Identification

Name
Phosphoramidon
Accession Number
DB02557  (EXPT02764)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Product Ingredients
IngredientUNIICASInChI Key
Phosphoramidon disodium3F7O684NXF164204-38-0OQKHVXFOYFBMDJ-ODIUWQMJSA-L
Categories
UNII
T3G94E2LB1
CAS number
36357-77-4
Weight
Average: 543.5039
Monoisotopic: 543.198180835
Chemical Formula
C23H34N3O10P
InChI Key
ZPHBZEQOLSRPAK-XLCYBJAPSA-N
InChI
InChI=1S/C23H34N3O10P/c1-11(2)8-16(26-37(33,34)36-23-20(29)19(28)18(27)12(3)35-23)21(30)25-17(22(31)32)9-13-10-24-15-7-5-4-6-14(13)15/h4-7,10-12,16-20,23-24,27-29H,8-9H2,1-3H3,(H,25,30)(H,31,32)(H2,26,33,34)/t12-,16-,17-,18-,19+,20+,23-/m0/s1
IUPAC Name
(2S)-2-{[(2S)-1-hydroxy-2-{[hydroxy({[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy})phosphoryl]amino}-4-methylpentylidene]amino}-3-(1H-indol-3-yl)propanoic acid
SMILES
[H][C@@](CC(C)C)(NP(O)(=O)O[C@]1([H])O[C@@]([H])(C)[C@]([H])(O)[C@@]([H])(O)[C@@]1([H])O)C(O)=N[C@@]([H])(CC1=CNC2=CC=CC=C12)C(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UNeprilysin
inhibitor
Human
UKell blood group glycoproteinNot 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
DrugInteraction
PitavastatinThe serum concentration of Pitavastatin can be decreased when it is combined with Phosphoramidon.
Food Interactions
Not Available

References

Synthesis Reference

Guillaume de Nanteuil, Georges Remond, Tony Verbeuren, "Preparation of phosphoramidon." U.S. Patent US5608045, issued December, 1989.

US5608045
General References
Not Available
External Links
KEGG Compound
C00563
PubChem Compound
445114
PubChem Substance
46506179
ChemSpider
392848
BindingDB
50251742
ChEBI
45353
ChEMBL
CHEMBL479579
Therapeutic Targets Database
DNC001121
HET
RDF
Wikipedia
Phosphoramidon
PDB Entries
1dmt / 1tlp / 3dbk / 3dwb / 3zuk / 4b52 / 4cth / 4zr5 / 6bh8

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 Solubility0.752 mg/mLALOGPS
logP0.1ALOGPS
logP0.98ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)2.49ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area214.16 Å2ChemAxon
Rotatable Bond Count11ChemAxon
Refractivity129.46 m3·mol-1ChemAxon
Polarizability51.5 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.6948
Blood Brain Barrier-0.9264
Caco-2 permeable-0.704
P-glycoprotein substrateSubstrate0.6813
P-glycoprotein inhibitor INon-inhibitor0.578
P-glycoprotein inhibitor IINon-inhibitor0.8717
Renal organic cation transporterNon-inhibitor0.9636
CYP450 2C9 substrateNon-substrate0.7455
CYP450 2D6 substrateNon-substrate0.7995
CYP450 3A4 substrateSubstrate0.6024
CYP450 1A2 substrateNon-inhibitor0.8286
CYP450 2C9 inhibitorNon-inhibitor0.8278
CYP450 2D6 inhibitorNon-inhibitor0.891
CYP450 2C19 inhibitorNon-inhibitor0.7963
CYP450 3A4 inhibitorNon-inhibitor0.746
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.759
Ames testNon AMES toxic0.6604
CarcinogenicityNon-carcinogens0.8752
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.7483 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9847
hERG inhibition (predictor II)Non-inhibitor0.8229
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/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
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-0000090000-bfa44de21c3535a87530
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-0006-0002090000-33b035434d6b84041094
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-0009010000-69688f69a2a7bcbc5163
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-8119000000-e07758fccb5a6b44deb1
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-9101000000-7cff0ab9b41737048aa3
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014m-0009030000-a5b6407e17e402eec55c
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014j-0319000000-38a8b18f710de46326b4
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a4i-0910000000-d18f2b765c3f2e8c04ce
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0a4i-0950000000-aab9a1e87c46971532dc
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-000b-0009840000-ef33a5933fe11f046ebd

Taxonomy

Description
This compound belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Dipeptides
Alternative Parents
Leucine and derivatives / N-acyl-L-alpha-amino acids / Alpha amino acid amides / Hexoses / Indolyl carboxylic acids and derivatives / 3-alkylindoles / Phosphoric monoester monoamides / Substituted pyrroles / Benzenoids / Phosphate esters
show 15 more
Substituents
Alpha-dipeptide / Leucine or derivatives / N-acyl-l-alpha-amino acid / N-acyl-alpha-amino acid / N-acyl-alpha amino acid or derivatives / Alpha-amino acid amide / Hexose monosaccharide / Indolyl carboxylic acid derivative / N-substituted-alpha-amino acid / Alpha-amino acid or derivatives
show 35 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
dipeptide, deoxyaldohexose phosphate (CHEBI:45353)

Targets

Details
1. Neprilysin
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Thermolysin-like specificity, but is almost confined on acting on polypeptides of up to 30 amino acids (PubMed:15283675, PubMed:8168535). Biologically important in the destruction of opioid peptide...
Gene Name
MME
Uniprot ID
P08473
Uniprot Name
Neprilysin
Molecular Weight
85513.225 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc endopeptidase with endothelin-3-converting enzyme activity. Cleaves EDN1, EDN2 and EDN3, with a marked preference for EDN3.
Specific Function
Metal ion binding
Gene Name
KEL
Uniprot ID
P23276
Uniprot Name
Kell blood group glycoprotein
Molecular Weight
82823.095 Da
References
  1. Claperon A, Rose C, Gane P, Collec E, Bertrand O, Ouimet T: The Kell protein of the common K2 phenotype is a catalytically active metalloprotease, whereas the rare Kell K1 antigen is inactive. Identification of novel substrates for the Kell protein. J Biol Chem. 2005 Jun 3;280(22):21272-83. Epub 2005 Mar 15. [PubMed:15769748]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 08:59