NP-MRD: Showing NP-Card for Armillaridin (NP0021893)

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Record Information

Version

2.0

Created at

2021-01-06 07:08:21 UTC

Updated at

2021-07-15 17:37:35 UTC

NP-MRD ID

NP0021893

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Armillaridin

Provided By

NPAtlas

Description

Armillaridin is found in Armillaria mellea and Armillaria ostoyae. Armillaridin was first documented in 1984 (PMID: 6548820). Based on a literature review a small amount of articles have been published on Armillaridin (PMID: 31488037) (PMID: 27592257) (PMID: 26952552).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242105193D          

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  Mrv1652306242105193D          

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    4.8398    1.1776    0.1536 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8127    2.3006    1.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0613    0.9364   -0.4877 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4601    1.9403   -0.1298 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.8291   -1.3884   -3.6621 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5862   -1.0088   -3.5286 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8283   -2.2666   -2.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2054   -1.6412   -2.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9496   -1.4257   -1.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2904    1.2575    1.8456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5961   -1.6213    1.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3554   -0.8850    2.8542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8225    1.1541    3.2164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7729    2.2533    2.2411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0571    1.0739    3.4383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6367   -0.6301    2.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4112    0.9088   -0.3794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4046    1.3037    1.1050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8598   -0.9661   -1.9896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4570    0.1833   -2.0651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1341    0.7617   -1.5341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0869   -0.9114    0.5176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9737   -0.3462    1.8477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5717    0.8313    0.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5792   -2.3933   -0.9394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9949   -2.3281    0.8511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6922   -2.5679    0.9581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2628   -1.9970   -1.5888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6618   -0.8452   -2.8453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5454    2.5300    0.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8200    2.8072    1.1423 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1115    3.1140    0.8445 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5919    1.9611    2.1537 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  1  6  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 23 26  1  0  0  0  0
 26 27  1  6  0  0  0
  7 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30  3  1  0  0  0  0
 26 11  1  0  0  0  0
 26 13  1  0  0  0  0
 21 15  1  0  0  0  0
  1 32  1  0  0  0  0
  1 33  1  0  0  0  0
  1 34  1  0  0  0  0
  4 35  1  0  0  0  0
  6 36  1  0  0  0  0
 11 37  1  1  0  0  0
 12 38  1  0  0  0  0
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 14 40  1  0  0  0  0
 14 41  1  0  0  0  0
 14 42  1  0  0  0  0
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 16 44  1  0  0  0  0
 16 45  1  0  0  0  0
 18 46  1  0  0  0  0
 18 47  1  0  0  0  0
 18 48  1  0  0  0  0
 19 49  1  0  0  0  0
 19 50  1  0  0  0  0
 19 51  1  0  0  0  0
 20 52  1  0  0  0  0
 20 53  1  0  0  0  0
 21 54  1  1  0  0  0
 22 55  1  0  0  0  0
 24 56  1  0  0  0  0
 27 57  1  0  0  0  0
 29 58  1  0  0  0  0
 29 59  1  0  0  0  0
 29 60  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0021893

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

> <INCHI_IDENTIFIER>
InChI=1S/C24H29ClO6/c1-12-19(16(27)7-17(30-5)20(12)25)21(28)31-18-10-23(4)15-9-22(2,3)8-13(15)6-14(11-26)24(18,23)29/h6-7,11,13,15,18,27,29H,8-10H2,1-5H3/t13-,15+,18-,23-,24+/m1/s1

> <INCHI_KEY>
QETHRCCHQRWBIJ-OXKPQTCESA-N

> <FORMULA>
C24H29ClO6

> <MOLECULAR_WEIGHT>
448.94

> <EXACT_MASS>
448.1652664

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
47.043915824029035

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,2aS,4aS,7aS,7bR)-3-formyl-2a-hydroxy-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>
4.35

