NP-MRD: Showing NP-Card for 8-(acetyloxy)-7-methyl-6-oxo-3-propyl-8,8a-dihydro-1h-isochromen-7-yl 3,5-dichloro-2,4-dimethoxy-6-methylbenzoate (NP0248312)

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Record Information

Version

2.0

Created at

2022-09-07 10:31:49 UTC

Updated at

2022-09-07 10:31:49 UTC

NP-MRD ID

NP0248312

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-(acetyloxy)-7-methyl-6-oxo-3-propyl-8,8a-dihydro-1h-isochromen-7-yl 3,5-dichloro-2,4-dimethoxy-6-methylbenzoate

Description

8-(Acetyloxy)-7-methyl-6-oxo-3-propyl-6,7,8,8a-tetrahydro-1H-isochromen-7-yl 3,5-dichloro-2,4-dimethoxy-6-methylbenzoate belongs to the class of organic compounds known as p-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 4 of the benzene ring is replaced by a methoxy group. 8-(acetyloxy)-7-methyl-6-oxo-3-propyl-8,8a-dihydro-1h-isochromen-7-yl 3,5-dichloro-2,4-dimethoxy-6-methylbenzoate is found in Aspergillus falconensis. 8-(Acetyloxy)-7-methyl-6-oxo-3-propyl-6,7,8,8a-tetrahydro-1H-isochromen-7-yl 3,5-dichloro-2,4-dimethoxy-6-methylbenzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241517582D          

 35 37  0  0  0  0            999 V2000
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    3.5724   -0.4125    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


  Mrv1533004241517582D          

 35 37  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0248312

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC1=CC2=CC(=O)C(C)(OC(=O)C3=C(C)C(Cl)=C(OC)C(Cl)=C3OC)C(OC(C)=O)C2CO1

> <INCHI_IDENTIFIER>
InChI=1S/C25H28Cl2O8/c1-7-8-15-9-14-10-17(29)25(4,23(34-13(3)28)16(14)11-33-15)35-24(30)18-12(2)19(26)22(32-6)20(27)21(18)31-5/h9-10,16,23H,7-8,11H2,1-6H3

> <INCHI_KEY>
GJJRTDHSSQUZNO-UHFFFAOYSA-N

> <FORMULA>
C25H28Cl2O8

> <MOLECULAR_WEIGHT>
527.39

> <EXACT_MASS>
526.1161233

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
52.66434581332638

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8-(acetyloxy)-7-methyl-6-oxo-3-propyl-6,7,8,8a-tetrahydro-1H-isochromen-7-yl 3,5-dichloro-2,4-dimethoxy-6-methylbenzoate

> <ALOGPS_LOGP>
4.60

> <JCHEM_LOGP>
4.749622893

> <ALOGPS_LOGS>
-5.83

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.673683367494469

> <JCHEM_PKA_STRONGEST_BASIC>
-4.404524401803046

> <JCHEM_POLAR_SURFACE_AREA>
97.36000000000003

> <JCHEM_REFRACTIVITY>
132.09869999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.79e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-(acetyloxy)-7-methyl-6-oxo-3-propyl-8,8a-dihydro-1H-isochromen-7-yl 3,5-dichloro-2,4-dimethoxy-6-methylbenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.185  -2.043   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.195  -3.757   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.712  -4.025   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       9.238  -5.472   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.702  -2.845   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.175  -1.398   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.658  -1.130   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.165  -0.218   0.000  0.00  0.00           C+0
HETATM   19 Cl   UNK     0       9.638   1.229   0.000  0.00  0.00          Cl+0
HETATM   20  C   UNK     0      11.681  -0.485   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      12.671   0.694   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      12.145   2.141   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.208  -1.933   0.000  0.00  0.00           C+0
HETATM   24 Cl   UNK     0      13.725  -2.200   0.000  0.00  0.00          Cl+0
HETATM   25  C   UNK     0      11.218  -3.112   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      11.745  -4.559   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      10.755  -5.739   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   35                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   33                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12   28                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   25                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   15   26                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   10   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30                                                            
CONECT   33   28    6   34                                                  
CONECT   34   33   35                                                       
CONECT   35   34    4                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   74    0
END

View in JSmol

Synonyms

Value	Source
8-(Acetyloxy)-7-methyl-6-oxo-3-propyl-6,7,8,8a-tetrahydro-1H-isochromen-7-yl 3,5-dichloro-2,4-dimethoxy-6-methylbenzoic acid	Generator

Chemical Formula

C₂₅H₂₈Cl₂O₈

Average Mass

527.3900 Da

Monoisotopic Mass

526.11612 Da

IUPAC Name

8-(acetyloxy)-7-methyl-6-oxo-3-propyl-6,7,8,8a-tetrahydro-1H-isochromen-7-yl 3,5-dichloro-2,4-dimethoxy-6-methylbenzoate

