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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-08-12 22:07:25 UTC
Update Date2019-07-23 05:45:48 UTC
HMDB IDHMDB0003503
Secondary Accession Numbers
  • HMDB03503
Metabolite Identification
Common Name3-(3,4-Dihydroxyphenyl)lactic acid
Description3-(3,4-Dihydroxyphenyl)lactic acid is a natural catecholamine metabolite present in normal newborns' plasma (PMID 1391254 ) and in normal urine (PMID 7460271 ).
Structure
Data?1563860748
Synonyms
ValueSource
3-(3,4-Dihydroxyphenyl)lactateChEBI
3,4-Dihydroxyphenyllactic acidKegg
3,4-DihydroxyphenyllactateGenerator
2-Hydroxy-3-(3,4-dihydroxyphenyl)propanoateHMDB
2-Hydroxy-3-(3,4-dihydroxyphenyl)propanoic acidHMDB
a-Hydroxyhydrocaffeic acidHMDB
alpha-HydroxyhydrocaffeateHMDB
alpha-Hydroxyhydrocaffeic acidHMDB
DanshensuHMDB
DL-b-(3,4-Dihydroxyphenyl)lactic acidHMDB
DL-beta-(3,4-Dihydroxyphenyl)lactic acidHMDB
(3,4-Dihydroxyphenyl)lactic acidHMDB
3,4-Dihydroxyphenyllactic acid, monosodium salt, (R)-isomerHMDB
3,4-Dihydroxyphenyllactic acid, (+-)-isomerHMDB
3,4-Dihydroxyphenyllactic acid, (R)-isomerHMDB
3,4-Dihydroxyphenyllactic acid, monosodium salt, (+-)-isomerHMDB
Salvianic acid a sodiumHMDB
3,4-Dihydroxyphenyllactic acid, monosodium saltHMDB
3-(3,4-Dihydroxyphenyl)lactic acidGenerator
Chemical FormulaC9H10O5
Average Molecular Weight198.1727
Monoisotopic Molecular Weight198.05282343
IUPAC Name3-(3,4-dihydroxyphenyl)-2-hydroxypropanoic acid
Traditional Namedanshensu
CAS Registry Number23028-17-3
SMILES
OC(CC1=CC(O)=C(O)C=C1)C(O)=O
InChI Identifier
InChI=1S/C9H10O5/c10-6-2-1-5(3-7(6)11)4-8(12)9(13)14/h1-3,8,10-12H,4H2,(H,13,14)
InChI KeyPAFLSMZLRSPALU-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.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassPhenylpropanoic acids
Sub ClassNot Available
Direct ParentPhenylpropanoic acids
Alternative Parents
Substituents
  • 3-phenylpropanoic-acid
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility6.7 g/LALOGPS
logP0.77ALOGPS
logP0.58ChemAxon
logS-1.5ALOGPS
pKa (Strongest Acidic)3.26ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity47.42 m³·mol⁻¹ChemAxon
Polarizability18.4 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00di-1900000000-4429ae1d67802f77638bJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-00xr-5039800000-242433a4eaee6ec21e37JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ff1-0900000000-c01f6f341825bf481916JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0fl1-0900000000-4ac5f7db2b698bf08063JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01bd-9600000000-384a42503ca93dcc002cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1900000000-badce4d6b7899f8089c8JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fmi-2900000000-73617118e281cf2316d7JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05fr-7900000000-e5db4da27043d9518b0eJSpectraViewer | MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue Locations
  • Fibroblasts
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified6.2 +/- 0.25 uMAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB023184
KNApSAcK IDC00031720
Chemspider ID388544
KEGG Compound IDC01207
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6942
PubChem Compound439435
PDB IDNot Available
ChEBI ID17807
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferencePoljanac, Mirela; Vasic-Racki, Durda; Hadolin, Majda; Bauman, Davor. Enzymatic preparation of Danshensu. Slovenski Kemijski Dnevi, Maribor, Slovenia, Sept. 25-26, 2003 (2003), 239-245.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Liu Q, Chao RB: [Determination of danshensu in urine and its pharmacokinetics in human]. Yao Xue Xue Bao. 2003 Oct;38(10):771-4. [PubMed:14730902 ]
  2. Li X, Yu C, Cai Y, Liu G, Jia J, Wang Y: Simultaneous determination of six phenolic constituents of danshen in human serum using liquid chromatography/tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Jun 5;820(1):41-7. Epub 2005 Apr 19. [PubMed:15866491 ]
  3. Jiang H, Ha T, Wei D: [A study on the mechanism of the biological roles of danshensu on fibroblast]. Zhonghua Shao Shang Za Zhi. 2001 Feb;17(1):36-8. [PubMed:11876909 ]
  4. Hirsimaki H, Kero P, Ekblad H, Scheinin M, Saraste M, Erkkola R: Mode of delivery, plasma catecholamines and Doppler-derived cardiac output in healthy term newborn infants. Biol Neonate. 1992;61(5):285-93. [PubMed:1391254 ]
  5. Muskiet FA, Stratingh MC, Stob GJ, Wolthers BG: Simultaneous determination of the four major catecholamine metabolites and estimation of a serotonin metabolite in urine by capillary gas chromatography of their tert-butyldimethylsilyl derivatives. Clin Chem. 1981 Feb;27(2):223-7. [PubMed:7460271 ]

Enzymes

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
3-(3,4-Dihydroxyphenyl)lactic acid → 3-(3,4-dihydroxyphenyl)-2-(sulfooxy)propanoic aciddetails
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
3-(3,4-Dihydroxyphenyl)lactic acid → 6-[4-(2-carboxy-2-hydroxyethyl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
3-(3,4-Dihydroxyphenyl)lactic acid → 6-[5-(2-carboxy-2-hydroxyethyl)-2-hydroxyphenoxy]-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
3-(3,4-Dihydroxyphenyl)lactic acid → 6-{[3-(3,4-dihydroxyphenyl)-2-hydroxypropanoyl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic aciddetails
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
3-(3,4-Dihydroxyphenyl)lactic acid → 2-hydroxy-3-[4-hydroxy-3-(sulfooxy)phenyl]propanoic aciddetails