NP-MRD: Showing NP-Card for Melledonal B (NP0048683)

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Record Information

Version

2.0

Created at

2022-03-17 21:00:32 UTC

Updated at

2022-03-17 21:00:32 UTC

NP-MRD ID

NP0048683

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Melledonal B

Description

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

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061309322D          

 32 35  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
   -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
   -3.3099    0.8565    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
    0.4685    0.7262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10  1  1  0  0  0  0
 11  6  2  0  0  0  0
 11  8  1  0  0  0  0
 12  5  2  0  0  0  0
 13  5  1  0  0  0  0
 14  7  1  0  0  0  0
 15 10  2  0  0  0  0
 15 12  1  0  0  0  0
 16 10  1  0  0  0  0
 16 13  2  0  0  0  0
 18 17  1  0  0  0  0
 19 15  1  0  0  0  0
 20  2  1  0  0  0  0
 20  3  1  0  0  0  0
 20  9  1  0  0  0  0
 20 18  1  0  0  0  0
 21  4  1  0  0  0  0
 21  7  1  0  0  0  0
 21 17  1  0  0  0  0
 22  6  1  0  0  0  0
 22  9  1  0  0  0  0
 22 17  1  0  0  0  0
 23 11  1  0  0  0  0
 23 14  1  0  0  0  0
 23 21  1  0  0  0  0
 24 16  1  0  0  0  0
 25  8  2  0  0  0  0
 26 12  1  0  0  0  0
 27 13  1  0  0  0  0
 28 18  1  0  0  0  0
 29 19  2  0  0  0  0
 30 22  1  0  0  0  0
 31 23  1  0  0  0  0
 32 14  1  0  0  0  0
 32 19  1  0  0  0  0
M  END


  Mrv0541 05061309322D          

 32 35  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
   -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
   -3.3099    0.8565    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
    0.4685    0.7262    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 10  1  1  0  0  0  0
 11  6  2  0  0  0  0
 11  8  1  0  0  0  0
 12  5  2  0  0  0  0
 13  5  1  0  0  0  0
 14  7  1  0  0  0  0
 15 10  2  0  0  0  0
 15 12  1  0  0  0  0
 16 10  1  0  0  0  0
 16 13  2  0  0  0  0
 18 17  1  0  0  0  0
 19 15  1  0  0  0  0
 20  2  1  0  0  0  0
 20  3  1  0  0  0  0
 20  9  1  0  0  0  0
 20 18  1  0  0  0  0
 21  4  1  0  0  0  0
 21  7  1  0  0  0  0
 21 17  1  0  0  0  0
 22  6  1  0  0  0  0
 22  9  1  0  0  0  0
 22 17  1  0  0  0  0
 23 11  1  0  0  0  0
 23 14  1  0  0  0  0
 23 21  1  0  0  0  0
 24 16  1  0  0  0  0
 25  8  2  0  0  0  0
 26 12  1  0  0  0  0
 27 13  1  0  0  0  0
 28 18  1  0  0  0  0
 29 19  2  0  0  0  0
 30 22  1  0  0  0  0
 31 23  1  0  0  0  0
 32 14  1  0  0  0  0
 32 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048683

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(C(=O)OC2CC3(C)C4C(O)C(C)(C)CC4(O)C=C(C=O)C23O)C(O)=CC(O)=C1Cl

> <INCHI_IDENTIFIER>
InChI=1S/C23H27ClO8/c1-10-15(12(26)5-13(27)16(10)24)19(29)32-14-7-21(4)17-18(28)20(2,3)9-22(17,30)6-11(8-25)23(14,21)31/h5-6,8,14,17-18,26-28,30-31H,7,9H2,1-4H3

> <INCHI_KEY>
HAJBXIZSTZMKOC-UHFFFAOYSA-N

> <FORMULA>
C23H27ClO8

> <MOLECULAR_WEIGHT>
466.909

> <EXACT_MASS>
466.139445547

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_AVERAGE_POLARIZABILITY>
46.501312497136595

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-formyl-2a,4a,7-trihydroxy-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>
2.13

> <JCHEM_LOGP>
2.4409735170000006

> <ALOGPS_LOGS>
-3.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.024754842931559

