NP-MRD: Showing NP-Card for 3-(2-hydroxy-6-methylphenyl)-7-methyl-6,8-dioxoisochromen-7-yl 2-methyloct-2-enoate (NP0269392)

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Record Information

Version

2.0

Created at

2022-09-08 14:51:38 UTC

Updated at

2022-09-08 14:51:38 UTC

NP-MRD ID

NP0269392

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(2-hydroxy-6-methylphenyl)-7-methyl-6,8-dioxoisochromen-7-yl 2-methyloct-2-enoate

Description

3-(2-Hydroxy-6-methylphenyl)-7-methyl-6,8-dioxo-7,8-dihydro-6H-isochromen-7-yl 2-methyloct-2-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. 3-(2-hydroxy-6-methylphenyl)-7-methyl-6,8-dioxoisochromen-7-yl 2-methyloct-2-enoate is found in Jackrogersella cohaerens. 3-(2-Hydroxy-6-methylphenyl)-7-methyl-6,8-dioxo-7,8-dihydro-6H-isochromen-7-yl 2-methyloct-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004171512352D          

 32 34  0  0  0  0            999 V2000
    5.0249   -0.5466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7394   -0.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4539   -0.5466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1683   -0.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8828   -0.5466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5973   -0.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3118   -0.5466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3118   -1.3716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0262   -0.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0262    0.6909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7407   -0.5466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7407   -1.3716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9282   -1.2283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5532   -1.2283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8353   -0.4531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0835   -1.8603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8013   -2.6355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3316   -3.2675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0494   -4.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2370   -4.1860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7067   -3.5540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9888   -2.7788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4585   -2.1468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6461   -2.2901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5797   -4.6748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3922   -4.5315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6744   -3.7563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9225   -5.1635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6403   -5.9387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8279   -6.0820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2976   -5.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4851   -5.5933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 12 23  1  0  0  0  0
 23 24  2  0  0  0  0
 19 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 25 31  1  0  0  0  0
 31 32  1  0  0  0  0
M  END


  Mrv1533004171512352D          

 32 34  0  0  0  0            999 V2000
    5.0249   -0.5466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7394   -0.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4539   -0.5466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1683   -0.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8828   -0.5466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5973   -0.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3118   -0.5466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3118   -1.3716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0262   -0.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0262    0.6909    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7407   -0.5466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7407   -1.3716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9282   -1.2283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5532   -1.2283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8353   -0.4531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0835   -1.8603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8013   -2.6355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3316   -3.2675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0494   -4.0428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2370   -4.1860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.7067   -3.5540    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9888   -2.7788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4585   -2.1468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6461   -2.2901    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5797   -4.6748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3922   -4.5315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6744   -3.7563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9225   -5.1635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6403   -5.9387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8279   -6.0820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2976   -5.4500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4851   -5.5933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  6  5  1  4  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  0  0  0  0
 12 23  1  0  0  0  0
 23 24  2  0  0  0  0
 19 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 25 31  1  0  0  0  0
 31 32  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0269392

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC=C(C)C(=O)OC1(C)C(=O)C=C2C=C(OC=C2C1=O)C1=C(C)C=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H28O6/c1-5-6-7-8-10-17(3)25(30)32-26(4)22(28)14-18-13-21(31-15-19(18)24(26)29)23-16(2)11-9-12-20(23)27/h9-15,27H,5-8H2,1-4H3

> <INCHI_KEY>
WJUXIDJEIYLXTQ-UHFFFAOYSA-N

> <FORMULA>
C26H28O6

> <MOLECULAR_WEIGHT>
436.504

> <EXACT_MASS>
436.188588622

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
46.96525717111448

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-(2-hydroxy-6-methylphenyl)-7-methyl-6,8-dioxo-7,8-dihydro-6H-isochromen-7-yl 2-methyloct-2-enoate