Traditional Name

8-(acetyloxy)-7-methyl-6-oxo-3-propyl-8,8a-dihydro-1H-isochromen-7-yl 3,5-dichloro-2,4-dimethoxy-6-methylbenzoate

CAS Registry Number

Not Available

SMILES

CCCC1=CC2=CC(=O)C(C)(OC(=O)C3=C(C)C(Cl)=C(OC)C(Cl)=C3OC)C(OC(C)=O)C2CO1

InChI Identifier

InChI=1S/C25H28Cl2O8/c1-7-8-15-9-14-10-17(29)25(4,23(34-13(3)28)16(14)11-33-15)35-24(30)18-12(2)19(26)22(32-6)20(27)21(18)31-5/h9-10,16,23H,7-8,11H2,1-6H3

InChI Key

GJJRTDHSSQUZNO-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
Emericella falconensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as p-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 4 of the benzene ring is replaced by a methoxy group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

P-methoxybenzoic acids and derivatives

Alternative Parents

Substituents

O-methoxybenzoic acid or derivatives
P-methoxybenzoic acid or derivatives
3-halobenzoic acid or derivatives
Halobenzoic acid or derivatives
Benzoate ester
Dimethoxybenzene
M-dimethoxybenzene
Phenoxy compound
1,3-dichlorobenzene
Phenol ether
Anisole
Benzoyl
Methoxybenzene
Toluene
Halobenzene
Cyclohexenone
Chlorobenzene
Alkyl aryl ether
Dicarboxylic acid or derivatives
Aryl chloride
Aryl halide
Cyclic ketone
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Ether
Organochloride
Organooxygen compound
Organic oxide
Carbonyl group
Organic oxygen compound
Hydrocarbon derivative
Organohalogen compound
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	4.6	ALOGPS
logP	4.75	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	12.67	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	97.36 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	132.1 m³·mol⁻¹	ChemAxon
Polarizability	52.66 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

85123657

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 8-(acetyloxy)-7-methyl-6-oxo-3-propyl-8,8a-dihydro-1h-isochromen-7-yl 3,5-dichloro-2,4-dimethoxy-6-methylbenzoate (NP0248312)

MOL for NP0248312 (8-(acetyloxy)-7-methyl-6-oxo-3-propyl-8,8a-dihydro-1h-isochromen-7-yl 3,5-dichloro-2,4-dimethoxy-6-methylbenzoate)

3D MOL for NP0248312 (8-(acetyloxy)-7-methyl-6-oxo-3-propyl-8,8a-dihydro-1h-isochromen-7-yl 3,5-dichloro-2,4-dimethoxy-6-methylbenzoate)

3D SDF for NP0248312 (8-(acetyloxy)-7-methyl-6-oxo-3-propyl-8,8a-dihydro-1h-isochromen-7-yl 3,5-dichloro-2,4-dimethoxy-6-methylbenzoate)

3D-SDF for NP0248312 (8-(acetyloxy)-7-methyl-6-oxo-3-propyl-8,8a-dihydro-1h-isochromen-7-yl 3,5-dichloro-2,4-dimethoxy-6-methylbenzoate)

PDB for NP0248312 (8-(acetyloxy)-7-methyl-6-oxo-3-propyl-8,8a-dihydro-1h-isochromen-7-yl 3,5-dichloro-2,4-dimethoxy-6-methylbenzoate)

3D PDB for NP0248312 (8-(acetyloxy)-7-methyl-6-oxo-3-propyl-8,8a-dihydro-1h-isochromen-7-yl 3,5-dichloro-2,4-dimethoxy-6-methylbenzoate)

SMILES for NP0248312 (8-(acetyloxy)-7-methyl-6-oxo-3-propyl-8,8a-dihydro-1h-isochromen-7-yl 3,5-dichloro-2,4-dimethoxy-6-methylbenzoate)

INCHI for NP0248312 (8-(acetyloxy)-7-methyl-6-oxo-3-propyl-8,8a-dihydro-1h-isochromen-7-yl 3,5-dichloro-2,4-dimethoxy-6-methylbenzoate)

Structure for NP0248312 (8-(acetyloxy)-7-methyl-6-oxo-3-propyl-8,8a-dihydro-1h-isochromen-7-yl 3,5-dichloro-2,4-dimethoxy-6-methylbenzoate)

3D Structure for NP0248312 (8-(acetyloxy)-7-methyl-6-oxo-3-propyl-8,8a-dihydro-1h-isochromen-7-yl 3,5-dichloro-2,4-dimethoxy-6-methylbenzoate)