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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2005-11-16 15:48:42 UTC

Update Date

2023-02-21 17:15:09 UTC

HMDB ID

HMDB0000755

Secondary Accession Numbers

HMDB00755

Metabolite Identification

Common Name

Hydroxyphenyllactic acid

Description

Hydroxyphenyllactic acid or 4-hydroxyphenyllactate (the L-form) is a tyrosine metabolite. The level of L-hydroxyphenyllactic acid is elevated in patients with a deficiency of the enzyme p-hydroxyphenylpyruvate oxidase (EC 1.14.2.2) (PMID: 4720815 ). L-hydroxyphenyllactate is present in relatively higher concentrations in the cerebrospinal fluid and urine of patients with phenylketonuria (PKU) and tyrosinemia (PMID: 3126358 ). However, the D-form of hydroxyphenyllactate is of bacterial origin and is also found in individuals with bacterial overgrowth or unusual gut microflora (PMID: 3126358 ). Microbial hydroxyphenyllactate is likely derived from phenolic or polyphenolic compounds in the diet. Bifidobacteria and lactobacilli produce considerable amounts of phenyllactic and p-hydroxyphenyllactic acids (PMID: 23061754 ). It has also been shown that hydroxyphenyllactate decreases ROS (reactive oxygen species) production in both mitochondria and neutrophils and so hydroxyphenyllactate may function as a natural anti-oxidant (PMID: 23061754 ). Hydroxyphenyllactic acid is a microbial metabolite found in Acinetobacter, Bacteroides, Bifidobacteria, Bifidobacterium, Clostridium, Enterococcus, Escherichia, Eubacterium, Klebsiella, Lactobacillus, Pseudomonas and Staphylococcus (PMID: 19961416 ).

Structure

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

<string xmlns="http://www.chemspider.com/">
  Mrv1652304222011122D          

 13 13  0  0  1  0            999 V2000
    5.1418   -2.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8388   -0.7763    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5409   -2.0060    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5619   -3.2507    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7029   -2.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1418   -2.0060    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4298   -1.5928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8388   -1.6027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9908   -1.6027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7029   -2.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2739   -2.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2739   -2.0110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9908   -3.2507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  2  8  2  0  0  0  0
  3  8  1  0  0  0  0
  4 11  1  0  0  0  0
  5  7  1  0  0  0  0
  5  9  2  0  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  9 12  1  0  0  0  0
 10 13  2  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000755

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8,10-11H,5H2,(H,12,13)

> <INCHI_KEY>
JVGVDSSUAVXRDY-UHFFFAOYSA-N

> <FORMULA>
C9H10O4

> <MOLECULAR_WEIGHT>
182.1733

> <EXACT_MASS>
182.057908808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
23

> <JCHEM_AVERAGE_POLARIZABILITY>
17.508950163763846

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-3-(4-hydroxyphenyl)propanoic acid

> <ALOGPS_LOGP>
0.87

> <JCHEM_LOGP>
0.8809315280000001

> <ALOGPS_LOGS>
-1.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.50382828900583

