NP-MRD: Showing NP-Card for 5-bromo-3-(2-hydroxy-6-methylphenyl)-7-methyl-6,8-dioxoisochromen-7-yl 2,4-dimethyldec-2-enoate (NP0323745)

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Record Information

Version

2.0

Created at

2022-09-12 03:22:24 UTC

Updated at

2022-09-12 03:22:24 UTC

NP-MRD ID

NP0323745

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-bromo-3-(2-hydroxy-6-methylphenyl)-7-methyl-6,8-dioxoisochromen-7-yl 2,4-dimethyldec-2-enoate

Description

5-Bromo-3-(2-hydroxy-6-methylphenyl)-7-methyl-6,8-dioxo-7,8-dihydro-6H-isochromen-7-yl 2,4-dimethyldec-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. 5-bromo-3-(2-hydroxy-6-methylphenyl)-7-methyl-6,8-dioxoisochromen-7-yl 2,4-dimethyldec-2-enoate is found in Penicillium simplicissimum. Based on a literature review very few articles have been published on 5-bromo-3-(2-hydroxy-6-methylphenyl)-7-methyl-6,8-dioxo-7,8-dihydro-6H-isochromen-7-yl 2,4-dimethyldec-2-enoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122205222D          

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M  END

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  Mrv1652309122205222D          

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 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 23 29  1  0  0  0  0
 29 30  1  0  0  0  0
 22 31  2  0  0  0  0
 31 32  1  0  0  0  0
 19 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 15 35  1  0  0  0  0
 35 36  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0323745

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C29H33BrO6/c1-6-7-8-9-11-17(2)14-19(4)28(34)36-29(5)26(32)21-16-35-23(15-20(21)25(30)27(29)33)24-18(3)12-10-13-22(24)31/h10,12-17,31H,6-9,11H2,1-5H3

> <INCHI_KEY>
AJUFJWUHEGAOEN-UHFFFAOYSA-N

> <FORMULA>
C29H33BrO6

> <MOLECULAR_WEIGHT>
557.481

> <EXACT_MASS>
556.146052

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
55.69076188883491

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-bromo-3-(2-hydroxy-6-methylphenyl)-7-methyl-6,8-dioxo-7,8-dihydro-6H-isochromen-7-yl 2,4-dimethyldec-2-enoate

> <JCHEM_LOGP>
7.662761013333334

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.06118346130801

> <JCHEM_PKA_STRONGEST_BASIC>
-5.267467967701863

> <JCHEM_POLAR_SURFACE_AREA>
89.9

> <JCHEM_REFRACTIVITY>
146.13459999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
5-bromo-3-(2-hydroxy-6-methylphenyl)-7-methyl-6,8-dioxoisochromen-7-yl 2,4-dimethyldec-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       7.183 -11.118   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.517 -10.348   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.851 -11.118   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.184 -10.348   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.518 -11.118   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.852 -10.348   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      15.185 -11.118   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.185 -12.658   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.519 -10.348   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.853 -11.118   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      17.853 -12.658   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      19.186 -10.348   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      19.186  -8.808   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      20.520 -11.118   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      20.520 -12.658   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      19.004 -12.390   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      22.037 -12.390   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      22.563 -10.943   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      23.027 -13.570   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      24.543 -13.303   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      25.533 -14.482   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      25.006 -15.930   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      25.996 -17.109   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      27.513 -16.842   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      28.040 -15.395   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      28.503 -18.022   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      27.976 -19.469   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      26.460 -19.736   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      25.470 -18.556   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      23.953 -18.824   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      23.490 -16.197   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      22.500 -15.017   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      20.983 -15.285   0.000  0.00  0.00           C+0
HETATM   34 Br   UNK     0      20.457 -16.732   0.000  0.00  0.00          Br+0
HETATM   35  C   UNK     0      19.993 -14.105   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      18.477 -14.372   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                                                       
CONECT   10    9   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-Bromo-3-(2-hydroxy-6-methylphenyl)-7-methyl-6,8-dioxo-7,8-dihydro-6H-isochromen-7-yl 2,4-dimethyldec-2-enoic acid	Generator