> <JCHEM_LOGP>
4.857467948

> <ALOGPS_LOGS>
-5.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.797544840705278

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.325375809042622

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7622191458403913

> <JCHEM_POLAR_SURFACE_AREA>
93.06000000000002

> <JCHEM_REFRACTIVITY>
117.33389999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.63e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,2aS,4aS,7aS,7bR)-3-formyl-2a-hydroxy-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

 60 63  0  0  0  0  0  0  0  0999 V2000
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    2.4814    0.6993    0.5871 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1718    0.3847    1.1435 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6305   -0.7320    1.7920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8130    0.1940    1.5809 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -6.2606   -0.2447    0.7806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4853   -1.8188   -0.0180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0330   -1.6523    0.4305 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1663   -1.3301   -0.7241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3107   -0.3198   -0.7740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5436   -0.1633   -1.9985 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2763    0.7869   -2.0746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0981    0.6348    0.3206 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2684    1.9730   -0.0060 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8398    1.1776    0.1536 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8127    2.3006    1.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0613    0.9364   -0.4877 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4601    1.9403   -0.1298 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.8291   -1.3884   -3.6621 H   0  0  0  0  0  0  0  0  0  0  0  0
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    7.8283   -2.2666   -2.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2054   -1.6412   -2.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9496   -1.4257   -1.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2904    1.2575    1.8456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5961   -1.6213    1.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3554   -0.8850    2.8542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8225    1.1541    3.2164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7729    2.2533    2.2411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0571    1.0739    3.4383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6367   -0.6301    2.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4112    0.9088   -0.3794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4046    1.3037    1.1050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8598   -0.9661   -1.9896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4570    0.1833   -2.0651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1341    0.7617   -1.5341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0869   -0.9114    0.5176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9737   -0.3462    1.8477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5717    0.8313    0.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5792   -2.3933   -0.9394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9949   -2.3281    0.8511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6922   -2.5679    0.9581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2628   -1.9970   -1.5888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6618   -0.8452   -2.8453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5454    2.5300    0.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8200    2.8072    1.1423 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1115    3.1140    0.8445 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5919    1.9611    2.1537 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  1  6
 17 19  1  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 23 26  1  0
 26 27  1  6
  7 28  1  0
 28 29  1  0
 28 30  2  0
 30 31  1  0
 30  3  1  0
 26 11  1  0
 26 13  1  0
 21 15  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
  6 36  1  0
 11 37  1  1
 12 38  1  0
 12 39  1  0
 14 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  1
 16 44  1  0
 16 45  1  0
 18 46  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 21 54  1  1
 22 55  1  0
 24 56  1  0
 27 57  1  0
 29 58  1  0
 29 59  1  0
 29 60  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       7.661  -1.278  -2.947  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.409  -0.279  -2.005  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.186  -0.076  -1.395  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.096  -0.846  -1.664  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.866  -0.612  -1.026  0.00  0.00           C+0
HETATM    6  O   UNK     0       2.861  -1.460  -1.390  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.723   0.400  -0.112  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.481   0.699   0.587  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.441   1.668   1.428  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.289   0.015   0.429  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.172   0.385   1.143  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.631  -0.732   1.792  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.813   0.194   1.581  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.865   1.223   2.665  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.121  -0.458   1.314  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.965   0.500   0.473  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.037  -0.424  -0.093  0.00  0.00           C+0
HETATM   18  C   UNK     0      -5.376  -0.059  -1.527  0.00  0.00           C+0
HETATM   19  C   UNK     0      -6.261  -0.245   0.781  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.485  -1.819  -0.018  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.033  -1.652   0.431  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.166  -1.330  -0.724  0.00  0.00           C+0
HETATM   23  C   UNK     0      -1.311  -0.320  -0.774  0.00  0.00           C+0
HETATM   24  C   UNK     0      -0.544  -0.163  -1.999  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.276   0.787  -2.075  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.098   0.635   0.321  0.00  0.00           C+0
HETATM   27  O   UNK     0      -1.268   1.973  -0.006  0.00  0.00           O+0