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5839647995095922

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8298154633716104

> <JCHEM_POLAR_SURFACE_AREA>
77.75999999999999

> <JCHEM_REFRACTIVITY>
45.439700000000016

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.79e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hydroxyphenyllactic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: <string xmlns="http://www.chemspider.com/">       
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-APR-20         0                                  
HETATM    1  O   UNK     0       9.598  -5.297   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0      10.899  -1.449   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      12.210  -3.745   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       2.916  -6.068   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       6.912  -3.754   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.598  -3.745   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.269  -2.973   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      10.899  -2.992   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.583  -2.992   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.912  -5.297   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.245  -5.297   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.245  -3.754   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.583  -6.068   0.000  0.00  0.00           C+0
CONECT    1    6                                                            
CONECT    2    8                                                            
CONECT    3    8                                                            
CONECT    4   11                                                            
CONECT    5    7    9   10                                                  
CONECT    6    1    7    8                                                  
CONECT    7    5    6                                                       
CONECT    8    2    3    6                                                  
CONECT    9    5   12                                                       
CONECT   10    5   13                                                       
CONECT   11    4   12   13                                                  
CONECT   12    9   11                                                       
CONECT   13   10   11                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Hydroxy-3-(4-hydroxyphenyl)propanoate	ChEBI
2-Hydroxy-3-(p-hydroxyphenyl)propionic acid	ChEBI
4-Hydroxyphenyllactic acid	ChEBI
beta-(4-Hydroxyphenyl)lactic acid	ChEBI
beta-(p-Hydroxyphenyl)lactic acid	ChEBI
DL-p-Hydroxyphenyllactic acid	ChEBI
p-Hydroxyphenyl lactic acid	ChEBI
4-Hydroxyphenyllactate	Kegg
p-Hydroxyphenyllactate	Kegg
2-Hydroxy-3-(4-hydroxyphenyl)propanoic acid	Generator
2-Hydroxy-3-(p-hydroxyphenyl)propionate	Generator
b-(4-Hydroxyphenyl)lactate	Generator
b-(4-Hydroxyphenyl)lactic acid	Generator
beta-(4-Hydroxyphenyl)lactate	Generator
Β-(4-hydroxyphenyl)lactate	Generator
Β-(4-hydroxyphenyl)lactic acid	Generator
b-(p-Hydroxyphenyl)lactate	Generator
b-(p-Hydroxyphenyl)lactic acid	Generator
beta-(p-Hydroxyphenyl)lactate	Generator
Β-(p-hydroxyphenyl)lactate	Generator
Β-(p-hydroxyphenyl)lactic acid	Generator
DL-p-Hydroxyphenyllactate	Generator
p-Hydroxyphenyl lactate	Generator
p-Hydroxyphenyllactic acid	Generator
Hydroxyphenyllactate	Generator
(RS)-3-(4-Hydroxyphenyl)lactate	HMDB
(RS)-3-(4-Hydroxyphenyl)lactic acid	HMDB
3-(4-Hydroxyphenyl)-DL-lactate	HMDB
3-(4-Hydroxyphenyl)-DL-lactic acid	HMDB
3-(4-Hydroxyphenyl)lactate	HMDB
3-(p-Hydroxyphenyl)-lactate	HMDB
3-(p-Hydroxyphenyl)-lactic acid	HMDB
a,4-Dihydroxybenzenepropanoate	HMDB
a,4-Dihydroxybenzenepropanoic acid	HMDB
b-(p-Hydroxyphenyl)-DL-lactate	HMDB
b-(p-Hydroxyphenyl)-DL-lactic acid	HMDB
beta-(p-Hydroxyphenyl)-DL-lactate	HMDB
beta-(p-Hydroxyphenyl)-DL-lactic acid	HMDB
DL-3-(4-Hydroxyphenyl)lactate	HMDB
DL-3-(4-Hydroxyphenyl)lactic acid	HMDB
HPLA	HMDB
4-Hydroxyphenyllactic acid, (DL)-isomer	HMDB
Para-hydroxyphenyllactic acid	HMDB
2-Hydroxyphloretate	HMDB
2-Hydroxy-3-(4'-hydroxyphenyl)propanoic acid	HMDB
2-Hydroxy-3-(4'-hydroxyphenyl)propanoic acid	HMDB

Chemical Formula

C₉H₁₀O₄

Average Molecular Weight

182.1733

Monoisotopic Molecular Weight

182.057908808

IUPAC Name

2-hydroxy-3-(4-hydroxyphenyl)propanoic acid

Traditional Name

hydroxyphenyllactic acid

CAS Registry Number

306-23-0

SMILES

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

InChI Identifier

InChI=1S/C9H10O4/c10-7-3-1-6(2-4-7)5-8(11)9(12)13/h1-4,8,10-11H,5H2,(H,12,13)

InChI Key

JVGVDSSUAVXRDY-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
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alpha-hydroxy acid
Monocyclic benzene moiety
Benzenoid
Hydroxy acid
Secondary alcohol
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Alcohol
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organic oxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:17385 )
2-hydroxy carboxylic acid (CHEBI:17385 )

Ontology

Physiological effect

Health effect

Observation

Supragingival Plaque (HMDB: HMDB0000755)

Respiratory system disorder

Supradiaphragmatic malignancy (HMDB: HMDB0000755)

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 9106023)
Cerebrospinal Fluid (CSF) (PMID: 10553836)
Saliva (PMID: 22308371)
Cerebrospinal fluid (HMDB: HMDB0000755)

Tissue

Epithelium

Epidermis (HMDB: HMDB0000755)

Organ

Prostate (HMDB: HMDB0000755)
Placenta (HMDB: HMDB0000755)

Excreta

Biofluid or Excreta

Urine (PMID: 8087979)
Feces (PMID: 19636438)

Cellular substructure

Organelle

Mitochondrion (HMDB: HMDB0000755)

