NAV

O-(((1R)-((N-PHENYLMETHOXYCARBONYL-L-ALANYL)AMINO)ETHYL)HYDROXYPHOSPHONO)-L-BENZYLACETIC ACID

Identification

Generic Name
O-(((1R)-((N-PHENYLMETHOXYCARBONYL-L-ALANYL)AMINO)ETHYL)HYDROXYPHOSPHONO)-L-BENZYLACETIC ACID
DrugBank Accession Number
DB08762
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 478.4321
Monoisotopic: 478.150502362
Chemical Formula
C22H27N2O8P
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UCarboxypeptidase A1Not AvailableHumans
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 alpha amino acid amides. These are amide derivatives of alpha amino acids.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Alpha amino acid amides
Alternative Parents
Phenylpropanoic acids / Alanine and derivatives / Benzyloxycarbonyls / Phosphonic acid esters / Carbamate esters / Organic phosphonic acids / Secondary carboxylic acid amides / Organic carbonic acids and derivatives / Carboxylic acids / Monocarboxylic acids and derivatives
show 6 more
Substituents
3-phenylpropanoic-acid / Alanine or derivatives / Alpha-amino acid amide / Aromatic homomonocyclic compound / Benzenoid / Benzyloxycarbonyl / Carbamic acid ester / Carbonic acid derivative / Carbonyl group / Carboxamide group
show 15 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
UPJNMOBJDSFRTI-FCEWJHQRSA-N
InChI
InChI=1S/C22H27N2O8P/c1-15(23-22(28)31-14-18-11-7-4-8-12-18)20(25)24-16(2)33(29,30)32-19(21(26)27)13-17-9-5-3-6-10-17/h3-12,15-16,19H,13-14H2,1-2H3,(H,23,28)(H,24,25)(H,26,27)(H,29,30)/t15-,16+,19-/m0/s1
IUPAC Name
(2S)-2-({[(1R)-1-[(2S)-2-{[(benzyloxy)carbonyl]amino}propanamido]ethyl](hydroxy)phosphoryl}oxy)-3-phenylpropanoic acid
SMILES
[H][C@@](C)(NC(=O)OCC1=CC=CC=C1)C(=O)N[C@@]([H])(C)[P@](O)(=O)O[C@@]([H])(CC1=CC=CC=C1)C(O)=O

References

General References
Not Available
PubChem Compound
5492457
PubChem Substance
99445233
ChemSpider
4591001
ZINC
ZINC000039313129
PDBe Ligand
ZAF
PDB Entries
6cpa

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 Solubility0.0187 mg/mLALOGPS
logP1.35ALOGPS
logP2.35Chemaxon
logS-4.4ALOGPS
pKa (Strongest Acidic)0.84Chemaxon
pKa (Strongest Basic)-4.9Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area151.26 Å2Chemaxon
Rotatable Bond Count12Chemaxon
Refractivity117.9 m3·mol-1Chemaxon
Polarizability45.73 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9163
Blood Brain Barrier+0.8155
Caco-2 permeable-0.6877
P-glycoprotein substrateNon-substrate0.5612
P-glycoprotein inhibitor INon-inhibitor0.685
P-glycoprotein inhibitor IINon-inhibitor0.9462
Renal organic cation transporterNon-inhibitor0.9513
CYP450 2C9 substrateNon-substrate0.7623
CYP450 2D6 substrateNon-substrate0.8247
CYP450 3A4 substrateNon-substrate0.5249
CYP450 1A2 substrateNon-inhibitor0.8444
CYP450 2C9 inhibitorNon-inhibitor0.7565
CYP450 2D6 inhibitorNon-inhibitor0.8921
CYP450 2C19 inhibitorNon-inhibitor0.8176
CYP450 3A4 inhibitorNon-inhibitor0.7272
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7089
Ames testNon AMES toxic0.5893
CarcinogenicityNon-carcinogens0.7819
BiodegradationNot ready biodegradable0.9909
Rat acute toxicity2.4085 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9915
hERG inhibition (predictor II)Non-inhibitor0.8322
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 MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-024i-1049600000-8f758ef736aa1e1e2e3c
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-08fr-0892000000-adae27bfae7369d76eb2
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0adi-3490000000-b5993e1af2d7862d226c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01r6-4459100000-c43334ca6ca67370a71f
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00b9-5679000000-1f3f2be26ef94b6041b0
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-9500000000-6fa54ecf530fbeaa09a8
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]-214.5806124
predicted
DarkChem Lite v0.1.0
[M-H]-198.3975
predicted
DeepCCS 1.0 (2019)
[M+H]+214.0493124
predicted
DarkChem Lite v0.1.0
[M+H]+200.29292
predicted
DeepCCS 1.0 (2019)
[M+Na]+213.8103124
predicted
DarkChem Lite v0.1.0
[M+Na]+206.07085
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Carboxypeptidase A1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Carboxypeptidase that catalyzes the release of a C-terminal amino acid, but has little or no action with -Asp, -Glu, -Arg, -Lys or -Pro.
Gene Name
CPA1
Uniprot ID
P15085
Uniprot Name
Carboxypeptidase A1
Molecular Weight
47139.86 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 21:34 / Updated at June 12, 2020 16:52