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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2021-09-14 15:00:08 UTC

HMDB ID

HMDB0000748

Secondary Accession Numbers

HMDB0000475
HMDB00475
HMDB00748

Metabolite Identification

Common Name

L-3-Phenyllactic acid

Description

L-3-Phenyllactic acid (or PLA) is a chiral aromatic compound involved in phenylalanine metabolism. It is likely produced from phenylpyruvate via the action of lactate dehydrogenase. The D-form of this organic acid is typically derived from bacterial sources while the L-form is almost certainly endogenous. Levels of phenyllactate are normally very low in blood or urine. High levels of PLA in the urine or blood are often indicative of phenylketonuria (PKU) and hyperphenylalaninemia (HPA). PKU is due to lack of the enzyme phenylalanine hydroxylase (PAH), so that phenylalanine is converted not to tyrosine but to phenylpyruvic acid (a precursor of phenylactate). In particular, excessive phenylalanine is typically metabolized into phenylketones through, a transaminase pathway route involving glutamate. Metabolites of this transamination reaction include phenylacetate, phenylpyruvate and phenethylamine. In persons with PKU, dietary phenylalanine either accumulates in the body or some of it is converted to phenylpyruvic acid and then to phenyllactate through the action of lactate dehydrogenase. Individuals with PKU tend to excrete large quantities of phenylpyruvate, phenylacetate and phenyllactate, along with phenylalanine, in their urine. If untreated, mental retardation effects and microcephaly are evident by the first year along with other symptoms which include: unusual irritability, epileptic seizures and skin lesions. Hyperactivity, EEG abnormalities and seizures, and severe learning disabilities are major clinical problems later in life. A "musty or mousy" odor of skin, hair, sweat and urine (due to phenylacetate accumulation); and a tendency to hypopigmentation and eczema are also observed. The neural-development effects of PKU are primarily due to the disruption of neurotransmitter synthesis. In particular, phenylalanine is a large, neutral amino acid which moves across the blood-brain barrier (BBB) via the large neutral amino acid transporter (LNAAT). Excessive phenylalanine in the blood saturates the transporter. Thus, excessive levels of phenylalanine significantly decrease the levels of other LNAAs in the brain. But since these amino acids are required for protein and neurotransmitter synthesis, phenylalanine accumulation disrupts brain development, leading to mental retardation.

Structure

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

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      31.732 -13.388   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      32.501 -12.054   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      31.732 -10.720   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      30.192 -10.720   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      29.422 -12.054   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      30.192 -13.388   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      29.422  -9.386   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      27.882  -9.386   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      27.112  -8.054   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      27.882  -6.720   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      25.572  -8.054   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      27.112 -10.720   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    8                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   24    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(R)-Phenyllactate	ChEBI
D-3-Phenyllactic acid	ChEBI
(R)-3-(Phenyl)lactate	Kegg
(R)-Phenyllactic acid	Generator
D-3-Phenyllactate	Generator
(R)-3-(Phenyl)lactic acid	Generator
L-3-Phenyllactate	Generator
(-)-2-Hydroxy-3-phenylpropanoate	HMDB
(-)-2-Hydroxy-3-phenylpropanoic acid	HMDB
(-)-2-Hydroxy-3-phenylpropionate	HMDB
(-)-2-Hydroxy-3-phenylpropionic acid	HMDB
(-)-3-Phenyllactate	HMDB
(-)-3-Phenyllactic acid	HMDB
(-)-b-Phenyllactate	HMDB
(-)-b-Phenyllactic acid	HMDB
(-)-beta-Phenyllactate	HMDB
(-)-beta-Phenyllactic acid	HMDB
(2S)-2-Hydroxy-3-phenylpropanoate	HMDB
(2S)-2-Hydroxy-3-phenylpropanoic acid	HMDB
(2S)-2-Hydroxy-3-phenylpropionate	HMDB
(2S)-2-Hydroxy-3-phenylpropionic acid	HMDB
(S)-3-Phenyl-lactate	HMDB
(S)-3-Phenyl-lactic acid	HMDB
(S)-3-Phenyllactic acid	HMDB
(S)-a-Hydroxy-benzenepropanoate	HMDB
(S)-a-Hydroxy-benzenepropanoic acid	HMDB
(S)-alpha-Hydroxy-benzenepropanoate	HMDB
(S)-alpha-Hydroxy-benzenepropanoic acid	HMDB
(S)-b-Phenyllactic	HMDB
(S)-beta-Phenyllactic	HMDB
alpha-Hydroxy-beta-phenyl-propionic acid	HMDB
HFA	HMDB
L-(-)-3-Phenyllactic acid	HMDB
L-2-Hydroxy-3-phenyl-propionic acid	HMDB
L-beta-Phenyllactic acid	HMDB
L-Phenyl lactate	HMDB
Phenyllactic acid	HMDB
(R)-3-Phenyllactate	HMDB

Chemical Formula

C₉H₁₀O₃

Average Molecular Weight

166.1739

Monoisotopic Molecular Weight

166.062994186

IUPAC Name

(2R)-2-hydroxy-3-phenylpropanoic acid

Traditional Name

(R)-phenyllactate

CAS Registry Number

20312-36-1

SMILES

O[C@H](CC1=CC=CC=C1)C(O)=O

InChI Identifier

InChI=1S/C9H10O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8,10H,6H2,(H,11,12)/t8-/m1/s1

InChI Key

VOXXWSYKYCBWHO-MRVPVSSYSA-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
Alpha-hydroxy acid
Monocyclic benzene moiety
Hydroxy acid
Benzenoid
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxygen compound
Alcohol
Carbonyl group
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

(2R)-2-hydroxy monocarboxylic acid (CHEBI:32978 )
3-phenyllactic acid (CHEBI:32978 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 2116554)
Saliva (HMDB: HMDB0000748)

Excreta

Biofluid or Excreta

Feces (PMID: 18085514)
Urine (PMID: 32966057)

Source

Exogenous

Exogenous (HMDB: HMDB0000748)

Food

Animal origin

Poultry

Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Endogenous

Endogenous (HMDB: HMDB0000748)

Plant

Plant (HMDB: HMDB0000748)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	121 - 125 °C	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	9.8 g/L	ALOGPS
logP	0.84	ALOGPS
logP	1.18	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	4.02	ChemAxon
pKa (Strongest Basic)	-3.8	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	43.46 m³·mol⁻¹	ChemAxon
Polarizability	16.73 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]+	137.296	31661259
DarkChem	[M-H]-	135.464	31661259
AllCCS	[M+H]+	136.532	32859911
AllCCS	[M-H]-	134.311	32859911
DeepCCS	[M+H]+	132.892	30932474
DeepCCS	[M-H]-	129.526	30932474
DeepCCS	[M-2H]-	166.743	30932474
DeepCCS	[M+Na]+	142.281	30932474
AllCCS	[M+H]+	136.5	32859911
AllCCS	[M+H-H2O]+	132.2	32859911
AllCCS	[M+NH4]+	140.6	32859911
AllCCS	[M+Na]+	141.8	32859911
AllCCS	[M-H]-	134.3	32859911
AllCCS	[M+Na-2H]-	135.3	32859911
AllCCS	[M+HCOO]-	136.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
L-3-Phenyllactic acid	O[C@H](CC1=CC=CC=C1)C(O)=O	2854.0	Standard polar	33892256
L-3-Phenyllactic acid	O[C@H](CC1=CC=CC=C1)C(O)=O	1466.5	Standard non polar	33892256
L-3-Phenyllactic acid	O[C@H](CC1=CC=CC=C1)C(O)=O	1528.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
L-3-Phenyllactic acid,1TMS,isomer #1	C[Si](C)(C)O[C@H](CC1=CC=CC=C1)C(=O)O	1550.2	Semi standard non polar	33892256
L-3-Phenyllactic acid,1TMS,isomer #2	C[Si](C)(C)OC(=O)[C@H](O)CC1=CC=CC=C1	1500.3	Semi standard non polar	33892256
L-3-Phenyllactic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)[C@@H](CC1=CC=CC=C1)O[Si](C)(C)C	1570.0	Semi standard non polar	33892256
L-3-Phenyllactic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)O[C@H](CC1=CC=CC=C1)C(=O)O	1783.8	Semi standard non polar	33892256
L-3-Phenyllactic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)[C@H](O)CC1=CC=CC=C1	1738.6	Semi standard non polar	33892256
L-3-Phenyllactic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CC1=CC=CC=C1)O[Si](C)(C)C(C)(C)C	2043.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - L-3-Phenyllactic acid GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-0007-0910000000-ee61dd1edcb64a115835	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - L-3-Phenyllactic acid EI-B (Non-derivatized)	splash10-0007-0920000000-7efa1766fa6121c5f695	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - L-3-Phenyllactic acid GC-EI-TOF (Non-derivatized)	splash10-0007-0910000000-ee61dd1edcb64a115835	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-3-Phenyllactic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9300000000-750e52d0df9e2b90be09	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-3-Phenyllactic acid GC-MS (2 TMS) - 70eV, Positive	splash10-006x-9540000000-c06e2865c7cf1c780f11	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-3-Phenyllactic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-3-Phenyllactic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-3-Phenyllactic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-3-Phenyllactic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-3-Phenyllactic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-3-Phenyllactic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - L-3-Phenyllactic acid GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-11-05	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-3-Phenyllactic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-00di-0900000000-c20feab32f47edc5bb94	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-3-Phenyllactic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-0f89-9500000000-598d564a5c5cb5a6febb	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-3-Phenyllactic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0ac0-9000000000-32b5f6f43141f16996a4	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-3-Phenyllactic acid 10V, Positive-QTOF	splash10-0kmi-1900000000-9df5ce396877a246e75a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-3-Phenyllactic acid 20V, Positive-QTOF	splash10-0ufr-5900000000-3ebebc6c015723d2e26d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-3-Phenyllactic acid 20V, Positive-QTOF	splash10-014i-0900000000-09797df3a57ff3212fae	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-3-Phenyllactic acid 40V, Positive-QTOF	splash10-004i-9000000000-55faf2887a4699d775df	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-3-Phenyllactic acid 40V, Negative-QTOF	splash10-002f-9000000000-5e9184f3d8f3a1c84cb5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-3-Phenyllactic acid 10V, Negative-QTOF	splash10-014i-1900000000-2173c51c5d8f4369c56a	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-3-Phenyllactic acid 40V, Positive-QTOF	splash10-014r-1900000000-30445b1c1ad4ff6c6cfe	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-3-Phenyllactic acid 10V, Positive-QTOF	splash10-014i-0900000000-68f9968ec4336192e093	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - L-3-Phenyllactic acid 20V, Negative-QTOF	splash10-00mo-9400000000-3fc7b7dbdcdb0c24a718	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-3-Phenyllactic acid 10V, Positive-QTOF	splash10-00ke-1900000000-b4165543fe4077bc8878	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-3-Phenyllactic acid 20V, Positive-QTOF	splash10-006y-4900000000-9cc77ecfa0e908d400f3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-3-Phenyllactic acid 40V, Positive-QTOF	splash10-0006-9100000000-8e08ba85783d44c725b8	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-3-Phenyllactic acid 10V, Negative-QTOF	splash10-014i-0900000000-c5b01c647718505d882a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-3-Phenyllactic acid 20V, Negative-QTOF	splash10-01bd-2900000000-2cd5c47ea7b35f76e87b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-3-Phenyllactic acid 40V, Negative-QTOF	splash10-00mo-9300000000-22457d19a65466f8e94d	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-3-Phenyllactic acid 10V, Positive-QTOF	splash10-00dl-5900000000-eb26ccce038261968168	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-3-Phenyllactic acid 20V, Positive-QTOF	splash10-0006-9300000000-aa44337c740dacf05e9c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-3-Phenyllactic acid 40V, Positive-QTOF	splash10-0006-9100000000-6509f4478fff1766b65a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-3-Phenyllactic acid 10V, Negative-QTOF	splash10-014i-3900000000-15a50bcc903d54af3f43	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-3-Phenyllactic acid 20V, Negative-QTOF	splash10-0006-9400000000-0d7b49d15700ae266645	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - L-3-Phenyllactic acid 40V, Negative-QTOF	splash10-0006-9300000000-ca99933d289067e5347a	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Feces
Saliva
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	18085514	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details
Saliva	Detected and Quantified	0.427 +/- 0.354 uM	Adult (>18 years old)	Not Specified	Normal	Sugimoto et al. (...	details
Saliva	Detected and Quantified	0.596 +/- 0.337 uM	Adult (>18 years old)	Not Specified	Normal	Sugimoto et al. (...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0-82.9 uM	Children (1-13 years old)	Both	Phenylketonuria	2116554	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	27015276	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details

Associated Disorders and Diseases

Disease References

Phenylketonuria
Clemens PC, Schunemann MH, Hoffmann GF, Kohlschutter A: Plasma concentrations of phenyllactic acid in phenylketonuria. J Inherit Metab Dis. 1990;13(2):227-8. [PubMed:2116554 ]
Colorectal cancer
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 ] 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 ]

Associated OMIM IDs

261600 (Phenylketonuria)
114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

643327

PDB ID

Not Available

ChEBI ID

32978

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

Tekewe A, Singh S, Singh M, Mohan U, Banerjee UC: Development and validation of HPLC method for the resolution of drug intermediates: DL-3-Phenyllactic acid, DL-O-acetyl-3-phenyllactic acid and (+/-)-mexiletine acetamide enantiomers. Talanta. 2008 Mar 15;75(1):239-45. doi: 10.1016/j.talanta.2007.11.004. Epub 2007 Nov 13. [PubMed:18371874 ]
(). Andrew D. Abell, John W. Blunt, Glenn J. Foulds and Murray H. G. Munro Chemistry of the mycalamides: antiviral and antitumour compounds from a New Zealand marine sponge. Part 6.1–3 The synthesis and testing of analogues of the C(7)–C(10) fragment. J. Chem. Soc., Perkin Trans. 1, 1997, 1647 - 1654,. .

Showing metabocard for L-3-Phenyllactic acid (HMDB0000748)

MOL for HMDB0000748 (L-3-Phenyllactic acid)

3D MOL for HMDB0000748 (L-3-Phenyllactic acid)

3D SDF for HMDB0000748 (L-3-Phenyllactic acid)

3D-SDF for HMDB0000748 (L-3-Phenyllactic acid)

PDB for HMDB0000748 (L-3-Phenyllactic acid)

3D PDB for HMDB0000748 (L-3-Phenyllactic acid)

SMILES for HMDB0000748 (L-3-Phenyllactic acid)

INCHI for HMDB0000748 (L-3-Phenyllactic acid)

Structure for HMDB0000748 (L-3-Phenyllactic acid)

3D Structure for HMDB0000748 (L-3-Phenyllactic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra