
 15 35  1  0  0  0  0
 18 36  1  0  0  0  0
 19 37  1  0  0  0  0
 20 38  1  0  0  0  0
 21 39  1  0  0  0  0
 22 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0023323

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C(OC([H])([H])[H])C(=O)C(=C(OC([H])([H])[H])C1=O)C1=C([H])C([H])=C([H])C([H])=C1[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H16O4/c1-23-19-15(13-9-5-3-6-10-13)18(22)20(24-2)16(17(19)21)14-11-7-4-8-12-14/h3-12H,1-2H3

> <INCHI_KEY>
WEOWAYMMZVELOQ-UHFFFAOYSA-N

> <FORMULA>
C20H16O4

> <MOLECULAR_WEIGHT>
320.344

> <EXACT_MASS>
320.104858995

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
34.44245536850851

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,5-dimethoxy-3,6-diphenylcyclohexa-2,5-diene-1,4-dione

> <ALOGPS_LOGP>
3.84

> <JCHEM_LOGP>
3.548628818

> <ALOGPS_LOGS>
-4.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.666832704016988

> <JCHEM_POLAR_SURFACE_AREA>
52.6

> <JCHEM_REFRACTIVITY>
93.37020000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.56e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,5-dimethoxy-3,6-diphenylcyclohexa-2,5-diene-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 40 42  0  0  0  0  0  0  0  0999 V2000
    1.6895   -3.1220   -1.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6654   -1.7264   -1.4277 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8676   -0.8609   -0.7037 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4585    0.0992   -0.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9108    0.2438   -0.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6285    0.1948   -1.1822 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0005    0.3073   -1.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7120    0.4758   -0.0339 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0153    0.5289    1.1643 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6191    0.4110    1.1496 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6012    1.0013    0.7372 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1424    1.9402    1.4134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8492    0.8573    0.7291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6621    1.7514    1.4596 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6431    3.1404    1.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4683   -0.0937    0.0497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9058   -0.2154    0.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5911   -0.5616   -1.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9447   -0.7101   -1.1874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6953   -0.5084   -0.0510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0914   -0.1652    1.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6954   -0.0233    1.1731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5713   -0.9971   -0.7035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270   -1.9195   -1.3666 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0336   -3.2564   -0.0766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6368   -3.5275   -1.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3402   -3.6661   -1.8688 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0422    0.0611   -2.1084 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5082    0.2691   -2.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8047    0.5700   -0.0186 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5668    0.6561    2.0616 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0962    0.4523    2.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9620    3.3365    0.0834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6014    3.4980    1.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3666    3.6515    1.8221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9800   -0.7089   -1.9878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4306   -0.9817   -2.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7898   -0.6393   -0.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6927   -0.0032    2.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2717    0.2405    2.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
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  2  3  1  0
  3  4  2  0
  4  5  1  0
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  4 11  1  0
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 21 39  1  0
 22 40  1  0
M  END

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       1.690  -3.122  -1.138  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.665  -1.726  -1.428  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.868  -0.861  -0.704  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.458   0.099  -0.012  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.911   0.244  -0.012  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.628   0.195  -1.182  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.000   0.307  -1.206  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.712   0.476  -0.034  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.015   0.529   1.164  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.619   0.411   1.150  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.601   1.001   0.737  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.142   1.940   1.413  0.00  0.00           O+0
HETATM   13  C   UNK     0      -0.849   0.857   0.729  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.662   1.751   1.460  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.643   3.140   1.142  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.468  -0.094   0.050  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.906  -0.215   0.061  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.591  -0.562  -1.109  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.945  -0.710  -1.187  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.695  -0.508  -0.051  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.091  -0.165   1.133  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.695  -0.023   1.173  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.571  -0.997  -0.704  0.00  0.00           C+0
HETATM   24  O   UNK     0      -1.127  -1.920  -1.367  0.00  0.00           O+0
HETATM   25  H   UNK     0       2.034  -3.256  -0.077  0.00  0.00           H+0
HETATM   26  H   UNK     0       0.637  -3.527  -1.153  0.00  0.00           H+0
HETATM   27  H   UNK     0       2.340  -3.666  -1.869  0.00  0.00           H+0
HETATM   28  H   UNK     0       3.042   0.061  -2.108  0.00  0.00           H+0
HETATM   29  H   UNK     0       5.508   0.269  -2.143  0.00  0.00           H+0
HETATM   30  H   UNK     0       6.805   0.570  -0.019  0.00  0.00           H+0
HETATM   31  H   UNK     0       5.567   0.656   2.062  0.00  0.00           H+0
HETATM   32  H   UNK     0       3.096   0.452   2.087  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.962   3.337   0.083  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.601   3.498   1.295  0.00  0.00           H+0
HETATM   35  H   UNK     0      -2.367   3.652   1.822  0.00  0.00           H+0
HETATM   36  H   UNK     0      -2.980  -0.709  -1.988  0.00  0.00           H+0
HETATM   37  H   UNK     0      -5.431  -0.982  -2.110  0.00  0.00           H+0
HETATM   38  H   UNK     0      -6.790  -0.639  -0.130  0.00  0.00           H+0
HETATM   39  H   UNK     0      -5.693  -0.003   2.039  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.272   0.241   2.129  0.00  0.00           H+0
CONECT    1    2   25   26   27                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   23                                                  
CONECT    4    3    5   11                                                  
CONECT    5    4    6   10                                                  
CONECT    6    5    7   28                                                  
CONECT    7    6    8   29                                                  
CONECT    8    7    9   30                                                  
CONECT    9    8   10   31                                                  
CONECT   10    9    5   32                                                  
CONECT   11    4   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   16                                                  
CONECT   14   13   15                                                       
CONECT   15   14   33   34   35                                             
CONECT   16   13   17   23                                                  
CONECT   17   16   18   22                                                  
CONECT   18   17   19   36                                                  
CONECT   19   18   20   37                                                  
CONECT   20   19   21   38                                                  
CONECT   21   20   22   39                                                  
CONECT   22   21   17   40                                                  
CONECT   23   16   24    3                                                  
CONECT   24   23                                                            
CONECT   25    1                                                            
CONECT   26    1                                                            
CONECT   27    1                                                            
CONECT   28    6                                                            
CONECT   29    7                                                            
CONECT   30    8                                                            
CONECT   31    9                                                            
CONECT   32   10                                                            
CONECT   33   15                                                            
CONECT   34   15                                                            
CONECT   35   15                                                            
CONECT   36   18                                                            
CONECT   37   19                                                            
CONECT   38   20                                                            
CONECT   39   21                                                            
CONECT   40   22                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   84    0
END

