NP-MRD: Showing NP-Card for Armillarikin (NP0006865)

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Record Information

Version

1.0

Created at

2020-12-09 03:46:55 UTC

Updated at

2021-07-15 16:56:01 UTC

NP-MRD ID

NP0006865

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Armillarikin

Provided By

NPAtlas

Description

Armillarikin is found in Armillaria mellea and Armillaria novae-zelandiae. It was first documented in 1989 (PMID: 17262464). Based on a literature review very few articles have been published on (2R,2aS,4aS,7R,7aS,7bR)-3-formyl-2a,7-dihydroxy-6,6,7b-trimethyl-1H,2H,2aH,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242118353D          

 61 64  0  0  0  0            999 V2000
    8.5325    0.8936   -0.3572 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2641    1.4159   -0.7102 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0925    0.6721   -0.5121 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1093   -0.5866    0.0272 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9014   -1.3034    0.2103 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0834   -2.5419    0.7581 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7055   -0.7400   -0.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4639   -1.4773    0.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3961   -2.6418    0.4873 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2211   -0.9307   -0.3385 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8389    2.8245   -1.5586 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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    7.0665   -1.0021    0.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4032   -3.2032    0.9726 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2634   -2.7412    0.2399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7157   -1.0671   -2.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8353   -2.9063    1.0832 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.2022   -0.8337   -1.9447 H   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
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 21 22  1  1  0  0  0
 16 23  1  0  0  0  0
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  7 29  1  0  0  0  0
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 30 59  1  0  0  0  0
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M  END

     RDKit          3D

 61 64  0  0  0  0  0  0  0  0999 V2000
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    7.2641    1.4159   -0.7102 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0925    0.6721   -0.5121 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0834   -2.5419    0.7581 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7055   -0.7400   -0.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4639   -1.4773    0.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.2211   -0.9307   -0.3385 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652306242118353D          

 61 64  0  0  0  0            999 V2000
    8.5325    0.8936   -0.3572 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2641    1.4159   -0.7102 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.4639   -1.4773    0.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3961   -2.6418    0.4873 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2211   -0.9307   -0.3385 O   0  0  0  0  0  0  0  0  0  0  0  0
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    4.8389    2.8245   -1.5586 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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    7.0665   -1.0021    0.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4032   -3.2032    0.9726 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2634   -2.7412    0.2399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7157   -1.0671   -2.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9261   -2.8205   -1.7715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8353   -2.9063    1.0832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6838   -2.7892   -0.5395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1636   -3.6765   -0.3613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2022   -0.8337   -1.9447 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4631    0.2413    2.5313 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.6065    0.7645   -0.2394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2418    2.4944   -0.4678 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.0485   -0.7642   -0.6452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7559   -1.4840    1.2840 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9324    0.5854   -1.9101 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.3070   -0.2744 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6634    2.2307   -1.5434 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 18 21  1  0  0  0  0
 21 22  1  1  0  0  0
 16 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 24 27  1  0  0  0  0
 27 28  1  0  0  0  0
  7 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31  3  1  0  0  0  0
 21 11  1  0  0  0  0
 21 13  1  0  0  0  0
 27 15  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
  4 36  1  0  0  0  0
  6 37  1  0  0  0  0
 11 38  1  1  0  0  0
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 17 46  1  0  0  0  0
 19 47  1  0  0  0  0
 22 48  1  0  0  0  0
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 23 50  1  0  0  0  0
 25 51  1  0  0  0  0
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 26 56  1  0  0  0  0
 27 57  1  6  0  0  0
 28 58  1  0  0  0  0
 30 59  1  0  0  0  0
 30 60  1  0  0  0  0
 30 61  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0006865

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C(C(=O)O[C@]2([H])C([H])([H])[C@]3(C([H])([H])[H])[C@]4([H])[C@]([H])(C([H])=C(C([H])=O)[C@]23O[H])C([H])([H])C(C([H])([H])[H])(C([H])([H])[H])[C@]4([H])O[H])C(=C(Cl)C(OC([H])([H])[H])=C1[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C24H29ClO7/c1-11-17(14(27)7-15(31-5)19(11)25)21(29)32-16-9-23(4)18-12(8-22(2,3)20(18)28)6-13(10-26)24(16,23)30/h6-7,10,12,16,18,20,27-28,30H,8-9H2,1-5H3/t12-,16-,18-,20-,23-,24+/m1/s1

> <INCHI_KEY>
LNEWYAZEAYTKQI-UEXMDZLUSA-N

> <FORMULA>
C24H29ClO7

> <MOLECULAR_WEIGHT>
464.94

> <EXACT_MASS>
464.160181

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
47.819068238772395

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,2aS,4aS,7R,7aS,7bR)-3-formyl-2a,7-dihydroxy-6,6,7b-trimethyl-1H,2H,2aH,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate

> <ALOGPS_LOGP>
2.99

> <JCHEM_LOGP>
3.7046106109999997

> <ALOGPS_LOGS>
-4.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.783824796788036

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.325371087604763

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0342593569572927

> <JCHEM_POLAR_SURFACE_AREA>
113.29

> <JCHEM_REFRACTIVITY>
118.77239999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.72e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,2aS,4aS,7R,7aS,7bR)-3-formyl-2a,7-dihydroxy-6,6,7b-trimethyl-1H,2H,4aH,5H,7H,7aH-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 61 64  0  0  0  0  0  0  0  0999 V2000
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    3.6864    0.5306   -0.6973 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4516    1.2173   -1.1357 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8783    1.2197   -0.8700 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8389    2.8245   -1.5586 Cl  0  0  0  0  0  0  0  0  0  0  0  0
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    8.4190    0.4693    0.6798 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0665   -1.0021    0.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4032   -3.2032    0.9726 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2634   -2.7412    0.2399 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.1636   -3.6765   -0.3613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2022   -0.8337   -1.9447 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.4631    0.2413    2.5313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2967   -0.9708    2.6069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2051    2.8664   -0.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9406    1.8929   -2.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.7559   -1.4840    1.2840 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9324    0.5854   -1.9101 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.3070   -0.2744 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6634    2.2307   -1.5434 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  1
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 18 21  1  0
 21 22  1  1
 16 23  1  0
 23 24  1  0
 24 25  1  1
 24 26  1  0
 24 27  1  0
 27 28  1  0
  7 29  1  0
 29 30  1  0
 29 31  2  0
 31 32  1  0
 31  3  1  0
 21 11  1  0
 21 13  1  0
 27 15  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  6 37  1  0
 11 38  1  1
 12 39  1  0
 12 40  1  0
 14 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  6
 16 45  1  6
 17 46  1  0
 19 47  1  0
 22 48  1  0
 23 49  1  0
 23 50  1  0
 25 51  1  0
 25 52  1  0
 25 53  1  0
 26 54  1  0
 26 55  1  0
 26 56  1  0
 27 57  1  6
 28 58  1  0
 30 59  1  0
 30 60  1  0
 30 61  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       8.533   0.894  -0.357  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.264   1.416  -0.710  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.093   0.672  -0.512  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.109  -0.587   0.027  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.901  -1.303   0.210  0.00  0.00           C+0
HETATM    6  O   UNK     0       5.083  -2.542   0.758  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.705  -0.740  -0.152  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.464  -1.477   0.018  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.396  -2.642   0.487  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.221  -0.931  -0.339  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.072  -1.711  -0.157  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.866  -1.796  -1.306  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.987  -1.484  -0.356  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.715  -2.761  -0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.932  -0.475  -0.929  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.318   0.890  -1.101  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.461   1.288   0.011  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.866   0.427   0.795  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.034   0.927   1.877  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.120   2.154   2.066  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.008  -1.025   0.630  0.00  0.00           C+0
HETATM   22  O   UNK     0      -1.091  -1.604   1.907  0.00  0.00           O+0
HETATM   23  C   UNK     0      -3.517   1.854  -1.075  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.504   1.215  -0.127  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.473   1.828   1.238  0.00  0.00           C+0
HETATM   26  C   UNK     0      -5.885   1.488  -0.713  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.175  -0.238  -0.155  0.00  0.00           C+0
HETATM   28  O   UNK     0      -4.136  -0.736   1.143  0.00  0.00           O+0
HETATM   29  C   UNK     0       3.686   0.531  -0.697  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.452   1.217  -1.136  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.878   1.220  -0.870  0.00  0.00           C+0
HETATM   32 Cl   UNK     0       4.839   2.825  -1.559  0.00  0.00          Cl+0
HETATM   33  H   UNK     0       9.306   1.688  -0.317  0.00  0.00           H+0
HETATM   34  H   UNK     0       8.801   0.066  -1.039  0.00  0.00           H+0
HETATM   35  H   UNK     0       8.419   0.469   0.680  0.00  0.00           H+0
HETATM   36  H   UNK     0       7.066  -1.002   0.302  0.00  0.00           H+0
HETATM   37  H   UNK     0       4.403  -3.203   0.973  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.263  -2.741   0.240  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.716  -1.067  -2.127  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.926  -2.821  -1.772  0.00  0.00           H+0
