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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2013-07-04 18:55:59 UTC

Update Date

2023-02-21 17:30:12 UTC

HMDB ID

HMDB0060734

Secondary Accession Numbers

HMDB60734

Metabolite Identification

Common Name

3-(3-Hydroxyphenyl)-2-methylpropionic acid

Description

3-(3-Hydroxyphenyl)-2-methylpropionic acid belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. 3-(3-Hydroxyphenyl)-2-methylpropionic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 3-(3-Hydroxyphenyl)-2-methylpropionic acid is a metabolite of carbidopa. Carbidopa (Lodosyn) is a drug given to people with Parkinson's disease in order to inhibit peripheral metabolism of levodopa. This property is significant in that it allows a greater proportion of peripheral levodopa to cross the blood brain barrier for central nervous system effect.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 07041311552D          

 13 13  0  0  0  0            999 V2000
   -0.7145    2.0625    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
    1.4289    0.8250    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    2.0625    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
    0.0000    2.4750    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
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  7  1  1  0  0  0  0
  7  5  1  0  0  0  0
  8  3  1  0  0  0  0
  8  5  1  0  0  0  0
  8  6  2  0  0  0  0
  9  4  2  0  0  0  0
  9  6  1  0  0  0  0
 10  7  1  0  0  0  0
 11  9  1  0  0  0  0
 12 10  2  0  0  0  0
 13 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0060734

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(CC1=CC(O)=CC=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H12O3/c1-7(10(12)13)5-8-3-2-4-9(11)6-8/h2-4,6-7,11H,5H2,1H3,(H,12,13)

> <INCHI_KEY>
ZTHRBJCNTAYZRE-UHFFFAOYSA-N

> <FORMULA>
C10H12O3

> <MOLECULAR_WEIGHT>
180.2005

> <EXACT_MASS>
180.07864425

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
18.476666917208675

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(3-hydroxyphenyl)-2-methylpropanoic acid

> <ALOGPS_LOGP>
1.65

> <JCHEM_LOGP>
2.294983727

> <ALOGPS_LOGS>
-2.10

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.466035792515322

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.278010079861143

> <JCHEM_PKA_STRONGEST_BASIC>
-5.964099261767733

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
48.522000000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.43e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(3-hydroxyphenyl)-2-methylpropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-JUL-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-JUL-13         0                                  
HETATM    1  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    3    4                                                       
CONECT    3    2    8                                                       
CONECT    4    2    9                                                       
CONECT    5    7    8                                                       
CONECT    6    8    9                                                       
CONECT    7    1    5   10                                                  
CONECT    8    3    5    6                                                  
CONECT    9    4    6   11                                                  
CONECT   10    7   12   13                                                  
CONECT   11    9                                                            
CONECT   12   10                                                            
CONECT   13   10                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-(3-Hydroxyphenyl)-2-methylpropionate	Generator
3-(3-Hydroxyphenyl)-2-methylpropanoate	Generator

Chemical Formula

C₁₀H₁₂O₃

Average Molecular Weight

180.2005

Monoisotopic Molecular Weight

180.07864425

IUPAC Name

3-(3-hydroxyphenyl)-2-methylpropanoic acid

Traditional Name

3-(3-hydroxyphenyl)-2-methylpropanoic acid

CAS Registry Number

Not Available

SMILES

CC(CC1=CC(O)=CC=C1)C(O)=O

InChI Identifier

InChI=1S/C10H12O3/c1-7(10(12)13)5-8-3-2-4-9(11)6-8/h2-4,6-7,11H,5H2,1H3,(H,12,13)

InChI Key

ZTHRBJCNTAYZRE-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Phenylpropanoic acids

