NP-MRD: Showing NP-Card for Melleolide C (NP0048681)

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Record Information

Version

2.0

Created at

2022-03-17 21:00:30 UTC

Updated at

2022-03-17 21:00:30 UTC

NP-MRD ID

NP0048681

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Melleolide C

Description

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

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061309312D          

 32 35  0  0  0  0            999 V2000
   -1.2154   -1.0878    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
   -1.9444    1.2774    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
   -1.4584   -0.2994    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
   -2.5056    0.6728    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
    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
    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
    1.0938    2.3785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5788    1.6983    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
 12  1  1  0  0  0  0
 12  6  2  0  0  0  0
 13  8  2  0  0  0  0
 13 10  1  0  0  0  0
 14  6  1  0  0  0  0
 14  7  2  0  0  0  0
 15  7  1  0  0  0  0
 16  9  1  0  0  0  0
 17 12  1  0  0  0  0
 17 15  2  0  0  0  0
 19 18  1  0  0  0  0
 20 17  1  0  0  0  0
 21  2  1  0  0  0  0
 21  3  1  0  0  0  0
 21 11  1  0  0  0  0
 21 19  1  0  0  0  0
 22  4  1  0  0  0  0
 22  9  1  0  0  0  0
 22 18  1  0  0  0  0
 23  8  1  0  0  0  0
 23 11  1  0  0  0  0
 23 18  1  0  0  0  0
 24 13  1  0  0  0  0
 24 16  1  0  0  0  0
 24 22  1  0  0  0  0
 25 10  1  0  0  0  0
 26 15  1  0  0  0  0
 27 19  1  0  0  0  0
 28 20  2  0  0  0  0
 29 23  1  0  0  0  0
 30 24  1  0  0  0  0
 31  5  1  0  0  0  0
 31 14  1  0  0  0  0
 32 16  1  0  0  0  0
 32 20  1  0  0  0  0
M  END


  Mrv0541 05061309312D          

 32 35  0  0  0  0            999 V2000
   -1.2154   -1.0878    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
   -1.9444    1.2774    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
   -1.4584   -0.2994    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
   -2.5056    0.6728    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
    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
    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
    1.0938    2.3785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5788    1.6983    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
 12  1  1  0  0  0  0
 12  6  2  0  0  0  0
 13  8  2  0  0  0  0
 13 10  1  0  0  0  0
 14  6  1  0  0  0  0
 14  7  2  0  0  0  0
 15  7  1  0  0  0  0
 16  9  1  0  0  0  0
 17 12  1  0  0  0  0
 17 15  2  0  0  0  0
 19 18  1  0  0  0  0
 20 17  1  0  0  0  0
 21  2  1  0  0  0  0
 21  3  1  0  0  0  0
 21 11  1  0  0  0  0
 21 19  1  0  0  0  0
 22  4  1  0  0  0  0
 22  9  1  0  0  0  0
 22 18  1  0  0  0  0
 23  8  1  0  0  0  0
 23 11  1  0  0  0  0
 23 18  1  0  0  0  0
 24 13  1  0  0  0  0
 24 16  1  0  0  0  0
 24 22  1  0  0  0  0
 25 10  1  0  0  0  0
 26 15  1  0  0  0  0
 27 19  1  0  0  0  0
 28 20  2  0  0  0  0
 29 23  1  0  0  0  0
 30 24  1  0  0  0  0
 31  5  1  0  0  0  0
 31 14  1  0  0  0  0
 32 16  1  0  0  0  0
 32 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048681

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C24H32O8/c1-12-6-14(31-5)7-15(26)17(12)20(28)32-16-9-22(4)18-19(27)21(2,3)11-23(18,29)8-13(10-25)24(16,22)30/h6-8,16,18-19,25-27,29-30H,9-11H2,1-5H3

> <INCHI_KEY>
XXMVVKDVYBWXPQ-UHFFFAOYSA-N

> <FORMULA>
C24H32O8

> <MOLECULAR_WEIGHT>
448.5061

> <EXACT_MASS>
448.209718

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
47.288087329334

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <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 2-hydroxy-4-methoxy-6-methylbenzoate