HETATM   28  C   UNK     0       4.840   1.178   0.154  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.813   2.301   1.121  0.00  0.00           C+0
HETATM   30  C   UNK     0       6.061   0.936  -0.488  0.00  0.00           C+0
HETATM   31 Cl   UNK     0       7.460   1.940  -0.130  0.00  0.00          Cl+0
HETATM   32  H   UNK     0       6.829  -1.388  -3.662  0.00  0.00           H+0
HETATM   33  H   UNK     0       8.586  -1.009  -3.529  0.00  0.00           H+0
HETATM   34  H   UNK     0       7.828  -2.267  -2.432  0.00  0.00           H+0
HETATM   35  H   UNK     0       5.205  -1.641  -2.381  0.00  0.00           H+0
HETATM   36  H   UNK     0       1.950  -1.426  -1.036  0.00  0.00           H+0
HETATM   37  H   UNK     0       0.290   1.258   1.846  0.00  0.00           H+0
HETATM   38  H   UNK     0      -0.596  -1.621   1.153  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.355  -0.885   2.854  0.00  0.00           H+0
HETATM   40  H   UNK     0      -2.822   1.154   3.216  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.773   2.253   2.241  0.00  0.00           H+0
HETATM   42  H   UNK     0      -1.057   1.074   3.438  0.00  0.00           H+0
HETATM   43  H   UNK     0      -3.637  -0.630   2.265  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.411   0.909  -0.379  0.00  0.00           H+0
HETATM   45  H   UNK     0      -4.405   1.304   1.105  0.00  0.00           H+0
HETATM   46  H   UNK     0      -5.860  -0.966  -1.990  0.00  0.00           H+0
HETATM   47  H   UNK     0      -4.457   0.183  -2.065  0.00  0.00           H+0
HETATM   48  H   UNK     0      -6.134   0.762  -1.534  0.00  0.00           H+0
HETATM   49  H   UNK     0      -7.087  -0.911   0.518  0.00  0.00           H+0
HETATM   50  H   UNK     0      -5.974  -0.346   1.848  0.00  0.00           H+0
HETATM   51  H   UNK     0      -6.572   0.831   0.650  0.00  0.00           H+0
HETATM   52  H   UNK     0      -4.579  -2.393  -0.939  0.00  0.00           H+0
HETATM   53  H   UNK     0      -4.995  -2.328   0.851  0.00  0.00           H+0
HETATM   54  H   UNK     0      -2.692  -2.568   0.958  0.00  0.00           H+0
HETATM   55  H   UNK     0      -2.263  -1.997  -1.589  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.662  -0.845  -2.845  0.00  0.00           H+0
HETATM   57  H   UNK     0      -0.545   2.530   0.395  0.00  0.00           H+0
HETATM   58  H   UNK     0       5.820   2.807   1.142  0.00  0.00           H+0
HETATM   59  H   UNK     0       4.112   3.114   0.845  0.00  0.00           H+0
HETATM   60  H   UNK     0       4.592   1.961   2.154  0.00  0.00           H+0
CONECT    1    2   32   33   34                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   30                                                  
CONECT    4    3    5   35                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5   36                                                       
CONECT    7    5    8   28                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   26   37                                             
CONECT   12   11   13   38   39                                             
CONECT   13   12   14   15   26                                             
CONECT   14   13   40   41   42                                             
CONECT   15   13   16   21   43                                             
CONECT   16   15   17   44   45                                             
CONECT   17   16   18   19   20                                             
CONECT   18   17   46   47   48                                             
CONECT   19   17   49   50   51                                             
CONECT   20   17   21   52   53                                             
CONECT   21   20   22   15   54                                             
CONECT   22   21   23   55                                                  
CONECT   23   22   24   26                                                  
CONECT   24   23   25   56                                                  
CONECT   25   24                                                            
CONECT   26   23   27   11   13                                             
CONECT   27   26   57                                                       
CONECT   28    7   29   30                                                  
CONECT   29   28   58   59   60                                             
CONECT   30   28   31    3                                                  
CONECT   31   30                                                            
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    4                                                            
CONECT   36    6                                                            
CONECT   37   11                                                            
CONECT   38   12                                                            
CONECT   39   12                                                            
CONECT   40   14                                                            
CONECT   41   14                                                            
CONECT   42   14                                                            
CONECT   43   15                                                            
CONECT   44   16                                                            
CONECT   45   16                                                            
CONECT   46   18                                                            
CONECT   47   18                                                            
CONECT   48   18                                                            
CONECT   49   19                                                            
CONECT   50   19                                                            
CONECT   51   19                                                            
CONECT   52   20                                                            
CONECT   53   20                                                            
CONECT   54   21                                                            
CONECT   55   22                                                            
CONECT   56   24                                                            
CONECT   57   27                                                            
CONECT   58   29                                                            
CONECT   59   29                                                            
CONECT   60   29                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  126    0
END

