NP-MRD: Showing NP-Card for 3,4-O-Dimethylgallic acid (NP0339467)

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Record Information

Version

2.0

Created at

2024-09-11 21:59:45 UTC

Updated at

2024-09-11 21:59:45 UTC

NP-MRD ID

NP0339467

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,4-O-Dimethylgallic acid

Description

3,4-O-Dimethylgallic acid, also known as 3,4-O-dimethylgallate or DMHBA, 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. 3,4-O-Dimethylgallic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02271201332D          

 14 14  0  0  0  0            999 V2000
   -0.0136    1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0136    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7009    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7009   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0136   -0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7280   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7280    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4425    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4154    1.0313    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7009   -1.8562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0136   -1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7280   -1.8562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1570    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7280    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  7  1  0  0  0  0
  3  4  1  0  0  0  0
  3  9  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5 11  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
  8 13  1  0  0  0  0
  1 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0339467

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC(O)=C1OC)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O5/c1-13-7-4-5(9(11)12)3-6(10)8(7)14-2/h3-4,10H,1-2H3,(H,11,12)

> <INCHI_KEY>
WFIBQVFJXGQICQ-UHFFFAOYSA-N

> <FORMULA>
C9H10O5

> <MOLECULAR_WEIGHT>
198.1727

> <EXACT_MASS>
198.05282343

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_AVERAGE_POLARIZABILITY>
18.79956282357437

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-hydroxy-4,5-dimethoxybenzoic acid

> <ALOGPS_LOGP>
1.38

> <JCHEM_LOGP>
1.0119208709999998

> <ALOGPS_LOGS>
-1.74

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.995749432981892

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.923463867916618

> <JCHEM_PKA_STRONGEST_BASIC>
-4.644423500403366

> <JCHEM_POLAR_SURFACE_AREA>
75.99

> <JCHEM_REFRACTIVITY>
48.2215

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.63e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-4,5-dimethoxybenzoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  O   UNK     0      -0.025   3.465   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.025   1.925   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.308   1.155   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.308  -0.385   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.025  -1.155   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.359  -0.385   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.359   1.155   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.693   1.925   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       2.642   1.925   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       1.308  -3.465   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -0.025  -2.695   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.359  -3.465   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -4.026   1.155   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.359   4.235   0.000  0.00  0.00           C+0
CONECT    1    2   14                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4    9                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   11                                                  
CONECT    6    5    7                                                       
CONECT    7    2    6    8                                                  
CONECT    8    7   13                                                       
CONECT    9    3                                                            
CONECT   10   11                                                            
CONECT   11    5   10   12                                                  
CONECT   12   11                                                            
CONECT   13    8                                                            
CONECT   14    1                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol

Synonyms

Value	Source
3,4-O-Dimethylgallate	Generator
DMHBA	HMDB
3,4-Dimethoxy-5-hydroxybenzoic acid	HMDB
3-Hydroxy-4,5-dimethoxybenzoate	Generator

Chemical Formula

C₉H₁₀O₅

Average Mass

198.1727 Da

Monoisotopic Mass

198.05282 Da

IUPAC Name

3-hydroxy-4,5-dimethoxybenzoic acid

Traditional Name

3-hydroxy-4,5-dimethoxybenzoic acid

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC(O)=C1OC)C(O)=O

InChI Identifier

InChI=1S/C9H10O5/c1-13-7-4-5(9(11)12)3-6(10)8(7)14-2/h3-4,10H,1-2H3,(H,11,12)

InChI Key

WFIBQVFJXGQICQ-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
M-methoxybenzoic acid or derivatives
O-dimethoxybenzene
Dimethoxybenzene
Methoxyphenol
Benzoic acid
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Carboxylic acid derivative
Carboxylic acid
Ether
Monocarboxylic acid or derivatives
Organooxygen compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	1.38	ALOGPS
logP	1.01	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	3.92	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	75.99 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	48.22 m³·mol⁻¹	ChemAxon
Polarizability	18.8 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

HMDB0041662

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029820

KNApSAcK ID

Not Available

Chemspider ID

67282

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

74709

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 3,4-O-Dimethylgallic acid (NP0339467)

MOL for NP0339467 (3,4-O-Dimethylgallic acid)

3D MOL for NP0339467 (3,4-O-Dimethylgallic acid)

3D SDF for NP0339467 (3,4-O-Dimethylgallic acid)

3D-SDF for NP0339467 (3,4-O-Dimethylgallic acid)

PDB for NP0339467 (3,4-O-Dimethylgallic acid)

3D PDB for NP0339467 (3,4-O-Dimethylgallic acid)

SMILES for NP0339467 (3,4-O-Dimethylgallic acid)

INCHI for NP0339467 (3,4-O-Dimethylgallic acid)

Structure for NP0339467 (3,4-O-Dimethylgallic acid)

3D Structure for NP0339467 (3,4-O-Dimethylgallic acid)