Cytoplasm (HMDB: HMDB0000755)
Extracellular (HMDB: HMDB0000755)

Source

Endogenous

Endogenous (HMDB: HMDB0000755)

Plant

Plant (HMDB: HMDB0000755)

Microbe

Microbe (HMDB: HMDB0000755)
Acinetobacter baumannii (HMDB: HMDB0000755)
Klebsiella pneumoniae (HMDB: HMDB0000755)
Pseudomonas aeruginosa (HMDB: HMDB0000755)
Enterococcus faecalis (HMDB: HMDB0000755)
Escherichia coli (HMDB: HMDB0000755)
Lactobacillus (HMDB: HMDB0000755)
Bacteroides fragilis (HMDB: HMDB0000755)
Clostridium (HMDB: HMDB0000755)
Klebsiella (HMDB: HMDB0000755)
Bacteroides thetaiotaomicron (HMDB: HMDB0000755)
Bifidobacteria (HMDB: HMDB0000755)
Bifidobacterium Bifidum (HMDB: HMDB0000755)
Enterococcus faecium (HMDB: HMDB0000755)
Eubacterium lentum (HMDB: HMDB0000755)
Lactobacillus fermentum (HMDB: HMDB0000755)
Staphylococcus (HMDB: HMDB0000755)
Staphylococcus aureus (HMDB: HMDB0000755)

Exogenous

Exogenous (HMDB: HMDB0000755)

Food

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Process

Naturally occurring process

Biological process

Biochemical pathway

Disease pathway

Tyrosinemia Type 2 (or Richner-Hanhart Syndrome) (HMDB: HMDB0000755)

Role

Biological role

Human metabolite (HMDB: HMDB0000755)
Bacterial metabolite (HMDB: HMDB0000755)

Industrial application

Pharmaceutical industry

Biomarker

Eosinophilic esophagitis (MarkerDB: MDB00029989)
Phenylketonuria (MarkerDB: MDB00029989)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	414.40 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	12.9 mg/mL at 16 °C	Not Available
LogP	0.310 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	MetCCS_train_neg	139.402	30932474
[M-H]-	Not Available	141.5	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000428

Predicted Molecular Properties

Property	Value	Source
Water Solubility	4.79 g/L	ALOGPS
logP	0.87	ALOGPS
logP	0.88	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	3.58	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	45.44 m³·mol⁻¹	ChemAxon
Polarizability	17.51 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]+	141.346	31661259
DarkChem	[M-H]-	136.358	31661259
AllCCS	[M+H]+	140.248	32859911
AllCCS	[M-H]-	137.895	32859911
DeepCCS	[M+H]+	134.298	30932474
DeepCCS	[M-H]-	130.471	30932474
DeepCCS	[M-2H]-	167.83	30932474
DeepCCS	[M+Na]+	143.369	30932474
AllCCS	[M+H]+	140.2	32859911
AllCCS	[M+H-H2O]+	136.0	32859911
AllCCS	[M+NH4]+	144.2	32859911
AllCCS	[M+Na]+	145.3	32859911
AllCCS	[M-H]-	137.9	32859911
AllCCS	[M+Na-2H]-	138.7	32859911
AllCCS	[M+HCOO]-	139.7	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.	2.96 minutes	32390414