RDKit          3D

60 63  0  0  0  0  0  0  0  0999 V2000
    7.6612   -1.2777   -2.9466 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4092   -0.2785   -2.0046 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1864   -0.0755   -1.3954 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0961   -0.8464   -1.6642 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8662   -0.6122   -1.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8614   -1.4596   -1.3904 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7228    0.3997   -0.1117 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4814    0.6993    0.5871 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4411    1.6679    1.4277 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2893    0.0152    0.4293 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1718    0.3847    1.1435 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6305   -0.7320    1.7920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8130    0.1940    1.5809 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8652    1.2231    2.6647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1214   -0.4576    1.3140 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9652    0.4999    0.4727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0367   -0.4237   -0.0925 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3756   -0.0587   -1.5269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2606   -0.2447    0.7806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4853   -1.8188   -0.0180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0330   -1.6523    0.4305 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1663   -1.3301   -0.7241 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3107   -0.3198   -0.7740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5436   -0.1633   -1.9985 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2763    0.7869   -2.0746 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0981    0.6348    0.3206 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.2684    1.9730   -0.0060 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8398    1.1776    0.1536 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8127    2.3006    1.1205 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0613    0.9364   -0.4877 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4601    1.9403   -0.1298 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.8291   -1.3884   -3.6621 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5862   -1.0088   -3.5286 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8283   -2.2666   -2.4318 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2054   -1.6412   -2.3811 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9496   -1.4257   -1.0364 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2904    1.2575    1.8456 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5961   -1.6213    1.1533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3554   -0.8850    2.8542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8225    1.1541    3.2164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7729    2.2533    2.2411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0571    1.0739    3.4383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6367   -0.6301    2.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4112    0.9088   -0.3794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4046    1.3037    1.1050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8598   -0.9661   -1.9896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4570    0.1833   -2.0651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1341    0.7617   -1.5341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0869   -0.9114    0.5176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9737   -0.3462    1.8477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5717    0.8313    0.6503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5792   -2.3933   -0.9394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9949   -2.3281    0.8511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6922   -2.5679    0.9581 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2628   -1.9970   -1.5888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6618   -0.8452   -2.8453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5454    2.5300    0.3954 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8200    2.8072    1.1423 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1115    3.1140    0.8445 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5919    1.9611    2.1537 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  1  6
 17 19  1  0
 17 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 23 26  1  0
 26 27  1  6
  7 28  1  0
 28 29  1  0
 28 30  2  0
 30 31  1  0
 30  3  1  0
 26 11  1  0
 26 13  1  0
 21 15  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  4 35  1  0
  6 36  1  0
 11 37  1  1
 12 38  1  0
 12 39  1  0
 14 40  1  0
 14 41  1  0
 14 42  1  0
 15 43  1  1
 16 44  1  0
 16 45  1  0
 18 46  1  0
 18 47  1  0
 18 48  1  0
 19 49  1  0
 19 50  1  0
 19 51  1  0
 20 52  1  0
 20 53  1  0
 21 54  1  1
 22 55  1  0
 24 56  1  0
 27 57  1  0
 29 58  1  0
 29 59  1  0
 29 60  1  0
M  END

