NP-MRD: Showing NP-Card for 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 (NP0273496)

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Record Information

Version

2.0

Created at

2022-09-08 20:34:01 UTC

Updated at

2022-09-08 20:34:01 UTC

NP-MRD ID

NP0273496

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Melleolide L 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 an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Melleolide L has been detected, but not quantified in, mushrooms. 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 is found in Armillaria novae-zelandiae. This could make melleolide L a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061308132D          

 31 34  0  0  0  0            999 V2000
   -0.8241   -1.2904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7863    1.5151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2702    2.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0897    2.3068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6180    0.0598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5079    0.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8695    0.8998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1480    1.9572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3548   -0.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3853   -0.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0567    0.7584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7935    0.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7036    0.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7509   -0.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7092    1.2586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1423    0.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6711    1.4877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1896   -0.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2455    2.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3380    0.2864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9862    1.7165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8467    1.5184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4079    0.8198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4326   -1.6579    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7404   -1.3375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4606    1.4957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5551   -0.4486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1041    2.8927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2232   -0.3182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8032    0.2585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0950    1.0748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10  1  1  0  0  0  0
 11  5  1  0  0  0  0
 11  7  1  0  0  0  0
 12  5  2  0  0  0  0
 12  9  1  0  0  0  0
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 16 10  2  0  0  0  0
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 18 14  2  0  0  0  0
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 20 16  1  0  0  0  0
 21  2  1  0  0  0  0
 21  3  1  0  0  0  0
 21  7  1  0  0  0  0
 21 19  1  0  0  0  0
 22  4  1  0  0  0  0
 22  8  1  0  0  0  0
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 26 13  1  0  0  0  0
 27 14  1  0  0  0  0
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 29 20  2  0  0  0  0
 30 23  1  0  0  0  0
 31 15  1  0  0  0  0
 31 20  1  0  0  0  0
M  END

     RDKit          3D

 58 61  0  0  0  0  0  0  0  0999 V2000
    3.8111   -1.4998    1.2664 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7487   -0.7725    0.3585 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.7050   -1.5722    2.1099 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    6.9981   -0.1497   -0.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8000    0.0642   -0.1939 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9958   -0.5824    1.0979 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8369   -1.2823    1.6205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8028   -1.6254    0.8927 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2676   -2.3275    1.5924 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1906   -2.5676    2.8222 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6851   -1.3220   -0.5612 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.0118   -2.4031   -1.3790 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5062    0.5286    2.0388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2939    1.4091    1.0457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5285    2.7435    1.6615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5286    0.6852    0.6057 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2993    1.4747   -0.1070 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8359    1.9247   -1.2810 O   0  0  0  0  0  0  0  0  0  0  0  0
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    7.2481    0.9727   -1.9094 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.5520    0.6106   -2.6186 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5331   -0.4543   -0.9268 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9009   -1.2914    1.0642 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1829   -2.6903    1.1292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0434   -3.2058   -0.7665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6966    1.0704    2.5243 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2317    0.1167    2.7545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5763    3.1645    2.0254 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.2149    2.6145    2.5279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4440    1.3450    0.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4463    0.1708   -0.3699 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.6522    1.5309   -1.6011 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 10  2  0
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 20 46  1  0
 22 47  1  0
 25 48  1  0
  9 37  1  0
  7 36  1  0
  6 35  1  0
M  END


  Mrv0541 05061308132D          

 31 34  0  0  0  0            999 V2000
   -0.8241   -1.2904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7863    1.5151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2702    2.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0897    2.3068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6180    0.0598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5079    0.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8695    0.8998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1480    1.9572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3548   -0.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3853   -0.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0567    0.7584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7935    0.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7036    0.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7509   -0.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7092    1.2586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1423    0.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6711    1.4877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1896   -0.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2455    2.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3380    0.2864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9862    1.7165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8467    1.5184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4079    0.8198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4326   -1.6579    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7404   -1.3375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4606    1.4957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5551   -0.4486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1041    2.8927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2232   -0.3182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8032    0.2585    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0950    1.0748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10  1  1  0  0  0  0
 11  5  1  0  0  0  0
 11  7  1  0  0  0  0
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 13  6  2  0  0  0  0
 14  6  1  0  0  0  0
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 18 10  1  0  0  0  0
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 21 19  1  0  0  0  0
 22  4  1  0  0  0  0
 22  8  1  0  0  0  0
 22 17  1  0  0  0  0
 23 12  1  0  0  0  0
 23 15  1  0  0  0  0
 23 22  1  0  0  0  0
 24 18  1  0  0  0  0
 25  9  2  0  0  0  0
 26 13  1  0  0  0  0
 27 14  1  0  0  0  0
 28 19  1  0  0  0  0
 29 20  2  0  0  0  0
 30 23  1  0  0  0  0
 31 15  1  0  0  0  0
 31 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0273496

