NP-MRD: Showing NP-Card for engelharquinone (NP0024730)

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Record Information

Version

2.0

Created at

2021-06-19 17:02:20 UTC

Updated at

2021-06-29 23:49:14 UTC

NP-MRD ID

NP0024730

Secondary Accession Numbers

None

Natural Product Identification

Common Name

engelharquinone

Provided By

JEOL Database JEOL Logo

Description

engelharquinone is found in Engelhardia roxburghiana. engelharquinone was first documented in 2007 (PMID: 17418287). Based on a literature review very few articles have been published on Engelharquinone (PMID: 28248526).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119023D          

 38 42  0  0  0  0            999 V2000
   -5.8762   -0.5326   -1.8311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7803   -0.0571   -2.0832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5562   -0.8293   -1.8882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3466   -0.3593   -2.2070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1367    0.9698   -2.7633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0146    1.3528   -3.0741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3375    1.8172   -2.9398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2162    3.1188   -3.4400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0188    3.6820   -3.7890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3459    3.9175   -3.6076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6084    3.4225   -3.2790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7432    2.1255   -2.7816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6095    1.3208   -2.6105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2945   -1.3799   -1.8937 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2240   -1.4098   -2.8082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1454   -2.6591   -2.0419 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4411   -2.2197   -1.3465 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1617   -2.1351    0.1553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0039   -2.3862    1.0129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7975   -1.6644    0.5706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4510   -1.5704    1.9208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3039   -1.8991    2.9375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1865   -1.1178    2.2843 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7354   -0.7503    1.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3993   -0.8331   -0.0518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8664   -1.2945   -0.4348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3010    3.0284   -3.6390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2414    4.9284   -3.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4881    4.0490   -3.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7326    1.7467   -2.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0517   -0.4888   -3.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3178   -2.9051   -3.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6801   -3.5392   -1.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2765   -2.8854   -1.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1652   -2.1686    2.5455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0810   -1.0481    3.3360 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7218   -0.3965    1.5947 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1346   -0.5410   -0.7993 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  2  0  0  0  0
 12 11  1  0  0  0  0
 11 10  2  0  0  0  0
 10  8  1  0  0  0  0
 20 26  2  0  0  0  0
 17 18  1  0  0  0  0
  4  5  1  0  0  0  0
  3  2  1  0  0  0  0
  2 13  1  0  0  0  0
  7  5  1  0  0  0  0
  7 13  1  0  0  0  0
 20 21  1  0  0  0  0
 26 25  1  0  0  0  0
 25 24  2  0  0  0  0
 24 23  1  0  0  0  0
 23 21  2  0  0  0  0
 14 26  1  0  0  0  0
  2  1  2  0  0  0  0
 18 20  1  0  0  0  0
  5  6  2  0  0  0  0
  4  3  2  0  0  0  0
  8  9  1  0  0  0  0
 18 19  2  0  0  0  0
  4 14  1  0  0  0  0
 21 22  1  0  0  0  0
  3 17  1  0  0  0  0
 14 15  1  6  0  0  0
  7  8  2  0  0  0  0
 17 16  1  0  0  0  0
 14 16  1  0  0  0  0
 17 34  1  1  0  0  0
 12 30  1  0  0  0  0
 11 29  1  0  0  0  0
 10 28  1  0  0  0  0
 25 38  1  0  0  0  0
 24 37  1  0  0  0  0
 23 36  1  0  0  0  0
  9 27  1  0  0  0  0
 22 35  1  0  0  0  0
 15 31  1  0  0  0  0
 16 32  1  0  0  0  0
 16 33  1  0  0  0  0
M  END

     RDKit          3D

 38 42  0  0  0  0  0  0  0  0999 V2000
   -5.8762   -0.5326   -1.8311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7803   -0.0571   -2.0832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5562   -0.8293   -1.8882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3466   -0.3593   -2.2070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1367    0.9698   -2.7633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0146    1.3528   -3.0741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3375    1.8172   -2.9398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2162    3.1188   -3.4400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0188    3.6820   -3.7890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3459    3.9175   -3.6076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6084    3.4225   -3.2790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7432    2.1255   -2.7816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6095    1.3208   -2.6105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2945   -1.3799   -1.8937 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2240   -1.4098   -2.8082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1454   -2.6591   -2.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4411   -2.2197   -1.3465 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1617   -2.1351    0.1553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0039   -2.3862    1.0129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7975   -1.6644    0.5706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4510   -1.5704    1.9208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3039   -1.8991    2.9375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1865   -1.1178    2.2843 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7354   -0.7503    1.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3993   -0.8331   -0.0518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8664   -1.2945   -0.4348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3010    3.0284   -3.6390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2414    4.9284   -3.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4881    4.0490   -3.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7326    1.7467   -2.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0517   -0.4888   -3.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3178   -2.9051   -3.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6801   -3.5392   -1.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2765   -2.8854   -1.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1652   -2.1686    2.5455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0810   -1.0481    3.3360 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7218   -0.3965    1.5947 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1346   -0.5410   -0.7993 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  2  0
 12 11  1  0
 11 10  2  0
 10  8  1  0
 20 26  2  0
 17 18  1  0
  4  5  1  0
  3  2  1  0
  2 13  1  0
  7  5  1  0
  7 13  1  0
 20 21  1  0
 26 25  1  0
 25 24  2  0
 24 23  1  0
 23 21  2  0
 14 26  1  0
  2  1  2  0
 18 20  1  0
  5  6  2  0
  4  3  2  0
  8  9  1  0
 18 19  2  0
  4 14  1  0
 21 22  1  0
  3 17  1  0
 14 15  1  6
  7  8  2  0
 17 16  1  0
 14 16  1  0
 17 34  1  1
 12 30  1  0
 11 29  1  0
 10 28  1  0
 25 38  1  0
 24 37  1  0
 23 36  1  0
  9 27  1  0
 22 35  1  0
 15 31  1  0
 16 32  1  0
 16 33  1  0
M  END


  Mrv1652306192119023D          

 38 42  0  0  0  0            999 V2000
   -5.8762   -0.5326   -1.8311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7803   -0.0571   -2.0832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5562   -0.8293   -1.8882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3466   -0.3593   -2.2070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1367    0.9698   -2.7633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0146    1.3528   -3.0741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3375    1.8172   -2.9398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2162    3.1188   -3.4400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0188    3.6820   -3.7890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3459    3.9175   -3.6076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6084    3.4225   -3.2790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7432    2.1255   -2.7816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6095    1.3208   -2.6105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2945   -1.3799   -1.8937 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2240   -1.4098   -2.8082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1454   -2.6591   -2.0419 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.4411   -2.2197   -1.3465 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1617   -2.1351    0.1553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0039   -2.3862    1.0129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7975   -1.6644    0.5706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4510   -1.5704    1.9208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3039   -1.8991    2.9375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1865   -1.1178    2.2843 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7354   -0.7503    1.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3993   -0.8331   -0.0518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8664   -1.2945   -0.4348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3010    3.0284   -3.6390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2414    4.9284   -3.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4881    4.0490   -3.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7326    1.7467   -2.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0517   -0.4888   -3.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3178   -2.9051   -3.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6801   -3.5392   -1.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2765   -2.8854   -1.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1652   -2.1686    2.5455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0810   -1.0481    3.3360 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7218   -0.3965    1.5947 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1346   -0.5410   -0.7993 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  2  0  0  0  0
 12 11  1  0  0  0  0
 11 10  2  0  0  0  0
 10  8  1  0  0  0  0
 20 26  2  0  0  0  0
 17 18  1  0  0  0  0
  4  5  1  0  0  0  0
  3  2  1  0  0  0  0
  2 13  1  0  0  0  0
  7  5  1  0  0  0  0
  7 13  1  0  0  0  0
 20 21  1  0  0  0  0
 26 25  1  0  0  0  0
 25 24  2  0  0  0  0
 24 23  1  0  0  0  0
 23 21  2  0  0  0  0
 14 26  1  0  0  0  0
  2  1  2  0  0  0  0
 18 20  1  0  0  0  0
  5  6  2  0  0  0  0
  4  3  2  0  0  0  0
  8  9  1  0  0  0  0
 18 19  2  0  0  0  0
  4 14  1  0  0  0  0
 21 22  1  0  0  0  0
  3 17  1  0  0  0  0
 14 15  1  6  0  0  0
  7  8  2  0  0  0  0
 17 16  1  0  0  0  0
 14 16  1  0  0  0  0
 17 34  1  1  0  0  0
 12 30  1  0  0  0  0
 11 29  1  0  0  0  0
 10 28  1  0  0  0  0
 25 38  1  0  0  0  0
 24 37  1  0  0  0  0
 23 36  1  0  0  0  0
  9 27  1  0  0  0  0
 22 35  1  0  0  0  0
 15 31  1  0  0  0  0
 16 32  1  0  0  0  0
 16 33  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0024730

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C([H])=C([H])C2=C1C(=O)[C@@]1([H])C3=C(C(=O)C4=C(O[H])C([H])=C([H])C([H])=C4C3=O)[C@]2(O[H])C1([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C20H12O6/c21-11-5-1-3-8-13(11)19(25)16-14(17(8)23)9-7-20(16,26)10-4-2-6-12(22)15(10)18(9)24/h1-6,9,21-22,26H,7H2/t9-,20+/m1/s1

> <INCHI_KEY>
YJGOKDWUHJGSPI-YBYGRFCBSA-N

> <FORMULA>
C20H12O6

> <MOLECULAR_WEIGHT>
348.31

> <EXACT_MASS>
348.063388106

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
33.5323020339646

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,12S)-8,12,17-trihydroxypentacyclo[10.7.1.0^{2,11}.0^{4,9}.0^{13,18}]icosa-2(11),4,6,8,13(18),14,16-heptaene-3,10,19-trione

> <ALOGPS_LOGP>
2.91

> <JCHEM_LOGP>
2.3802995586666666

> <ALOGPS_LOGS>
-2.96

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.5942444322698

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.967683853169079

> <JCHEM_PKA_STRONGEST_BASIC>
-3.670730506504258

> <JCHEM_POLAR_SURFACE_AREA>
111.90000000000002

> <JCHEM_REFRACTIVITY>
91.6747

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.78e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,12S)-8,12,17-trihydroxypentacyclo[10.7.1.0^{2,11}.0^{4,9}.0^{13,18}]icosa-2(11),4,6,8,13(18),14,16-heptaene-3,10,19-trione

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 38 42  0  0  0  0  0  0  0  0999 V2000
   -5.8762   -0.5326   -1.8311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7803   -0.0571   -2.0832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5562   -0.8293   -1.8882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3466   -0.3593   -2.2070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1367    0.9698   -2.7633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0146    1.3528   -3.0741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3375    1.8172   -2.9398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2162    3.1188   -3.4400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0188    3.6820   -3.7890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3459    3.9175   -3.6076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6084    3.4225   -3.2790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7432    2.1255   -2.7816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6095    1.3208   -2.6105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2945   -1.3799   -1.8937 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2240   -1.4098   -2.8082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1454   -2.6591   -2.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4411   -2.2197   -1.3465 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1617   -2.1351    0.1553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0039   -2.3862    1.0129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7975   -1.6644    0.5706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4510   -1.5704    1.9208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3039   -1.8991    2.9375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1865   -1.1178    2.2843 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7354   -0.7503    1.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3993   -0.8331   -0.0518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8664   -1.2945   -0.4348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3010    3.0284   -3.6390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2414    4.9284   -3.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4881    4.0490   -3.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7326    1.7467   -2.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0517   -0.4888   -3.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3178   -2.9051   -3.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6801   -3.5392   -1.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2765   -2.8854   -1.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1652   -2.1686    2.5455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0810   -1.0481    3.3360 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7218   -0.3965    1.5947 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1346   -0.5410   -0.7993 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  2  0
 12 11  1  0
 11 10  2  0
 10  8  1  0
 20 26  2  0
 17 18  1  0
  4  5  1  0
  3  2  1  0
  2 13  1  0
  7  5  1  0
  7 13  1  0
 20 21  1  0
 26 25  1  0
 25 24  2  0
 24 23  1  0
 23 21  2  0
 14 26  1  0
  2  1  2  0
 18 20  1  0
  5  6  2  0
  4  3  2  0
  8  9  1  0
 18 19  2  0
  4 14  1  0
 21 22  1  0
  3 17  1  0
 14 15  1  6
  7  8  2  0
 17 16  1  0
 14 16  1  0
 17 34  1  1
 12 30  1  0
 11 29  1  0
 10 28  1  0
 25 38  1  0
 24 37  1  0
 23 36  1  0
  9 27  1  0
 22 35  1  0
 15 31  1  0
 16 32  1  0
 16 33  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  O   UNK     0      -5.876  -0.533  -1.831  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.780  -0.057  -2.083  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.556  -0.829  -1.888  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.347  -0.359  -2.207  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.137   0.970  -2.763  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.015   1.353  -3.074  0.00  0.00           O+0
HETATM    7  C   UNK     0      -3.337   1.817  -2.940  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.216   3.119  -3.440  0.00  0.00           C+0
HETATM    9  O   UNK     0      -2.019   3.682  -3.789  0.00  0.00           O+0
HETATM   10  C   UNK     0      -4.346   3.918  -3.608  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.608   3.422  -3.279  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.743   2.126  -2.782  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.609   1.321  -2.611  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.295  -1.380  -1.894  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.224  -1.410  -2.808  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.145  -2.659  -2.042  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.441  -2.220  -1.347  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.162  -2.135   0.155  0.00  0.00           C+0
HETATM   19  O   UNK     0      -4.004  -2.386   1.013  0.00  0.00           O+0
HETATM   20  C   UNK     0      -1.798  -1.664   0.571  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.451  -1.570   1.921  0.00  0.00           C+0
HETATM   22  O   UNK     0      -2.304  -1.899   2.938  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.187  -1.118   2.284  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.735  -0.750   1.302  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.399  -0.833  -0.052  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.866  -1.295  -0.435  0.00  0.00           C+0
HETATM   27  H   UNK     0      -1.301   3.028  -3.639  0.00  0.00           H+0
HETATM   28  H   UNK     0      -4.241   4.928  -3.996  0.00  0.00           H+0
HETATM   29  H   UNK     0      -6.488   4.049  -3.411  0.00  0.00           H+0
HETATM   30  H   UNK     0      -6.733   1.747  -2.528  0.00  0.00           H+0
HETATM   31  H   UNK     0      -0.052  -0.489  -3.090  0.00  0.00           H+0
HETATM   32  H   UNK     0      -2.318  -2.905  -3.100  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.680  -3.539  -1.580  0.00  0.00           H+0
HETATM   34  H   UNK     0      -4.277  -2.885  -1.572  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.165  -2.169   2.546  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.081  -1.048   3.336  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.722  -0.397   1.595  0.00  0.00           H+0
HETATM   38  H   UNK     0       1.135  -0.541  -0.799  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    3   13    1                                                  
CONECT    3    2    4   17                                                  
CONECT    4    5    3   14                                                  
CONECT    5    4    7    6                                                  
CONECT    6    5                                                            
CONECT    7    5   13    8                                                  
CONECT    8   10    9    7                                                  
CONECT    9    8   27                                                       
CONECT   10   11    8   28                                                  
CONECT   11   12   10   29                                                  
CONECT   12   13   11   30                                                  
CONECT   13   12    2    7                                                  
CONECT   14   26    4   15   16                                             
CONECT   15   14   31                                                       
CONECT   16   17   14   32   33                                             
CONECT   17   18    3   16   34                                             
CONECT   18   17   20   19                                                  
CONECT   19   18                                                            
CONECT   20   26   21   18                                                  
CONECT   21   20   23   22                                                  
CONECT   22   21   35                                                       
CONECT   23   24   21   36                                                  
CONECT   24   25   23   37                                                  
CONECT   25   26   24   38                                                  
CONECT   26   20   25   14                                                  
CONECT   27    9                                                            
CONECT   28   10                                                            
CONECT   29   11                                                            
CONECT   30   12                                                            
CONECT   31   15                                                            
CONECT   32   16                                                            
CONECT   33   16                                                            
CONECT   34   17                                                            
CONECT   35   22                                                            
CONECT   36   23                                                            
CONECT   37   24                                                            
CONECT   38   25                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

