NP-MRD: Showing NP-Card for 4-methoxy-3,5-dimethyl-6-[2-methyl-3-(4-methyl-5-{2,4,5-trimethyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl}penta-2,4-dien-2-yl)oxiran-2-yl]pyran-2-one (NP0311273)

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Record Information

Version

2.0

Created at

2022-09-11 07:09:43 UTC

Updated at

2022-09-11 07:09:43 UTC

NP-MRD ID

NP0311273

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-methoxy-3,5-dimethyl-6-[2-methyl-3-(4-methyl-5-{2,4,5-trimethyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl}penta-2,4-dien-2-yl)oxiran-2-yl]pyran-2-one

Description

Verrucosidin belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone. Tremorgenic mycotoxins affect central nervous system activity and have been implicated in a number of neurologic diseases of cattle collectively known as "staggers syndromes". They cause a neurological disease of cattle known as "staggers syndrome", which is characterized by muscle tremors, hyperexcitability, convulsions and ataxia. Verrucosidin is an extremely weak basic (essentially neutral) compound (based on its pKa). Verrucosidin is a potentially toxic compound. Tremorgenic mycotoxins exert their toxic effects by interfering with neurotransmitter release, possibly by causing degeneration of nerve terminals. This would initially increase neurotransmitter levels, potentiating the GABA-induced chloride current, then lead to decreased levels of neurotransmitter in the synapse. Tremorgenic mycotoxins affect central nervous system activity. It may be found in contaminated cereal crops such as oats, barley, millet, corn and rice. Verrucosidin is a tremorgenic mycotoxin that has been found in fungi of the genera Penicillium and Aspergillus. Generalized seizures may be treated with diazepam followed by methocarbamol or a barbiturate such as pentobarbital sodium. 4-methoxy-3,5-dimethyl-6-[2-methyl-3-(4-methyl-5-{2,4,5-trimethyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl}penta-2,4-dien-2-yl)oxiran-2-yl]pyran-2-one is found in Penicillium aurantiogriseum and Penicillium verrucosum. Gastric lavage should be performed and activated charcoal administered to limit further absorption of toxins.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241212552D          

 30 33  0  0  0  0            999 V2000
   -1.3169   -6.9052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5718   -6.1205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3564   -5.8656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3564   -5.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0709   -5.4531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5718   -4.7857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0869   -5.4531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7349   -3.9769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9645   -4.2272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1773   -4.4740    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0027   -5.2791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4300   -3.9155    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2172   -4.1622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3972   -4.9674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8245   -3.6038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0712   -2.8166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6297   -3.4239    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4620   -2.2603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3856   -2.0538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8822   -1.4002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0144   -0.5283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv0541 02241212552D          

 30 33  0  0  0  0            999 V2000
   -1.3169   -6.9052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5718   -6.1205    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3564   -5.8656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3564   -5.0406    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0709   -5.4531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5718   -4.7857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0311273

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(C)C(=O)OC(=C1C)C1(C)OC1C(C)=CC(C)=CC1(C)OC(C)C2(C)OC12

> <INCHI_IDENTIFIER>
InChI=1S/C24H32O6/c1-12(11-22(6)21-23(7,30-21)16(5)28-22)10-13(2)18-24(8,29-18)19-14(3)17(26-9)15(4)20(25)27-19/h10-11,16,18,21H,1-9H3

> <INCHI_KEY>
JSVLNARHSWZARV-UHFFFAOYSA-N

> <FORMULA>
C24H32O6

> <MOLECULAR_WEIGHT>
416.5073

> <EXACT_MASS>
416.219888756

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
46.09718530167251

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-methoxy-3,5-dimethyl-6-[2-methyl-3-(4-methyl-5-{2,4,5-trimethyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl}penta-2,4-dien-2-yl)oxiran-2-yl]-2H-pyran-2-one

> <ALOGPS_LOGP>
4.53

> <JCHEM_LOGP>
3.3868057600000006

> <ALOGPS_LOGS>
-4.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7595583304774327

> <JCHEM_POLAR_SURFACE_AREA>
69.82000000000001

> <JCHEM_REFRACTIVITY>
115.55769999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.34e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-methoxy-3,5-dimethyl-6-[2-methyl-3-(4-methyl-5-{2,4,5-trimethyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl}penta-2,4-dien-2-yl)oxiran-2-yl]pyran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -2.458 -12.890   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.934 -11.425   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.399 -10.949   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.399  -9.409   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -5.732 -10.179   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.934  -8.933   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.029 -10.179   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -3.238  -7.424   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.800  -7.891   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.331  -8.351   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.005  -9.854   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.803  -7.309   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.272  -7.769   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.608  -9.272   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.406  -6.727   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.866  -5.258   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       4.909  -6.391   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.729  -4.219   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.453  -3.834   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.513  -2.614   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.100  -1.190   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.627  -0.986   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.567  -2.206   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.093  -2.003   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       5.980  -3.630   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.214   0.438   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       3.161   0.030   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       3.748   1.454   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.987  -2.817   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -5.025 -12.356   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4    5   30                                             
CONECT    4    3    5    6                                                  
CONECT    5    4    3                                                       
CONECT    6    4    7    8    9                                             
CONECT    7    6    2                                                       
CONECT    8    6                                                            
CONECT    9    6   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15   17   18   19                                             
CONECT   17   16   15                                                       
CONECT   18   16                                                            
CONECT   19   16   20   25                                                  
CONECT   20   19   21   29                                                  
CONECT   21   20   22   27                                                  
CONECT   22   21   23   26                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   19                                                       
CONECT   26   22                                                            
CONECT   27   21   28                                                       
CONECT   28   27                                                            
CONECT   29   20                                                            
CONECT   30    3                                                            
MASTER        0    0    0    0    0    0    0    0   30    0   66    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₂O₆

Average Mass

416.5073 Da

Monoisotopic Mass

416.21989 Da

IUPAC Name

4-methoxy-3,5-dimethyl-6-[2-methyl-3-(4-methyl-5-{2,4,5-trimethyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl}penta-2,4-dien-2-yl)oxiran-2-yl]-2H-pyran-2-one

Traditional Name

4-methoxy-3,5-dimethyl-6-[2-methyl-3-(4-methyl-5-{2,4,5-trimethyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl}penta-2,4-dien-2-yl)oxiran-2-yl]pyran-2-one

CAS Registry Number

Not Available

SMILES

COC1=C(C)C(=O)OC(=C1C)C1(C)OC1C(C)=CC(C)=CC1(C)OC(C)C2(C)OC12

InChI Identifier

InChI=1S/C24H32O6/c1-12(11-22(6)21-23(7,30-21)16(5)28-22)10-13(2)18-24(8,29-18)19-14(3)17(26-9)15(4)20(25)27-19/h10-11,16,18,21H,1-9H3

InChI Key

JSVLNARHSWZARV-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Penicillium aurantiogriseum	LOTUS Database	35616633
Penicillium verrucosum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrans

Sub Class

Pyranones and derivatives

Direct Parent

Pyranones and derivatives

Alternative Parents

Substituents

Alkyl aryl ether
Pyranone
Para-dioxane
Tetrahydrofuran
Vinylogous ester
Heteroaromatic compound
Lactone
Ether
Oxirane
Dialkyl ether
Oxacycle
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	4.53	ALOGPS
logP	3.39	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	69.82 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	115.56 m³·mol⁻¹	ChemAxon
Polarizability	46.1 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Verrucosidin

METLIN ID

Not Available

PubChem Compound

74202876

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-methoxy-3,5-dimethyl-6-[2-methyl-3-(4-methyl-5-{2,4,5-trimethyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl}penta-2,4-dien-2-yl)oxiran-2-yl]pyran-2-one (NP0311273)

MOL for NP0311273 (4-methoxy-3,5-dimethyl-6-[2-methyl-3-(4-methyl-5-{2,4,5-trimethyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl}penta-2,4-dien-2-yl)oxiran-2-yl]pyran-2-one)

3D MOL for NP0311273 (4-methoxy-3,5-dimethyl-6-[2-methyl-3-(4-methyl-5-{2,4,5-trimethyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl}penta-2,4-dien-2-yl)oxiran-2-yl]pyran-2-one)

3D SDF for NP0311273 (4-methoxy-3,5-dimethyl-6-[2-methyl-3-(4-methyl-5-{2,4,5-trimethyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl}penta-2,4-dien-2-yl)oxiran-2-yl]pyran-2-one)

3D-SDF for NP0311273 (4-methoxy-3,5-dimethyl-6-[2-methyl-3-(4-methyl-5-{2,4,5-trimethyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl}penta-2,4-dien-2-yl)oxiran-2-yl]pyran-2-one)

PDB for NP0311273 (4-methoxy-3,5-dimethyl-6-[2-methyl-3-(4-methyl-5-{2,4,5-trimethyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl}penta-2,4-dien-2-yl)oxiran-2-yl]pyran-2-one)

3D PDB for NP0311273 (4-methoxy-3,5-dimethyl-6-[2-methyl-3-(4-methyl-5-{2,4,5-trimethyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl}penta-2,4-dien-2-yl)oxiran-2-yl]pyran-2-one)

SMILES for NP0311273 (4-methoxy-3,5-dimethyl-6-[2-methyl-3-(4-methyl-5-{2,4,5-trimethyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl}penta-2,4-dien-2-yl)oxiran-2-yl]pyran-2-one)

INCHI for NP0311273 (4-methoxy-3,5-dimethyl-6-[2-methyl-3-(4-methyl-5-{2,4,5-trimethyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl}penta-2,4-dien-2-yl)oxiran-2-yl]pyran-2-one)

Structure for NP0311273 (4-methoxy-3,5-dimethyl-6-[2-methyl-3-(4-methyl-5-{2,4,5-trimethyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl}penta-2,4-dien-2-yl)oxiran-2-yl]pyran-2-one)

3D Structure for NP0311273 (4-methoxy-3,5-dimethyl-6-[2-methyl-3-(4-methyl-5-{2,4,5-trimethyl-3,6-dioxabicyclo[3.1.0]hexan-2-yl}penta-2,4-dien-2-yl)oxiran-2-yl]pyran-2-one)