NP-MRD: Showing NP-Card for Armillaricin (NP0049200)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-03-17 21:08:41 UTC

Updated at

2022-03-17 21:08:41 UTC

NP-MRD ID

NP0049200

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Armillaricin

Description

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

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061310352D          

 30 33  0  0  0  0            999 V2000
   -0.8241   -1.2904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7863    1.5151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2702    2.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0897    2.3068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1164    0.1561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6180    0.0598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5079    0.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8695    0.8998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2455    2.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1480    1.9572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3548   -0.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3853   -0.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0567    0.7584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7935    0.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6711    1.4877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7036    0.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7509   -0.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7092    1.2586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1423    0.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4079    0.8198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1896   -0.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3380    0.2864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9862    1.7165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8467    1.5184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4326   -1.6579    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7404   -1.3375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4606    1.4957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2232   -0.3182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5551   -0.4486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0950    1.0748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 12  1  1  0  0  0  0
 13  6  1  0  0  0  0
 13  8  1  0  0  0  0
 14  6  1  0  0  0  0
 14 11  1  0  0  0  0
 15  9  1  0  0  0  0
 15 13  1  0  0  0  0
 16  7  2  0  0  0  0
 17  7  1  0  0  0  0
 18 10  1  0  0  0  0
 19 12  2  0  0  0  0
 19 16  1  0  0  0  0
 20 14  2  0  0  0  0
 20 18  1  0  0  0  0
 21 12  1  0  0  0  0
 21 17  2  0  0  0  0
 22 19  1  0  0  0  0
 23  2  1  0  0  0  0
 23  3  1  0  0  0  0
 23  8  1  0  0  0  0
 23  9  1  0  0  0  0
 24  4  1  0  0  0  0
 24 10  1  0  0  0  0
 24 15  1  0  0  0  0
 24 20  1  0  0  0  0
 25 21  1  0  0  0  0
 26 11  2  0  0  0  0
 27 16  1  0  0  0  0
 28 22  2  0  0  0  0
 29  5  1  0  0  0  0
 29 17  1  0  0  0  0
 30 18  1  0  0  0  0
 30 22  1  0  0  0  0
M  END


  Mrv0541 05061310352D          

 30 33  0  0  0  0            999 V2000
   -0.8241   -1.2904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7863    1.5151    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2702    2.4911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0897    2.3068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1164    0.1561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6180    0.0598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5079    0.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8695    0.8998    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2455    2.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1480    1.9572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3548   -0.6082    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3853   -0.6857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0567    0.7584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7935    0.0905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6711    1.4877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7036    0.7073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7509   -0.2648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7092    1.2586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1423    0.1027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4079    0.8198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1896   -0.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3380    0.2864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9862    1.7165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8467    1.5184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4326   -1.6579    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.7404   -1.3375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4606    1.4957    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2232   -0.3182    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5551   -0.4486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0950    1.0748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 12  1  1  0  0  0  0
 13  6  1  0  0  0  0
 13  8  1  0  0  0  0
 14  6  1  0  0  0  0
 14 11  1  0  0  0  0
 15  9  1  0  0  0  0
 15 13  1  0  0  0  0
 16  7  2  0  0  0  0
 17  7  1  0  0  0  0
 18 10  1  0  0  0  0
 19 12  2  0  0  0  0
 19 16  1  0  0  0  0
 20 14  2  0  0  0  0
 20 18  1  0  0  0  0
 21 12  1  0  0  0  0
 21 17  2  0  0  0  0
 22 19  1  0  0  0  0
 23  2  1  0  0  0  0
 23  3  1  0  0  0  0
 23  8  1  0  0  0  0
 23  9  1  0  0  0  0
 24  4  1  0  0  0  0
 24 10  1  0  0  0  0
 24 15  1  0  0  0  0
 24 20  1  0  0  0  0
 25 21  1  0  0  0  0
 26 11  2  0  0  0  0
 27 16  1  0  0  0  0
 28 22  2  0  0  0  0
 29  5  1  0  0  0  0
 29 17  1  0  0  0  0
 30 18  1  0  0  0  0
 30 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049200

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(Cl)C(C)=C(C(=O)OC2CC3(C)C4CC(C)(C)CC4CC(C=O)=C23)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C24H29ClO5/c1-12-19(16(27)7-17(29-5)21(12)25)22(28)30-18-10-24(4)15-9-23(2,3)8-13(15)6-14(11-26)20(18)24/h7,11,13,15,18,27H,6,8-10H2,1-5H3

> <INCHI_KEY>
HTYGPZSURXEEQG-UHFFFAOYSA-N

> <FORMULA>
C24H29ClO5

> <MOLECULAR_WEIGHT>
432.937

> <EXACT_MASS>
432.170351745

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
47.101411915069356

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-formyl-6,6,7b-trimethyl-1H,2H,4H,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate

> <ALOGPS_LOGP>
4.43

> <JCHEM_LOGP>
5.661294968333333

> <ALOGPS_LOGS>
-5.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.324082817381406

> <JCHEM_PKA_STRONGEST_BASIC>
-4.348577960083337

> <JCHEM_POLAR_SURFACE_AREA>
72.83

> <JCHEM_REFRACTIVITY>
115.84719999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.27e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-formyl-6,6,7b-trimethyl-1H,2H,4H,4aH,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      -1.538  -2.409   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.934   2.828   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.971   4.650   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.901   4.306   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.684   0.291   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.887   0.112   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.681   0.977   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.223   1.680   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.058   3.882   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.143   3.653   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.529  -1.135   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.586  -1.280   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.706   1.416   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.348   0.169   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.986   2.777   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.180   1.320   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -5.135  -0.494   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.324   2.349   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.132   0.192   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.628   1.530   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.087  -1.623   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.631   0.535   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.441   3.204   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.447   2.834   0.000  0.00  0.00           C+0
HETATM   25 Cl   UNK     0      -4.541  -3.095   0.000  0.00  0.00          Cl+0
HETATM   26  O   UNK     0       3.249  -2.497   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      -2.726   2.792   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       0.417  -0.594   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -6.636  -0.837   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -0.177   2.006   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   23                                                            
CONECT    3   23                                                            
CONECT    4   24                                                            
CONECT    5   29                                                            
CONECT    6   13   14                                                       
CONECT    7   16   17                                                       
CONECT    8   13   23                                                       
CONECT    9   15   23                                                       
CONECT   10   18   24                                                       
CONECT   11   14   26                                                       
CONECT   12    1   19   21                                                  
CONECT   13    6    8   15                                                  
CONECT   14    6   11   20                                                  
CONECT   15    9   13   24                                                  
CONECT   16    7   19   27                                                  
CONECT   17    7   21   29                                                  
CONECT   18   10   20   30                                                  
CONECT   19   12   16   22                                                  
CONECT   20   14   18   24                                                  
CONECT   21   12   17   25                                                  
CONECT   22   19   28   30                                                  
CONECT   23    2    3    8    9                                             
CONECT   24    4   10   15   20                                             
CONECT   25   21                                                            
CONECT   26   11                                                            
CONECT   27   16                                                            
CONECT   28   22                                                            
CONECT   29    5   17                                                       
CONECT   30   18   22                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Value	Source
3-Formyl-6,6,7b-trimethyl-1H,2H,4H,4ah,5H,6H,7H,7ah,7BH-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoic acid	Generator

Chemical Formula

C₂₄H₂₉ClO₅

Average Mass

432.9370 Da

Monoisotopic Mass

432.17035 Da

IUPAC Name

3-formyl-6,6,7b-trimethyl-1H,2H,4H,4aH,5H,6H,7H,7aH,7bH-cyclobuta[e]inden-2-yl 3-chloro-6-hydroxy-4-methoxy-2-methylbenzoate

Traditional Name

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

CAS Registry Number

119516-62-0

SMILES

COC1=C(Cl)C(C)=C(C(=O)OC2CC3(C)C4CC(C)(C)CC4CC(C=O)=C23)C(O)=C1

InChI Identifier

InChI=1S/C24H29ClO5/c1-12-19(16(27)7-17(29-5)21(12)25)22(28)30-18-10-24(4)15-9-23(2,3)8-13(15)6-14(11-26)20(18)24/h7,11,13,15,18,27H,6,8-10H2,1-5H3

InChI Key

HTYGPZSURXEEQG-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
Benzoyl
4-halophenol
Phenoxy compound
M-cresol
Anisole
4-chlorophenol
Phenol ether
Methoxybenzene
Chlorobenzene
Alkyl aryl ether
Halobenzene
Phenol
1-hydroxy-2-unsubstituted benzenoid
Toluene
Aryl halide
Monocyclic benzene moiety
Aryl chloride
Benzenoid
Vinylogous acid
Carboxylic acid ester
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Aldehyde
Organohalogen compound
Organochloride
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Carbonyl group
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	4.43	ALOGPS
logP	5.66	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	9.32	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	115.85 m³·mol⁻¹	ChemAxon
Polarizability	47.1 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0038686

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018090

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

131752426

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Armillaricin (NP0049200)

MOL for NP0049200 (Armillaricin)

3D MOL for NP0049200 (Armillaricin)

3D SDF for NP0049200 (Armillaricin)

3D-SDF for NP0049200 (Armillaricin)

PDB for NP0049200 (Armillaricin)

3D PDB for NP0049200 (Armillaricin)

SMILES for NP0049200 (Armillaricin)

INCHI for NP0049200 (Armillaricin)

Structure for NP0049200 (Armillaricin)

3D Structure for NP0049200 (Armillaricin)