View in JSmol View NMR Assignments

Synonyms

Value	Source
(2R,2AS,4as,7as,7BR)-3-formyl-2a-hydroxy-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

C₂₄H₂₉ClO₆

Average Mass

448.9400 Da

Monoisotopic Mass

448.16527 Da

IUPAC Name

(2R,2aS,4aS,7aS,7bR)-3-formyl-2a-hydroxy-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,7aS,7bR)-3-formyl-2a-hydroxy-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]4CC(C)(C)C[C@H]4C=C(C=O)[C@]23O)C(O)=C1

InChI Identifier

InChI=1S/C24H29ClO6/c1-12-19(16(27)7-17(30-5)20(12)25)21(28)31-18-10-23(4)15-9-22(2,3)8-13(15)6-14(11-26)24(18,23)29/h6-7,11,13,15,18,27,29H,8-10H2,1-5H3/t13-,15+,18-,23-,24+/m1/s1

InChI Key

QETHRCCHQRWBIJ-OXKPQTCESA-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
Agaricus bisporus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Armillaria mellea	NPAtlas	6548820
Armillaria ostoyae	LOTUS Database	35616633
Pleurotus ostreatus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...

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	4.35	ALOGPS
logP	4.86	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	9.33	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	117.33 m³·mol⁻¹	ChemAxon
Polarizability	47.04 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

NPA018512

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00021454

Chemspider ID

26345562

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

51351607

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Yang JS, Chen YW, Feng XZ, Yu DQ, Liang XT: Chemical constituents of Armillaria mellea mycelium. I. Isolation and characterization of armillarin and armillaridin. Planta Med. 1984 Aug;50(4):288-90. doi: 10.1055/s-2007-969711. [PubMed:6548820 ]
Leu YS, Chen YJ, Chen CC, Huang HL: Induction of Autophagic Death of Human Hepatocellular Carcinoma Cells by Armillaridin from Armillaria mellea. Am J Chin Med. 2019;47(6):1365-1380. doi: 10.1142/S0192415X19500708. Epub 2019 Sep 5. [PubMed:31488037 ]
Chang WH, Huang HL, Huang WP, Chen CC, Chen YJ: Armillaridin induces autophagy-associated cell death in human chronic myelogenous leukemia K562 cells. Tumour Biol. 2016 Oct;37(10):14291-14300. doi: 10.1007/s13277-016-5208-6. Epub 2016 Sep 3. [PubMed:27592257 ]
Li Z, Wang Y, Jiang B, Li W, Zheng L, Yang X, Bao Y, Sun L, Huang Y, Li Y: Structure, cytotoxic activity and mechanism of protoilludane sesquiterpene aryl esters from the mycelium of Armillaria mellea. J Ethnopharmacol. 2016 May 26;184:119-27. doi: 10.1016/j.jep.2016.02.044. Epub 2016 Mar 4. [PubMed:26952552 ]

Showing NP-Card for Armillaridin (NP0021893)

MOL for NP0021893 (Armillaridin)

3D MOL for NP0021893 (Armillaridin)

3D SDF for NP0021893 (Armillaridin)

3D-SDF for NP0021893 (Armillaridin)

PDB for NP0021893 (Armillaridin)

3D PDB for NP0021893 (Armillaridin)

SMILES for NP0021893 (Armillaridin)

INCHI for NP0021893 (Armillaridin)

Structure for NP0021893 (Armillaridin)

3D Structure for NP0021893 (Armillaridin)