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Showing metabocard for p-Anisic acid (HMDB0001101)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:15:26 UTC
HMDB IDHMDB0001101
Secondary Accession Numbers
  • HMDB01101
Metabolite 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 HMDB0001101 (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 HMDB0001101 (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 HMDB0001101 (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>
HMDB0001101

> <DATABASE_NAME>
hmdb

> <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 HMDB0001101 (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
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PDB for HMDB0001101 (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 HMDB0001101 (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 HMDB0001101 (p-Anisic acid)

COC1=CC=C(C=C1)C(O)=O
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INCHI for HMDB0001101 (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 JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC8H8O3
Average Molecular Weight152.1473
Monoisotopic Molecular Weight152.047344122
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
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
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Industrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point185 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.53 mg/mL at 37 °CNot Available
LogP1.96HANSCH,C ET AL. (1995)
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Male
Normal		 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02795
Phenol Explorer Compound ID425
FooDB IDFDB010587
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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
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 ]

Enzymes

Enzyme Details
1. UDP-glucuronosyltransferase 1-1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
p-Anisic acid → 3,4,5-trihydroxy-6-(4-methoxybenzoyloxy)oxane-2-carboxylic aciddetails
Enzyme Details
2. Glycine N-acyltransferase
General function:
Involved in glycine N-acyltransferase activity
Specific function:
Mitochondrial acyltransferase which transfers an acyl group to the N-terminus of glycine and glutamine, although much less efficiently. Can conjugate numerous substrates to form a variety of N-acylglycines, with a preference for benzoyl-CoA over phenylacetyl-CoA as acyl donors. Thereby detoxify xenobiotics, such as benzoic acid or salicylic acid, and endogenous organic acids, such as isovaleric acid.
Gene Name:
GLYAT
Uniprot ID:
Q6IB77
Molecular weight:
18506.33
Reactions
p-Anisic acid → 2-[(4-methoxyphenyl)formamido]acetic aciddetails