NP-MRD: Showing NP-Card for Melleolide D (NP0048682)

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Record Information

Version

2.0

Created at

2022-03-17 21:00:31 UTC

Updated at

2022-03-17 21:00:31 UTC

NP-MRD ID

NP0048682

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Melleolide D

Description

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

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061309312D          

 33 36  0  0  0  0            999 V2000
   -0.5788    1.6983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3497    0.2859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8336   -0.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6532   -0.5058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8712    0.2519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2626   -0.1156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1815    1.7412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7115   -0.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9182    2.4092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4330    0.9012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1401    1.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3570    1.7105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4584   -0.2994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5056    0.6728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2727    0.5424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8971    0.3053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9444    1.2774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2346    0.3132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8090   -0.2789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0928    0.1215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5497    0.0844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4102    0.2826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6202    1.0426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9714    0.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1874    2.0658    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.0938    2.3785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2154   -1.0878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6676   -1.0917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1502   -0.6669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0800    1.7276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3667    1.5425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3099    0.8565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4685    0.7262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 11  1  1  0  0  0  0
 12  7  2  0  0  0  0
 12  9  1  0  0  0  0
 13  6  2  0  0  0  0
 14  6  1  0  0  0  0
 15  8  1  0  0  0  0
 16 11  2  0  0  0  0
 16 13  1  0  0  0  0
 17 11  1  0  0  0  0
 17 14  2  0  0  0  0
 19 18  1  0  0  0  0
 20 16  1  0  0  0  0
 21  2  1  0  0  0  0
 21  3  1  0  0  0  0
 21 10  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
 22 18  1  0  0  0  0
 23  7  1  0  0  0  0
 23 10  1  0  0  0  0
 23 18  1  0  0  0  0
 24 12  1  0  0  0  0
 24 15  1  0  0  0  0
 24 22  1  0  0  0  0
 25 17  1  0  0  0  0
 26  9  1  0  0  0  0
 27 13  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 24  1  0  0  0  0
 32  5  1  0  0  0  0
 32 14  1  0  0  0  0
 33 15  1  0  0  0  0
 33 20  1  0  0  0  0
M  END


  Mrv0541 05061309312D          

 33 36  0  0  0  0            999 V2000
   -0.5788    1.6983    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3497    0.2859    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8336   -0.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6532   -0.5058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8712    0.2519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2626   -0.1156    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1815    1.7412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7115   -0.1562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9182    2.4092    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4330    0.9012    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1401    1.0937    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3570    1.7105    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4584   -0.2994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5056    0.6728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2727    0.5424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8971    0.3053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9444    1.2774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2346    0.3132    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8090   -0.2789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0928    0.1215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5497    0.0844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4102    0.2826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6202    1.0426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9714    0.9812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1874    2.0658    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.0938    2.3785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2154   -1.0878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6676   -1.0917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1502   -0.6669    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0800    1.7276    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3667    1.5425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3099    0.8565    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4685    0.7262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 11  1  1  0  0  0  0
 12  7  2  0  0  0  0
 12  9  1  0  0  0  0
 13  6  2  0  0  0  0
 14  6  1  0  0  0  0
 15  8  1  0  0  0  0
 16 11  2  0  0  0  0
 16 13  1  0  0  0  0
 17 11  1  0  0  0  0
 17 14  2  0  0  0  0
 19 18  1  0  0  0  0
 20 16  1  0  0  0  0
 21  2  1  0  0  0  0
 21  3  1  0  0  0  0
 21 10  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
 22 18  1  0  0  0  0
 23  7  1  0  0  0  0
 23 10  1  0  0  0  0
 23 18  1  0  0  0  0
 24 12  1  0  0  0  0
 24 15  1  0  0  0  0
 24 22  1  0  0  0  0
 25 17  1  0  0  0  0
 26  9  1  0  0  0  0
 27 13  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 24  1  0  0  0  0
 32  5  1  0  0  0  0
 32 14  1  0  0  0  0
 33 15  1  0  0  0  0
 33 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048682

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(Cl)C(C)=C(C(=O)OC2CC3(C)C4C(O)C(C)(C)CC4(O)C=C(CO)C23O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H31ClO8/c1-11-16(13(27)6-14(32-5)17(11)25)20(29)33-15-8-22(4)18-19(28)21(2,3)10-23(18,30)7-12(9-26)24(15,22)31/h6-7,15,18-19,26-28,30-31H,8-10H2,1-5H3

> <INCHI_KEY>
PSCSRVBGZZBKIW-UHFFFAOYSA-N

> <FORMULA>
C24H31ClO8

> <MOLECULAR_WEIGHT>
482.951

> <EXACT_MASS>
482.170745675

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
49.423593622203086

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2a,4a,7-trihydroxy-3-(hydroxymethyl)-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>
1.75

> <JCHEM_LOGP>
2.273020069666667

> <ALOGPS_LOGS>
-3.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.86531284626945