Chemical Formula

C₂₉H₃₃BrO₆

Average Mass

557.4810 Da

Monoisotopic Mass

556.14605 Da

IUPAC Name

5-bromo-3-(2-hydroxy-6-methylphenyl)-7-methyl-6,8-dioxo-7,8-dihydro-6H-isochromen-7-yl 2,4-dimethyldec-2-enoate

Traditional Name

5-bromo-3-(2-hydroxy-6-methylphenyl)-7-methyl-6,8-dioxoisochromen-7-yl 2,4-dimethyldec-2-enoate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C29H33BrO6/c1-6-7-8-9-11-17(2)14-19(4)28(34)36-29(5)26(32)21-16-35-23(15-20(21)25(30)27(29)33)24-18(3)12-10-13-22(24)31/h10,12-17,31H,6-9,11H2,1-5H3

InChI Key

AJUFJWUHEGAOEN-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 simplicissimum	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
Cyclohexenone
Alpha-acyloxy ketone
Toluene
Phenol
Fatty acid ester
Fatty acyl
Benzenoid
Pyran
Monocyclic benzene moiety
Alpha-haloketone
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Cyclic ketone
Ketone
Carboxylic acid ester
Oxacycle
Bromoalkene
Haloalkene
Vinyl halide
Vinyl bromide
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organobromide
Organohalogen 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	7.66	ChemAxon
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	10	ChemAxon
Refractivity	146.13 m³·mol⁻¹	ChemAxon
Polarizability	55.69 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	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

162816411

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-bromo-3-(2-hydroxy-6-methylphenyl)-7-methyl-6,8-dioxoisochromen-7-yl 2,4-dimethyldec-2-enoate (NP0323745)

MOL for NP0323745 (5-bromo-3-(2-hydroxy-6-methylphenyl)-7-methyl-6,8-dioxoisochromen-7-yl 2,4-dimethyldec-2-enoate)

3D MOL for NP0323745 (5-bromo-3-(2-hydroxy-6-methylphenyl)-7-methyl-6,8-dioxoisochromen-7-yl 2,4-dimethyldec-2-enoate)

3D SDF for NP0323745 (5-bromo-3-(2-hydroxy-6-methylphenyl)-7-methyl-6,8-dioxoisochromen-7-yl 2,4-dimethyldec-2-enoate)

3D-SDF for NP0323745 (5-bromo-3-(2-hydroxy-6-methylphenyl)-7-methyl-6,8-dioxoisochromen-7-yl 2,4-dimethyldec-2-enoate)

PDB for NP0323745 (5-bromo-3-(2-hydroxy-6-methylphenyl)-7-methyl-6,8-dioxoisochromen-7-yl 2,4-dimethyldec-2-enoate)

3D PDB for NP0323745 (5-bromo-3-(2-hydroxy-6-methylphenyl)-7-methyl-6,8-dioxoisochromen-7-yl 2,4-dimethyldec-2-enoate)

SMILES for NP0323745 (5-bromo-3-(2-hydroxy-6-methylphenyl)-7-methyl-6,8-dioxoisochromen-7-yl 2,4-dimethyldec-2-enoate)

INCHI for NP0323745 (5-bromo-3-(2-hydroxy-6-methylphenyl)-7-methyl-6,8-dioxoisochromen-7-yl 2,4-dimethyldec-2-enoate)

Structure for NP0323745 (5-bromo-3-(2-hydroxy-6-methylphenyl)-7-methyl-6,8-dioxoisochromen-7-yl 2,4-dimethyldec-2-enoate)

3D Structure for NP0323745 (5-bromo-3-(2-hydroxy-6-methylphenyl)-7-methyl-6,8-dioxoisochromen-7-yl 2,4-dimethyldec-2-enoate)