NP-MRD: Showing NP-Card for Atraric acid (NP0075127)

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Record Information

Version

2.0

Created at

2022-04-28 20:26:01 UTC

Updated at

2022-04-28 20:26:01 UTC

NP-MRD ID

NP0075127

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Atraric acid

Description

Methyl 2,4-dihydroxy-3,6-dimethylbenzoate, also known as atraric acid, belongs to the class of organic compounds known as p-hydroxybenzoic acid alkyl esters. These are aromatic compounds containing a benzoic acid, which is esterified with an alkyl group and para-substituted with a hydroxyl group. Methyl 2,4-dihydroxy-3,6-dimethylbenzoate is an extremely weak basic (essentially neutral) compound (based on its pKa). There is evidence to suggest that it has antiandrogenic activity in humans and its use in treatment of benign prostate hyperplasia, prostate cancer, and spinal and bulbar muscular atrophy has been investigated. It occurs in the root-bark of Pygeum africanum and Evernia prunastri (Oakmoss). Atraric acid is found in Acer nikoense, Asahinea chrysantha, Asahinea scholanderi, Buddleja cordata, Dianella revoluta, Ekebergia pterophylla, Frullania brasiliensis, Frullania falciloba, Frullania fugax, Frullania monocera, Frullania probosciphora, Lethariella cladonioides, Liriodendron tulipifera, Newbouldia laevis, Parmotrema reticulatum, Prunus africana, Pygeum africanum, Stereocaulon alpinum, Usnea articulata, Usnea undulata and Xylosma longifolia. Atraric Acid is a naturally occurring phenolic compound and ester with the IUPAC name methyl 2,4-dihydroxy-3,6-dimethylbenzoate and molecular formula C10H12O4.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004151517492D          

 14 14  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
    2.1434    1.2375    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
    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
    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 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
   -0.7145    1.2375    0.0000 O   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
  6  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  5 13  1  0  0  0  0
 13 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0075127

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=C(C)C=C(O)C(C)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C10H12O4/c1-5-4-7(11)6(2)9(12)8(5)10(13)14-3/h4,11-12H,1-3H3

> <INCHI_KEY>
UUQHKWMIDYRWHH-UHFFFAOYSA-N

> <FORMULA>
C10H12O4

> <MOLECULAR_WEIGHT>
196.202

> <EXACT_MASS>
196.073558866

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
19.987326436946468

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 2,4-dihydroxy-3,6-dimethylbenzoate

> <ALOGPS_LOGP>
1.67

> <JCHEM_LOGP>
3.0464349153333328

> <ALOGPS_LOGS>
-1.89

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.872610489895765

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.107984240395071

> <JCHEM_PKA_STRONGEST_BASIC>
-3.9803622482394827

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
52.127500000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.54e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 2,4-dihydroxy-3,6-dimethylbenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-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       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.000   0.000   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  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   14  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    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   13                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    5   14                                                  
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol

Synonyms

Value	Source
Methyl 2,4-dihydroxy-3,6-dimethylbenzoic acid	Generator
Atraric acid	MeSH
Methyl Beta-orcinolcarboxylate	ChEMBL
Methyl-Beta-orcinol carboxylate	ChEMBL
Methyl b-orcinolcarboxylate	Generator
Methyl b-orcinolcarboxylic acid	Generator
Methyl beta-orcinolcarboxylic acid	Generator
Methyl β-orcinolcarboxylate	Generator
Methyl β-orcinolcarboxylic acid	Generator
ATRARate	Generator
Methyl-b-orcinol carboxylate	Generator
Methyl-b-orcinol carboxylic acid	Generator
Methyl-beta-orcinol carboxylic acid	Generator
Methyl-β-orcinol carboxylate	Generator
Methyl-β-orcinol carboxylic acid	Generator

Chemical Formula

C₁₀H₁₂O₄

Average Mass

196.2020 Da

Monoisotopic Mass

196.07356 Da

IUPAC Name

methyl 2,4-dihydroxy-3,6-dimethylbenzoate

Traditional Name

methyl 2,4-dihydroxy-3,6-dimethylbenzoate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=C(C)C=C(O)C(C)=C1O

InChI Identifier

InChI=1S/C10H12O4/c1-5-4-7(11)6(2)9(12)8(5)10(13)14-3/h4,11-12H,1-3H3

InChI Key

UUQHKWMIDYRWHH-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Acer nikoense	LOTUS Database	35616633
Asahinea chrysantha	LOTUS Database	35616633
Asahinea scholanderi	LOTUS Database	35616633
Buddleja cordata	LOTUS Database	35616633
Dianella revoluta	LOTUS Database	35616633
Ekebergia pterophylla	Plant	KNApSAcK
Frullania brasiliensis	Plant	KNApSAcK
Frullania falciloba	Plant	KNApSAcK
Frullania fugax	Plant	KNApSAcK
Frullania monocera	Plant	KNApSAcK
Frullania probosciphora	Plant	KNApSAcK
Lethariella Lethariella cladonioides	LOTUS Database	35616633
Liriodendron tulipifera	LOTUS Database	35616633
Newbouldia laevis	LOTUS Database	35616633
Parmotrema reticulatum	LOTUS Database	35616633
Prunus africana	LOTUS Database	35616633
Pygeum africanum	Plant	KNApSAcK
Stereocaulon alpinum	LOTUS Database	35616633
Usnea articulata	LOTUS Database	35616633
Usnea undulata	LOTUS Database	35616633
Xylosma longifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as p-hydroxybenzoic acid alkyl esters. These are aromatic compounds containing a benzoic acid, which is esterified with an alkyl group and para-substituted with a hydroxyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

p-Hydroxybenzoic acid alkyl esters

Alternative Parents

Substituents

P-hydroxybenzoic acid alkyl ester
O-hydroxybenzoic acid ester
Dihydroxybenzoic acid
Salicylic acid or derivatives
P-xylenol
Xylenol
Benzoyl
P-xylene
Xylene
M-cresol
O-cresol
Resorcinol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Vinylogous acid
Methyl ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
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	1.67	ALOGPS
logP	3.05	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	9.11	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	52.13 m³·mol⁻¹	ChemAxon
Polarizability	19.99 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

Atraric acid

METLIN ID

Not Available

PubChem Compound

78435

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Atraric acid (NP0075127)

MOL for NP0075127 (Atraric acid)

3D MOL for NP0075127 (Atraric acid)

3D SDF for NP0075127 (Atraric acid)

3D-SDF for NP0075127 (Atraric acid)

PDB for NP0075127 (Atraric acid)

3D PDB for NP0075127 (Atraric acid)

SMILES for NP0075127 (Atraric acid)

INCHI for NP0075127 (Atraric acid)

Structure for NP0075127 (Atraric acid)

3D Structure for NP0075127 (Atraric acid)