NP-MRD: Showing NP-Card for Armillasin (NP0049208)

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Record Information

Version

2.0

Created at

2022-03-17 21:08:49 UTC

Updated at

2022-03-17 21:08:49 UTC

NP-MRD ID

NP0049208

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Armillasin

Description

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

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061310372D          

 27 30  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
    3.1815    1.7412    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
   -2.2626   -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
    4.4330    0.9012    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
   -1.4584   -0.2994    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
   -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
   -1.1401    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
   -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
    1.9714    0.9812    0.0000 C   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
   -0.5788    1.6983    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
    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
  6  5  2  0  0  0  0
 12  1  1  0  0  0  0
 12  7  2  0  0  0  0
 13  5  1  0  0  0  0
 13  9  1  0  0  0  0
 14  7  1  0  0  0  0
 14  8  2  0  0  0  0
 15 10  1  0  0  0  0
 15 13  1  0  0  0  0
 16  8  1  0  0  0  0
 17 11  1  0  0  0  0
 18 12  1  0  0  0  0
 18 16  2  0  0  0  0
 19 18  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 10  1  0  0  0  0
 21  4  1  0  0  0  0
 21 11  1  0  0  0  0
 21 15  1  0  0  0  0
 22  6  1  0  0  0  0
 22 17  1  0  0  0  0
 22 21  1  0  0  0  0
 23 14  1  0  0  0  0
 24 16  1  0  0  0  0
 25 19  2  0  0  0  0
 26 22  1  0  0  0  0
 27 17  1  0  0  0  0
 27 19  1  0  0  0  0
M  END


  Mrv0541 05061310372D          

 27 30  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
    3.1815    1.7412    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
   -2.2626   -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
    4.4330    0.9012    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
   -1.4584   -0.2994    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
   -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
   -1.1401    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
   -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
    1.9714    0.9812    0.0000 C   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
   -0.5788    1.6983    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
    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
  6  5  2  0  0  0  0
 12  1  1  0  0  0  0
 12  7  2  0  0  0  0
 13  5  1  0  0  0  0
 13  9  1  0  0  0  0
 14  7  1  0  0  0  0
 14  8  2  0  0  0  0
 15 10  1  0  0  0  0
 15 13  1  0  0  0  0
 16  8  1  0  0  0  0
 17 11  1  0  0  0  0
 18 12  1  0  0  0  0
 18 16  2  0  0  0  0
 19 18  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 10  1  0  0  0  0
 21  4  1  0  0  0  0
 21 11  1  0  0  0  0
 21 15  1  0  0  0  0
 22  6  1  0  0  0  0
 22 17  1  0  0  0  0
 22 21  1  0  0  0  0
 23 14  1  0  0  0  0
 24 16  1  0  0  0  0
 25 19  2  0  0  0  0
 26 22  1  0  0  0  0
 27 17  1  0  0  0  0
 27 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049208

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=CC12O

> <INCHI_IDENTIFIER>
InChI=1S/C22H28O5/c1-12-7-14(23)8-16(24)18(12)19(25)27-17-11-21(4)15-10-20(2,3)9-13(15)5-6-22(17,21)26/h5-8,13,15,17,23-24,26H,9-11H2,1-4H3

> <INCHI_KEY>
AFPPVJHFFGBKOB-UHFFFAOYSA-N

> <FORMULA>
C22H28O5

> <MOLECULAR_WEIGHT>
372.4547

> <EXACT_MASS>
372.193674006

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
40.75105105863582

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2a-hydroxy-6,6,7b-trimethyl-1H,2H,2aH,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate

> <ALOGPS_LOGP>
3.68

> <JCHEM_LOGP>
4.831091597333334

> <ALOGPS_LOGS>
-3.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.554908855716997

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.697540911126874

> <JCHEM_PKA_STRONGEST_BASIC>
-3.612866087656098

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
102.97299999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.75e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2a-hydroxy-6,6,7b-trimethyl-1H,2H,4aH,5H,7H,7aH-cyclobuta[e]inden-2-yl 2,4-dihydroxy-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       5.939   3.250   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.400   3.193   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.224  -0.216   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -3.630   2.384   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       7.110  -0.521   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.195  -0.292   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       6.758   1.946   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       6.038   0.585   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.128   2.042   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      -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       3.680   1.832   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -6.178   1.599   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -1.080   3.170   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       0.280  -1.245   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       2.551   2.879   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       0.875   1.356   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   20                                                            
CONECT    3   20                                                            
CONECT    4   21                                                            
CONECT    5    6   13                                                       
CONECT    6    5   22                                                       
CONECT    7   12   14                                                       
CONECT    8   14   16                                                       
CONECT    9   13   20                                                       
CONECT   10   15   20                                                       
CONECT   11   17   21                                                       
CONECT   12    1    7   18                                                  
CONECT   13    5    9   15                                                  
CONECT   14    7    8   23                                                  
CONECT   15   10   13   21                                                  
CONECT   16    8   18   24                                                  
CONECT   17   11   22   27                                                  
CONECT   18   12   16   19                                                  
CONECT   19   18   25   27                                                  
CONECT   20    2    3    9   10                                             
CONECT   21    4   11   15   22                                             
CONECT   22    6   17   21   26                                             
CONECT   23   14                                                            
CONECT   24   16                                                            
CONECT   25   19                                                            
CONECT   26   22                                                            
CONECT   27   17   19                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   60    0
END

View in JSmol

Synonyms

Value	Source
2a-Hydroxy-6,6,7b-trimethyl-1H,2H,2ah,4ah,5H,6H,7H,7ah,7BH-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoic acid	Generator

Chemical Formula

C₂₂H₂₈O₅

Average Mass

372.4547 Da

Monoisotopic Mass

372.19367 Da

IUPAC Name

2a-hydroxy-6,6,7b-trimethyl-1H,2H,2aH,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-2-yl 2,4-dihydroxy-6-methylbenzoate

Traditional Name

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

CAS Registry Number

139051-16-4

SMILES

CC1=CC(O)=CC(O)=C1C(=O)OC1CC2(C)C3CC(C)(C)CC3C=CC12O

InChI Identifier

InChI=1S/C22H28O5/c1-12-7-14(23)8-16(24)18(12)19(25)27-17-11-21(4)15-10-20(2,3)9-13(15)5-6-22(17,21)26/h5-8,13,15,17,23-24,26H,9-11H2,1-4H3

InChI Key

AFPPVJHFFGBKOB-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-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
O-hydroxybenzoic acid ester
Dihydroxybenzoic acid
Benzoate ester
Salicylic acid or derivatives
Benzoic acid or derivatives
M-cresol
Benzoyl
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Toluene
Phenol
Monocyclic benzene moiety
Benzenoid
Vinylogous acid
Tertiary alcohol
Carboxylic acid ester
Cyclobutanol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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	3.68	ALOGPS
logP	4.83	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	8.7	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	102.97 m³·mol⁻¹	ChemAxon
Polarizability	40.75 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

HMDB0038742

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018153

KNApSAcK ID

Not Available

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

131752445

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Armillasin (NP0049208)

MOL for NP0049208 (Armillasin)

3D MOL for NP0049208 (Armillasin)

3D SDF for NP0049208 (Armillasin)

3D-SDF for NP0049208 (Armillasin)

PDB for NP0049208 (Armillasin)

3D PDB for NP0049208 (Armillasin)

SMILES for NP0049208 (Armillasin)

INCHI for NP0049208 (Armillasin)

Structure for NP0049208 (Armillasin)

3D Structure for NP0049208 (Armillasin)