(2S)-3-[(R)-[(1S)-1-amino-3-phenylpropyl](hydroxy)phosphoryl]-2-benzylpropanoic acid

Identification

Name
(2S)-3-[(R)-[(1S)-1-amino-3-phenylpropyl](hydroxy)phosphoryl]-2-benzylpropanoic acid
Accession Number
DB07448
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 361.3719
Monoisotopic: 361.144294773
Chemical Formula
C19H24NO4P
InChI Key
QELOIXSGJMIHBZ-MSOLQXFVSA-N
InChI
InChI=1S/C19H24NO4P/c20-18(12-11-15-7-3-1-4-8-15)25(23,24)14-17(19(21)22)13-16-9-5-2-6-10-16/h1-10,17-18H,11-14,20H2,(H,21,22)(H,23,24)/t17-,18+/m1/s1
IUPAC Name
(2S)-3-{[(1S)-1-amino-3-phenylpropyl](hydroxy)phosphoryl}-2-benzylpropanoic acid
SMILES
[H][[email protected]@](CC1=CC=CC=C1)(C[[email protected]](O)(=O)[[email protected]]([H])(N)CCC1=CC=CC=C1)C(O)=O

Pharmacology

Indication
Not Available
Structured Indications
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UCytosol aminopeptidaseNot AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
25138289
PubChem Substance
99443919
ChemSpider
23296554
ChEMBL
CHEMBL393949
HET
BEY
PDB Entries
3ebi / 3kr5

Clinical Trials

Clinical Trials
Not Available

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 Solubility0.0709 mg/mLALOGPS
logP-0.11ALOGPS
logP1.5ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)-0.057ChemAxon
pKa (Strongest Basic)9.92ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area100.62 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity97.68 m3·mol-1ChemAxon
Polarizability37.12 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.8182
Blood Brain Barrier+0.5851
Caco-2 permeable-0.7021
P-glycoprotein substrateNon-substrate0.5592
P-glycoprotein inhibitor INon-inhibitor0.9567
P-glycoprotein inhibitor IINon-inhibitor0.9957
Renal organic cation transporterNon-inhibitor0.8747
CYP450 2C9 substrateNon-substrate0.7798
CYP450 2D6 substrateNon-substrate0.8432
CYP450 3A4 substrateNon-substrate0.6312
CYP450 1A2 substrateNon-inhibitor0.8196
CYP450 2C9 inhibitorNon-inhibitor0.9373
CYP450 2D6 inhibitorNon-inhibitor0.9144
CYP450 2C19 inhibitorNon-inhibitor0.936
CYP450 3A4 inhibitorNon-inhibitor0.6792
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9846
Ames testNon AMES toxic0.7332
CarcinogenicityNon-carcinogens0.9097
BiodegradationNot ready biodegradable0.8688
Rat acute toxicity2.0622 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9389
hERG inhibition (predictor II)Non-inhibitor0.7723
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-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Benzene and substituted derivatives / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organophosphorus compounds / Organic oxides / Monoalkylamines / Hydrocarbon derivatives / Carbonyl compounds
Substituents
3-phenylpropanoic-acid / Monocyclic benzene moiety / Benzenoid / Carboxylic acid derivative / Carboxylic acid / Monocarboxylic acid or derivatives / Organic nitrogen compound / Hydrocarbon derivative / Organophosphorus compound / Organooxygen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Targets

Details
1. Cytosol aminopeptidase
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Metalloexopeptidase activity
Specific Function
Presumably involved in the processing and regular turnover of intracellular proteins. Catalyzes the removal of unsubstituted N-terminal amino acids from various peptides.
Gene Name
LAP3
Uniprot ID
P28838
Uniprot Name
Cytosol aminopeptidase
Molecular Weight
56165.84 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. [PubMed:10592235]

Drug created on September 15, 2010 15:21 / Updated on December 01, 2017 15:51