Predicted by Siyang on May 30, 2022	9.8335 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	3.65 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	115.4 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1075.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	289.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	93.6 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	167.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	83.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	310.3 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	287.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	335.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	672.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	293.0 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	918.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	205.9 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	242.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	489.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	273.5 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	208.1 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Hydroxyphenyllactic acid	OC(CC1=CC=C(O)C=C1)C(O)=O	3554.1	Standard polar	33892256
Hydroxyphenyllactic acid	OC(CC1=CC=C(O)C=C1)C(O)=O	1782.4	Standard non polar	33892256
Hydroxyphenyllactic acid	OC(CC1=CC=C(O)C=C1)C(O)=O	1841.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Hydroxyphenyllactic acid,1TMS,isomer #1	C[Si](C)(C)OC(CC1=CC=C(O)C=C1)C(=O)O	1886.2	Semi standard non polar	33892256
Hydroxyphenyllactic acid,1TMS,isomer #2	C[Si](C)(C)OC1=CC=C(CC(O)C(=O)O)C=C1	1835.4	Semi standard non polar	33892256
Hydroxyphenyllactic acid,1TMS,isomer #3	C[Si](C)(C)OC(=O)C(O)CC1=CC=C(O)C=C1	1846.2	Semi standard non polar	33892256
Hydroxyphenyllactic acid,2TMS,isomer #1	C[Si](C)(C)OC1=CC=C(CC(O[Si](C)(C)C)C(=O)O)C=C1	1887.2	Semi standard non polar	33892256
Hydroxyphenyllactic acid,2TMS,isomer #2	C[Si](C)(C)OC(=O)C(CC1=CC=C(O)C=C1)O[Si](C)(C)C	1884.2	Semi standard non polar	33892256
Hydroxyphenyllactic acid,2TMS,isomer #3	C[Si](C)(C)OC(=O)C(O)CC1=CC=C(O[Si](C)(C)C)C=C1	1856.0	Semi standard non polar	33892256
Hydroxyphenyllactic acid,3TMS,isomer #1	C[Si](C)(C)OC(=O)C(CC1=CC=C(O[Si](C)(C)C)C=C1)O[Si](C)(C)C	1910.8	Semi standard non polar	33892256
Hydroxyphenyllactic acid,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(CC1=CC=C(O)C=C1)C(=O)O	2132.7	Semi standard non polar	33892256
Hydroxyphenyllactic acid,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1=CC=C(CC(O)C(=O)O)C=C1	2096.9	Semi standard non polar	33892256
Hydroxyphenyllactic acid,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(O)CC1=CC=C(O)C=C1	2101.6	Semi standard non polar	33892256
Hydroxyphenyllactic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1=CC=C(CC(O[Si](C)(C)C(C)(C)C)C(=O)O)C=C1	2386.3	Semi standard non polar	33892256
Hydroxyphenyllactic acid,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=C(O)C=C1)O[Si](C)(C)C(C)(C)C	2338.7	Semi standard non polar	33892256
Hydroxyphenyllactic acid,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC(=O)C(O)CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1	2376.6	Semi standard non polar	33892256
Hydroxyphenyllactic acid,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C(CC1=CC=C(O[Si](C)(C)C(C)(C)C)C=C1)O[Si](C)(C)C(C)(C)C	2604.8	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Mitochondria

Biospecimen Locations

Blood
Cerebrospinal Fluid (CSF)
Feces
Saliva
Urine

Tissue Locations

Epidermis
Placenta
Prostate

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
Blood	Detected and Quantified	0.64 +/- 0.24 uM	Adult (>18 years old)	Both	Normal	9106023	details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Female	Normal	27355821	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27065191	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Specified	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Infant (0-1 year old)	Not Available	Normal	24628373	details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Normal	19636438	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	19636438	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
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Saliva	Detected and Quantified	25.10 +/- 14.93 uM	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Normal	22308371	details
Urine	Detected and Quantified	33.513 +/- 76.957 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	4837567	details
Urine	Detected and Quantified	22.342 +/- 30.410 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	4837567	details
Urine	Detected and Quantified	17.377 +/- 21.101 umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	4837567	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	26269369	details
Urine	Detected and Quantified	0-1.0 umol/mmol creatinine	Infant (0-1 year old)	Male	Normal	31963255	details
Urine	Detected and Quantified	0-1.0 umol/mmol creatinine	Infant (0-1 year old)	Female	Normal	31963255	details
Urine	Detected and Quantified	0-2 umol/mmol creatinine	Infant (0-1 year old)	Male	Normal	31963255	details
Urine	Detected and Quantified	0-2.3 umol/mmol creatinine	Infant (0-1 year old)	Female	Normal	31963255	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected and Quantified	5.393 +/- 4.849 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected and Quantified	0.51-0.94 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	27012787	details
Urine	Detected and Quantified	0.55-1.2 umol/mmol creatinine	Adult (>18 years old)	Female	Normal	27012787	details
Urine	Detected and Quantified	<50.12 umol/mmol creatinine	Children (1 - 18 years old)	Both	Normal	BC Children's Hos...	details
Urine	Detected and Quantified	3.7 (0.1-11.5) umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	8087979	details
Urine	Detected and Quantified	35.939 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Normal	Analysis of 30 no...	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	3.2 (1.5-3.9) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	2.8 (2.6-3.0) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	24023812	details
Urine	Detected and Quantified	1.1 (0.2-2.6) umol/mmol creatinine	Adult (>18 years old)	Both	Normal	2702744	details
Urine	Detected and Quantified	1.05 +/- 0.43 umol/mmol creatinine	Adult (>18 years old)	Male	Normal	Geigy Scientific ...	details
Urine	Detected and Quantified	1.0 (0.4-7.3) umol/mmol creatinine	Adolescent (13-18 years old)	Both	Normal	8087979	details
Urine	Detected and Quantified	1.5 (0.1-8.7) umol/mmol creatinine	Children (1-13 years old)	Both	Normal	8087979	details
Urine	Detected and Quantified	1.6 (0.3-5.8) umol/mmol creatinine	Children (1-13 years old)	Both	Normal	8087979	details
Urine	Detected and Quantified	4.8 (2.7-5.3) umol/mmol creatinine	Infant (0-1 year old)	Both	Normal	8087979	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Cerebrospinal Fluid (CSF)	Detected and Quantified	0.80 +/- 0.10 uM	Adult (>18 years old)	Both	Morphine treatment	10553836	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	CCD	19636438	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ileal Crohn's disease	19636438	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Supragingival Plaque	31026179	details
Urine	Detected and Quantified	12.6 +/- 36.00 umol/mmol creatinine	Newborn (0-30 days old)	Both	Phenylketonuria	2091926	details
Urine	Detected and Quantified	6.21 +/- 4.38 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected and Quantified	5.879 +/- 5.443 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Eosinophilic esophagitis	Analysis of 30 no...	details
Urine	Detected and Quantified	8.512 +/- 4.226 umol/mmol creatinine	Children (1 - 13 years old)	Not Specified	Gastroesophageal reflux disease	Analysis of 30 no...	details
Urine	Detected and Quantified	139.639 +/- 122.882 umol/mmol creatinine	Children (1-13 years old)	Both	Phenylketonuria	4837567	details
Urine	Detected and Quantified	74.474 +/- 94.334 umol/mmol creatinine	Children (1-13 years old)	Both	Phenylketonuria	4837567	details
Urine	Detected and Quantified	75.0948 +/- 98.678 umol/mmol creatinine	Children (1-13 years old)	Both	Phenylketonuria	4837567	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] 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 ]
Supragingival Plaque
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Phenylketonuria
Monch E, Kneer J, Jakobs C, Arnold M, Diehl H, Batzler U: Examination of urine metabolites in the newborn period and during protein loading tests at 6 months of age--Part 1. Eur J Pediatr. 1990;149 Suppl 1:S17-24. [PubMed:2091926 ] Rampini S, Vollmin JA, Bosshard HR, Muller M, Curtius HC: Aromatic acids in urine of healthy infants, persistent hyperphenylalaninemia, and phenylketonuria, before and after phenylalanine load. Pediatr Res. 1974 Jul;8(7):704-9. [PubMed:4837567 ]
Eosinophilic esophagitis
Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.

Associated OMIM IDs

114500 (Colorectal cancer)
261600 (Phenylketonuria)
610247 (Eosinophilic esophagitis)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

