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

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Record Information
Version1.0
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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View in JSmol
Synonyms
ValueSource
4-Anisic acidChEBI
Anisic acidChEBI
Draconic acidChEBI
p-Methoxybenzoic acidChEBI
4-Methoxybenzoic acidKegg
4-AnisateGenerator
AnisateGenerator
DraconateGenerator
p-MethoxybenzoateGenerator
4-MethoxybenzoateGenerator
p-AnisateGenerator
4-Anisic acid, copper (+2) saltHMDB
4-Anisic acid, 14C-carboxyHMDB
4-Anisic acid, potassium saltHMDB
4-Anisic acid, sodium saltHMDB
Para-anisic acidHMDB
p-Anisic acidChEBI
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
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Aconitum forrestiiLOTUS Database
Aegle marmelosLOTUS Database
Aleuritopteris kuhniiLOTUS Database
Anas platyrhynchosFooDB
Anastatica hierochunticaLOTUS Database
AnatidaeFooDB
Annona purpureaKNApSAcK Database
Anser anserFooDB
Artemisia dracunculusFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capparis spinosaLOTUS Database
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
Chaenomeles speciosaLOTUS Database
Colchicum bornmuelleri FreynLOTUS Database
ColumbaFooDB
ColumbidaeFooDB
Cota palaestinaLOTUS Database
Cotoneaster orbicularisLOTUS Database
Croton draco Schltdl.& Cham.KNApSAcK Database
Cyathobasis fruticulosaLOTUS Database
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Euphorbia aleppicaLOTUS Database
Ferula sinaicaPlant
Ficus mucusoLOTUS Database
Foeniculum vulgareFooDB
Gallus gallusFooDB
Illicium verumLOTUS Database
Isatis tinctoriaLOTUS Database
Lagopus mutaFooDB
Lagotis yunnanensisLOTUS Database
LeporidaeFooDB
Lepus timidusFooDB
Licaria triandraLOTUS Database
Lysionotus denticulosusLOTUS Database
Malva silvestrisKNApSAcK Database
Matricaria recutitaFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Momordica charantiaLOTUS Database
Nelumbo nuciferaLOTUS Database
Neolitsea acuminatissimaKNApSAcK Database
Neolitsea hiiranensisLOTUS Database
Numida meleagrisFooDB
Nymphaea caeruleaKNApSAcK Database
Nymphaea guineensisLOTUS Database
OdocoileusFooDB
Ophiocordyceps sinensisLOTUS Database
OryctolagusFooDB
Ovis ariesFooDB
Palicourea coriaceaKNApSAcK Database
Parthenium hysterophorusLOTUS Database
Parthenium hysterophorus L.KNApSAcK Database
Pentagramma triangularisLOTUS Database
Peperomia heyneanaLOTUS Database
PhasianidaeFooDB
Phasianus colchicusFooDB
Pimpinella anisumKNApSAcK Database
Piper aduncumLOTUS Database
Piper philippinumKNApSAcK Database
Polycarpa aurataLOTUS Database
Populus deltoidesLOTUS Database
Posidonia oceanicaKNApSAcK Database
Pulicaria paludosaLOTUS Database
Rhododendron dauricumLOTUS Database
Rhododendron ferrugineumLOTUS Database
Rostrinucula dependensLOTUS Database
Salsola collinaLOTUS Database
Scapholeberis mucronataLOTUS Database
Soroseris hookerianaLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Tabebuia avellanedaeKNApSAcK Database
Taraxacum formosanumKNApSAcK Database
Taraxacum mongolicumLOTUS Database
Thaxterogaster vibratilisLOTUS Database
Theobroma cacaoFooDB
Trianthema portulacastrumKNApSAcK Database
Vaccinium macrocarponLOTUS Database
Vanilla planifolia Jacks.LOTUS Database
Vanilla pomponaLOTUS Database
Viburnum dilatatumLOTUS Database
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. Todoriki H, Hayashi T, Naruse H: High-performance liquid chromatographic method for screening disorders of aromatic acid metabolism using a multi-detection system. J Chromatogr. 1984 Oct 12;310(2):273-81. [PubMed:6511847 ]
  2. Thoma H, Reiner J, Spiteller G: Profiles of strongly polar and less polar acids obtained from human blood, plasma and serum by two-step ultrafiltration. J Chromatogr. 1984 Jul 13;309(1):17-32. [PubMed:6480763 ]
  3. 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 ]
  4. 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 ]
  5. Seephonkai P, Popescu R, Zehl M, Krupitza G, Urban E, Kopp B: Ferruginenes A-C from Rhododendron ferrugineum and their cytotoxic evaluation. J Nat Prod. 2011 Apr 25;74(4):712-7. doi: 10.1021/np100778k. Epub 2011 Mar 28. [PubMed:21443171 ]