> <ALOGPS_LOGP>
5.42

> <JCHEM_LOGP>
5.932944321333333

> <ALOGPS_LOGS>
-5.49

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.06346501453964

> <JCHEM_PKA_STRONGEST_BASIC>
-5.261973298941847

> <JCHEM_POLAR_SURFACE_AREA>
89.90000000000002

> <JCHEM_REFRACTIVITY>
124.77469999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.41e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(2-hydroxy-6-methylphenyl)-7-methyl-6,8-dioxoisochromen-7-yl 2-methyloct-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       9.380  -1.020   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.714  -0.250   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.047  -1.020   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.381  -0.250   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.715  -1.020   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.048  -0.250   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.382  -1.020   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.382  -2.560   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.716  -0.250   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      18.716   1.290   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      20.049  -1.020   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      20.049  -2.560   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      18.533  -2.293   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      21.566  -2.293   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      22.093  -0.846   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      22.556  -3.473   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      22.029  -4.920   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      23.019  -6.099   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      22.492  -7.547   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      20.976  -7.814   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      19.986  -6.634   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      20.512  -5.187   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      19.523  -4.007   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      18.006  -4.275   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      23.482  -8.726   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      24.999  -8.459   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      25.525  -7.012   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      25.989  -9.639   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      25.462 -11.086   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      23.945 -11.353   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      22.955 -10.173   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      21.439 -10.441   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14   23                                             
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   22                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   25                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   17   23                                                  
CONECT   23   22   12   24                                                  
CONECT   24   23                                                            
CONECT   25   19   26   31                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   25   32                                                  
CONECT   32   31                                                            
MASTER        0    0    0    0    0    0    0    0   32    0   68    0
END

View in JSmol

Synonyms

Value	Source
3-(2-Hydroxy-6-methylphenyl)-7-methyl-6,8-dioxo-7,8-dihydro-6H-isochromen-7-yl 2-methyloct-2-enoic acid	Generator

Chemical Formula

C₂₆H₂₈O₆

Average Mass

436.5040 Da

Monoisotopic Mass

436.18859 Da

IUPAC Name

3-(2-hydroxy-6-methylphenyl)-7-methyl-6,8-dioxo-7,8-dihydro-6H-isochromen-7-yl 2-methyloct-2-enoate

Traditional Name

3-(2-hydroxy-6-methylphenyl)-7-methyl-6,8-dioxoisochromen-7-yl 2-methyloct-2-enoate

CAS Registry Number

Not Available

SMILES

CCCCCC=C(C)C(=O)OC1(C)C(=O)C=C2C=C(OC=C2C1=O)C1=C(C)C=CC=C1O

InChI Identifier

InChI=1S/C26H28O6/c1-5-6-7-8-10-17(3)25(30)32-26(4)22(28)14-18-13-21(31-15-19(18)24(26)29)23-16(2)11-9-12-20(23)27/h9-15,27H,5-8H2,1-4H3

InChI Key

WJUXIDJEIYLXTQ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Jackrogersella cohaerens	LOTUS Database	35616633

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
M-cresol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Cyclohexenone
Phenol
Alpha-acyloxy ketone
Toluene
Monocyclic benzene moiety
Fatty acyl
Benzenoid
Pyran
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Ketone
Cyclic ketone
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Oxacycle
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organooxygen compound
Carbonyl group
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	5.42	ALOGPS
logP	5.93	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	8.06	ChemAxon
pKa (Strongest Basic)	-5.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	89.9 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	124.77 m³·mol⁻¹	ChemAxon
Polarizability	46.97 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

73804572

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-(2-hydroxy-6-methylphenyl)-7-methyl-6,8-dioxoisochromen-7-yl 2-methyloct-2-enoate (NP0269392)

MOL for NP0269392 (3-(2-hydroxy-6-methylphenyl)-7-methyl-6,8-dioxoisochromen-7-yl 2-methyloct-2-enoate)

3D MOL for NP0269392 (3-(2-hydroxy-6-methylphenyl)-7-methyl-6,8-dioxoisochromen-7-yl 2-methyloct-2-enoate)

3D SDF for NP0269392 (3-(2-hydroxy-6-methylphenyl)-7-methyl-6,8-dioxoisochromen-7-yl 2-methyloct-2-enoate)

3D-SDF for NP0269392 (3-(2-hydroxy-6-methylphenyl)-7-methyl-6,8-dioxoisochromen-7-yl 2-methyloct-2-enoate)

PDB for NP0269392 (3-(2-hydroxy-6-methylphenyl)-7-methyl-6,8-dioxoisochromen-7-yl 2-methyloct-2-enoate)

3D PDB for NP0269392 (3-(2-hydroxy-6-methylphenyl)-7-methyl-6,8-dioxoisochromen-7-yl 2-methyloct-2-enoate)

SMILES for NP0269392 (3-(2-hydroxy-6-methylphenyl)-7-methyl-6,8-dioxoisochromen-7-yl 2-methyloct-2-enoate)

INCHI for NP0269392 (3-(2-hydroxy-6-methylphenyl)-7-methyl-6,8-dioxoisochromen-7-yl 2-methyloct-2-enoate)

Structure for NP0269392 (3-(2-hydroxy-6-methylphenyl)-7-methyl-6,8-dioxoisochromen-7-yl 2-methyloct-2-enoate)

3D Structure for NP0269392 (3-(2-hydroxy-6-methylphenyl)-7-methyl-6,8-dioxoisochromen-7-yl 2-methyloct-2-enoate)