NP-MRD: Showing NP-Card for pycnanthuquinone B (NP0029961)

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Record Information

Version

1.0

Created at

2021-06-19 21:26:50 UTC

Updated at

2021-06-29 23:57:39 UTC

NP-MRD ID

NP0029961

Secondary Accession Numbers

None

Natural Product Identification

Common Name

pycnanthuquinone B

Provided By

JEOL Database JEOL Logo

Description

pycnanthuquinone B is found in Pycnanthus angolensis. It was first documented in 2000 (Fort, D. M., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192123263D          

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M  END

     RDKit          3D

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M  END


  Mrv1652306192123263D          

 70 72  0  0  0  0            999 V2000
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    0.4698    1.6089    5.8293 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8295    1.7907    5.1339 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8319    1.5639    3.6456 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9468    2.0878    2.7714 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8942    1.8247    1.2857 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.2362    0.4725    0.9620 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3340   -0.0098   -0.5247 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1549   -1.4792   -0.5636 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7600    0.0198   -1.1223 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0200    0.4130   -2.3896 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4193    0.5324   -2.8925 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6399    0.7237   -4.0858 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5238    0.4826   -1.9085 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8669    0.9275   -2.3997 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2697    0.0704   -0.6622 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2591    0.0719    0.3081 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9116   -0.4053   -0.2726 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7797   -1.0963    0.7353 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9627    0.8179   -3.4003 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1006    0.0263   -4.5835 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4588    0.5969   -2.8882 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5570    0.9258   -1.3967 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0698    0.9731   -1.1421 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7163    1.2910   -2.5043 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5525    1.4928   -3.4891 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9212    1.1479   -4.9251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1502    2.8639   -3.4306 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8458    0.6220    3.1375 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8319    0.9059    2.4794 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4629   -0.6412    3.3811 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1756    2.7566    3.1473 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9027    1.8982    0.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3224    2.6369    0.8224 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6470   -0.3044    1.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8218    0.5283    1.2538 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4752   -2.1260    0.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1326   -1.9007   -1.5736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1742   -1.5811   -0.1792 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2115    0.2770   -3.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8139    1.9542   -2.7773 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6308    0.9067   -1.6164 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7964    0.1374    1.1767 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1214    1.8665   -3.6770 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9946    0.2241   -4.9366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7530   -0.4469   -3.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1879    1.9540   -1.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3144    1.7456   -0.4046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4714    0.0291   -0.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3567    2.1764   -2.4287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3431    0.4422   -2.8030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1922    0.0928   -5.0322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7681    1.7554   -5.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0919    1.3664   -5.6062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8551    3.3978   -3.8385 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9096   -1.1740    2.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  1  0  0  0
 11 26  1  0  0  0  0
 10  9  1  0  0  0  0
 25 23  1  0  0  0  0
  9  8  1  0  0  0  0
 25 26  1  0  0  0  0
  8  7  2  0  0  0  0
 15 17  1  0  0  0  0
  7  6  1  0  0  0  0
 17 19  2  0  0  0  0
  6  5  1  0  0  0  0
 14 13  2  0  0  0  0
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  4  2  2  3  0  0  0
 21 13  1  0  0  0  0
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 26 27  1  0  0  0  0
 21 22  2  0  0  0  0
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 17 18  1  0  0  0  0
 28 29  1  0  0  0  0
 19 20  1  0  0  0  0
 29 25  1  0  0  0  0
 29 30  1  0  0  0  0
 21 19  1  0  0  0  0
 29 31  1  6  0  0  0
 11 12  1  0  0  0  0
  7 32  1  0  0  0  0
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  2  1  1  0  0  0  0
 23 24  1  0  0  0  0
  2  3  1  0  0  0  0
 13 11  1  0  0  0  0
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 31 69  1  0  0  0  0
 34 70  1  0  0  0  0
  1 35  1  0  0  0  0
  1 36  1  0  0  0  0
  1 37  1  0  0  0  0
  3 38  1  0  0  0  0
  3 39  1  0  0  0  0
  3 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0029961

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC(=O)C(=C(\[H])C([H])([H])C([H])([H])[C@@]1(C2=C(C(=O)C(=C(O[H])C2=O)C([H])([H])[H])[C@@]([H])(O[H])[C@@]2([H])[C@@]1([H])C([H])([H])C([H])([H])[C@]2(O[H])C([H])([H])[H])C([H])([H])[H])\C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C27H36O7/c1-14(2)8-6-9-16(25(32)33)10-7-12-26(4)17-11-13-27(5,34)19(17)23(30)18-20(26)24(31)22(29)15(3)21(18)28/h8,10,17,19,23,29-30,34H,6-7,9,11-13H2,1-5H3,(H,32,33)/b16-10-/t17-,19-,23-,26+,27-/m1/s1

> <INCHI_KEY>
HBGRAOUXLANZCC-IXXIDZNVSA-N

> <FORMULA>
C27H36O7

> <MOLECULAR_WEIGHT>
472.578

> <EXACT_MASS>
472.246103499

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
50.892313999539

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2Z)-2-{3-[(1R,3aR,4S,9S,9aR)-1,6,9-trihydroxy-1,4,7-trimethyl-5,8-dioxo-1H,2H,3H,3aH,4H,5H,8H,9H,9aH-cyclopenta[b]naphthalen-4-yl]propylidene}-6-methylhept-5-enoic acid

> <ALOGPS_LOGP>
2.77

> <JCHEM_LOGP>
3.5531448769999994

> <ALOGPS_LOGS>
-4.13

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.910673631182353

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.289874848018259

> <JCHEM_PKA_STRONGEST_BASIC>
-2.935834207009867

> <JCHEM_POLAR_SURFACE_AREA>
132.13

> <JCHEM_REFRACTIVITY>
131.35679999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.53e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-2-{3-[(1R,3aR,4S,9S,9aR)-1,6,9-trihydroxy-1,4,7-trimethyl-5,8-dioxo-2H,3H,3aH,9H,9aH-cyclopenta[b]naphthalen-4-yl]propylidene}-6-methylhept-5-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 70 72  0  0  0  0  0  0  0  0999 V2000
   -1.6036   -1.6312    5.0398 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2386   -0.1702    5.1079 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2551    0.7434    4.4824 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0815    0.2154    5.6812 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4698    1.6089    5.8293 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8295    1.7907    5.1339 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8319    1.5639    3.6456 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9468    2.0878    2.7714 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8942    1.8247    1.2857 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2362    0.4725    0.9620 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3340   -0.0098   -0.5247 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1549   -1.4792   -0.5636 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7600    0.0198   -1.1223 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0200    0.4130   -2.3896 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4193    0.5324   -2.8925 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6399    0.7237   -4.0858 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5238    0.4826   -1.9085 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8669    0.9275   -2.3997 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2697    0.0704   -0.6622 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2591    0.0719    0.3081 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9116   -0.4053   -0.2726 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7797   -1.0963    0.7353 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9627    0.8179   -3.4003 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.1006    0.0263   -4.5835 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4588    0.5969   -2.8882 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5570    0.9258   -1.3967 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0698    0.9731   -1.1421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7163    1.2910   -2.5043 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5525    1.4928   -3.4891 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9212    1.1479   -4.9251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1502    2.8639   -3.4306 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8458    0.6220    3.1375 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8319    0.9059    2.4794 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4629   -0.6412    3.3811 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7153   -1.9448    3.9966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8446   -2.2729    5.4994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5496   -1.8101    5.5612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3900    0.4874    3.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2200    0.6331    4.9885 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9838    1.7995    4.5278 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5685   -0.5590    6.0913 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2291    2.3742    5.4822 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6054    1.7990    6.9016 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1935    2.8077    5.3281 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5557    1.1200    5.6130 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1756    2.7566    3.1473 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9027    1.8982    0.8686 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3224    2.6369    0.8224 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6470   -0.3044    1.6142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8218    0.5283    1.2538 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4752   -2.1260    0.0581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1326   -1.9007   -1.5736 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1742   -1.5811   -0.1792 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2115    0.2770   -3.2105 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8139    1.9542   -2.7773 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6308    0.9067   -1.6164 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7964    0.1374    1.1767 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1214    1.8665   -3.6770 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9946    0.2241   -4.9366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7530   -0.4469   -3.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1879    1.9540   -1.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3144    1.7456   -0.4046 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4714    0.0291   -0.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3567    2.1764   -2.4287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3431    0.4422   -2.8030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1922    0.0928   -5.0322 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7681    1.7554   -5.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0919    1.3664   -5.6062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8551    3.3978   -3.8385 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9096   -1.1740    2.6815 H   0  0  0  0  0  0  0  0  0  0  0  0
 11 10  1  1
 11 26  1  0
 10  9  1  0
 25 23  1  0
  9  8  1  0
 25 26  1  0
  8  7  2  0
 15 17  1  0
  7  6  1  0
 17 19  2  0
  6  5  1  0
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  5  4  1  0
  4  2  2  3
 21 13  1  0
 15 16  2  0
 26 27  1  0
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 27 28  1  0
 17 18  1  0
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 21 19  1  0
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  7 32  1  0
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 14 23  1  0
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 34 70  1  0
  1 35  1  0
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  3 38  1  0
  3 39  1  0
  3 40  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.604  -1.631   5.040  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.239  -0.170   5.108  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.255   0.743   4.482  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.082   0.215   5.681  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.470   1.609   5.829  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.829   1.791   5.134  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.832   1.564   3.646  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.947   2.088   2.771  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.894   1.825   1.286  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.236   0.473   0.962  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.334  -0.010  -0.525  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.155  -1.479  -0.564  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.760   0.020  -1.122  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.020   0.413  -2.390  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.419   0.532  -2.893  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.640   0.724  -4.086  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.524   0.483  -1.909  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.867   0.928  -2.400  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.270   0.070  -0.662  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.259   0.072   0.308  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.912  -0.405  -0.273  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.780  -1.096   0.735  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.963   0.818  -3.400  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.101   0.026  -4.583  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.459   0.597  -2.888  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.557   0.926  -1.397  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.070   0.973  -1.142  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.716   1.291  -2.504  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.553   1.493  -3.489  0.00  0.00           C+0
HETATM   30  C   UNK     0      -1.921   1.148  -4.925  0.00  0.00           C+0
HETATM   31  O   UNK     0      -1.150   2.864  -3.431  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.846   0.622   3.138  0.00  0.00           C+0
HETATM   33  O   UNK     0       3.832   0.906   2.479  0.00  0.00           O+0
HETATM   34  O   UNK     0       2.463  -0.641   3.381  0.00  0.00           O+0
HETATM   35  H   UNK     0      -1.715  -1.945   3.997  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.845  -2.273   5.499  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.550  -1.810   5.561  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.390   0.487   3.426  0.00  0.00           H+0
HETATM   39  H   UNK     0      -3.220   0.633   4.989  0.00  0.00           H+0
HETATM   40  H   UNK     0      -1.984   1.800   4.528  0.00  0.00           H+0
HETATM   41  H   UNK     0       0.569  -0.559   6.091  0.00  0.00           H+0
HETATM   42  H   UNK     0      -0.229   2.374   5.482  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.605   1.799   6.902  0.00  0.00           H+0
HETATM   44  H   UNK     0       2.193   2.808   5.328  0.00  0.00           H+0
HETATM   45  H   UNK     0       2.556   1.120   5.613  0.00  0.00           H+0
HETATM   46  H   UNK     0       0.176   2.757   3.147  0.00  0.00           H+0
HETATM   47  H   UNK     0       1.903   1.898   0.869  0.00  0.00           H+0
HETATM   48  H   UNK     0       0.322   2.637   0.822  0.00  0.00           H+0
HETATM   49  H   UNK     0       0.647  -0.304   1.614  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.822   0.528   1.254  0.00  0.00           H+0
HETATM   51  H   UNK     0       0.475  -2.126   0.058  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.133  -1.901  -1.574  0.00  0.00           H+0
HETATM   53  H   UNK     0      -1.174  -1.581  -0.179  0.00  0.00           H+0
HETATM   54  H   UNK     0       6.212   0.277  -3.211  0.00  0.00           H+0
HETATM   55  H   UNK     0       5.814   1.954  -2.777  0.00  0.00           H+0
HETATM   56  H   UNK     0       6.631   0.907  -1.616  0.00  0.00           H+0
HETATM   57  H   UNK     0       4.796   0.137   1.177  0.00  0.00           H+0
HETATM   58  H   UNK     0       1.121   1.867  -3.677  0.00  0.00           H+0
HETATM   59  H   UNK     0       1.995   0.224  -4.937  0.00  0.00           H+0
HETATM   60  H   UNK     0      -0.753  -0.447  -3.068  0.00  0.00           H+0
HETATM   61  H   UNK     0      -0.188   1.954  -1.259  0.00  0.00           H+0
HETATM   62  H   UNK     0      -2.314   1.746  -0.405  0.00  0.00           H+0
HETATM   63  H   UNK     0      -2.471   0.029  -0.765  0.00  0.00           H+0
HETATM   64  H   UNK     0      -3.357   2.176  -2.429  0.00  0.00           H+0
HETATM   65  H   UNK     0      -3.343   0.442  -2.803  0.00  0.00           H+0
HETATM   66  H   UNK     0      -2.192   0.093  -5.032  0.00  0.00           H+0
HETATM   67  H   UNK     0      -2.768   1.755  -5.264  0.00  0.00           H+0
HETATM   68  H   UNK     0      -1.092   1.366  -5.606  0.00  0.00           H+0
HETATM   69  H   UNK     0      -1.855   3.398  -3.838  0.00  0.00           H+0
HETATM   70  H   UNK     0       2.910  -1.174   2.682  0.00  0.00           H+0
CONECT    1    2   35   36   37                                             
CONECT    2    4    1    3                                                  
CONECT    3    2   38   39   40                                             
CONECT    4    5    2   41                                                  
CONECT    5    6    4   42   43                                             
CONECT    6    7    5   44   45                                             
CONECT    7    8    6   32                                                  
CONECT    8    9    7   46                                                  
CONECT    9   10    8   47   48                                             
CONECT   10   11    9   49   50                                             
CONECT   11   10   26   12   13                                             
CONECT   12   11   51   52   53                                             
CONECT   13   14   21   11                                                  
CONECT   14   13   15   23                                                  
CONECT   15   17   16   14                                                  
CONECT   16   15                                                            
CONECT   17   15   19   18                                                  
CONECT   18   17   54   55   56                                             
CONECT   19   17   20   21                                                  
CONECT   20   19   57                                                       
CONECT   21   13   22   19                                                  
CONECT   22   21                                                            
CONECT   23   25   14   24   58                                             
CONECT   24   23   59                                                       
CONECT   25   23   26   29   60                                             
CONECT   26   11   25   27   61                                             
CONECT   27   26   28   62   63                                             
CONECT   28   27   29   64   65                                             
CONECT   29   28   25   30   31                                             
CONECT   30   29   66   67   68                                             
CONECT   31   29   69                                                       
CONECT   32    7   34   33                                                  
CONECT   33   32                                                            
CONECT   34   32   70                                                       
CONECT   35    1                                                            
CONECT   36    1                                                            
CONECT   37    1                                                            
CONECT   38    3                                                            
CONECT   39    3                                                            
CONECT   40    3                                                            
CONECT   41    4                                                            
CONECT   42    5                                                            
CONECT   43    5                                                            
CONECT   44    6                                                            
CONECT   45    6                                                            
CONECT   46    8                                                            
CONECT   47    9                                                            
CONECT   48    9                                                            
CONECT   49   10                                                            
CONECT   50   10                                                            
CONECT   51   12                                                            
CONECT   52   12                                                            
CONECT   53   12                                                            
CONECT   54   18                                                            
CONECT   55   18                                                            
CONECT   56   18                                                            
CONECT   57   20                                                            
CONECT   58   23                                                            
CONECT   59   24                                                            
CONECT   60   25                                                            
CONECT   61   26                                                            
CONECT   62   27                                                            
CONECT   63   27                                                            
CONECT   64   28                                                            
CONECT   65   28                                                            
CONECT   66   30                                                            
CONECT   67   30                                                            
CONECT   68   30                                                            
CONECT   69   31                                                            
CONECT   70   34                                                            
MASTER        0    0    0    0    0    0    0    0   70    0  144    0
END

