NP-MRD: Showing NP-Card for methyl 3,5-bis(acetyloxy)-4-methoxybenzoate (NP0159967)

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Record Information

Version

2.0

Created at

2022-09-02 17:49:03 UTC

Updated at

2022-09-02 17:49:03 UTC

NP-MRD ID

NP0159967

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 3,5-bis(acetyloxy)-4-methoxybenzoate

Description

Methyl 3,5-bis(acetyloxy)-4-methoxybenzoate belongs to the class of organic compounds known as gallic acid and derivatives. Gallic acid and derivatives are compounds containing a 3,4,5-trihydroxybenzoic acid moiety. methyl 3,5-bis(acetyloxy)-4-methoxybenzoate is found in Phoenix dactylifera. Methyl 3,5-bis(acetyloxy)-4-methoxybenzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 34  0  0  0  0  0  0  0  0999 V2000
    4.7486   -2.4390   -1.4687 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6654   -1.5724   -1.1893 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4205   -2.0978   -0.9188 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2742   -3.3372   -0.9261 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2898   -1.2384   -0.6286 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0382   -1.7522   -0.3561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0221   -0.9137   -0.0829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2946   -1.4193    0.1947 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7299   -1.7316    1.4614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1021   -2.2630    1.6447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9493   -1.5571    2.4321 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8473    0.4646   -0.0776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9330    1.3082    0.2017 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7362    1.7554   -0.8719 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3950    1.0018   -0.3471 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5113    2.3852   -0.3280 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8332    3.1062    0.7977 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9615    4.5815    0.8364 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0307    2.4649    1.8620 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4224    0.1495   -0.6132 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6041   -1.9145   -1.9256 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3941   -3.2967   -2.0808 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1343   -2.8454   -0.4876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1177   -2.8413   -0.3562 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1601   -3.0217    2.4591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7736   -1.4227    1.8945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4723   -2.7094    0.6945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4799    2.7981   -1.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6039    1.1522   -1.7860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8205    1.6992   -0.5885 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1419    5.0818    0.2592 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9080    4.9166    0.3409 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8767    4.9458    1.8779 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3925    0.5625   -0.8239 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  2  0
  7 12  2  0
 12 13  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 17 19  2  0
 15 20  2  0
 20  5  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  6 24  1  0
 10 25  1  0
 10 26  1  0
 10 27  1  0
 14 28  1  0
 14 29  1  0
 14 30  1  0
 18 31  1  0
 18 32  1  0
 18 33  1  0
 20 34  1  0
M  END


  Mrv1533004241513462D          

 20 20  0  0  0  0            999 V2000
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  7 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 15 20  2  0  0  0  0
  5 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0159967

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CC(OC(C)=O)=C(OC)C(OC(C)=O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H14O7/c1-7(14)19-10-5-9(13(16)18-4)6-11(12(10)17-3)20-8(2)15/h5-6H,1-4H3

> <INCHI_KEY>
MVCZQEYADKZPAR-UHFFFAOYSA-N

> <FORMULA>
C13H14O7

> <MOLECULAR_WEIGHT>
282.248

> <EXACT_MASS>
282.073952791

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
27.682960723652975

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 3,5-bis(acetyloxy)-4-methoxybenzoate

> <ALOGPS_LOGP>
1.49

> <JCHEM_LOGP>
1.033573463

> <ALOGPS_LOGS>
-3.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.989435404953649

> <JCHEM_POLAR_SURFACE_AREA>
88.13

> <JCHEM_REFRACTIVITY>
66.81130000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.76e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 3,5-bis(acetyloxy)-4-methoxybenzoate

> <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       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.001  -0.770   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   20                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    7   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   20                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   15    5                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

View in JSmol

Synonyms

Value	Source
Methyl 3,5-bis(acetyloxy)-4-methoxybenzoic acid	Generator

Chemical Formula

C₁₃H₁₄O₇

Average Mass

282.2480 Da

Monoisotopic Mass

282.07395 Da

IUPAC Name

methyl 3,5-bis(acetyloxy)-4-methoxybenzoate

Traditional Name

methyl 3,5-bis(acetyloxy)-4-methoxybenzoate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CC(OC(C)=O)=C(OC)C(OC(C)=O)=C1

InChI Identifier

InChI=1S/C13H14O7/c1-7(14)19-10-5-9(13(16)18-4)6-11(12(10)17-3)20-8(2)15/h5-6H,1-4H3

InChI Key

MVCZQEYADKZPAR-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
Phoenix dactylifera	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as gallic acid and derivatives. Gallic acid and derivatives are compounds containing a 3,4,5-trihydroxybenzoic acid moiety.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Gallic acid and derivatives

Alternative Parents

Substituents

Gallic acid or derivatives
P-methoxybenzoic acid or derivatives
Benzoate ester
Phenol ester
Tricarboxylic acid or derivatives
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Benzoyl
Alkyl aryl ether
Methyl ester
Carboxylic acid ester
Ether
Carboxylic acid derivative
Organic oxygen compound
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxide
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	1.49	ALOGPS
logP	1.03	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Basic)	-5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	88.13 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	66.81 m³·mol⁻¹	ChemAxon
Polarizability	27.68 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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 3,5-bis(acetyloxy)-4-methoxybenzoate (NP0159967)

MOL for NP0159967 (methyl 3,5-bis(acetyloxy)-4-methoxybenzoate)

3D MOL for NP0159967 (methyl 3,5-bis(acetyloxy)-4-methoxybenzoate)

3D SDF for NP0159967 (methyl 3,5-bis(acetyloxy)-4-methoxybenzoate)

3D-SDF for NP0159967 (methyl 3,5-bis(acetyloxy)-4-methoxybenzoate)

PDB for NP0159967 (methyl 3,5-bis(acetyloxy)-4-methoxybenzoate)

3D PDB for NP0159967 (methyl 3,5-bis(acetyloxy)-4-methoxybenzoate)

SMILES for NP0159967 (methyl 3,5-bis(acetyloxy)-4-methoxybenzoate)

INCHI for NP0159967 (methyl 3,5-bis(acetyloxy)-4-methoxybenzoate)

Structure for NP0159967 (methyl 3,5-bis(acetyloxy)-4-methoxybenzoate)

3D Structure for NP0159967 (methyl 3,5-bis(acetyloxy)-4-methoxybenzoate)