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Showing metabocard for Methylparaben (HMDB0032572)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 17:50:34 UTC
Update Date2023-02-21 17:22:23 UTC
HMDB IDHMDB0032572
Secondary Accession Numbers
  • HMDB32572
Metabolite Identification
Common NameMethylparaben
DescriptionMethylparaben, also known as methyl 4-hydroxybenzoate or p-carbomethoxyphenol, 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. Methylparaben is an antimicrobial agent, preservative, and flavouring agent. methylparaben has been detected, but not quantified, in a few different foods, such as alcoholic beverages, saffrons, and fruits (particularly blueberries). It is also a constituent of cloudberry, yellow passion fruit, white wine, botrytized wine, and Bourbon vanilla. Methylparaben is the most frequently used antimicrobial preservative in cosmetics.
Structure
Data?1677000143
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0032572 (Methylparaben)

  Mrv1652311141917252D          

 11 11  0  0  0  0            999 V2000
    9.6973   -4.8920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4116   -5.3046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1263   -4.8920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1263   -4.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4116   -3.6546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6973   -4.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9828   -5.3046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8407   -3.6546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5552   -4.0670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2695   -3.6546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8407   -2.8296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  6  1  2  0  0  0  0
  7  1  1  0  0  0  0
  3  2  2  0  0  0  0
  4  3  1  0  0  0  0
  5  4  2  0  0  0  0
  8  4  1  0  0  0  0
  6  5  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
  8 11  2  0  0  0  0
M  END
Download

3D MOL for HMDB0032572 (Methylparaben)

HMDB0032572
     RDKit          3D
Methylparaben
 19 19  0  0  0  0  0  0  0  0999 V2000
    3.6298    0.6320    0.8349 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2588    0.3093    0.7626 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4755    0.4737   -0.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9734    0.9441   -1.3940 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0616    0.1241   -0.3659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5225   -0.3969    0.7734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8596   -0.7365    0.7790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6664   -0.5724   -0.3432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0099   -0.9202   -0.3176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0683   -0.0530   -1.4668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7191    0.2950   -1.4889 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7317    1.7150    1.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1349    0.0050    1.6025 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0924    0.3448   -0.1378 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1052   -0.5308    1.6653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3253   -1.1481    1.6757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4154   -1.2943    0.5113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6411    0.1050   -2.3903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2358    0.7041   -2.3646 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11  5  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  6 15  1  0
  7 16  1  0
  9 17  1  0
 10 18  1  0
 11 19  1  0
M  END
Download

3D SDF for HMDB0032572 (Methylparaben)

  Mrv1652311141917252D          

 11 11  0  0  0  0            999 V2000
    9.6973   -4.8920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4116   -5.3046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1263   -4.8920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1263   -4.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4116   -3.6546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6973   -4.0670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9828   -5.3046    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8407   -3.6546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5552   -4.0670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.2695   -3.6546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8407   -2.8296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  6  1  2  0  0  0  0
  7  1  1  0  0  0  0
  3  2  2  0  0  0  0
  4  3  1  0  0  0  0
  5  4  2  0  0  0  0
  8  4  1  0  0  0  0
  6  5  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
  8 11  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032572

> <DATABASE_NAME>
hmdb

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

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

> <INCHI_KEY>
LXCFILQKKLGQFO-UHFFFAOYSA-N

> <FORMULA>
C8H8O3

> <MOLECULAR_WEIGHT>
152.1473

> <EXACT_MASS>
152.047344122

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
15.146895116351764

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 4-hydroxybenzoate

> <ALOGPS_LOGP>
2.17

> <JCHEM_LOGP>
1.6731574583333335

> <ALOGPS_LOGS>
-1.62

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.50311531147631

> <JCHEM_PKA_STRONGEST_BASIC>
-6.0642205225851145

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
40.0642

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.69e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
paraben

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0032572 (Methylparaben)

HMDB0032572
     RDKit          3D
Methylparaben
 19 19  0  0  0  0  0  0  0  0999 V2000
    3.6298    0.6320    0.8349 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2588    0.3093    0.7626 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4755    0.4737   -0.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9734    0.9441   -1.3940 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0616    0.1241   -0.3659 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5225   -0.3969    0.7734 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8596   -0.7365    0.7790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6664   -0.5724   -0.3432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0099   -0.9202   -0.3176 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0683   -0.0530   -1.4668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7191    0.2950   -1.4889 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7317    1.7150    1.0395 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1349    0.0050    1.6025 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0924    0.3448   -0.1378 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1052   -0.5308    1.6653 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3253   -1.1481    1.6757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4154   -1.2943    0.5113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6411    0.1050   -2.3903 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2358    0.7041   -2.3646 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
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  2  0
 11  5  1  0
  1 12  1  0
  1 13  1  0
  1 14  1  0
  6 15  1  0
  7 16  1  0
  9 17  1  0
 10 18  1  0
 11 19  1  0
M  END
Download

