NAV

Phloretic acid

Identification

Generic Name
Phloretic acid
DrugBank Accession Number
DB03897
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 166.1739
Monoisotopic: 166.062994186
Chemical Formula
C9H10O3
Synonyms
  • 3-(4-Hydroxyphenyl)propionic acid
  • 3-(p-hydroxyphenyl)propionic acid
  • 4-Hydroxyphenylpropionic acid
  • Desaminotyrosine
  • Dihydro-p-coumaric acid
  • Hydroxyphenyl propionic acid
  • p-Hydroxyhydrocinnamic acid
  • p-hydroxyphenylpropionic acid
  • Phloretic acid
  • Phloretinic acid
  • β-(p-hydroxyphenyl)propionic acid
External IDs
  • NSC-40949
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UTyrosine phenol-lyaseNot AvailableCitrobacter freundii
UPrephenate dehydrogenaseNot AvailableAquifex aeolicus (strain VF5)
UTyrosine phenol-lyaseNot AvailableEscherichia intermedia
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
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
1-hydroxy-2-unsubstituted benzenoids / Benzene and substituted derivatives / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
1-hydroxy-2-unsubstituted benzenoid / 3-phenylpropanoic-acid / Aromatic homomonocyclic compound / Benzenoid / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Hydrocarbon derivative / Monocarboxylic acid or derivatives / Monocyclic benzene moiety
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
hydroxy monocarboxylic acid (CHEBI:32980)
Affected organisms
Not Available

Chemical Identifiers

UNII
6QNC6P18SR
CAS number
501-97-3
InChI Key
NMHMNPHRMNGLLB-UHFFFAOYSA-N
InChI
InChI=1S/C9H10O3/c10-8-4-1-7(2-5-8)3-6-9(11)12/h1-2,4-5,10H,3,6H2,(H,11,12)
IUPAC Name
3-(4-hydroxyphenyl)propanoic acid
SMILES
OC(=O)CCC1=CC=C(O)C=C1

References

General References
Not Available
Human Metabolome Database
HMDB0002199
KEGG Compound
C01744
PubChem Compound
10394
PubChem Substance
46504920
ChemSpider
9965
BindingDB
231636
ChEBI
32980
ChEMBL
CHEMBL1172560
ZINC
ZINC000008383206
PDBe Ligand
HPP
Wikipedia
Phloretic_acid
PDB Entries
2tpl / 3ggp / 5sxf / 5whl

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 Solubility2.71 mg/mLALOGPS
logP1.15ALOGPS
logP1.75Chemaxon
logS-1.8ALOGPS
pKa (Strongest Acidic)4.21Chemaxon
pKa (Strongest Basic)-6Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area57.53 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity43.95 m3·mol-1Chemaxon
Polarizability16.97 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9789
Blood Brain Barrier+0.5264
Caco-2 permeable+0.7259
P-glycoprotein substrateNon-substrate0.6677
P-glycoprotein inhibitor INon-inhibitor0.976
P-glycoprotein inhibitor IINon-inhibitor0.9753
Renal organic cation transporterNon-inhibitor0.8951
CYP450 2C9 substrateNon-substrate0.8217
CYP450 2D6 substrateNon-substrate0.903
CYP450 3A4 substrateNon-substrate0.7114
CYP450 1A2 substrateNon-inhibitor0.944
CYP450 2C9 inhibitorNon-inhibitor0.9796
CYP450 2D6 inhibitorNon-inhibitor0.9731
CYP450 2C19 inhibitorNon-inhibitor0.9212
CYP450 3A4 inhibitorNon-inhibitor0.94
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9615
Ames testNon AMES toxic0.9434
CarcinogenicityNon-carcinogens0.9148
BiodegradationReady biodegradable0.8949
Rat acute toxicity1.9895 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8951
hERG inhibition (predictor II)Non-inhibitor0.9547
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-MSsplash10-0ab9-3900000000-424e95de0b8037c4aa20
GC-MS Spectrum - EI-BGC-MSsplash10-066r-9800000000-44e113d8fc2602ffba88
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-004l-0900000000-5ae3f727b5218398aa83
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-00kv-5900000000-db98339dadc21116c7aa
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-052r-9400000000-7d2340d4f6981ee8aecb
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-00bi-9100000000-cac6ca239c2cbe36238d
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, NegativeLC-MS/MSsplash10-014i-0900000000-e131522c5a7352167afb
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, NegativeLC-MS/MSsplash10-014i-3900000000-5c5920f4693d31baa640
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, NegativeLC-MS/MSsplash10-0a4i-9500000000-49bd07916272cdc49e68
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, NegativeLC-MS/MSsplash10-0a6u-9100000000-683b03c9384a9a750863
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, NegativeLC-MS/MSsplash10-00di-9000000000-d4af6cba1b370fd620ed
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-014i-0900000000-514be816ed648e5588b7
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-014i-3900000000-5c5920f4693d31baa640
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a4i-9500000000-49bd07916272cdc49e68
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0a6u-9100000000-683b03c9384a9a750863
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-00di-9000000000-d4af6cba1b370fd620ed
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0axr-1900000000-d979818d83c0e8598f43
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-1900000000-72a53a01cd16b7e41fd7
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0uk9-2900000000-2366bc85f6ff900ff4b4
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a6r-6900000000-533e6556eafbc03e23bc
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fdo-7900000000-bcd1a0aba1e8e729cce3
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-9500000000-e147da6ec3136e35db4f
1H NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-139.4078379
predicted
DarkChem Lite v0.1.0
[M-H]-139.1901379
predicted
DarkChem Lite v0.1.0
[M-H]-139.3075379
predicted
DarkChem Lite v0.1.0
[M-H]-132.4182
predicted
DeepCCS 1.0 (2019)
[M+H]+140.2175379
predicted
DarkChem Lite v0.1.0
[M+H]+138.9740379
predicted
DarkChem Lite v0.1.0
[M+H]+138.9689379
predicted
DarkChem Lite v0.1.0
[M+H]+135.36142
predicted
DeepCCS 1.0 (2019)
[M+Na]+138.4594379
predicted
DarkChem Lite v0.1.0
[M+Na]+138.6474379
predicted
DarkChem Lite v0.1.0
[M+Na]+138.5315379
predicted
DarkChem Lite v0.1.0
[M+Na]+144.8766
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Details1. Tyrosine phenol-lyase
Kind
Protein
Organism
Citrobacter freundii
Pharmacological action
Unknown
General Function
Tyrosine phenol-lyase activity
Specific Function
Not Available
Gene Name
tpl
Uniprot ID
P31013
Uniprot Name
Tyrosine phenol-lyase
Molecular Weight
51499.525 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]
Details2. Prephenate dehydrogenase
Kind
Protein
Organism
Aquifex aeolicus (strain VF5)
Pharmacological action
Unknown
General Function
Prephenate dehydrogenase activity
Specific Function
Not Available
Gene Name
tyrA
Uniprot ID
O67636
Uniprot Name
Prephenate dehydrogenase
Molecular Weight
34849.26 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]
Details3. Tyrosine phenol-lyase
Kind
Protein
Organism
Escherichia intermedia
Pharmacological action
Unknown
General Function
Tyrosine phenol-lyase activity
Specific Function
Not Available
Gene Name
tpl
Uniprot ID
P31012
Uniprot Name
Tyrosine phenol-lyase
Molecular Weight
51441.485 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52