NP-MRD: Showing NP-Card for Melleolide L (NP0003258)

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Record Information

Version

1.0

Created at

2020-12-09 00:32:26 UTC

Updated at

2021-07-15 16:45:56 UTC

NP-MRD ID

NP0003258

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Melleolide L

Provided By

NPAtlas

Description

(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-4,6-dihydroxy-2-methylbenzoate belongs to the class of organic compounds known as melleolides and analogues. Melleolides and analogues are compounds with a structure characterized by the presence of a 2-hydroxy-4-methoxy-6-methylbenzoic acid derivative linked to a 3,6,6,7b-tetramethyl-cyclobuta[e]indene moiety. Melleolide L is found in Armillaria mellea , Armillaria novae-zelandiae, Armillariella and Armillariella mellea (Vahl. ex Fr.) Karst . It was first documented in 2000 (PMID: 10805573). 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-4,6-dihydroxy-2-methylbenzoate.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306242117463D          

 58 61  0  0  0  0            999 V2000
    3.0674   -1.6576    0.6422 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3781   -0.9347    0.6076 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5413   -1.6632    0.7342 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5018   -3.4195    0.9170 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.7561   -1.0244    0.7194 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9176   -1.7879    0.8496 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7653    0.3291    0.5777 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5656    1.0794    0.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6766    2.4352    0.3089 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3411    0.4517    0.4599 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0694    1.1601    0.3500 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9881    2.4072    0.2370 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8177    0.5339    0.3587 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6348    1.2869    0.2638 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3696    1.0447    1.3641 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4261    1.3611    0.3308 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.5379   -0.5381   -0.9920 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3408   -1.1031   -2.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1835   -0.4112   -2.6442 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4235    0.8859   -0.7033 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3703    1.7167   -1.8350 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.3858   -0.7473   -0.6307 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -3.5904    0.5534   -0.6777 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0623    0.6649   -1.9340 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2851    1.7854    2.1858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3405   -0.0100    1.6698 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  2  0  0  0  0
  3  4  1  0  0  0  0
  3  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  1  0  0  0  0
  8 10  2  0  0  0  0
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 11 13  1  0  0  0  0
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 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
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 19 26  1  0  0  0  0
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 10  2  1  0  0  0  0
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M  END

     RDKit          3D

 58 61  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306242117463D          

 58 61  0  0  0  0            999 V2000
    3.0674   -1.6576    0.6422 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3781   -0.9347    0.6076 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5413   -1.6632    0.7342 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5018   -3.4195    0.9170 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.7561   -1.0244    0.7194 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9176   -1.7879    0.8496 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7653    0.3291    0.5777 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5656    1.0794    0.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.3411    0.4517    0.4599 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0694    1.1601    0.3500 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.8177    0.5339    0.3587 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6348    1.2869    0.2638 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -0.3703    1.7167   -1.8350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7028   -1.5721    0.4394 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.3858   -0.7473   -0.6307 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8275   -0.4514   -0.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3426   -1.4727   -1.9463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5904    0.5534   -0.6777 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0623    0.6649   -1.9340 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2803   -2.7396    0.8751 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4965   -1.3056    1.5240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5347   -1.5514   -0.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8249   -1.3223    0.8399 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6982    0.8697    0.5613 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9639    3.0754    0.2088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8114    2.4006    0.2065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2851    1.7854    2.1858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3405   -0.0100    1.6698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4515    3.3669    1.1328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7924    2.9425   -0.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1448    3.3075   -0.6215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1871    0.8819    1.3705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0034   -1.1861    1.6679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3875   -2.3959   -0.6989 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3107   -2.1561   -2.3011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4830    1.2072   -2.6741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2946   -1.4760    1.3755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5888   -2.6307    0.1674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1042    0.4916   -0.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5234   -1.2387   -0.6899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9970   -0.2709    0.7756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3021   -0.7170   -2.7730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3882   -2.0441   -2.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2239   -2.1333   -2.0649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2944    1.4138   -0.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5420    1.2677   -2.5412 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  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  1  0  0  0  0
  8 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  6  0  0  0
 19 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 27 29  1  0  0  0  0
 27 30  1  0  0  0  0
 30 31  1  0  0  0  0
 10  2  1  0  0  0  0
 24 14  1  0  0  0  0
 24 16  1  0  0  0  0
 30 18  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
  6 35  1  0  0  0  0
  7 36  1  0  0  0  0
  9 37  1  0  0  0  0
 14 38  1  6  0  0  0
 15 39  1  0  0  0  0
 15 40  1  0  0  0  0
 17 41  1  0  0  0  0
 17 42  1  0  0  0  0
 17 43  1  0  0  0  0
 18 44  1  1  0  0  0
 19 45  1  1  0  0  0
 20 46  1  0  0  0  0
 22 47  1  0  0  0  0
 25 48  1  0  0  0  0
 26 49  1  0  0  0  0
 26 50  1  0  0  0  0
 28 51  1  0  0  0  0
 28 52  1  0  0  0  0
 28 53  1  0  0  0  0
 29 54  1  0  0  0  0
 29 55  1  0  0  0  0
 29 56  1  0  0  0  0
 30 57  1  1  0  0  0
 31 58  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0003258

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC1=C([H])C(O[H])=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(=C1Cl)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C23H27ClO7/c1-10-16(13(26)6-14(27)18(10)24)20(29)31-15-8-22(4)17-11(7-21(2,3)19(17)28)5-12(9-25)23(15,22)30/h5-6,9,11,15,17,19,26-28,30H,7-8H2,1-4H3/t11-,15-,17-,19-,22-,23+/m1/s1

> <INCHI_KEY>
QXPGYRDUXBYJHG-NDVLAHOZSA-N

> <FORMULA>
C23H27ClO7

> <MOLECULAR_WEIGHT>
450.91

> <EXACT_MASS>
450.1445309

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
46.082589764312594

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <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-4,6-dihydroxy-2-methylbenzoate

> <ALOGPS_LOGP>
2.80

> <JCHEM_LOGP>
3.5587165549999997

> <ALOGPS_LOGS>
-3.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.024834478034853

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.208684562783208

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0342593569572927

> <JCHEM_POLAR_SURFACE_AREA>
124.29000000000002

> <JCHEM_REFRACTIVITY>
114.29009999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.66e-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-4,6-dihydroxy-2-methylbenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 58 61  0  0  0  0  0  0  0  0999 V2000
    3.0674   -1.6576    0.6422 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3781   -0.9347    0.6076 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5413   -1.6632    0.7342 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5018   -3.4195    0.9170 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.7561   -1.0244    0.7194 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9176   -1.7879    0.8496 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7653    0.3291    0.5777 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5656    1.0794    0.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6766    2.4352    0.3089 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3411    0.4517    0.4599 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0694    1.1601    0.3500 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9881    2.4072    0.2370 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8177    0.5339    0.3587 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6348    1.2869    0.2638 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3696    1.0447    1.3641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4261    1.3611    0.3308 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7323    2.8212    0.1992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6482    0.5230    0.4546 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3308   -0.9398    0.6502 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3822   -1.3637   -0.4038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5379   -0.5381   -0.9920 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3408   -1.1031   -2.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1835   -0.4112   -2.6442 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4235    0.8859   -0.7033 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3703    1.7167   -1.8350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7028   -1.5721    0.4394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3858   -0.7473   -0.6307 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8275   -0.4514   -0.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3426   -1.4727   -1.9463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5904    0.5534   -0.6777 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0623    0.6649   -1.9340 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2803   -2.7396    0.8751 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4965   -1.3056    1.5240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5347   -1.5514   -0.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8249   -1.3223    0.8399 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6982    0.8697    0.5613 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9639    3.0754    0.2088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8114    2.4006    0.2065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2851    1.7854    2.1858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3405   -0.0100    1.6698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4515    3.3669    1.1328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7924    2.9425   -0.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1448    3.3075   -0.6215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1871    0.8819    1.3705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0034   -1.1861    1.6679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3875   -2.3959   -0.6989 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3107   -2.1561   -2.3011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4830    1.2072   -2.6741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2946   -1.4760    1.3755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5888   -2.6307    0.1674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1042    0.4916   -0.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5234   -1.2387   -0.6899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9970   -0.2709    0.7756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3021   -0.7170   -2.7730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3882   -2.0441   -2.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2239   -2.1333   -2.0649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2944    1.4138   -0.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5420    1.2677   -2.5412 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  6
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 21 24  1  0
 24 25  1  6
 19 26  1  0
 26 27  1  0
 27 28  1  1
 27 29  1  0
 27 30  1  0
 30 31  1  0
 10  2  1  0
 24 14  1  0
 24 16  1  0
 30 18  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  6 35  1  0
  7 36  1  0
  9 37  1  0
 14 38  1  6
 15 39  1  0
 15 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  1
 19 45  1  1
 20 46  1  0
 22 47  1  0
 25 48  1  0
 26 49  1  0
 26 50  1  0
 28 51  1  0
 28 52  1  0
 28 53  1  0
 29 54  1  0
 29 55  1  0
 29 56  1  0
 30 57  1  1
 31 58  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       3.067  -1.658   0.642  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.378  -0.935   0.608  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.541  -1.663   0.734  0.00  0.00           C+0
HETATM    4 Cl   UNK     0       5.502  -3.420   0.917  0.00  0.00          Cl+0
HETATM    5  C   UNK     0       6.756  -1.024   0.719  0.00  0.00           C+0
HETATM    6  O   UNK     0       7.918  -1.788   0.850  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.765   0.329   0.578  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.566   1.079   0.447  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.677   2.435   0.309  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.341   0.452   0.460  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.069   1.160   0.350  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.988   2.407   0.237  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.818   0.534   0.359  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.635   1.287   0.264  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.370   1.045   1.364  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.426   1.361   0.331  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.732   2.821   0.199  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.648   0.523   0.455  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.331  -0.940   0.650  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.382  -1.364  -0.404  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.538  -0.538  -0.992  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.341  -1.103  -2.021  0.00  0.00           C+0
HETATM   23  O   UNK     0       1.184  -0.411  -2.644  0.00  0.00           O+0
HETATM   24  C   UNK     0      -0.424   0.886  -0.703  0.00  0.00           C+0
HETATM   25  O   UNK     0      -0.370   1.717  -1.835  0.00  0.00           O+0
HETATM   26  C   UNK     0      -3.703  -1.572   0.439  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.386  -0.747  -0.631  0.00  0.00           C+0
HETATM   28  C   UNK     0      -5.827  -0.451  -0.292  0.00  0.00           C+0
HETATM   29  C   UNK     0      -4.343  -1.473  -1.946  0.00  0.00           C+0
HETATM   30  C   UNK     0      -3.590   0.553  -0.678  0.00  0.00           C+0
HETATM   31  O   UNK     0      -3.062   0.665  -1.934  0.00  0.00           O+0
HETATM   32  H   UNK     0       3.280  -2.740   0.875  0.00  0.00           H+0
HETATM   33  H   UNK     0       2.497  -1.306   1.524  0.00  0.00           H+0
HETATM   34  H   UNK     0       2.535  -1.551  -0.302  0.00  0.00           H+0
HETATM   35  H   UNK     0       8.825  -1.322   0.840  0.00  0.00           H+0
HETATM   36  H   UNK     0       7.698   0.870   0.561  0.00  0.00           H+0
HETATM   37  H   UNK     0       4.964   3.075   0.209  0.00  0.00           H+0
HETATM   38  H   UNK     0       0.811   2.401   0.207  0.00  0.00           H+0
HETATM   39  H   UNK     0      -0.285   1.785   2.186  0.00  0.00           H+0
HETATM   40  H   UNK     0      -0.341  -0.010   1.670  0.00  0.00           H+0
HETATM   41  H   UNK     0      -1.452   3.367   1.133  0.00  0.00           H+0
HETATM   42  H   UNK     0      -2.792   2.942  -0.069  0.00  0.00           H+0
HETATM   43  H   UNK     0      -1.145   3.308  -0.622  0.00  0.00           H+0
HETATM   44  H   UNK     0      -3.187   0.882   1.371  0.00  0.00           H+0
HETATM   45  H   UNK     0      -2.003  -1.186   1.668  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.387  -2.396  -0.699  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.311  -2.156  -2.301  0.00  0.00           H+0
HETATM   48  H   UNK     0      -0.483   1.207  -2.674  0.00  0.00           H+0
HETATM   49  H   UNK     0      -4.295  -1.476   1.375  0.00  0.00           H+0
HETATM   50  H   UNK     0      -3.589  -2.631   0.167  0.00  0.00           H+0
HETATM   51  H   UNK     0      -6.104   0.492  -0.835  0.00  0.00           H+0
HETATM   52  H   UNK     0      -6.523  -1.239  -0.690  0.00  0.00           H+0
HETATM   53  H   UNK     0      -5.997  -0.271   0.776  0.00  0.00           H+0
HETATM   54  H   UNK     0      -4.302  -0.717  -2.773  0.00  0.00           H+0
HETATM   55  H   UNK     0      -3.388  -2.044  -2.007  0.00  0.00           H+0
HETATM   56  H   UNK     0      -5.224  -2.133  -2.065  0.00  0.00           H+0
HETATM   57  H   UNK     0      -4.294   1.414  -0.534  0.00  0.00           H+0
HETATM   58  H   UNK     0      -3.542   1.268  -2.541  0.00  0.00           H+0
CONECT    1    2   32   33   34                                             
CONECT    2    1    3   10                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5   35                                                       
CONECT    7    5    8   36                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8   37                                                       
CONECT   10    8   11    2                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   24   38                                             
CONECT   15   14   16   39   40                                             
CONECT   16   15   17   18   24                                             
CONECT   17   16   41   42   43                                             
CONECT   18   16   19   30   44                                             
CONECT   19   18   20   26   45                                             
CONECT   20   19   21   46                                                  
CONECT   21   20   22   24                                                  
CONECT   22   21   23   47                                                  
CONECT   23   22                                                            
CONECT   24   21   25   14   16                                             
CONECT   25   24   48                                                       
CONECT   26   19   27   49   50                                             
CONECT   27   26   28   29   30                                             
CONECT   28   27   51   52   53                                             
CONECT   29   27   54   55   56                                             
CONECT   30   27   31   18   57                                             
CONECT   31   30   58                                                       
CONECT   32    1                                                            
CONECT   33    1                                                            
CONECT   34    1                                                            
CONECT   35    6                                                            
CONECT   36    7                                                            
CONECT   37    9                                                            
CONECT   38   14                                                            
CONECT   39   15                                                            
CONECT   40   15                                                            
CONECT   41   17                                                            
CONECT   42   17                                                            
CONECT   43   17                                                            
CONECT   44   18                                                            
CONECT   45   19                                                            
CONECT   46   20                                                            
CONECT   47   22                                                            
CONECT   48   25                                                            
CONECT   49   26                                                            
CONECT   50   26                                                            
CONECT   51   28                                                            
CONECT   52   28                                                            
CONECT   53   28                                                            
CONECT   54   29                                                            
CONECT   55   29                                                            
CONECT   56   29                                                            
CONECT   57   30                                                            
CONECT   58   31                                                            
MASTER        0    0    0    0    0    0    0    0   58    0  122    0
END