Sub Class

Not Available

Direct Parent

Phenylpropanoic acids

Alternative Parents

Substituents

3-phenylpropanoic-acid
Phenylpropane
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monocyclic benzene moiety
Benzenoid
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Carbonyl group
Organic oxygen compound
Organooxygen compound
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.43 g/L	ALOGPS
logP	1.65	ALOGPS
logP	2.29	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	4.28	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	48.52 m³·mol⁻¹	ChemAxon
Polarizability	18.48 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	142.101	31661259
DarkChem	[M-H]-	136.33	31661259
DeepCCS	[M+H]+	135.344	30932474
DeepCCS	[M-H]-	131.517	30932474
DeepCCS	[M-2H]-	168.834	30932474
DeepCCS	[M+Na]+	144.373	30932474
AllCCS	[M+H]+	138.6	32859911
AllCCS	[M+H-H2O]+	134.3	32859911
AllCCS	[M+NH4]+	142.5	32859911
AllCCS	[M+Na]+	143.7	32859911
AllCCS	[M-H]-	138.3	32859911
AllCCS	[M+Na-2H]-	139.1	32859911
AllCCS	[M+HCOO]-	140.1	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.22 minutes	32390414
Predicted by Siyang on May 30, 2022	10.6846 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.48 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1422.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	314.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	126.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	181.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	103.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	400.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	397.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	101.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	853.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	385.2 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	981.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	250.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	328.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	362.6 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	226.4 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	96.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-(3-Hydroxyphenyl)-2-methylpropionic acid	CC(CC1=CC(O)=CC=C1)C(O)=O	3113.0	Standard polar	33892256
3-(3-Hydroxyphenyl)-2-methylpropionic acid	CC(CC1=CC(O)=CC=C1)C(O)=O	1649.8	Standard non polar	33892256
3-(3-Hydroxyphenyl)-2-methylpropionic acid	CC(CC1=CC(O)=CC=C1)C(O)=O	1750.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-(3-Hydroxyphenyl)-2-methylpropionic acid,1TMS,isomer #1	CC(CC1=CC=CC(O[Si](C)(C)C)=C1)C(=O)O	1707.1	Semi standard non polar	33892256
3-(3-Hydroxyphenyl)-2-methylpropionic acid,1TMS,isomer #2	CC(CC1=CC=CC(O)=C1)C(=O)O[Si](C)(C)C	1752.6	Semi standard non polar	33892256
3-(3-Hydroxyphenyl)-2-methylpropionic acid,2TMS,isomer #1	CC(CC1=CC=CC(O[Si](C)(C)C)=C1)C(=O)O[Si](C)(C)C	1708.9	Semi standard non polar	33892256
3-(3-Hydroxyphenyl)-2-methylpropionic acid,1TBDMS,isomer #1	CC(CC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)C(=O)O	1941.0	Semi standard non polar	33892256
3-(3-Hydroxyphenyl)-2-methylpropionic acid,1TBDMS,isomer #2	CC(CC1=CC=CC(O)=C1)C(=O)O[Si](C)(C)C(C)(C)C	1990.5	Semi standard non polar	33892256
3-(3-Hydroxyphenyl)-2-methylpropionic acid,2TBDMS,isomer #1	CC(CC1=CC=CC(O[Si](C)(C)C(C)(C)C)=C1)C(=O)O[Si](C)(C)C(C)(C)C	2178.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(3-Hydroxyphenyl)-2-methylpropionic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-2900000000-f101a3d0640c765a3b95	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(3-Hydroxyphenyl)-2-methylpropionic acid GC-MS (2 TMS) - 70eV, Positive	splash10-0adr-9884000000-1a63ec7c513dde6f711b	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-(3-Hydroxyphenyl)-2-methylpropionic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3-Hydroxyphenyl)-2-methylpropionic acid 10V, Positive-QTOF	splash10-001i-0900000000-80976148077085f44e0d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3-Hydroxyphenyl)-2-methylpropionic acid 20V, Positive-QTOF	splash10-01p9-2900000000-d2745bd7d5ea27868949	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3-Hydroxyphenyl)-2-methylpropionic acid 40V, Positive-QTOF	splash10-0006-9700000000-8741896259794b43f910	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3-Hydroxyphenyl)-2-methylpropionic acid 10V, Negative-QTOF	splash10-004i-0900000000-dede99ddffadd009443d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3-Hydroxyphenyl)-2-methylpropionic acid 20V, Negative-QTOF	splash10-004r-0900000000-a9cc83f7936fb3754866	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3-Hydroxyphenyl)-2-methylpropionic acid 40V, Negative-QTOF	splash10-01bl-7900000000-f56d7c83ceef5057aa53	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3-Hydroxyphenyl)-2-methylpropionic acid 10V, Positive-QTOF	splash10-001i-0900000000-c5c6f19eccc3584a2939	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3-Hydroxyphenyl)-2-methylpropionic acid 20V, Positive-QTOF	splash10-0a4l-7900000000-146b7c90900b28439632	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3-Hydroxyphenyl)-2-methylpropionic acid 40V, Positive-QTOF	splash10-00kf-9200000000-cd3840d07696162d3d82	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3-Hydroxyphenyl)-2-methylpropionic acid 10V, Negative-QTOF	splash10-056r-0900000000-388d5724bc65ec139015	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3-Hydroxyphenyl)-2-methylpropionic acid 20V, Negative-QTOF	splash10-066r-0900000000-fa546a417f74422cf6c7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-(3-Hydroxyphenyl)-2-methylpropionic acid 40V, Negative-QTOF	splash10-0a4i-5900000000-dba0bb601d0b38a8fe81	2021-10-12	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Membrane (predicted from logP)

Biospecimen Locations

Blood
Urine

Tissue Locations

Kidney
Liver

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Normal	Not Available	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB 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

Not Available

METLIN ID

Not Available

PubChem Compound

23378291

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 3-(3-Hydroxyphenyl)-2-methylpropionic acid (HMDB0060734)

MOL for HMDB0060734 (3-(3-Hydroxyphenyl)-2-methylpropionic acid)

3D MOL for HMDB0060734 (3-(3-Hydroxyphenyl)-2-methylpropionic acid)

3D SDF for HMDB0060734 (3-(3-Hydroxyphenyl)-2-methylpropionic acid)

3D-SDF for HMDB0060734 (3-(3-Hydroxyphenyl)-2-methylpropionic acid)

PDB for HMDB0060734 (3-(3-Hydroxyphenyl)-2-methylpropionic acid)

3D PDB for HMDB0060734 (3-(3-Hydroxyphenyl)-2-methylpropionic acid)

SMILES for HMDB0060734 (3-(3-Hydroxyphenyl)-2-methylpropionic acid)

INCHI for HMDB0060734 (3-(3-Hydroxyphenyl)-2-methylpropionic acid)

Structure for HMDB0060734 (3-(3-Hydroxyphenyl)-2-methylpropionic acid)

3D Structure for HMDB0060734 (3-(3-Hydroxyphenyl)-2-methylpropionic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra