NP-MRD: Showing NP-Card for Botrysphin E (NP0016709)

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Record Information

Version

2.0

Created at

2021-01-06 01:36:47 UTC

Updated at

2021-07-15 17:23:27 UTC

NP-MRD ID

NP0016709

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Botrysphin E

Provided By

NPAtlas

Description

Botrysphin E is found in Botryosphaeria laricina. Based on a literature review very few articles have been published on (1R,5S,6R)-5,6-dihydroxy-4-methoxy-2-oxocyclohex-3-en-1-yl (4aR,4bR,7R)-7-ethenyl-4b,10-dihydroxy-1,1,7-trimethyl-9-oxo-1,2,3,4,4a,4b,5,6,7,9-decahydrophenanthrene-4a-carboxylate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242104163D          

 70 73  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652306242104163D          

 70 73  0  0  0  0            999 V2000
   -5.9632    3.0116    1.2423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6500    2.9106    1.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0299    2.5726   -0.1414 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6197    3.3611   -1.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1173    1.1450   -0.4933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2572    0.2328   -0.0868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4352   -1.1730   -0.4934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5280   -1.4855   -1.0612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3804   -2.1191   -0.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5704   -3.4608   -0.6257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2535   -1.7504    0.3560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2649   -2.8258    0.5636 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9614   -4.1023    1.0787 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2458   -3.1928   -0.8415 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8759   -2.5419    1.4473 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8327   -1.3142    2.2735 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3339   -0.4256    2.1237 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9527   -0.3682    0.7369 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0736    0.2288   -0.1631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1501    1.0569   -1.0677 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4432   -0.1221   -0.0525 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4269    0.4089   -0.8723 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3454    1.2279   -0.0284 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8519    2.1369    0.6983 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7868    1.0094   -0.0193 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3219    0.4955   -1.1131 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6844    0.2742   -1.1417 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6233    1.2023   -0.6221 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4061    0.1926   -2.2395 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0238   -0.5055   -3.2588 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2312   -0.6059   -1.6545 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7096   -1.6260   -0.8661 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1483    0.5530    0.7868 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6935    0.2839    2.1144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8467    1.9951    0.8144 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5307    2.8854   -0.1778 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.5744    2.8435    0.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4702    3.2615    2.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0385    3.0841    2.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9684    3.1285   -2.1816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6335    2.9995   -1.5706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5568    4.4471   -1.1509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9554    0.8228   -1.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4853   -3.8416   -0.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9992   -4.8920    0.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3381   -4.5698    1.9006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9197   -3.8760    1.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1704   -2.6528   -1.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5121   -2.9201   -1.6123 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3711   -4.2998   -0.9320 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8314   -2.6436    0.8558 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9846   -3.4086    2.1793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8209   -0.7786    2.1200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8949   -1.5686    3.3837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1323    0.6082    2.4876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1619   -0.7987    2.7927 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9358    1.1166   -1.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3987    1.2610    0.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6390    0.7850   -0.7695 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5065    2.2116   -1.0162 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4839    1.2702    0.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0013    1.1633   -2.6198 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9292   -0.7530   -3.0140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6016   -0.9487   -2.5013 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6283   -1.3993   -0.5782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2117   -0.5423    2.0485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7607    2.2419    0.7460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1155    2.4674    1.8304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2048    2.6715   -1.1879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3544    3.9443    0.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  3  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
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 26 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 18 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36  3  1  0  0  0  0
 33  6  1  0  0  0  0
 18 11  1  0  0  0  0
 31 22  1  0  0  0  0
  1 37  1  0  0  0  0
  1 38  1  0  0  0  0
  2 39  1  0  0  0  0
  4 40  1  0  0  0  0
  4 41  1  0  0  0  0
  4 42  1  0  0  0  0
  5 43  1  0  0  0  0
 10 44  1  0  0  0  0
 13 45  1  0  0  0  0
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 13 47  1  0  0  0  0
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 15 51  1  0  0  0  0
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 17 55  1  0  0  0  0
 17 56  1  0  0  0  0
 22 57  1  6  0  0  0
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 28 59  1  0  0  0  0
 28 60  1  0  0  0  0
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 29 62  1  6  0  0  0
 30 63  1  0  0  0  0
 31 64  1  6  0  0  0
 32 65  1  0  0  0  0
 34 66  1  0  0  0  0
 35 67  1  0  0  0  0
 35 68  1  0  0  0  0
 36 69  1  0  0  0  0
 36 70  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0016709

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C2[C@](C(=O)O[C@@]3([H])C(=O)C([H])=C(OC([H])([H])[H])[C@@]([H])(O[H])[C@@]3([H])O[H])(C([H])([H])C([H])([H])C([H])([H])C2(C([H])([H])[H])C([H])([H])[H])[C@]2(O[H])C(=C([H])[C@](C([H])=C([H])[H])(C([H])([H])[H])C([H])([H])C2([H])[H])C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H34O9/c1-6-25(4)10-11-27(34)14(13-25)17(29)20(32)22-24(2,3)8-7-9-26(22,27)23(33)36-21-15(28)12-16(35-5)18(30)19(21)31/h6,12-13,18-19,21,30-32,34H,1,7-11H2,2-5H3/t18-,19-,21+,25+,26+,27-/m1/s1

> <INCHI_KEY>
QRKUDJZMRTVQRY-SJJDIPSKSA-N

> <FORMULA>
C27H34O9

> <MOLECULAR_WEIGHT>
502.56

> <EXACT_MASS>
502.220282675

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
51.837604383222526

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,5S,6R)-5,6-dihydroxy-4-methoxy-2-oxocyclohex-3-en-1-yl (4aR,4bR,7R)-7-ethenyl-4b,10-dihydroxy-1,1,7-trimethyl-9-oxo-1,2,3,4,4a,4b,5,6,7,9-decahydrophenanthrene-4a-carboxylate

> <ALOGPS_LOGP>
1.53

> <JCHEM_LOGP>
1.559520591

> <ALOGPS_LOGS>
-3.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.534948552245652

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.034427732341168

> <JCHEM_PKA_STRONGEST_BASIC>
-3.560291611814278

> <JCHEM_POLAR_SURFACE_AREA>
150.59

> <JCHEM_REFRACTIVITY>
131.74939999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.61e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,5S,6R)-5,6-dihydroxy-4-methoxy-2-oxocyclohex-3-en-1-yl (4aR,4bR,7R)-7-ethenyl-4b,10-dihydroxy-1,1,7-trimethyl-9-oxo-3,4,5,6-tetrahydro-2H-phenanthrene-4a-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 70 73  0  0  0  0  0  0  0  0999 V2000
   -5.9632    3.0116    1.2423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6500    2.9106    1.1390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0299    2.5726   -0.1414 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.6197    3.3611   -1.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1173    1.1450   -0.4933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2572    0.2328   -0.0868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4352   -1.1730   -0.4934 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5280   -1.4855   -1.0612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3804   -2.1191   -0.2344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5704   -3.4608   -0.6257 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2535   -1.7504    0.3560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2649   -2.8258    0.5636 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9614   -4.1023    1.0787 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2458   -3.1928   -0.8415 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8759   -2.5419    1.4473 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8327   -1.3142    2.2735 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3339   -0.4256    2.1237 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9527   -0.3682    0.7369 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0736    0.2288   -0.1631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1501    1.0569   -1.0677 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4432   -0.1221   -0.0525 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4269    0.4089   -0.8723 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3454    1.2279   -0.0284 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8519    2.1369    0.6983 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7868    1.0094   -0.0193 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3219    0.4955   -1.1131 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6844    0.2742   -1.1417 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6233    1.2023   -0.6221 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4061    0.1926   -2.2395 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0238   -0.5055   -3.2588 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2312   -0.6059   -1.6545 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7096   -1.6260   -0.8661 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1483    0.5530    0.7868 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6935    0.2839    2.1144 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8467    1.9951    0.8144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5307    2.8854   -0.1778 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5744    2.8435    0.3777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4702    3.2615    2.1772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0385    3.0841    2.0248 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9684    3.1285   -2.1816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6335    2.9995   -1.5706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5568    4.4471   -1.1509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9554    0.8228   -1.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4853   -3.8416   -0.4197 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9992   -4.8920    0.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3381   -4.5698    1.9006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9197   -3.8760    1.5645 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1704   -2.6528   -1.0915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5121   -2.9201   -1.6123 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3711   -4.2998   -0.9320 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8314   -2.6436    0.8558 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9846   -3.4086    2.1793 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8209   -0.7786    2.1200 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8949   -1.5686    3.3837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1323    0.6082    2.4876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1619   -0.7987    2.7927 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9358    1.1166   -1.5813 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3987    1.2610    0.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6390    0.7850   -0.7695 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5065    2.2116   -1.0162 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4839    1.2702    0.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0013    1.1633   -2.6198 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9292   -0.7530   -3.0140 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6016   -0.9487   -2.5013 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6283   -1.3993   -0.5782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2117   -0.5423    2.0485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7607    2.2419    0.7460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1155    2.4674    1.8304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2048    2.6715   -1.1879 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3544    3.9443    0.1277 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  3  2  1  1
  3  4  1  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  9 10  1  0
  9 11  2  0
 11 12  1  0
 12 13  1  1
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 16 17  1  0
 17 18  1  0
 18 19  1  6
 19 20  2  0
 19 21  1  0
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 31 32  1  0
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 10 44  1  0
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 34 66  1  0
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 35 68  1  0
 36 69  1  0
 36 70  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      -5.963   3.012   1.242  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.650   2.911   1.139  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.030   2.573  -0.141  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.620   3.361  -1.302  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.117   1.145  -0.493  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.257   0.233  -0.087  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.435  -1.173  -0.493  0.00  0.00           C+0
HETATM    8  O   UNK     0      -4.528  -1.486  -1.061  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.380  -2.119  -0.234  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.570  -3.461  -0.626  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.254  -1.750   0.356  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.265  -2.826   0.564  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.961  -4.102   1.079  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.246  -3.193  -0.842  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.876  -2.542   1.447  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.833  -1.314   2.273  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.334  -0.426   2.124  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.953  -0.368   0.737  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.074   0.229  -0.163  0.00  0.00           C+0
HETATM   20  O   UNK     0      -0.150   1.057  -1.068  0.00  0.00           O+0
HETATM   21  O   UNK     0       1.443  -0.122  -0.053  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.427   0.409  -0.872  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.345   1.228  -0.028  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.852   2.137   0.698  0.00  0.00           O+0
HETATM   25  C   UNK     0       4.787   1.009  -0.019  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.322   0.496  -1.113  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.684   0.274  -1.142  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.623   1.202  -0.622  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.406   0.193  -2.240  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.024  -0.505  -3.259  0.00  0.00           O+0
HETATM   31  C   UNK     0       3.231  -0.606  -1.655  0.00  0.00           C+0
HETATM   32  O   UNK     0       3.710  -1.626  -0.866  0.00  0.00           O+0
HETATM   33  C   UNK     0      -2.148   0.553   0.787  0.00  0.00           C+0
HETATM   34  O   UNK     0      -2.693   0.284   2.114  0.00  0.00           O+0
HETATM   35  C   UNK     0      -1.847   1.995   0.814  0.00  0.00           C+0
HETATM   36  C   UNK     0      -2.531   2.885  -0.178  0.00  0.00           C+0
HETATM   37  H   UNK     0      -6.574   2.844   0.378  0.00  0.00           H+0
HETATM   38  H   UNK     0      -6.470   3.261   2.177  0.00  0.00           H+0
HETATM   39  H   UNK     0      -4.038   3.084   2.025  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.968   3.128  -2.182  0.00  0.00           H+0
HETATM   41  H   UNK     0      -5.633   2.999  -1.571  0.00  0.00           H+0
HETATM   42  H   UNK     0      -4.557   4.447  -1.151  0.00  0.00           H+0
HETATM   43  H   UNK     0      -4.955   0.823  -1.136  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.485  -3.842  -0.420  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.999  -4.892   0.303  0.00  0.00           H+0
HETATM   46  H   UNK     0      -0.338  -4.570   1.901  0.00  0.00           H+0
HETATM   47  H   UNK     0      -1.920  -3.876   1.565  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.170  -2.653  -1.091  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.512  -2.920  -1.612  0.00  0.00           H+0
HETATM   50  H   UNK     0       0.371  -4.300  -0.932  0.00  0.00           H+0
HETATM   51  H   UNK     0       1.831  -2.644   0.856  0.00  0.00           H+0
HETATM   52  H   UNK     0       0.985  -3.409   2.179  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.821  -0.779   2.120  0.00  0.00           H+0
HETATM   54  H   UNK     0       0.895  -1.569   3.384  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.132   0.608   2.488  0.00  0.00           H+0
HETATM   56  H   UNK     0      -1.162  -0.799   2.793  0.00  0.00           H+0
HETATM   57  H   UNK     0       1.936   1.117  -1.581  0.00  0.00           H+0
HETATM   58  H   UNK     0       5.399   1.261   0.857  0.00  0.00           H+0
HETATM   59  H   UNK     0       8.639   0.785  -0.770  0.00  0.00           H+0
HETATM   60  H   UNK     0       7.506   2.212  -1.016  0.00  0.00           H+0
HETATM   61  H   UNK     0       7.484   1.270   0.485  0.00  0.00           H+0
HETATM   62  H   UNK     0       4.001   1.163  -2.620  0.00  0.00           H+0
HETATM   63  H   UNK     0       5.929  -0.753  -3.014  0.00  0.00           H+0
HETATM   64  H   UNK     0       2.602  -0.949  -2.501  0.00  0.00           H+0
HETATM   65  H   UNK     0       4.628  -1.399  -0.578  0.00  0.00           H+0
HETATM   66  H   UNK     0      -3.212  -0.542   2.049  0.00  0.00           H+0
HETATM   67  H   UNK     0      -0.761   2.242   0.746  0.00  0.00           H+0
HETATM   68  H   UNK     0      -2.115   2.467   1.830  0.00  0.00           H+0
HETATM   69  H   UNK     0      -2.205   2.672  -1.188  0.00  0.00           H+0
HETATM   70  H   UNK     0      -2.354   3.944   0.128  0.00  0.00           H+0
CONECT    1    2   37   38                                                  
CONECT    2    1    3   39                                                  
CONECT    3    2    4    5   36                                             
CONECT    4    3   40   41   42                                             
CONECT    5    3    6   43                                                  
CONECT    6    5    7   33                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9   44                                                       
CONECT   11    9   12   18                                                  
CONECT   12   11   13   14   15                                             
CONECT   13   12   45   46   47                                             
CONECT   14   12   48   49   50                                             
CONECT   15   12   16   51   52                                             
CONECT   16   15   17   53   54                                             
CONECT   17   16   18   55   56                                             
CONECT   18   17   19   33   11                                             
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   31   57                                             
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   58                                                  
CONECT   26   25   27   29                                                  
CONECT   27   26   28                                                       
CONECT   28   27   59   60   61                                             
CONECT   29   26   30   31   62                                             
CONECT   30   29   63                                                       
CONECT   31   29   32   22   64                                             
CONECT   32   31   65                                                       
CONECT   33   18   34   35    6                                             
CONECT   34   33   66                                                       
CONECT   35   33   36   67   68                                             
CONECT   36   35    3   69   70                                             
CONECT   37    1                                                            
CONECT   38    1                                                            
CONECT   39    2                                                            
CONECT   40    4                                                            
CONECT   41    4                                                            
CONECT   42    4                                                            
CONECT   43    5                                                            
CONECT   44   10                                                            
CONECT   45   13                                                            
CONECT   46   13                                                            
CONECT   47   13                                                            
CONECT   48   14                                                            
CONECT   49   14                                                            
CONECT   50   14                                                            
CONECT   51   15                                                            
CONECT   52   15                                                            
CONECT   53   16                                                            
CONECT   54   16                                                            
CONECT   55   17                                                            
CONECT   56   17                                                            
CONECT   57   22                                                            
CONECT   58   25                                                            
CONECT   59   28                                                            
CONECT   60   28                                                            
CONECT   61   28                                                            
CONECT   62   29                                                            
CONECT   63   30                                                            
CONECT   64   31                                                            
CONECT   65   32                                                            
CONECT   66   34                                                            
CONECT   67   35                                                            
CONECT   68   35                                                            
CONECT   69   36                                                            
CONECT   70   36                                                            
MASTER        0    0    0    0    0    0    0    0   70    0  146    0
END

RDKit          3D

70 73  0  0  0  0  0  0  0  0999 V2000
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  1  2  2  3
  3  2  1  1
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  5  6  2  0
  6  7  1  0
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  9 10  1  0
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 33 35  1  0
 35 36  1  0
 36  3  1  0
 33  6  1  0
 18 11  1  0
 31 22  1  0
  1 37  1  0
  1 38  1  0
  2 39  1  0
  4 40  1  0
  4 41  1  0
  4 42  1  0
  5 43  1  0
 10 44  1  0
 13 45  1  0
 13 46  1  0
 13 47  1  0
 14 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  0
 15 52  1  0
 16 53  1  0
 16 54  1  0
 17 55  1  0
 17 56  1  0
 22 57  1  6
 25 58  1  0
 28 59  1  0
 28 60  1  0
 28 61  1  0
 29 62  1  6
 30 63  1  0
 31 64  1  6
 32 65  1  0
 34 66  1  0
 35 67  1  0
 35 68  1  0
 36 69  1  0
 36 70  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(1R,5S,6R)-5,6-Dihydroxy-4-methoxy-2-oxocyclohex-3-en-1-yl (4ar,4BR,7R)-7-ethenyl-4b,10-dihydroxy-1,1,7-trimethyl-9-oxo-1,2,3,4,4a,4b,5,6,7,9-decahydrophenanthrene-4a-carboxylic acid	Generator

Chemical Formula

C₂₇H₃₄O₉

Average Mass

502.5600 Da

Monoisotopic Mass

502.22028 Da

IUPAC Name

(1R,5S,6R)-5,6-dihydroxy-4-methoxy-2-oxocyclohex-3-en-1-yl (4aR,4bR,7R)-7-ethenyl-4b,10-dihydroxy-1,1,7-trimethyl-9-oxo-1,2,3,4,4a,4b,5,6,7,9-decahydrophenanthrene-4a-carboxylate

Traditional Name

(1R,5S,6R)-5,6-dihydroxy-4-methoxy-2-oxocyclohex-3-en-1-yl (4aR,4bR,7R)-7-ethenyl-4b,10-dihydroxy-1,1,7-trimethyl-9-oxo-3,4,5,6-tetrahydro-2H-phenanthrene-4a-carboxylate

CAS Registry Number

Not Available

SMILES

COC1=CC(=O)[C@H](OC(=O)[C@]23CCCC(C)(C)C2=C(O)C(=O)C2=C[C@](C)(CC[C@]32O)C=C)[C@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C27H34O9/c1-6-25(4)10-11-27(34)14(13-25)17(29)20(32)22-24(2,3)8-7-9-26(22,27)23(33)36-21-15(28)12-16(35-5)18(30)19(21)31/h6,12-13,18-19,21,30-32,34H,1,7-11H2,2-5H3/t18-,19-,21+,25+,26+,27-/m1/s1

InChI Key

QRKUDJZMRTVQRY-SJJDIPSKSA-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
Botryosphaeria laricina	NPAtlas	28609099

Chemical Taxonomy

Classification

Not classified

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.53	ALOGPS
logP	1.56	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	9.03	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	150.59 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	131.75 m³·mol⁻¹	ChemAxon
Polarizability	51.84 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA022361

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78441642

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

132487898

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Botrysphin E (NP0016709)

MOL for NP0016709 (Botrysphin E)

3D MOL for NP0016709 (Botrysphin E)

3D SDF for NP0016709 (Botrysphin E)

3D-SDF for NP0016709 (Botrysphin E)

PDB for NP0016709 (Botrysphin E)

3D PDB for NP0016709 (Botrysphin E)

SMILES for NP0016709 (Botrysphin E)

INCHI for NP0016709 (Botrysphin E)

Structure for NP0016709 (Botrysphin E)

3D Structure for NP0016709 (Botrysphin E)