NP-MRD: Showing NP-Card for methyl 4-{4-[2-(acetyloxy)-4-methoxy-6-methylbenzoyloxy]-2-hydroxy-6-methylbenzoyloxy}-2-hydroxy-6-methylbenzoate (NP0196406)

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Record Information

Version

2.0

Created at

2022-09-04 14:29:29 UTC

Updated at

2022-09-04 14:29:29 UTC

NP-MRD ID

NP0196406

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 4-{4-[2-(acetyloxy)-4-methoxy-6-methylbenzoyloxy]-2-hydroxy-6-methylbenzoyloxy}-2-hydroxy-6-methylbenzoate

Description

3-Hydroxy-4-{[3-hydroxy-4-(methoxycarbonyl)-5-methylphenoxy]carbonyl}-5-methylphenyl 2-(acetyloxy)-4-methoxy-6-methylbenzoate belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone). methyl 4-{4-[2-(acetyloxy)-4-methoxy-6-methylbenzoyloxy]-2-hydroxy-6-methylbenzoyloxy}-2-hydroxy-6-methylbenzoate is found in Pseudocyphellaria neglecta. 3-Hydroxy-4-{[3-hydroxy-4-(methoxycarbonyl)-5-methylphenoxy]carbonyl}-5-methylphenyl 2-(acetyloxy)-4-methoxy-6-methylbenzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 04121517362D          

 39 41  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv0541 04121517362D          

 39 41  0  0  0  0            999 V2000
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 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 25 28  1  0  0  0  0
 28 29  2  0  0  0  0
 21 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 17 34  1  0  0  0  0
 34 35  2  0  0  0  0
 13 35  1  0  0  0  0
 35 36  1  0  0  0  0
  9 37  1  0  0  0  0
 37 38  2  0  0  0  0
  5 38  1  0  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0196406

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=C(C)C=C(OC(=O)C2=C(C)C=C(OC(=O)C3=C(C)C=C(OC)C=C3OC(C)=O)C=C2O)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C28H26O11/c1-13-8-18(10-20(30)23(13)26(32)36-6)38-27(33)24-14(2)9-19(11-21(24)31)39-28(34)25-15(3)7-17(35-5)12-22(25)37-16(4)29/h7-12,30-31H,1-6H3

> <INCHI_KEY>
BUCICDCMTFJVJR-UHFFFAOYSA-N

> <FORMULA>
C28H26O11

> <MOLECULAR_WEIGHT>
538.505

> <EXACT_MASS>
538.147511657

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
52.89527265048276

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 4-{4-[2-(acetyloxy)-4-methoxy-6-methylbenzoyloxy]-2-hydroxy-6-methylbenzoyloxy}-2-hydroxy-6-methylbenzoate

> <ALOGPS_LOGP>
4.13

> <JCHEM_LOGP>
6.982316838666665

> <ALOGPS_LOGS>
-5.11

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.592438867166909

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.988045130683362

> <JCHEM_PKA_STRONGEST_BASIC>
-4.3596280030536585

> <JCHEM_POLAR_SURFACE_AREA>
154.89

> <JCHEM_REFRACTIVITY>
138.37009999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.21e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 4-{4-[2-(acetyloxy)-4-methoxy-6-methylbenzoyloxy]-2-hydroxy-6-methylbenzoyloxy}-2-hydroxy-6-methylbenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-APR-15         0                                  
HETATM    1  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.001 -16.170   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.335 -16.940   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.668 -16.170   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.335 -18.480   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668 -19.250   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002 -18.480   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668 -20.790   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335 -21.560   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.335 -23.100   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       6.668 -23.870   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.002 -23.100   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.668 -25.410   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.002 -26.180   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.336 -25.410   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.002 -27.720   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.668 -28.490   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       6.668 -30.030   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       8.002 -30.800   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.335 -27.720   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.335 -26.180   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       4.001 -25.410   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.667 -26.180   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.667 -27.720   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       1.334 -25.410   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.001 -20.790   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.001 -19.250   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       2.667 -18.480   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       1.334 -11.550   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   38                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   37                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   35                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18   34                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   29                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25   29                                                       
CONECT   29   28   21   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   17   35                                                       
CONECT   35   34   13   36                                                  
CONECT   36   35                                                            
CONECT   37    9   38                                                       
CONECT   38   37    5   39                                                  
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   82    0
END

View in JSmol

Synonyms

Value	Source
3-Hydroxy-4-{[3-hydroxy-4-(methoxycarbonyl)-5-methylphenoxy]carbonyl}-5-methylphenyl 2-(acetyloxy)-4-methoxy-6-methylbenzoic acid	Generator

