NAV

(2S,3S)-3-(4-fluorophenyl)-2,3-dihydroxypropanoic acid

Identification

Generic Name
(2S,3S)-3-(4-fluorophenyl)-2,3-dihydroxypropanoic acid
DrugBank Accession Number
DB06946
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 200.1638
Monoisotopic: 200.048486981
Chemical Formula
C9H9FO4
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UMIO-dependent tyrosine 2,3-aminomutaseNot AvailableStreptomyces globisporus
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as phenylpropanoic acids. These 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
Sugar acids and derivatives / Fluorobenzenes / Beta hydroxy acids and derivatives / Monosaccharides / Aryl fluorides / Alpha hydroxy acids and derivatives / Secondary alcohols / 1,2-diols / Monocarboxylic acids and derivatives / Carboxylic acids
show 5 more
Substituents
1,2-diol / 3-phenylpropanoic-acid / Alcohol / Alpha-hydroxy acid / Aromatic alcohol / Aromatic homomonocyclic compound / Aryl fluoride / Aryl halide / Benzenoid / Beta-hydroxy acid
show 17 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
DWYLYIVEFVSGCP-YUMQZZPRSA-N
InChI
InChI=1S/C9H9FO4/c10-6-3-1-5(2-4-6)7(11)8(12)9(13)14/h1-4,7-8,11-12H,(H,13,14)/t7-,8-/m0/s1
IUPAC Name
(2S,3S)-3-(4-fluorophenyl)-2,3-dihydroxypropanoic acid
SMILES
[H][C@@](O)(C(O)=O)[C@@]([H])(O)C1=CC=C(F)C=C1

References

General References
Not Available
PubChem Compound
23644579
PubChem Substance
99443417
ChemSpider
25057390
PDBe Ligand
295
PDB Entries
2rjr

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility7.39 mg/mLALOGPS
logP0.28ALOGPS
logP0.41Chemaxon
logS-1.4ALOGPS
pKa (Strongest Acidic)3.27Chemaxon
pKa (Strongest Basic)-3.6Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area77.76 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity44.88 m3·mol-1Chemaxon
Polarizability17.61 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.8252
Blood Brain Barrier+0.8927
Caco-2 permeable+0.5192
P-glycoprotein substrateNon-substrate0.6985
P-glycoprotein inhibitor INon-inhibitor0.9772
P-glycoprotein inhibitor IINon-inhibitor0.991
Renal organic cation transporterNon-inhibitor0.9463
CYP450 2C9 substrateNon-substrate0.8802
CYP450 2D6 substrateNon-substrate0.9166
CYP450 3A4 substrateNon-substrate0.7524
CYP450 1A2 substrateNon-inhibitor0.7407
CYP450 2C9 inhibitorNon-inhibitor0.9129
CYP450 2D6 inhibitorNon-inhibitor0.9166
CYP450 2C19 inhibitorNon-inhibitor0.9453
CYP450 3A4 inhibitorNon-inhibitor0.7643
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9533
Ames testNon AMES toxic0.9279
CarcinogenicityNon-carcinogens0.7577
BiodegradationNot ready biodegradable0.8223
Rat acute toxicity2.1883 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9914
hERG inhibition (predictor II)Non-inhibitor0.9581
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-00b9-5900000000-dc1e8a75743424d4f18e
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-05n0-0900000000-fdffb3c281110102e297
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0019-1900000000-c9e40b9d3544a7ae79c6
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-056r-2900000000-4cf27d06d30618c53aaf
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0571-9400000000-80e274260897acafd04e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-5900000000-9a64931d2504fec9df79
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4r-9500000000-8670a42c3415328849ab
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-142.81387
predicted
DeepCCS 1.0 (2019)
[M+H]+145.20995
predicted
DeepCCS 1.0 (2019)
[M+Na]+151.37459
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. MIO-dependent tyrosine 2,3-aminomutase
Kind
Protein
Organism
Streptomyces globisporus
Pharmacological action
Unknown
General Function
Tyrosine ammonia-lyase activity
Specific Function
Involved in the biosynthesis of the enediyne antitumor antibiotic C-1027. Catalyzes the MIO-dependent deamination of L-tyrosine generating the corresponding alpha,beta-unsaturated acid, (S)-beta-ty...
Gene Name
Not Available
Uniprot ID
Q8GMG0
Uniprot Name
MIO-dependent tyrosine 2,3-aminomutase
Molecular Weight
58138.44 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at September 15, 2010 21:17 / Updated at June 12, 2020 16:52