Showing NP-Card for p-Anisic acid (NP0000019)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-10-07 20:40:08 UTC
NP-MRD IDNP0000019
Secondary Accession NumbersNone
Natural Product Identification
Common Namep-Anisic acid
DescriptionP-Anisic acid, also known as 4-anisate or draconic acid, belongs to the class of organic compounds known as p-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 4 of the benzene ring is replaced by a methoxy group. P-Anisic acid is a drug. P-Anisic acid exists in all eukaryotes, ranging from yeast to humans. P-Anisic acid is a faint, sweet, and cadaverous tasting compound. Outside of the human body, p-anisic acid has been detected, but not quantified in several different foods, such as anises, cocoa beans, fennels, and german camomiles. This could make p-anisic acid a potential biomarker for the consumption of these foods. It is a white crystalline solid which is insoluble in water, highly soluble in alcohols and soluble in ether, and ethyl acetate. P-Anisic acid has antiseptic properties. It is also used as an intermediate in the preparation of more complex organic compounds. It is generally obtained by the oxidation of anethole or p-methoxyacetophenone. The term "anisic acid" often refers to this form specifically. P-Anisic acid is found naturally in anise.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000019 (p-Anisic acid)

  Mrv1652305201900042D          

 11 11  0  0  0  0            999 V2000
    1.4289   -1.6500    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
    0.7145   -0.4125    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
    0.0000    0.8250    0.0000 C   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
    0.7145    2.0625    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
    1.4289    2.4750    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
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
M  END
Download

3D MOL for NP0000019 (p-Anisic acid)

HMDB0001101
     RDKit          3D
p-Anisic acid
 19 19  0  0  0  0  0  0  0  0999 V2000
    3.3332    0.1926    0.9102 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5637    0.3305   -0.2402 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1895    0.1777   -0.2545 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4805    0.3266   -1.4269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8773    0.1723   -1.4234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5358   -0.1332   -0.2425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9783   -0.2957   -0.2465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6624   -0.1639   -1.3168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6502   -0.6015    0.9286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8366   -0.2840    0.9336 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5426   -0.1262    0.9248 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3584    0.5894    0.6725 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4762   -0.8524    1.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8972    0.7345    1.7784 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9790    0.5687   -2.3763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4475    0.2835   -2.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5631   -0.1444    1.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3360   -0.5224    1.8637 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0670   -0.2521    1.8727 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  6 10  1  0
 10 11  2  0
 11  3  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  4 15  1  0
  5 16  1  0
  9 17  1  0
 10 18  1  0
 11 19  1  0
M  END
Download

3D SDF for NP0000019 (p-Anisic acid)

  Mrv1652305201900042D          

 11 11  0  0  0  0            999 V2000
    1.4289   -1.6500    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
    0.7145   -0.4125    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
    0.0000    0.8250    0.0000 C   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
    0.7145    2.0625    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
    1.4289    2.4750    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
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0000019

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C8H8O3/c1-11-7-4-2-6(3-5-7)8(9)10/h2-5H,1H3,(H,9,10)

> <INCHI_KEY>
ZEYHEAKUIGZSGI-UHFFFAOYSA-N

> <FORMULA>
C8H8O3

> <MOLECULAR_WEIGHT>
152.1473

> <EXACT_MASS>
152.047344122

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
14.987426796627265

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-methoxybenzoic acid

> <ALOGPS_LOGP>
1.63

> <JCHEM_LOGP>
1.4731574583333336

> <ALOGPS_LOGS>
-1.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.366688111140357

> <JCHEM_PKA_STRONGEST_BASIC>
-4.845611234615028

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
39.7774

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.00e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
P-anisic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000019 (p-Anisic acid)

HMDB0001101
     RDKit          3D
p-Anisic acid
 19 19  0  0  0  0  0  0  0  0999 V2000
    3.3332    0.1926    0.9102 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5637    0.3305   -0.2402 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1895    0.1777   -0.2545 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4805    0.3266   -1.4269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8773    0.1723   -1.4234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5358   -0.1332   -0.2425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9783   -0.2957   -0.2465 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6624   -0.1639   -1.3168 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6502   -0.6015    0.9286 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8366   -0.2840    0.9336 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5426   -0.1262    0.9248 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3584    0.5894    0.6725 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4762   -0.8524    1.2396 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8972    0.7345    1.7784 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9790    0.5687   -2.3763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4475    0.2835   -2.3226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5631   -0.1444    1.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3360   -0.5224    1.8637 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0670   -0.2521    1.8727 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
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  7  9  1  0
  6 10  1  0
 10 11  2  0
 11  3  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  4 15  1  0
  5 16  1  0
  9 17  1  0
 10 18  1  0
 11 19  1  0
M  END
Download

PDB for NP0000019 (p-Anisic acid)

HEADER    PROTEIN                                 20-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAY-19         0                                  
HETATM    1  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   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   3.850   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3                                                       
CONECT    9    6   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for NP0000019 (p-Anisic acid)

COMPND    HMDB0001101
HETATM    1  C1  UNL     1       3.333   0.193   0.910  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.564   0.330  -0.240  1.00  0.00           O  
HETATM    3  C2  UNL     1       1.189   0.178  -0.254  1.00  0.00           C  
HETATM    4  C3  UNL     1       0.480   0.327  -1.427  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.877   0.172  -1.423  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.536  -0.133  -0.242  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.978  -0.296  -0.246  1.00  0.00           C  
HETATM    8  O2  UNL     1      -3.662  -0.164  -1.317  1.00  0.00           O  
HETATM    9  O3  UNL     1      -3.650  -0.602   0.929  1.00  0.00           O  
HETATM   10  C7  UNL     1      -0.837  -0.284   0.934  1.00  0.00           C  
HETATM   11  C8  UNL     1       0.543  -0.126   0.925  1.00  0.00           C  
HETATM   12  H1  UNL     1       4.358   0.589   0.673  1.00  0.00           H  
HETATM   13  H2  UNL     1       3.476  -0.852   1.240  1.00  0.00           H  
HETATM   14  H3  UNL     1       2.897   0.734   1.778  1.00  0.00           H  
HETATM   15  H4  UNL     1       0.979   0.569  -2.376  1.00  0.00           H  
HETATM   16  H5  UNL     1      -1.447   0.284  -2.323  1.00  0.00           H  
HETATM   17  H6  UNL     1      -4.563  -0.144   1.057  1.00  0.00           H  
HETATM   18  H7  UNL     1      -1.336  -0.522   1.864  1.00  0.00           H  
HETATM   19  H8  UNL     1       1.067  -0.252   1.873  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3
CONECT    3    4    4   11
CONECT    4    5   15
CONECT    5    6    6   16
CONECT    6    7   10
CONECT    7    8    8    9
CONECT    9   17
CONECT   10   11   11   18
CONECT   11   19
END
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SMILES for NP0000019 (p-Anisic acid)

COC1=CC=C(C=C1)C(O)=O
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INCHI for NP0000019 (p-Anisic acid)

InChI=1S/C8H8O3/c1-11-7-4-2-6(3-5-7)8(9)10/h2-5H,1H3,(H,9,10)
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Synonyms
Chemical FormulaC8H8O3
Average Mass152.1473 Da
Monoisotopic Mass152.04734 Da
IUPAC Name4-methoxybenzoic acid
Traditional NameP-anisic acid
CAS Registry Number100-09-4
SMILES
COC1=CC=C(C=C1)C(O)=O
InChI Identifier
InChI=1S/C8H8O3/c1-11-7-4-2-6(3-5-7)8(9)10/h2-5H,1H3,(H,9,10)
InChI KeyZEYHEAKUIGZSGI-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl3, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Not Available
Species
Species of Origin
Chemical Taxonomy
Description Belongs to the class of organic compounds known as p-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 4 of the benzene ring is replaced by a methoxy group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentP-methoxybenzoic acids and derivatives
Alternative Parents
Substituents
  • P-methoxybenzoic acid or derivatives
  • Benzoic acid
  • Anisole
  • Phenoxy compound
  • Benzoyl
  • Phenol ether
  • Methoxybenzene
  • Alkyl aryl ether
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point185 °Chttps://en.wikipedia.org/wiki/P-Anisic_acid
Boiling Point275 - 280 °Chttps://en.wikipedia.org/wiki/P-Anisic_acid
Water Solubility0.53 mg/mL at 37 °Chttps://en.wikipedia.org/wiki/P-Anisic_acid
LogP1.96Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).
Predicted Properties
PropertyValueSource
Water Solubility2 g/LALOGPS
logP1.63ALOGPS
logP1.47ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)4.37ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity39.78 m³·mol⁻¹ChemAxon
Polarizability14.99 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001101
DrugBank IDDB02795
Phenol Explorer Compound ID425
FoodDB IDFDB008969
KNApSAcK IDC00029536
Chemspider ID10181338
KEGG Compound IDC02519
BioCyc IDCPD-1076
BiGG IDNot Available
Wikipedia LinkP-Anisic_acid
METLIN IDNot Available
PubChem Compound7478
PDB IDNot Available
ChEBI ID40813
Good Scents IDrw1411761
References
General References
  1. Kubo I, Chen QX, Nihei K, Calderon JS, Cespedes CL: Tyrosinase inhibition kinetics of anisic acid. Z Naturforsch C. 2003 Sep-Oct;58(9-10):713-8. [PubMed:14577637 ]
  2. Shirane M, Nakamura K: Aniracetam enhances cortical dopamine and serotonin release via cholinergic and glutamatergic mechanisms in SHRSP. Brain Res. 2001 Oct 19;916(1-2):211-21. [PubMed:11597608 ]