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.208684411197303

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0722485964669746

> <JCHEM_POLAR_SURFACE_AREA>
144.52

> <JCHEM_REFRACTIVITY>
115.71939999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.47e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-formyl-2a,4a,7-trihydroxy-6,6,7b-trimethyl-1H,2H,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      -1.080   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      -4.224  -0.216   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.939   3.250   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.195  -0.292   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.581   4.497   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.275   1.682   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.128   2.042   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.400   3.193   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      -4.677   1.256   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.376   1.012   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.675   0.570   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.630   2.384   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.038   0.585   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.110  -0.521   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -0.173   0.227   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.493   0.158   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.499   0.528   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.758   1.946   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.680   1.832   0.000  0.00  0.00           C+0
HETATM   24 Cl   UNK     0      -4.083   3.856   0.000  0.00  0.00          Cl+0
HETATM   25  O   UNK     0       2.042   4.440   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -2.269  -2.031   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -6.178   1.599   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       0.875   1.356   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   20                                                            
CONECT    3   20                                                            
CONECT    4   21                                                            
CONECT    5   12   13                                                       
CONECT    6   11   22                                                       
CONECT    7   14   21                                                       
CONECT    8   11   25                                                       
CONECT    9   20   22                                                       
CONECT   10    1   15   16                                                  
CONECT   11    6    8   23                                                  
CONECT   12    5   15   26                                                  
CONECT   13    5   16   27                                                  
CONECT   14    7   23   32                                                  
CONECT   15   10   12   19                                                  
CONECT   16   10   13   24                                                  
CONECT   17   18   21   22                                                  
CONECT   18   17   20   28                                                  
CONECT   19   15   29   32                                                  
CONECT   20    2    3    9   18                                             
CONECT   21    4    7   17   23                                             
CONECT   22    6    9   17   30                                             
CONECT   23   11   14   21   31                                             
CONECT   24   16                                                            
CONECT   25    8                                                            
CONECT   26   12                                                            
CONECT   27   13                                                            
CONECT   28   18                                                            
CONECT   29   19                                                            
CONECT   30   22                                                            
CONECT   31   23                                                            
CONECT   32   14   19                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
3-Formyl-2a,4a,7-trihydroxy-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

Chemical Formula

C₂₃H₂₇ClO₈

Average Mass

466.9090 Da

Monoisotopic Mass

466.13945 Da

IUPAC Name

3-formyl-2a,4a,7-trihydroxy-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,4a,7-trihydroxy-6,6,7b-trimethyl-1H,2H,5H,7H,7aH-cyclobuta[e]inden-2-yl 3-chloro-4,6-dihydroxy-2-methylbenzoate

CAS Registry Number

117458-36-3

SMILES

CC1=C(C(=O)OC2CC3(C)C4C(O)C(C)(C)CC4(O)C=C(C=O)C23O)C(O)=CC(O)=C1Cl

InChI Identifier

InChI=1S/C23H27ClO8/c1-10-15(12(26)5-13(27)16(10)24)19(29)32-14-7-21(4)17-18(28)20(2,3)9-22(17,30)6-11(8-25)23(14,21)31/h5-6,8,14,17-18,26-28,30-31H,7,9H2,1-4H3

InChI Key

HAJBXIZSTZMKOC-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
Armillaria novae-zelandiae	LOTUS Database	35616633
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-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
O-hydroxybenzoic acid ester
Dihydroxybenzoic acid
Salicylic acid or derivatives
3-halobenzoic acid or derivatives
Halobenzoic acid or derivatives
Benzoate ester
Benzoic acid or derivatives
4-chlorophenol
Resorcinol
M-cresol
2-chlorophenol
2-halophenol
4-halophenol
Benzoyl
1-hydroxy-2-unsubstituted benzenoid
Chlorobenzene
Halobenzene
Toluene
Phenol
Aryl halide
Monocyclic benzene moiety
Aryl chloride
Benzenoid
Tertiary alcohol
Vinylogous acid
Cyclic alcohol
Secondary alcohol
Carboxylic acid ester
Cyclobutanol
Polyol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Aldehyde
Carbonyl group
Organic oxide
Organic oxygen compound
Alcohol
Organohalogen compound
Organochloride
Organooxygen compound
Hydrocarbon derivative
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	2.13	ALOGPS
logP	2.44	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	7.21	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	144.52 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	115.72 m³·mol⁻¹	ChemAxon
Polarizability	46.5 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

HMDB0037043

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016025

KNApSAcK ID

C00021466

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

76046882

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Melledonal B (NP0048683)

MOL for NP0048683 (Melledonal B)

3D MOL for NP0048683 (Melledonal B)

3D SDF for NP0048683 (Melledonal B)

3D-SDF for NP0048683 (Melledonal B)

PDB for NP0048683 (Melledonal B)

3D PDB for NP0048683 (Melledonal B)

SMILES for NP0048683 (Melledonal B)

INCHI for NP0048683 (Melledonal B)

Structure for NP0048683 (Melledonal B)

3D Structure for NP0048683 (Melledonal B)