NAV

Nα-[(2S)-2-{[(S)-[(1S)-1-{[(Benzyloxy)carbonyl]amino}-2-phenylethyl](hydroxy)phosphoryl]methyl}-5-phenylpentanoyl]-L-tryptophanamide

Identification

Generic Name
Nα-[(2S)-2-{[(S)-[(1S)-1-{[(Benzyloxy)carbonyl]amino}-2-phenylethyl](hydroxy)phosphoryl]methyl}-5-phenylpentanoyl]-L-tryptophanamide
DrugBank Accession Number
DB04318
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Similar Structures
Weight
Average: 694.7557
Monoisotopic: 694.29202164
Chemical Formula
C39H43N4O6P
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UStromelysin-3Not 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 n-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid (or a derivative thereof) which bears an acyl group at its terminal nitrogen atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
N-acyl-alpha amino acids and derivatives
Alternative Parents
Tryptamines and derivatives / 3-alkylindoles / Benzyloxycarbonyls / Substituted pyrroles / N-acyl amines / Carbamate esters / Heteroaromatic compounds / Secondary carboxylic acid amides / Primary carboxylic acid amides / Organic carbonic acids and derivatives
show 7 more
Substituents
3-alkylindole / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Benzyloxycarbonyl / Carbamic acid ester / Carbonic acid derivative / Carbonyl group / Carboxamide group / Fatty acyl
show 21 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
YQEMFOGNUTYMTJ-JNBVYXHXSA-N
InChI
InChI=1S/C39H43N4O6P/c40-37(44)35(24-32-25-41-34-22-11-10-21-33(32)34)42-38(45)31(20-12-19-28-13-4-1-5-14-28)27-50(47,48)36(23-29-15-6-2-7-16-29)43-39(46)49-26-30-17-8-3-9-18-30/h1-11,13-18,21-22,25,31,35-36,41H,12,19-20,23-24,26-27H2,(H2,40,44)(H,42,45)(H,43,46)(H,47,48)/t31-,35+,36+/m1/s1
IUPAC Name
[(1S)-1-{[(benzyloxy)carbonyl]amino}-2-phenylethyl][(2S)-2-{[(1S)-1-carbamoyl-2-(1H-indol-3-yl)ethyl]carbamoyl}-2-(3-phenylpropyl)ethyl]phosphinic acid
SMILES
[H]N([H])C(=O)[C@H](CC1=CN([H])C2=CC=CC=C12)N([H])C(=O)[C@H](CCCC1=CC=CC=C1)CP(O)(=O)[C@@H](CC1=CC=CC=C1)N([H])C(=O)OCC1=CC=CC=C1

References

General References
Not Available
PubChem Compound
446143
PubChem Substance
46504852
ChemSpider
393578
ZINC
ZINC000026576087
PDBe Ligand
RXP
PDB Entries
1hv5

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 Solubility0.000359 mg/mLALOGPS
logP4.02ALOGPS
logP5.79Chemaxon
logS-6.3ALOGPS
pKa (Strongest Acidic)1.54Chemaxon
pKa (Strongest Basic)-1.2Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area163.61 Å2Chemaxon
Rotatable Bond Count18Chemaxon
Refractivity192.79 m3·mol-1Chemaxon
Polarizability73.5 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.628
Blood Brain Barrier+0.6648
Caco-2 permeable-0.7693
P-glycoprotein substrateSubstrate0.6154
P-glycoprotein inhibitor INon-inhibitor0.8523
P-glycoprotein inhibitor IINon-inhibitor0.9836
Renal organic cation transporterNon-inhibitor0.8776
CYP450 2C9 substrateNon-substrate0.826
CYP450 2D6 substrateNon-substrate0.8021
CYP450 3A4 substrateNon-substrate0.5653
CYP450 1A2 substrateNon-inhibitor0.8086
CYP450 2C9 inhibitorNon-inhibitor0.7826
CYP450 2D6 inhibitorNon-inhibitor0.8724
CYP450 2C19 inhibitorNon-inhibitor0.7022
CYP450 3A4 inhibitorNon-inhibitor0.6146
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.778
Ames testNon AMES toxic0.6681
CarcinogenicityNon-carcinogens0.9276
BiodegradationNot ready biodegradable0.9918
Rat acute toxicity2.4732 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.959
hERG inhibition (predictor II)Non-inhibitor0.5811
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/MSsplash10-0002-0000169000-7b0b5be758033e3c7bf2
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-05mo-0100296000-b29734388c75e23ad021
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0109444000-396548d306c936b68519
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-1101490000-8e0d3d5214c44d526a39
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-5921102000-75fa77693f8fa8cfa009
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0bt9-5039351000-ef61c3d2069fa17c37ac
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-225.95238
predicted
DeepCCS 1.0 (2019)
[M+H]+227.7773
predicted
DeepCCS 1.0 (2019)
[M+Na]+233.43033
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Stromelysin-3
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
May play an important role in the progression of epithelial malignancies.
Gene Name
MMP11
Uniprot ID
P24347
Uniprot Name
Stromelysin-3
Molecular Weight
54589.395 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]
  3. 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