RDKit          3D

40 42  0  0  0  0  0  0  0  0999 V2000
    1.6895   -3.1220   -1.1380 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6654   -1.7264   -1.4277 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8676   -0.8609   -0.7037 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4585    0.0992   -0.0119 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9108    0.2438   -0.0123 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6285    0.1948   -1.1822 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0005    0.3073   -1.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7120    0.4758   -0.0339 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0153    0.5289    1.1643 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6191    0.4110    1.1496 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6012    1.0013    0.7372 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1424    1.9402    1.4134 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8492    0.8573    0.7291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6621    1.7514    1.4596 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6431    3.1404    1.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4683   -0.0937    0.0497 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9058   -0.2154    0.0609 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5911   -0.5616   -1.1090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9447   -0.7101   -1.1874 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6953   -0.5084   -0.0510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0914   -0.1652    1.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6954   -0.0233    1.1731 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5713   -0.9971   -0.7035 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270   -1.9195   -1.3666 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0336   -3.2564   -0.0766 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6368   -3.5275   -1.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3402   -3.6661   -1.8688 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0422    0.0611   -2.1084 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5082    0.2691   -2.1427 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8047    0.5700   -0.0186 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5668    0.6561    2.0616 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0962    0.4523    2.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9620    3.3365    0.0834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6014    3.4980    1.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3666    3.6515    1.8221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9800   -0.7089   -1.9878 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4306   -0.9817   -2.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7898   -0.6393   -0.1295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6927   -0.0032    2.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2717    0.2405    2.1286 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  2  0
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 23  3  1  0
 10  5  1  0
 22 17  1  0
  1 25  1  0
  1 26  1  0
  1 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
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 10 32  1  0
 15 33  1  0
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 15 35  1  0
 18 36  1  0
 19 37  1  0
 20 38  1  0
 21 39  1  0
 22 40  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Not Available

Chemical Formula

C₂₀H₁₆O₄

Average Mass

320.3440 Da

Monoisotopic Mass

320.10486 Da

IUPAC Name

2,5-dimethoxy-3,6-diphenylcyclohexa-2,5-diene-1,4-dione

Traditional Name

2,5-dimethoxy-3,6-diphenylcyclohexa-2,5-diene-1,4-dione

CAS Registry Number

Not Available

SMILES

COC1=C(C(=O)C(OC)=C(C1=O)C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1S/C20H16O4/c1-23-19-15(13-9-5-3-6-10-13)18(22)20(24-2)16(17(19)21)14-11-7-4-8-12-14/h3-12H,1-2H3

InChI Key

WEOWAYMMZVELOQ-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Cylindropuntia versicolor	LOTUS Database	35616633
Lenzites	NPAtlas	8946751
Lenzites betulinus	LOTUS Database	35616633

Species Where Detected

Species Name	Source	Reference
Aspergillus terreus	KNApSAcK Database	22123792
Lenzites betulina	KNApSAcK Database	22123792

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as p-benzoquinones. These are benzoquinones where the two C=O groups are attached at the 1- and 4-positions, respectively.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

P-benzoquinones

Alternative Parents

Substituents

P-benzoquinone
Benzenoid
Monocyclic benzene moiety
Vinylogous ester
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	3.84	ALOGPS
logP	3.55	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	52.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	93.37 m³·mol⁻¹	ChemAxon
Polarizability	34.44 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

NPAtlas ID

NPA000698

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00043311

Chemspider ID

157077

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

180510

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Betulinan A (NP0023323)

MOL for NP0023323 (Betulinan A)

3D MOL for NP0023323 (Betulinan A)

3D SDF for NP0023323 (Betulinan A)

3D-SDF for NP0023323 (Betulinan A)

PDB for NP0023323 (Betulinan A)

3D PDB for NP0023323 (Betulinan A)

SMILES for NP0023323 (Betulinan A)

INCHI for NP0023323 (Betulinan A)

Structure for NP0023323 (Betulinan A)

3D Structure for NP0023323 (Betulinan A)