4-HYDROXYPHENYLLACTATE

BiGG ID

2392410

Wikipedia Link

Not Available

METLIN ID

5723

PubChem Compound

9378

PDB ID

Not Available

ChEBI ID

17385

Food Biomarker Ontology

Not Available

VMH ID

34HPL

MarkerDB ID

MDB00029989

Good Scents ID

rw1622271

References

Synthesis Reference

Deng, Xi-ling; Wang, Xin-bing; Xiang, Ying; Zhu, Shi-fa. Synthesis of b-(4-hydroxyphenyl)lactic acid. Shihezi Daxue Xuebao, Ziran Kexueban (2005), 23(1), 11-13.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
Raw I, Schmidt BJ, Merzel J: Catecholamines and congenital pain insensitivity. Braz J Med Biol Res. 1984;17(3-4):271-9. [PubMed:6085021 ]
Bennett MJ, Ragni MC, Hood I, Hale DE: Comparison of post-mortem urinary and vitreous humour organic acids. Ann Clin Biochem. 1992 Sep;29 ( Pt 5):541-5. [PubMed:1444166 ]
Roth K, Cohn R, Yandrasitz J, Preti G, Dodd P, Segal S: Beta-methylcrotonic aciduria associated with lactic acidosis. J Pediatr. 1976 Feb;88(2):229-35. [PubMed:1249684 ]
Spaapen LJ, Ketting D, Wadman SK, Bruinvis L, Duran M: Urinary D-4-hydroxyphenyllactate, D-phenyllactate and D-2-hydroxyisocaproate, abnormalities of bacterial origin. J Inherit Metab Dis. 1987;10(4):383-90. [PubMed:3126358 ]
Deutsch JC: Determination of p-hydroxyphenylpyruvate, p-hydroxyphenyllactate and tyrosine in normal human plasma by gas chromatography-mass spectrometry isotope-dilution assay. J Chromatogr B Biomed Sci Appl. 1997 Mar 7;690(1-2):1-6. [PubMed:9106023 ]
Mrochek JE, Dinsmore SR, Ohrt DW: Monitoring phenylalanine-tyrosine metabolism by high-resolution liquid chromatography of urine. Clin Chem. 1973 Aug;19(8):927-36. [PubMed:4720815 ]
Higa S, Kishimoto S: Isolation of 2-hydroxycarboxylic acids with a boronate affinity gel. Anal Biochem. 1986 Apr;154(1):71-4. [PubMed:3706738 ]
Jakobs C, Sweetman L, Nyhan WL: Chemical analysis of succinylacetone and 4-hydroxyphenyllactate in amniotic fluid using selective ion monitoring. Prenat Diagn. 1984 May-Jun;4(3):187-94. [PubMed:6463026 ]
Beloborodova N, Bairamov I, Olenin A, Shubina V, Teplova V, Fedotcheva N: Effect of phenolic acids of microbial origin on production of reactive oxygen species in mitochondria and neutrophils. J Biomed Sci. 2012 Oct 12;19:89. doi: 10.1186/1423-0127-19-89. [PubMed:23061754 ]
Beloborodova NV, Khodakova AS, Bairamov IT, Olenin AY: Microbial origin of phenylcarboxylic acids in the human body. Biochemistry (Mosc). 2009 Dec;74(12):1350-5. [PubMed:19961416 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
(). Charles Scriver, Arthur Beaudet, William Sly, David Valle, Barton Childs, Kenneth Kinzler, Bert Vogelstein. The Metabolic and Molecular Bases of Inherited Disease. McGraw-Hill Professional; 8 edition (Dec 15 2000). . . [ISBN:978-0079130358 ]

Enzymes

Enzyme Details

1. Sulfotransferase family cytosolic 2B member 1

General function:: Involved in sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of many hormones, neurotransmitters, drugs and xenobiotic compounds. Sulfonation increases the water solubility of most compounds, and therefore their renal excretion, but it can also result in bioactivation to form active metabolites. Sulfates hydroxysteroids like DHEA. Isoform 1 preferentially sulfonates cholesterol, and isoform 2 avidly sulfonates pregnenolone but not cholesterol.
Gene Name:: SULT2B1
Uniprot ID:: O00204
Molecular weight:: 39598.595

Reactions

Hydroxyphenyllactic acid → 3-(4-hydroxyphenyl)-2-(sulfooxy)propanoic acid	details

Enzyme Details

2. 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

Hydroxyphenyllactic acid → 6-[4-(2-carboxy-2-hydroxyethyl)phenoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid	details
Hydroxyphenyllactic acid → 3,4,5-trihydroxy-6-{[2-hydroxy-3-(4-hydroxyphenyl)propanoyl]oxy}oxane-2-carboxylic acid	details

Enzyme Details

3. Sulfotransferase 1A3

General function:: sulfotransferase activity
Specific function:: Sulfotransferase that utilizes 3'-phospho-5'-adenylyl sulfate (PAPS) as sulfonate donor to catalyze the sulfate conjugation of phenolic monoamines (neurotransmitters such as dopamine, norepinephrine and serotonin) and phenolic and catechol drugs.
Gene Name:: SULT1A3
Uniprot ID:: P0DMM9
Molecular weight:: 34195.96

Reactions

Hydroxyphenyllactic acid → 2-hydroxy-3-[4-(sulfooxy)phenyl]propanoic acid	details

Showing metabocard for Hydroxyphenyllactic acid (HMDB0000755)

MOL for HMDB0000755 (Hydroxyphenyllactic acid)

3D MOL for HMDB0000755 (Hydroxyphenyllactic acid)

3D SDF for HMDB0000755 (Hydroxyphenyllactic acid)

3D-SDF for HMDB0000755 (Hydroxyphenyllactic acid)

PDB for HMDB0000755 (Hydroxyphenyllactic acid)

3D PDB for HMDB0000755 (Hydroxyphenyllactic acid)

SMILES for HMDB0000755 (Hydroxyphenyllactic acid)

INCHI for HMDB0000755 (Hydroxyphenyllactic acid)

Structure for HMDB0000755 (Hydroxyphenyllactic acid)

3D Structure for HMDB0000755 (Hydroxyphenyllactic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

Enzymes

Reactions

Reactions

Reactions