NP-MRD: Showing NP-Card for 5-chloro-7-methyl-3-(2-methyl-6-oxocyclohex-1-en-1-yl)-6,8-dioxoisochromen-7-yl 3-(acetyloxy)-2,4-dimethylhex-4-enoate (NP0279751)

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Record Information

Version

2.0

Created at

2022-09-09 05:15:15 UTC

Updated at

2022-09-09 05:15:15 UTC

NP-MRD ID

NP0279751

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-chloro-7-methyl-3-(2-methyl-6-oxocyclohex-1-en-1-yl)-6,8-dioxoisochromen-7-yl 3-(acetyloxy)-2,4-dimethylhex-4-enoate

Description

5-Chloro-7-methyl-3-(2-methyl-6-oxocyclohex-1-en-1-yl)-6,8-dioxo-7,8-dihydro-6H-isochromen-7-yl 3-(acetyloxy)-2,4-dimethylhex-4-enoate belongs to the class of organic compounds known as azaphilones. These are a structurally variable family of fungal polyketide metabolites possessing a highly oxygenated pyranoquinone bicyclic core, usually known as isochromene, and a quaternary carbon center. Based on a literature review very few articles have been published on 5-chloro-7-methyl-3-(2-methyl-6-oxocyclohex-1-en-1-yl)-6,8-dioxo-7,8-dihydro-6H-isochromen-7-yl 3-(acetyloxy)-2,4-dimethylhex-4-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092207152D          

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M  END

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  Mrv1652309092207152D          

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M  END
> <DATABASE_ID>
NP0279751

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC=C(C)C(OC(C)=O)C(C)C(=O)OC1(C)C(=O)C(Cl)=C2C=C(OC=C2C1=O)C1=C(C)CCCC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H29ClO8/c1-7-13(2)23(35-16(5)29)15(4)26(33)36-27(6)24(31)18-12-34-20(11-17(18)22(28)25(27)32)21-14(3)9-8-10-19(21)30/h7,11-12,15,23H,8-10H2,1-6H3

> <INCHI_KEY>
HASSXTLCIPVJFU-UHFFFAOYSA-N

> <FORMULA>
C27H29ClO8

> <MOLECULAR_WEIGHT>
516.97

> <EXACT_MASS>
516.1550956

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
51.968965421108024

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-chloro-7-methyl-3-(2-methyl-6-oxocyclohex-1-en-1-yl)-6,8-dioxo-7,8-dihydro-6H-isochromen-7-yl 3-(acetyloxy)-2,4-dimethylhex-4-enoate

> <JCHEM_LOGP>
4.0251059346666676

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-5.092279920079117

> <JCHEM_POLAR_SURFACE_AREA>
113.04000000000002

> <JCHEM_REFRACTIVITY>
135.2582

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
5-chloro-7-methyl-3-(2-methyl-6-oxocyclohex-1-en-1-yl)-6,8-dioxoisochromen-7-yl 3-(acetyloxy)-2,4-dimethylhex-4-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       0.948 -12.602   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.718 -11.268   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.258 -11.268   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.028 -12.602   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.028  -9.935   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       3.258  -8.601   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       1.718  -8.601   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.948  -9.935   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.948  -7.267   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.568  -9.935   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.338 -11.268   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.338  -8.601   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       5.568  -7.267   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       7.878  -8.601   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       8.648  -9.935   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.200 -10.461   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.827  -8.945   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.560  -7.428   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      11.274  -9.472   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      12.454  -8.482   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      13.901  -9.008   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      14.169 -10.525   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      15.616 -11.052   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      16.796 -10.062   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      16.528  -8.545   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      18.243 -10.589   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      18.510 -12.105   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      17.330 -13.095   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      15.883 -12.568   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      14.704 -13.558   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      12.989 -11.515   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.542 -10.988   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      10.362 -11.978   0.000  0.00  0.00           C+0
HETATM   34 Cl   UNK     0      10.630 -13.495   0.000  0.00  0.00          Cl+0
HETATM   35  C   UNK     0       8.915 -11.451   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       7.735 -12.441   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    5   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   17   35                                             
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   32                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   31                                                  
CONECT   23   22   24   29                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   23   30                                                  
CONECT   30   29                                                            
CONECT   31   22   32                                                       
CONECT   32   31   19   33                                                  
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   15   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Value	Source
5-Chloro-7-methyl-3-(2-methyl-6-oxocyclohex-1-en-1-yl)-6,8-dioxo-7,8-dihydro-6H-isochromen-7-yl 3-(acetyloxy)-2,4-dimethylhex-4-enoic acid	Generator

Chemical Formula

C₂₇H₂₉ClO₈

Average Mass

516.9700 Da

Monoisotopic Mass

516.15510 Da

IUPAC Name

5-chloro-7-methyl-3-(2-methyl-6-oxocyclohex-1-en-1-yl)-6,8-dioxo-7,8-dihydro-6H-isochromen-7-yl 3-(acetyloxy)-2,4-dimethylhex-4-enoate

Traditional Name

5-chloro-7-methyl-3-(2-methyl-6-oxocyclohex-1-en-1-yl)-6,8-dioxoisochromen-7-yl 3-(acetyloxy)-2,4-dimethylhex-4-enoate

CAS Registry Number

Not Available

SMILES

CC=C(C)C(OC(C)=O)C(C)C(=O)OC1(C)C(=O)C(Cl)=C2C=C(OC=C2C1=O)C1=C(C)CCCC1=O

InChI Identifier

InChI=1S/C27H29ClO8/c1-7-13(2)23(35-16(5)29)15(4)26(33)36-27(6)24(31)18-12-34-20(11-17(18)22(28)25(27)32)21-14(3)9-8-10-19(21)30/h7,11-12,15,23H,8-10H2,1-6H3

InChI Key

HASSXTLCIPVJFU-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as azaphilones. These are a structurally variable family of fungal polyketide metabolites possessing a highly oxygenated pyranoquinone bicyclic core, usually known as isochromene, and a quaternary carbon center.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Azaphilones

Sub Class

Not Available

Direct Parent

Azaphilones

Alternative Parents

Substituents

Azaphilone
Cyclohexenone
Alpha-acyloxy ketone
Fatty acid ester
Fatty acyl
Pyran
Dicarboxylic acid or derivatives
Alpha-haloketone
Alpha-chloroketone
Vinylogous ester
Cyclic ketone
Ketone
Carboxylic acid ester
Oxacycle
Chloroalkene
Haloalkene
Vinyl halide
Vinyl chloride
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organochloride
Organohalogen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	4.03	ChemAxon
pKa (Strongest Basic)	-5.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	113.04 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	135.26 m³·mol⁻¹	ChemAxon
Polarizability	51.97 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

Not Available

METLIN ID

Not Available

PubChem Compound

162814372

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-chloro-7-methyl-3-(2-methyl-6-oxocyclohex-1-en-1-yl)-6,8-dioxoisochromen-7-yl 3-(acetyloxy)-2,4-dimethylhex-4-enoate (NP0279751)

MOL for NP0279751 (5-chloro-7-methyl-3-(2-methyl-6-oxocyclohex-1-en-1-yl)-6,8-dioxoisochromen-7-yl 3-(acetyloxy)-2,4-dimethylhex-4-enoate)

3D MOL for NP0279751 (5-chloro-7-methyl-3-(2-methyl-6-oxocyclohex-1-en-1-yl)-6,8-dioxoisochromen-7-yl 3-(acetyloxy)-2,4-dimethylhex-4-enoate)

3D SDF for NP0279751 (5-chloro-7-methyl-3-(2-methyl-6-oxocyclohex-1-en-1-yl)-6,8-dioxoisochromen-7-yl 3-(acetyloxy)-2,4-dimethylhex-4-enoate)

3D-SDF for NP0279751 (5-chloro-7-methyl-3-(2-methyl-6-oxocyclohex-1-en-1-yl)-6,8-dioxoisochromen-7-yl 3-(acetyloxy)-2,4-dimethylhex-4-enoate)

PDB for NP0279751 (5-chloro-7-methyl-3-(2-methyl-6-oxocyclohex-1-en-1-yl)-6,8-dioxoisochromen-7-yl 3-(acetyloxy)-2,4-dimethylhex-4-enoate)

3D PDB for NP0279751 (5-chloro-7-methyl-3-(2-methyl-6-oxocyclohex-1-en-1-yl)-6,8-dioxoisochromen-7-yl 3-(acetyloxy)-2,4-dimethylhex-4-enoate)

SMILES for NP0279751 (5-chloro-7-methyl-3-(2-methyl-6-oxocyclohex-1-en-1-yl)-6,8-dioxoisochromen-7-yl 3-(acetyloxy)-2,4-dimethylhex-4-enoate)

INCHI for NP0279751 (5-chloro-7-methyl-3-(2-methyl-6-oxocyclohex-1-en-1-yl)-6,8-dioxoisochromen-7-yl 3-(acetyloxy)-2,4-dimethylhex-4-enoate)

Structure for NP0279751 (5-chloro-7-methyl-3-(2-methyl-6-oxocyclohex-1-en-1-yl)-6,8-dioxoisochromen-7-yl 3-(acetyloxy)-2,4-dimethylhex-4-enoate)

3D Structure for NP0279751 (5-chloro-7-methyl-3-(2-methyl-6-oxocyclohex-1-en-1-yl)-6,8-dioxoisochromen-7-yl 3-(acetyloxy)-2,4-dimethylhex-4-enoate)