RDKit          3D

70 72  0  0  0  0  0  0  0  0999 V2000
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    0.3340   -0.0098   -0.5247 C   0  0  2  0  0  0  0  0  0  0  0  0
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    2.0200    0.4130   -2.3896 C   0  0  0  0  0  0  0  0  0  0  0  0
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 30 66  1  0
 30 67  1  0
 30 68  1  0
 31 69  1  0
 34 70  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  3 38  1  0
  3 39  1  0
  3 40  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₆O₇

Average Mass

472.5780 Da

Monoisotopic Mass

472.24610 Da

IUPAC Name

(2Z)-2-{3-[(1R,3aR,4S,9S,9aR)-1,6,9-trihydroxy-1,4,7-trimethyl-5,8-dioxo-1H,2H,3H,3aH,4H,5H,8H,9H,9aH-cyclopenta[b]naphthalen-4-yl]propylidene}-6-methylhept-5-enoic acid

Traditional Name

(2Z)-2-{3-[(1R,3aR,4S,9S,9aR)-1,6,9-trihydroxy-1,4,7-trimethyl-5,8-dioxo-2H,3H,3aH,9H,9aH-cyclopenta[b]naphthalen-4-yl]propylidene}-6-methylhept-5-enoic acid

CAS Registry Number

Not Available

SMILES

[H]OC(=O)C(=C(\[H])C([H])([H])C([H])([H])[C@@]1(C2=C(C(=O)C(=C(O[H])C2=O)C([H])([H])[H])[C@@]([H])(O[H])[C@@]2([H])[C@@]1([H])C([H])([H])C([H])([H])[C@]2(O[H])C([H])([H])[H])C([H])([H])[H])\C([H])([H])C([H])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C27H36O7/c1-14(2)8-6-9-16(25(32)33)10-7-12-26(4)17-11-13-27(5,34)19(17)23(30)18-20(26)24(31)22(29)15(3)21(18)28/h8,10,17,19,23,29-30,34H,6-7,9,11-13H2,1-5H3,(H,32,33)/b16-10-/t17-,19-,23-,26+,27-/m1/s1

InChI Key

HBGRAOUXLANZCC-IXXIDZNVSA-N

Experimental Spectra

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

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Pycnanthus angolensis	JEOL database	Fort, D. M., et al, J. Org. Chem. 65, 6534 (2000)

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	2.77	ALOGPS
logP	3.55	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	4.29	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	132.13 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	131.36 m³·mol⁻¹	ChemAxon
Polarizability	50.89 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

Not Available

References

General References

Fort, D. M., et al. (2000). Fort, D. M., et al, J. Org. Chem. 65, 6534 (2000). J. Org. Chem..

Showing NP-Card for pycnanthuquinone B (NP0029961)

MOL for NP0029961 (pycnanthuquinone B)

3D MOL for NP0029961 (pycnanthuquinone B)

3D SDF for NP0029961 (pycnanthuquinone B)

3D-SDF for NP0029961 (pycnanthuquinone B)

PDB for NP0029961 (pycnanthuquinone B)

3D PDB for NP0029961 (pycnanthuquinone B)

SMILES for NP0029961 (pycnanthuquinone B)

INCHI for NP0029961 (pycnanthuquinone B)

Structure for NP0029961 (pycnanthuquinone B)

3D Structure for NP0029961 (pycnanthuquinone B)