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(C(=O)OC2CC3(C)C4C(CC(C)(C)C4O)C=C(C=O)C23O)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

> <INCHI_KEY>
QXPGYRDUXBYJHG-UHFFFAOYSA-N

> <FORMULA>
C23H27ClO7

> <MOLECULAR_WEIGHT>
450.909

> <EXACT_MASS>
450.144530925

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
45.64896883375807

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
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>
10.024834478034856

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.208684562783208

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0342593569572927

> <JCHEM_POLAR_SURFACE_AREA>
124.29000000000002

> <JCHEM_REFRACTIVITY>
114.29009999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.66e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
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

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -1.538  -2.409   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.934   2.828   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.971   4.650   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.901   4.306   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.887   0.112   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.681   0.977   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.223   1.680   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.143   3.653   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.529  -1.135   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.586  -1.280   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.706   1.416   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.348   0.169   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.180   1.320   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.135  -0.494   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.324   2.349   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.132   0.192   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.986   2.777   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -4.087  -1.623   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.058   3.882   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.631   0.535   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.441   3.204   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.447   2.834   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.628   1.530   0.000  0.00  0.00           C+0
HETATM   24 Cl   UNK     0      -4.541  -3.095   0.000  0.00  0.00          Cl+0
HETATM   25  O   UNK     0       3.249  -2.497   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -2.726   2.792   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -6.636  -0.837   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       5.794   5.400   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       0.417  -0.594   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       1.499   0.483   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -0.177   2.006   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   21                                                            
CONECT    3   21                                                            
CONECT    4   22                                                            
CONECT    5   11   12                                                       
CONECT    6   13   14                                                       
CONECT    7   11   21                                                       
CONECT    8   15   22                                                       
CONECT    9   12   25                                                       
CONECT   10    1   16   18                                                  
CONECT   11    5    7   17                                                  
CONECT   12    5    9   23                                                  
CONECT   13    6   16   26                                                  
CONECT   14    6   18   27                                                  
CONECT   15    8   23   31                                                  
CONECT   16   10   13   20                                                  
CONECT   17   11   19   22                                                  
CONECT   18   10   14   24                                                  
CONECT   19   17   21   28                                                  
CONECT   20   16   29   31                                                  
CONECT   21    2    3    7   19                                             
CONECT   22    4    8   17   23                                             
CONECT   23   12   15   22   30                                             
CONECT   24   18                                                            
CONECT   25    9                                                            
CONECT   26   13                                                            
CONECT   27   14                                                            
CONECT   28   19                                                            
CONECT   29   20                                                            
CONECT   30   23                                                            
CONECT   31   15   20                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Value	Source
6'-Chloro-10a-hydroxymelleolide	HMDB
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
Melleolide L	MeSH

Chemical Formula

C₂₃H₂₇ClO₇

Average Mass

450.9090 Da

Monoisotopic Mass

450.14453 Da

IUPAC Name

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

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)OC2CC3(C)C4C(CC(C)(C)C4O)C=C(C=O)C23O)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

InChI Key

QXPGYRDUXBYJHG-UHFFFAOYSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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 novae-zelandiae	LOTUS Database	35616633

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	45.65 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

HMDB ID

HMDB0035067

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB013691

KNApSAcK ID

C00015496

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

85116077

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 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 (NP0273496)

MOL for NP0273496 (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)

3D MOL for NP0273496 (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)

3D SDF for NP0273496 (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)

3D-SDF for NP0273496 (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)

PDB for NP0273496 (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)

3D PDB for NP0273496 (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)

SMILES for NP0273496 (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)

INCHI for NP0273496 (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)

Structure for NP0273496 (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)

3D Structure for NP0273496 (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)