NAV

N-[(Furan-2-Yl)Carbonyl]-(S)-Leucyl-(R)-[1-Amino-2(1h-Indol-3-Yl)Ethyl]-Phosphonic Acid

Identification

Generic Name
N-[(Furan-2-Yl)Carbonyl]-(S)-Leucyl-(R)-[1-Amino-2(1h-Indol-3-Yl)Ethyl]-Phosphonic Acid
DrugBank Accession Number
DB02046
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 447.4214
Monoisotopic: 447.155922091
Chemical Formula
C21H26N3O6P
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UDisintegrin and metalloproteinase domain-containing protein 28Not 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 leucine and derivatives. These are compounds containing leucine or a derivative thereof resulting from reaction of leucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Leucine and derivatives
Alternative Parents
N-acyl-alpha amino acids and derivatives / Alpha amino acid amides / 3-alkylindoles / 2-heteroaryl carboxamides / Furoic acid and derivatives / Substituted pyrroles / Benzenoids / N-acyl amines / Heteroaromatic compounds / Organic phosphonic acids
show 9 more
Substituents
2-heteroaryl carboxamide / 3-alkylindole / Alpha-amino acid amide / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxamide group / Fatty acyl / Fatty amide
show 23 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
indoles, L-leucine derivative (CHEBI:42450)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
WHPKSASOSKNDPY-PKOBYXMFSA-N
InChI
InChI=1S/C21H26N3O6P/c1-13(2)10-17(23-21(26)18-8-5-9-30-18)20(25)24-19(31(27,28)29)11-14-12-22-16-7-4-3-6-15(14)16/h3-9,12-13,17,19,22H,10-11H2,1-2H3,(H,23,26)(H,24,25)(H2,27,28,29)/t17-,19+/m0/s1
IUPAC Name
[(1R)-1-[(2S)-2-[(furan-2-yl)formamido]-4-methylpentanamido]-2-(1H-indol-3-yl)ethyl]phosphonic acid
SMILES
[H][C@@](CC(C)C)(NC(=O)C1=CC=CO1)C(=O)N[C@@]([H])(CC1=CNC2=C1C=CC=C2)P(O)(O)=O

References

General References
Not Available
PubChem Compound
449500
PubChem Substance
46505506
ChemSpider
396015
ZINC
ZINC000024985889
PDBe Ligand
FLX
PDB Entries
4aig

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 Solubility0.0688 mg/mLALOGPS
logP1.57ALOGPS
logP1.64Chemaxon
logS-3.8ALOGPS
pKa (Strongest Acidic)1.49Chemaxon
pKa (Strongest Basic)-2.9Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area144.66 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity114.37 m3·mol-1Chemaxon
Polarizability44.02 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.5069
Blood Brain Barrier+0.7584
Caco-2 permeable-0.6885
P-glycoprotein substrateSubstrate0.6387
P-glycoprotein inhibitor INon-inhibitor0.8376
P-glycoprotein inhibitor IINon-inhibitor0.9659
Renal organic cation transporterNon-inhibitor0.9618
CYP450 2C9 substrateNon-substrate0.8029
CYP450 2D6 substrateNon-substrate0.7375
CYP450 3A4 substrateSubstrate0.5249
CYP450 1A2 substrateNon-inhibitor0.7685
CYP450 2C9 inhibitorNon-inhibitor0.7817
CYP450 2D6 inhibitorNon-inhibitor0.8893
CYP450 2C19 inhibitorNon-inhibitor0.7308
CYP450 3A4 inhibitorNon-inhibitor0.8039
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8119
Ames testNon AMES toxic0.6779
CarcinogenicityNon-carcinogens0.8378
BiodegradationNot ready biodegradable0.9875
Rat acute toxicity2.5271 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9906
hERG inhibition (predictor II)Non-inhibitor0.9169
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/MSsplash10-0002-2024900000-1f1db66d925f33bf8834
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0011900000-0eaebd9817c09b3b3219
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00ks-9100000000-5a07f0b6177e5bdee39f
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03fr-9228200000-faf5ce597215d0a8d70d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-9100000000-8e3d62f0062a05ed9cbe
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0403-9300100000-fd18f7873724c3d94797
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]-198.75594
predicted
DeepCCS 1.0 (2019)
[M+H]+201.15149
predicted
DeepCCS 1.0 (2019)
[M+Na]+208.30974
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Disintegrin and metalloproteinase domain-containing protein 28
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
May play a role in the adhesive and proteolytic events that occur during lymphocyte emigration or may function in ectodomain shedding of lymphocyte surface target proteins, such as FASL and CD40L. ...
Gene Name
ADAM28
Uniprot ID
Q9UKQ2
Uniprot Name
Disintegrin and metalloproteinase domain-containing protein 28
Molecular Weight
87147.04 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 June 13, 2005 13:24 / Updated at June 12, 2020 16:52