NP-MRD: Showing NP-Card for Armillarinin (NP0047309)

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Record Information

Version

2.0

Created at

2022-03-17 20:38:02 UTC

Updated at

2022-03-17 20:38:02 UTC

NP-MRD ID

NP0047309

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Armillarinin

Description

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

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061306042D          

 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
    4.8336   -0.6902    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
    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
    3.8090   -0.2789    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
    3.2346    0.3132    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
   -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
    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
 13  7  2  0  0  0  0
 13 10  1  0  0  0  0
 14  6  2  0  0  0  0
 15  6  1  0  0  0  0
 16  8  1  0  0  0  0
 17  9  1  0  0  0  0
 18 12  2  0  0  0  0
 18 14  1  0  0  0  0
 19 12  1  0  0  0  0
 19 15  2  0  0  0  0
 20 18  1  0  0  0  0
 21  2  1  0  0  0  0
 21  3  1  0  0  0  0
 21  8  1  0  0  0  0
 21 11  1  0  0  0  0
 22  4  1  0  0  0  0
 22  9  1  0  0  0  0
 22 16  1  0  0  0  0
 23  7  1  0  0  0  0
 23 11  1  0  0  0  0
 23 16  1  0  0  0  0
 24 13  1  0  0  0  0
 24 17  1  0  0  0  0
 24 22  1  0  0  0  0
 25 19  1  0  0  0  0
 26 10  2  0  0  0  0
 27 14  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 15  1  0  0  0  0
 32 17  1  0  0  0  0
 32 20  1  0  0  0  0
M  END


  Mrv0541 05061306042D          

 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
    4.8336   -0.6902    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
    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
    3.8090   -0.2789    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
    3.2346    0.3132    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
   -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
    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
 13  7  2  0  0  0  0
 13 10  1  0  0  0  0
 14  6  2  0  0  0  0
 15  6  1  0  0  0  0
 16  8  1  0  0  0  0
 17  9  1  0  0  0  0
 18 12  2  0  0  0  0
 18 14  1  0  0  0  0
 19 12  1  0  0  0  0
 19 15  2  0  0  0  0
 20 18  1  0  0  0  0
 21  2  1  0  0  0  0
 21  3  1  0  0  0  0
 21  8  1  0  0  0  0
 21 11  1  0  0  0  0
 22  4  1  0  0  0  0
 22  9  1  0  0  0  0
 22 16  1  0  0  0  0
 23  7  1  0  0  0  0
 23 11  1  0  0  0  0
 23 16  1  0  0  0  0
 24 13  1  0  0  0  0
 24 17  1  0  0  0  0
 24 22  1  0  0  0  0
 25 19  1  0  0  0  0
 26 10  2  0  0  0  0
 27 14  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 15  1  0  0  0  0
 32 17  1  0  0  0  0
 32 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047309

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(Cl)C(C)=C(C(=O)OC2CC3(C)C4CC(C)(C)CC4(O)C=C(C=O)C23O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H29ClO7/c1-12-18(14(27)6-15(31-5)19(12)25)20(28)32-17-9-22(4)16-8-21(2,3)11-23(16,29)7-13(10-26)24(17,22)30/h6-7,10,16-17,27,29-30H,8-9,11H2,1-5H3

> <INCHI_KEY>
XOGUZUVXPLTDMB-UHFFFAOYSA-N

> <FORMULA>
C24H29ClO7

> <MOLECULAR_WEIGHT>
464.936

> <EXACT_MASS>
464.160180989

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
48.08896430983783

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-formyl-2a,4a-dihydroxy-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>
2.95

> <JCHEM_LOGP>
3.7761219129999994

> <ALOGPS_LOGS>
-4.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.759490633044269

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.32536236365188

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2083614593839442

> <JCHEM_POLAR_SURFACE_AREA>
113.29

> <JCHEM_REFRACTIVITY>
118.78499999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.10e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-formyl-2a,4a-dihydroxy-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       9.023  -1.288   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.986   0.534   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       7.110  -0.521   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      -2.128   2.042   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      -2.722  -0.559   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.677   1.256   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.038   0.585   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.376   1.012   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.675   0.570   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.630   2.384   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       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   14   15                                                       
CONECT    7   13   23                                                       
CONECT    8   16   21                                                       
CONECT    9   17   22                                                       
CONECT   10   13   26                                                       
CONECT   11   21   23                                                       
CONECT   12    1   18   19                                                  
CONECT   13    7   10   24                                                  
CONECT   14    6   18   27                                                  
CONECT   15    6   19   31                                                  
CONECT   16    8   22   23                                                  
CONECT   17    9   24   32                                                  
CONECT   18   12   14   20                                                  
CONECT   19   12   15   25                                                  
CONECT   20   18   28   32                                                  
CONECT   21    2    3    8   11                                             
CONECT   22    4    9   16   24                                             
CONECT   23    7   11   16   29                                             
CONECT   24   13   17   22   30                                             
CONECT   25   19                                                            
CONECT   26   10                                                            
CONECT   27   14                                                            
CONECT   28   20                                                            
CONECT   29   23                                                            
CONECT   30   24                                                            
CONECT   31    5   15                                                       
CONECT   32   17   20                                                       
MASTER        0    0    0    0    0    0    0    0   32    0   70    0
END

View in JSmol

Synonyms

Value	Source
3-Formyl-2a,4a-dihydroxy-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
Armillarinin	MeSH

Chemical Formula

C₂₄H₂₉ClO₇

Average Mass

464.9360 Da

Monoisotopic Mass

464.16018 Da

IUPAC Name

3-formyl-2a,4a-dihydroxy-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

3-formyl-2a,4a-dihydroxy-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

127486-63-9

SMILES

COC1=C(Cl)C(C)=C(C(=O)OC2CC3(C)C4CC(C)(C)CC4(O)C=C(C=O)C23O)C(O)=C1

InChI Identifier

InChI=1S/C24H29ClO7/c1-12-18(14(27)6-15(31-5)19(12)25)20(28)32-17-9-22(4)16-8-21(2,3)11-23(16,29)7-13(10-26)24(17,22)30/h6-7,10,16-17,27,29-30H,8-9,11H2,1-5H3

InChI Key

XOGUZUVXPLTDMB-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
P-methoxybenzoic acid or derivatives
O-hydroxybenzoic acid ester
Salicylic acid or derivatives
Methoxyphenol
3-halobenzoic acid or derivatives
Halobenzoic acid or derivatives
Benzoate ester
Benzoic acid or derivatives
Anisole
Phenoxy compound
4-chlorophenol
M-cresol
4-halophenol
Methoxybenzene
Benzoyl
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Chlorobenzene
Halobenzene
Toluene
Phenol
Aryl chloride
Benzenoid
Aryl halide
Monocyclic benzene moiety
Tertiary alcohol
Vinylogous acid
Cyclic alcohol
Carboxylic acid ester
Cyclobutanol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Ether
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aldehyde
Organooxygen compound
Organohalogen compound
Organochloride
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	2.95	ALOGPS
logP	3.78	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	9.33	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	113.29 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	118.78 m³·mol⁻¹	ChemAxon
Polarizability	48.09 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

HMDB0031674

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB008334

KNApSAcK ID

Not Available

Chemspider ID

19994085

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

21126387

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Armillarinin (NP0047309)

MOL for NP0047309 (Armillarinin)

3D MOL for NP0047309 (Armillarinin)

3D SDF for NP0047309 (Armillarinin)

3D-SDF for NP0047309 (Armillarinin)

PDB for NP0047309 (Armillarinin)

3D PDB for NP0047309 (Armillarinin)

SMILES for NP0047309 (Armillarinin)

INCHI for NP0047309 (Armillarinin)

Structure for NP0047309 (Armillarinin)

3D Structure for NP0047309 (Armillarinin)