Chemical Formula

C₂₈H₂₆O₁₁

Average Mass

538.5050 Da

Monoisotopic Mass

538.14751 Da

IUPAC Name

methyl 4-{4-[2-(acetyloxy)-4-methoxy-6-methylbenzoyloxy]-2-hydroxy-6-methylbenzoyloxy}-2-hydroxy-6-methylbenzoate

Traditional Name

methyl 4-{4-[2-(acetyloxy)-4-methoxy-6-methylbenzoyloxy]-2-hydroxy-6-methylbenzoyloxy}-2-hydroxy-6-methylbenzoate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=C(C)C=C(OC(=O)C2=C(C)C=C(OC(=O)C3=C(C)C=C(OC)C=C3OC(C)=O)C=C2O)C=C1O

InChI Identifier

InChI=1S/C28H26O11/c1-13-8-18(10-20(30)23(13)26(32)36-6)38-27(33)24-14(2)9-19(11-21(24)31)39-28(34)25-15(3)7-17(35-5)12-22(25)37-16(4)29/h7-12,30-31H,1-6H3

InChI Key

BUCICDCMTFJVJR-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
Pseudocyphellaria neglecta	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as depsides and depsidones. These are polycyclic compounds that is either a polyphenolic compound composed of two or more monocyclic aromatic units linked by an ester bond (depside), or a compound containing the depsidone structure (depsidone).

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Depsides and depsidones

Sub Class

Not Available

Direct Parent

Depsides and depsidones

Alternative Parents

Substituents

Depside backbone
Tetracarboxylic acid or derivatives
Acylsalicylic acid or derivatives
O-hydroxybenzoic acid ester
P-methoxybenzoic acid or derivatives
Benzoate ester
Phenol ester
Salicylic acid or derivatives
Benzoic acid or derivatives
Anisole
Phenoxy compound
Benzoyl
M-cresol
Phenol ether
Methoxybenzene
Phenol
Alkyl aryl ether
Toluene
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Methyl ester
Carboxylic acid ester
Ether
Carboxylic acid derivative
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	4.13	ALOGPS
logP	6.98	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	8.99	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	154.89 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	138.37 m³·mol⁻¹	ChemAxon
Polarizability	52.9 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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 4-{4-[2-(acetyloxy)-4-methoxy-6-methylbenzoyloxy]-2-hydroxy-6-methylbenzoyloxy}-2-hydroxy-6-methylbenzoate (NP0196406)

MOL for NP0196406 (methyl 4-{4-[2-(acetyloxy)-4-methoxy-6-methylbenzoyloxy]-2-hydroxy-6-methylbenzoyloxy}-2-hydroxy-6-methylbenzoate)

3D MOL for NP0196406 (methyl 4-{4-[2-(acetyloxy)-4-methoxy-6-methylbenzoyloxy]-2-hydroxy-6-methylbenzoyloxy}-2-hydroxy-6-methylbenzoate)

3D SDF for NP0196406 (methyl 4-{4-[2-(acetyloxy)-4-methoxy-6-methylbenzoyloxy]-2-hydroxy-6-methylbenzoyloxy}-2-hydroxy-6-methylbenzoate)

3D-SDF for NP0196406 (methyl 4-{4-[2-(acetyloxy)-4-methoxy-6-methylbenzoyloxy]-2-hydroxy-6-methylbenzoyloxy}-2-hydroxy-6-methylbenzoate)

PDB for NP0196406 (methyl 4-{4-[2-(acetyloxy)-4-methoxy-6-methylbenzoyloxy]-2-hydroxy-6-methylbenzoyloxy}-2-hydroxy-6-methylbenzoate)

3D PDB for NP0196406 (methyl 4-{4-[2-(acetyloxy)-4-methoxy-6-methylbenzoyloxy]-2-hydroxy-6-methylbenzoyloxy}-2-hydroxy-6-methylbenzoate)

SMILES for NP0196406 (methyl 4-{4-[2-(acetyloxy)-4-methoxy-6-methylbenzoyloxy]-2-hydroxy-6-methylbenzoyloxy}-2-hydroxy-6-methylbenzoate)

INCHI for NP0196406 (methyl 4-{4-[2-(acetyloxy)-4-methoxy-6-methylbenzoyloxy]-2-hydroxy-6-methylbenzoyloxy}-2-hydroxy-6-methylbenzoate)

Structure for NP0196406 (methyl 4-{4-[2-(acetyloxy)-4-methoxy-6-methylbenzoyloxy]-2-hydroxy-6-methylbenzoyloxy}-2-hydroxy-6-methylbenzoate)

3D Structure for NP0196406 (methyl 4-{4-[2-(acetyloxy)-4-methoxy-6-methylbenzoyloxy]-2-hydroxy-6-methylbenzoyloxy}-2-hydroxy-6-methylbenzoate)