RDKit          3D

58 61  0  0  0  0  0  0  0  0999 V2000
    3.0674   -1.6576    0.6422 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3781   -0.9347    0.6076 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5413   -1.6632    0.7342 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5018   -3.4195    0.9170 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.7561   -1.0244    0.7194 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9176   -1.7879    0.8496 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7653    0.3291    0.5777 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5656    1.0794    0.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6766    2.4352    0.3089 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3411    0.4517    0.4599 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0694    1.1601    0.3500 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9881    2.4072    0.2370 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8177    0.5339    0.3587 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6348    1.2869    0.2638 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3696    1.0447    1.3641 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4261    1.3611    0.3308 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.7323    2.8212    0.1992 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6482    0.5230    0.4546 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3308   -0.9398    0.6502 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3822   -1.3637   -0.4038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5379   -0.5381   -0.9920 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3408   -1.1031   -2.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1835   -0.4112   -2.6442 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4235    0.8859   -0.7033 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3703    1.7167   -1.8350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7028   -1.5721    0.4394 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3858   -0.7473   -0.6307 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.8275   -0.4514   -0.2922 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3426   -1.4727   -1.9463 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5904    0.5534   -0.6777 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0623    0.6649   -1.9340 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2803   -2.7396    0.8751 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4965   -1.3056    1.5240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5347   -1.5514   -0.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8249   -1.3223    0.8399 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6982    0.8697    0.5613 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9639    3.0754    0.2088 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8114    2.4006    0.2065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2851    1.7854    2.1858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3405   -0.0100    1.6698 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4515    3.3669    1.1328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7924    2.9425   -0.0688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1448    3.3075   -0.6215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1871    0.8819    1.3705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0034   -1.1861    1.6679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3875   -2.3959   -0.6989 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3107   -2.1561   -2.3011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4830    1.2072   -2.6741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2946   -1.4760    1.3755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5888   -2.6307    0.1674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1042    0.4916   -0.8349 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5234   -1.2387   -0.6899 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9970   -0.2709    0.7756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3021   -0.7170   -2.7730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3882   -2.0441   -2.0075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2239   -2.1333   -2.0649 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2944    1.4138   -0.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5420    1.2677   -2.5412 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  6
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 21 24  1  0
 24 25  1  6
 19 26  1  0
 26 27  1  0
 27 28  1  1
 27 29  1  0
 27 30  1  0
 30 31  1  0
 10  2  1  0
 24 14  1  0
 24 16  1  0
 30 18  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  6 35  1  0
  7 36  1  0
  9 37  1  0
 14 38  1  6
 15 39  1  0
 15 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
 18 44  1  1
 19 45  1  1
 20 46  1  0
 22 47  1  0
 25 48  1  0
 26 49  1  0
 26 50  1  0
 28 51  1  0
 28 52  1  0
 28 53  1  0
 29 54  1  0
 29 55  1  0
 29 56  1  0
 30 57  1  1
 31 58  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-4,6-dihydroxy-2-methylbenzoic acid	Generator
Melleolide-L	MeSH

Chemical Formula

C₂₃H₂₇ClO₇

Average Mass

450.9100 Da

Monoisotopic Mass

450.14453 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-4,6-dihydroxy-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-4,6-dihydroxy-2-methylbenzoate

CAS Registry Number

Not Available

SMILES

CC1=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)=CC(O)=C1Cl

InChI Identifier

InChI=1S/C23H27ClO7/c1-10-16(13(26)6-14(27)18(10)24)20(29)31-15-8-22(4)17-11(7-21(2,3)19(17)28)5-12(9-25)23(15,22)30/h5-6,9,11,15,17,19,26-28,30H,7-8H2,1-4H3/t11-,15-,17-,19-,22-,23+/m1/s1

InChI Key

QXPGYRDUXBYJHG-NDVLAHOZSA-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	Fungi	KNApSAcK
Armillaria novae-zelandiae	LOTUS Database	35616633
Armillariella	NPAtlas	10805573
Armillariella mellea (Vahl. ex Fr.) Karst	Fungi	KNApSAcK
Pleurotus ostreatus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...

Species Where Detected

Species Name	Source	Reference
Armillariella mellea	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as melleolides and analogues. Melleolides and analogues are compounds with a structure characterized by the presence of a 2-hydroxy-4-methoxy-6-methylbenzoic acid derivative linked to a 3,6,6,7b-tetramethyl-cyclobuta[e]indene moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Melleolides and analogues

Alternative Parents

Substituents

Melleolide-skeleton
P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
O-hydroxybenzoic acid ester
Dihydroxybenzoic acid
Benzoate ester
Salicylic acid or derivatives
3-halobenzoic acid or derivatives
Halobenzoic acid or derivatives
Benzoic acid or derivatives
Benzoyl
4-halophenol
2-halophenol
M-cresol
2-chlorophenol
4-chlorophenol
Resorcinol
Toluene
1-hydroxy-2-unsubstituted benzenoid
Phenol
Chlorobenzene
Halobenzene
Monocyclic benzene moiety
Benzenoid
Aryl halide
Aryl chloride
Tertiary alcohol
Vinylogous acid
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Cyclobutanol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organochloride
Carbonyl group
Alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organohalogen compound
Aldehyde
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

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	2.8	ALOGPS
logP	3.56	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	7.21	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	124.29 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	114.29 m³·mol⁻¹	ChemAxon
Polarizability	46.08 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

NPA005890

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00054139

Chemspider ID

8519236

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10343777

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Momose I, Sekizawa R, Hosokawa N, Iinuma H, Matsui S, Nakamura H, Naganawa H, Hamada M, Takeuchi T: Melleolides K, L and M, new melleolides from Armillariella mellea. J Antibiot (Tokyo). 2000 Feb;53(2):137-43. doi: 10.7164/antibiotics.53.137. [PubMed:10805573 ]

Showing NP-Card for Melleolide L (NP0003258)

MOL for NP0003258 (Melleolide L)

3D MOL for NP0003258 (Melleolide L)

3D SDF for NP0003258 (Melleolide L)

3D-SDF for NP0003258 (Melleolide L)

PDB for NP0003258 (Melleolide L)

3D PDB for NP0003258 (Melleolide L)

SMILES for NP0003258 (Melleolide L)

INCHI for NP0003258 (Melleolide L)

Structure for NP0003258 (Melleolide L)

3D Structure for NP0003258 (Melleolide L)