> <ALOGPS_LOGP>
1.11

> <JCHEM_LOGP>
1.668975393333334

> <ALOGPS_LOGS>
-3.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.86551010760936

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.762842871934216

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7719665684205426

> <JCHEM_POLAR_SURFACE_AREA>
136.68

> <JCHEM_REFRACTIVITY>
116.37979999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.44e-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 2-hydroxy-4-methoxy-6-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      -2.269  -2.031   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      -3.630   2.384   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.939   3.250   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.195  -0.292   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.581   4.497   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.275   1.682   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.722  -0.559   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.400   3.193   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      -2.128   2.042   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.376   1.012   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.675   0.570   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  O   UNK     0       2.042   4.440   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -1.080   3.170   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       6.846  -2.038   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       0.280  -1.245   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       7.616   3.225   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       2.551   2.879   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -6.178   1.599   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       0.875   1.356   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   21                                                            
CONECT    3   21                                                            
CONECT    4   22                                                            
CONECT    5   31                                                            
CONECT    6   12   14                                                       
CONECT    7   14   15                                                       
CONECT    8   13   23                                                       
CONECT    9   16   22                                                       
CONECT   10   13   25                                                       
CONECT   11   21   23                                                       
CONECT   12    1    6   17                                                  
CONECT   13    8   10   24                                                  
CONECT   14    6    7   31                                                  
CONECT   15    7   17   26                                                  
CONECT   16    9   24   32                                                  
CONECT   17   12   15   20                                                  
CONECT   18   19   22   23                                                  
CONECT   19   18   21   27                                                  
CONECT   20   17   28   32                                                  
CONECT   21    2    3   11   19                                             
CONECT   22    4    9   18   24                                             
CONECT   23    8   11   18   29                                             
CONECT   24   13   16   22   30                                             
CONECT   25   10                                                            
CONECT   26   15                                                            
CONECT   27   19                                                            
CONECT   28   20                                                            
CONECT   29   23                                                            
CONECT   30   24                                                            
CONECT   31    5   14                                                       
CONECT   32   16   20                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   70    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 2-hydroxy-4-methoxy-6-methylbenzoic acid	Generator

Chemical Formula

C₂₄H₃₂O₈

Average Mass

448.5061 Da

Monoisotopic Mass

448.20972 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 2-hydroxy-4-methoxy-6-methylbenzoate

Traditional Name

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

CAS Registry Number

101901-56-8

SMILES

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

InChI Identifier

InChI=1S/C24H32O8/c1-12-6-14(31-5)7-15(26)17(12)20(28)32-16-9-22(4)18-19(27)21(2,3)11-23(18,29)8-13(10-25)24(16,22)30/h6-8,16,18-19,25-27,29-30H,9-11H2,1-5H3

InChI Key

XXMVVKDVYBWXPQ-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	LOTUS Database	35616633
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
P-methoxybenzoic acid or derivatives
O-hydroxybenzoic acid ester
Methoxyphenol
Salicylic acid or derivatives
Benzoate ester
Benzoic acid or derivatives
Methoxybenzene
Phenoxy compound
Benzoyl
M-cresol
Phenol ether
Anisole
Toluene
1-hydroxy-4-unsubstituted benzenoid
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Tertiary alcohol
Cyclic alcohol
Carboxylic acid ester
Secondary alcohol
Cyclobutanol
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Ether
Organooxygen compound
Hydrocarbon derivative
Alcohol
Organic oxygen compound
Organic oxide
Primary alcohol
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	1.11	ALOGPS
logP	1.67	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	9.76	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	116.38 m³·mol⁻¹	ChemAxon
Polarizability	47.29 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

HMDB0037041

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016023

KNApSAcK ID

C00021461

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

14166113

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Melleolide C (NP0048681)

MOL for NP0048681 (Melleolide C)

3D MOL for NP0048681 (Melleolide C)

3D SDF for NP0048681 (Melleolide C)

3D-SDF for NP0048681 (Melleolide C)

PDB for NP0048681 (Melleolide C)

3D PDB for NP0048681 (Melleolide C)

SMILES for NP0048681 (Melleolide C)

INCHI for NP0048681 (Melleolide C)

Structure for NP0048681 (Melleolide C)

3D Structure for NP0048681 (Melleolide C)