HETATM   41  H   UNK     0      -2.835  -2.906   1.083  0.00  0.00           H+0
HETATM   42  H   UNK     0      -3.684  -2.789  -0.540  0.00  0.00           H+0
HETATM   43  H   UNK     0      -2.164  -3.676  -0.361  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.202  -0.834  -1.945  0.00  0.00           H+0
HETATM   45  H   UNK     0      -1.767   1.023  -2.048  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.315   2.349   0.190  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.463   0.241   2.531  0.00  0.00           H+0
HETATM   48  H   UNK     0      -1.297  -0.971   2.607  0.00  0.00           H+0
HETATM   49  H   UNK     0      -3.205   2.866  -0.766  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.941   1.893  -2.095  0.00  0.00           H+0
HETATM   51  H   UNK     0      -4.422   1.121   2.066  0.00  0.00           H+0
HETATM   52  H   UNK     0      -3.581   2.506   1.314  0.00  0.00           H+0
HETATM   53  H   UNK     0      -5.351   2.484   1.396  0.00  0.00           H+0
HETATM   54  H   UNK     0      -6.606   0.765  -0.239  0.00  0.00           H+0
HETATM   55  H   UNK     0      -6.242   2.494  -0.468  0.00  0.00           H+0
HETATM   56  H   UNK     0      -5.888   1.378  -1.817  0.00  0.00           H+0
HETATM   57  H   UNK     0      -5.048  -0.764  -0.645  0.00  0.00           H+0
HETATM   58  H   UNK     0      -4.756  -1.484   1.284  0.00  0.00           H+0
HETATM   59  H   UNK     0       1.932   0.585  -1.910  0.00  0.00           H+0
HETATM   60  H   UNK     0       1.780   1.307  -0.274  0.00  0.00           H+0
HETATM   61  H   UNK     0       2.663   2.231  -1.543  0.00  0.00           H+0
CONECT    1    2   33   34   35                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   31                                                  
CONECT    4    3    5   36                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5   37                                                       
CONECT    7    5    8   29                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   21   38                                             
CONECT   12   11   13   39   40                                             
CONECT   13   12   14   15   21                                             
CONECT   14   13   41   42   43                                             
CONECT   15   13   16   27   44                                             
CONECT   16   15   17   23   45                                             
CONECT   17   16   18   46                                                  
CONECT   18   17   19   21                                                  
CONECT   19   18   20   47                                                  
CONECT   20   19                                                            
CONECT   21   18   22   11   13                                             
CONECT   22   21   48                                                       
CONECT   23   16   24   49   50                                             
CONECT   24   23   25   26   27                                             
CONECT   25   24   51   52   53                                             
CONECT   26   24   54   55   56                                             
CONECT   27   24   28   15   57                                             
CONECT   28   27   58                                                       
CONECT   29    7   30   31                                                  
CONECT   30   29   59   60   61                                             
CONECT   31   29   32    3                                                  
CONECT   32   31                                                            
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    4                                                            
CONECT   37    6                                                            
CONECT   38   11                                                            
CONECT   39   12                                                            
CONECT   40   12                                                            
CONECT   41   14                                                            
CONECT   42   14                                                            
CONECT   43   14                                                            
CONECT   44   15                                                            
CONECT   45   16                                                            
CONECT   46   17                                                            
CONECT   47   19                                                            
CONECT   48   22                                                            
CONECT   49   23                                                            
CONECT   50   23                                                            
CONECT   51   25                                                            
CONECT   52   25                                                            
CONECT   53   25                                                            
CONECT   54   26                                                            
CONECT   55   26                                                            
CONECT   56   26                                                            
CONECT   57   27                                                            
CONECT   58   28                                                            
CONECT   59   30                                                            
CONECT   60   30                                                            
CONECT   61   30                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  128    0
END

RDKit          3D

61 64  0  0  0  0  0  0  0  0999 V2000
    8.5325    0.8936   -0.3572 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2641    1.4159   -0.7102 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0925    0.6721   -0.5121 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1093   -0.5866    0.0272 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9014   -1.3034    0.2103 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0834   -2.5419    0.7581 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7055   -0.7400   -0.1521 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4639   -1.4773    0.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3961   -2.6418    0.4873 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2211   -0.9307   -0.3385 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0716   -1.7112   -0.1571 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8661   -1.7961   -1.3062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9868   -1.4836   -0.3564 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7154   -2.7609   -0.0001 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9321   -0.4748   -0.9286 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3180    0.8896   -1.1008 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4611    1.2877    0.0112 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8664    0.4269    0.7945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0338    0.9269    1.8768 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1196    2.1541    2.0664 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0082   -1.0250    0.6297 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0907   -1.6040    1.9070 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5168    1.8536   -1.0751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5042    1.2149   -0.1271 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.4730    1.8279    1.2378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8847    1.4877   -0.7126 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1751   -0.2376   -0.1548 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.1359   -0.7356    1.1435 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6864    0.5306   -0.6973 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4516    1.2173   -1.1357 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8783    1.2197   -0.8700 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8389    2.8245   -1.5586 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    9.3061    1.6878   -0.3173 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8012    0.0660   -1.0391 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4190    0.4693    0.6798 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0665   -1.0021    0.3016 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4032   -3.2032    0.9726 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2634   -2.7412    0.2399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7157   -1.0671   -2.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9261   -2.8205   -1.7715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8353   -2.9063    1.0832 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6838   -2.7892   -0.5395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1636   -3.6765   -0.3613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2022   -0.8337   -1.9447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7673    1.0227   -2.0477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3154    2.3485    0.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4631    0.2413    2.5313 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2967   -0.9708    2.6069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2051    2.8664   -0.7661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9406    1.8929   -2.0951 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4219    1.1214    2.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5807    2.5055    1.3144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3507    2.4836    1.3961 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6065    0.7645   -0.2394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2418    2.4944   -0.4678 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8879    1.3781   -1.8174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0485   -0.7642   -0.6452 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7559   -1.4840    1.2840 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9324    0.5854   -1.9101 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.3070   -0.2744 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6634    2.2307   -1.5434 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  1
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 18 21  1  0
 21 22  1  1
 16 23  1  0
 23 24  1  0
 24 25  1  1
 24 26  1  0
 24 27  1  0
 27 28  1  0
  7 29  1  0
 29 30  1  0
 29 31  2  0
 31 32  1  0
 31  3  1  0
 21 11  1  0
 21 13  1  0
 27 15  1  0
  1 33  1  0
  1 34  1  0
  1 35  1  0
  4 36  1  0
  6 37  1  0
 11 38  1  1
 12 39  1  0
 12 40  1  0
 14 41  1  0
 14 42  1  0
 14 43  1  0
 15 44  1  6
 16 45  1  6
 17 46  1  0
 19 47  1  0
 22 48  1  0
 23 49  1  0
 23 50  1  0
 25 51  1  0
 25 52  1  0
 25 53  1  0
 26 54  1  0
 26 55  1  0
 26 56  1  0
 27 57  1  6
 28 58  1  0
 30 59  1  0
 30 60  1  0
 30 61  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(2R,2AS,4as,7R,7as,7BR)-3-formyl-2a,7-dihydroxy-6,6,7b-trimethyl-1H,2H,2ah,4ah,5H,6H,7H,7ah,7BH-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoic acid	Generator

Chemical Formula

C₂₄H₂₉ClO₇

Average Mass

464.9400 Da

Monoisotopic Mass

464.16018 Da

IUPAC Name

(2R,2aS,4aS,7R,7aS,7bR)-3-formyl-2a,7-dihydroxy-6,6,7b-trimethyl-1H,2H,2aH,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate

Traditional Name

(2R,2aS,4aS,7R,7aS,7bR)-3-formyl-2a,7-dihydroxy-6,6,7b-trimethyl-1H,2H,4aH,5H,7H,7aH-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate

CAS Registry Number

Not Available

SMILES

COC1=C(Cl)C(C)=C(C(=O)O[C@@H]2C[C@]3(C)[C@@H]4[C@@H](CC(C)(C)[C@@H]4O)C=C(C=O)[C@]23O)C(O)=C1

InChI Identifier

InChI=1S/C24H29ClO7/c1-11-17(14(27)7-15(31-5)19(11)25)21(29)32-16-9-23(4)18-12(8-22(2,3)20(18)28)6-13(10-26)24(16,23)30/h6-7,10,12,16,18,20,27-28,30H,8-9H2,1-5H3/t12-,16-,18-,20-,23-,24+/m1/s1

InChI Key

LNEWYAZEAYTKQI-UEXMDZLUSA-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
Armillaria mellea	NPAtlas	17262464
Armillaria novae-zelandiae	LOTUS Database	35616633

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	2.99	ALOGPS
logP	3.7	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	9.33	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	118.77 m³·mol⁻¹	ChemAxon
Polarizability	47.82 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

NPAtlas ID

NPA003281

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

78439615

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

129320386

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yang JS, Su YL, Wang YL, Feng XZ, Yu DQ, Cong PZ, Tamai M, Obuchi T, Kondoh H, Liang XT: Isolation and structures of two new sesquiterpenoid aromatic esters: armillarigin and armillarikin1. Planta Med. 1989 Oct;55(5):479-81. doi: 10.1055/s-2006-962070. [PubMed:17262464 ]

Showing NP-Card for Armillarikin (NP0006865)

MOL for NP0006865 (Armillarikin)

3D MOL for NP0006865 (Armillarikin)

3D SDF for NP0006865 (Armillarikin)

3D-SDF for NP0006865 (Armillarikin)

PDB for NP0006865 (Armillarikin)

3D PDB for NP0006865 (Armillarikin)

SMILES for NP0006865 (Armillarikin)

INCHI for NP0006865 (Armillarikin)

Structure for NP0006865 (Armillarikin)

3D Structure for NP0006865 (Armillarikin)