RDKit          3D

38 42  0  0  0  0  0  0  0  0999 V2000
   -5.8762   -0.5326   -1.8311 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7803   -0.0571   -2.0832 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5562   -0.8293   -1.8882 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3466   -0.3593   -2.2070 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1367    0.9698   -2.7633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0146    1.3528   -3.0741 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3375    1.8172   -2.9398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2162    3.1188   -3.4400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0188    3.6820   -3.7890 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3459    3.9175   -3.6076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6084    3.4225   -3.2790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7432    2.1255   -2.7816 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6095    1.3208   -2.6105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2945   -1.3799   -1.8937 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2240   -1.4098   -2.8082 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1454   -2.6591   -2.0419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4411   -2.2197   -1.3465 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.1617   -2.1351    0.1553 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0039   -2.3862    1.0129 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7975   -1.6644    0.5706 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4510   -1.5704    1.9208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3039   -1.8991    2.9375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1865   -1.1178    2.2843 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7354   -0.7503    1.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3993   -0.8331   -0.0518 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8664   -1.2945   -0.4348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3010    3.0284   -3.6390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2414    4.9284   -3.9960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4881    4.0490   -3.4114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7326    1.7467   -2.5282 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0517   -0.4888   -3.0899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3178   -2.9051   -3.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6801   -3.5392   -1.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2765   -2.8854   -1.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1652   -2.1686    2.5455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0810   -1.0481    3.3360 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7218   -0.3965    1.5947 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1346   -0.5410   -0.7993 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  2  0
 12 11  1  0
 11 10  2  0
 10  8  1  0
 20 26  2  0
 17 18  1  0
  4  5  1  0
  3  2  1  0
  2 13  1  0
  7  5  1  0
  7 13  1  0
 20 21  1  0
 26 25  1  0
 25 24  2  0
 24 23  1  0
 23 21  2  0
 14 26  1  0
  2  1  2  0
 18 20  1  0
  5  6  2  0
  4  3  2  0
  8  9  1  0
 18 19  2  0
  4 14  1  0
 21 22  1  0
  3 17  1  0
 14 15  1  6
  7  8  2  0
 17 16  1  0
 14 16  1  0
 17 34  1  1
 12 30  1  0
 11 29  1  0
 10 28  1  0
 25 38  1  0
 24 37  1  0
 23 36  1  0
  9 27  1  0
 22 35  1  0
 15 31  1  0
 16 32  1  0
 16 33  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₁₂O₆

Average Mass

348.3100 Da

Monoisotopic Mass

348.06339 Da

IUPAC Name

(1R,12S)-8,12,17-trihydroxypentacyclo[10.7.1.0^{2,11}.0^{4,9}.0^{13,18}]icosa-2(11),4,6,8,13(18),14,16-heptaene-3,10,19-trione

Traditional Name

(1R,12S)-8,12,17-trihydroxypentacyclo[10.7.1.0^{2,11}.0^{4,9}.0^{13,18}]icosa-2(11),4,6,8,13(18),14,16-heptaene-3,10,19-trione

CAS Registry Number

Not Available

SMILES

[H]OC1=C([H])C([H])=C([H])C2=C1C(=O)[C@@]1([H])C3=C(C(=O)C4=C(O[H])C([H])=C([H])C([H])=C4C3=O)[C@]2(O[H])C1([H])[H]

InChI Identifier

InChI=1S/C20H12O6/c21-11-5-1-3-8-13(11)19(25)16-14(17(8)23)9-7-20(16,26)10-4-2-6-12(22)15(10)18(9)24/h1-6,9,21-22,26H,7H2/t9-,20+/m1/s1

InChI Key

YJGOKDWUHJGSPI-YBYGRFCBSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Engelhardia roxburghiana	JEOL database	Wu, C.-C. et al, Phytochemistry 68, 1338 (2007)

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	2.91	ALOGPS
logP	2.38	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	7.97	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	111.9 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	91.67 m³·mol⁻¹	ChemAxon
Polarizability	33.53 Å³	ChemAxon
Number of Rings	5	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00034500

Chemspider ID

17613916

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16681261

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Fukazawa T, Ando Y, Ohmori K, Hayashi T, Suzuki K: Enantioselective Access to Bicyclo[3.2.1]octadienone Skeleton: Total Syntheses of (+)-Engelharquinone and Its Epoxide. Org Lett. 2017 Mar 17;19(6):1470-1473. doi: 10.1021/acs.orglett.7b00464. Epub 2017 Mar 1. [PubMed:28248526 ]
Wu CC, Peng CF, Tsai IL, Abd El-Razek MH, Huang HS, Chen IS: Secondary metabolites from the roots of Engelhardia roxburghiana and their antitubercular activities. Phytochemistry. 2007 May;68(9):1338-43. doi: 10.1016/j.phytochem.2007.01.018. Epub 2007 Apr 5. [PubMed:17418287 ]
Wu, C.-C. et al. (2007). Wu, C.-C. et al, Phytochemistry 68, 1338 (2007). Phytochem..

Showing NP-Card for engelharquinone (NP0024730)

MOL for NP0024730 (engelharquinone)

3D MOL for NP0024730 (engelharquinone)

3D SDF for NP0024730 (engelharquinone)

3D-SDF for NP0024730 (engelharquinone)

PDB for NP0024730 (engelharquinone)

3D PDB for NP0024730 (engelharquinone)

SMILES for NP0024730 (engelharquinone)

INCHI for NP0024730 (engelharquinone)

Structure for NP0024730 (engelharquinone)

3D Structure for NP0024730 (engelharquinone)