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.325406793907701

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7719665684205514

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
121.18459999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.65e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2a,4a,7-trihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,5H,7H,7aH-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-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      -1.080   3.170   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.986   0.534   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.023  -1.288   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.953  -0.944   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.226   0.470   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.224  -0.216   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.939   3.250   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.195  -0.292   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.581   4.497   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.275   1.682   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.128   2.042   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.400   3.193   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.722  -0.559   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.677   1.256   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.376   1.012   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.675   0.570   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -3.630   2.384   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.038   0.585   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.110  -0.521   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -0.173   0.227   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.493   0.158   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.499   0.528   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.758   1.946   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.680   1.832   0.000  0.00  0.00           C+0
HETATM   25 Cl   UNK     0      -4.083   3.856   0.000  0.00  0.00          Cl+0
HETATM   26  O   UNK     0       2.042   4.440   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -2.269  -2.031   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       6.846  -2.038   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       0.280  -1.245   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       7.616   3.225   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       2.551   2.879   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -6.178   1.599   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       0.875   1.356   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   21                                                            
CONECT    3   21                                                            
CONECT    4   22                                                            
CONECT    5   32                                                            
CONECT    6   13   14                                                       
CONECT    7   12   23                                                       
CONECT    8   15   22                                                       
CONECT    9   12   26                                                       
CONECT   10   21   23                                                       
CONECT   11    1   16   17                                                  
CONECT   12    7    9   24                                                  
CONECT   13    6   16   27                                                  
CONECT   14    6   17   32                                                  
CONECT   15    8   24   33                                                  
CONECT   16   11   13   20                                                  
CONECT   17   11   14   25                                                  
CONECT   18   19   22   23                                                  
CONECT   19   18   21   28                                                  
CONECT   20   16   29   33                                                  
CONECT   21    2    3   10   19                                             
CONECT   22    4    8   18   24                                             
CONECT   23    7   10   18   30                                             
CONECT   24   12   15   22   31                                             
CONECT   25   17                                                            
CONECT   26    9                                                            
CONECT   27   13                                                            
CONECT   28   19                                                            
CONECT   29   20                                                            
CONECT   30   23                                                            
CONECT   31   24                                                            
CONECT   32    5   14                                                       
CONECT   33   15   20                                                       
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
2a,4a,7-Trihydroxy-3-(hydroxymethyl)-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

C₂₄H₃₁ClO₈

Average Mass

482.9510 Da

Monoisotopic Mass

482.17075 Da

IUPAC Name

2a,4a,7-trihydroxy-3-(hydroxymethyl)-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

2a,4a,7-trihydroxy-3-(hydroxymethyl)-6,6,7b-trimethyl-1H,2H,5H,7H,7aH-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate

CAS Registry Number

101922-80-9

SMILES

COC1=C(Cl)C(C)=C(C(=O)OC2CC3(C)C4C(O)C(C)(C)CC4(O)C=C(CO)C23O)C(O)=C1

InChI Identifier

InChI=1S/C24H31ClO8/c1-11-16(13(27)6-14(32-5)17(11)25)20(29)33-15-8-22(4)18-19(28)21(2,3)10-23(18,30)7-12(9-26)24(15,22)31/h6-7,15,18-19,26-28,30-31H,8-10H2,1-5H3

InChI Key

PSCSRVBGZZBKIW-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

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
Pleurotus ostreatus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...

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
O-hydroxybenzoic acid ester
P-methoxybenzoic acid or derivatives
Methoxyphenol
Benzoate ester
Salicylic acid or derivatives
3-halobenzoic acid or derivatives
Halobenzoic acid or derivatives
Benzoic acid or derivatives
4-halophenol
Phenoxy compound
M-cresol
Benzoyl
4-chlorophenol
Anisole
Phenol ether
Methoxybenzene
Phenol
Chlorobenzene
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Halobenzene
Toluene
Aryl chloride
Monocyclic benzene moiety
Aryl halide
Benzenoid
Cyclic alcohol
Tertiary alcohol
Vinylogous acid
Secondary alcohol
Carboxylic acid ester
Cyclobutanol
Carboxylic acid derivative
Polyol
Monocarboxylic acid or derivatives
Ether
Organohalogen compound
Organic oxygen compound
Organochloride
Organooxygen compound
Primary alcohol
Alcohol
Hydrocarbon derivative
Organic oxide
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	1.75	ALOGPS
logP	2.27	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	9.33	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	136.68 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	121.18 m³·mol⁻¹	ChemAxon
Polarizability	49.42 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0037042

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016024

KNApSAcK ID

C00021462

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

14166115

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Melleolide D (NP0048682)

MOL for NP0048682 (Melleolide D)

3D MOL for NP0048682 (Melleolide D)

3D SDF for NP0048682 (Melleolide D)

3D-SDF for NP0048682 (Melleolide D)

PDB for NP0048682 (Melleolide D)

3D PDB for NP0048682 (Melleolide D)

SMILES for NP0048682 (Melleolide D)

INCHI for NP0048682 (Melleolide D)

Structure for NP0048682 (Melleolide D)

3D Structure for NP0048682 (Melleolide D)