PDB for HMDB0032572 (Methylparaben)

HEADER    PROTEIN                                 14-NOV-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   14-NOV-19         0                                  
HETATM    1  C   UNK     0      18.102  -9.132   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      19.435  -9.902   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      20.769  -9.132   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      20.769  -7.592   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      19.435  -6.822   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.102  -7.592   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      16.768  -9.902   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      22.103  -6.822   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      23.436  -7.592   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      24.770  -6.822   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      22.103  -5.282   0.000  0.00  0.00           O+0
CONECT    1    2    6    7                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5                                                       
CONECT    7    1                                                            
CONECT    8    4    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END
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3D PDB for HMDB0032572 (Methylparaben)

COMPND    HMDB0032572
HETATM    1  C1  UNL     1       3.630   0.632   0.835  1.00  0.00           C  
HETATM    2  O1  UNL     1       2.259   0.309   0.763  1.00  0.00           O  
HETATM    3  C2  UNL     1       1.476   0.474  -0.343  1.00  0.00           C  
HETATM    4  O2  UNL     1       1.973   0.944  -1.394  1.00  0.00           O  
HETATM    5  C3  UNL     1       0.062   0.124  -0.366  1.00  0.00           C  
HETATM    6  C4  UNL     1      -0.522  -0.397   0.773  1.00  0.00           C  
HETATM    7  C5  UNL     1      -1.860  -0.737   0.779  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.666  -0.572  -0.343  1.00  0.00           C  
HETATM    9  O3  UNL     1      -4.010  -0.920  -0.318  1.00  0.00           O  
HETATM   10  C7  UNL     1      -2.068  -0.053  -1.467  1.00  0.00           C  
HETATM   11  C8  UNL     1      -0.719   0.295  -1.489  1.00  0.00           C  
HETATM   12  H1  UNL     1       3.732   1.715   1.040  1.00  0.00           H  
HETATM   13  H2  UNL     1       4.135   0.005   1.602  1.00  0.00           H  
HETATM   14  H3  UNL     1       4.092   0.345  -0.138  1.00  0.00           H  
HETATM   15  H4  UNL     1       0.105  -0.531   1.665  1.00  0.00           H  
HETATM   16  H5  UNL     1      -2.325  -1.148   1.676  1.00  0.00           H  
HETATM   17  H6  UNL     1      -4.415  -1.294   0.511  1.00  0.00           H  
HETATM   18  H7  UNL     1      -2.641   0.105  -2.390  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.236   0.704  -2.365  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3
CONECT    3    4    4    5
CONECT    5    6    6   11
CONECT    6    7   15
CONECT    7    8    8   16
CONECT    8    9   10
CONECT    9   17
CONECT   10   11   11   18
CONECT   11   19
END
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SMILES for HMDB0032572 (Methylparaben)

COC(=O)C1=CC=C(O)C=C1
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INCHI for HMDB0032572 (Methylparaben)

InChI=1S/C8H8O3/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5,9H,1H3
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
Chemical FormulaC8H8O3
Average Molecular Weight152.1473
Monoisotopic Molecular Weight152.047344122
IUPAC Namemethyl 4-hydroxybenzoate
Traditional Nameparaben
CAS Registry Number99-76-3
SMILES
COC(=O)C1=CC=C(O)C=C1
InChI Identifier
InChI=1S/C8H8O3/c1-11-8(10)6-2-4-7(9)5-3-6/h2-5,9H,1H3
InChI KeyLXCFILQKKLGQFO-UHFFFAOYSA-N
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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct Parentp-Hydroxybenzoic acid alkyl esters
Alternative Parents
Substituents
  • P-hydroxybenzoic acid alkyl ester
  • Benzoyl
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Methyl ester
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Industrial applicationBiological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point131 °CNot Available
Boiling Point275.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility2.5 mg/mL at 25 °CNot Available
LogP1.96Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Feces
  • Saliva
  • Sweat
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
UrineDetected and Quantified0.0480 (0.0424-0.0545) umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal
    • National Health a...
 details
UrineDetected and Quantified0.0328 (0.0265-0.0406) umol/mmol creatinineChildren (1-13 years old)Not SpecifiedNormal
    • National Health a...
 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
SweatDetected but not QuantifiedNot QuantifiedInfant (0-1 year old)Not Specifiedscreen-positive CF details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  2. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Cystic fibrosis
  1. Adriana Nori de Macedo. Robust capillary electrophoresis methods for biomarker discovery and routine measurements in clinical and epidemiological applications. March 2017 [Link]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB010509
KNApSAcK IDC00030751
Chemspider ID7176
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMethylparaben
METLIN IDNot Available
PubChem Compound7456
PDB IDMPB
ChEBI ID31835
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1032731
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Gupta S, Kaisheva E: Development of a multidose formulation for a humanized monoclonal antibody using experimental design techniques. AAPS PharmSci. 2003;5(2):E8. [PubMed:12866935 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .