NAV

(2s,3r)-3-Amino-2-Hydroxy-5-(Ethylsulfanyl)Pentanoyl-((S)-(-)-(1-Naphthyl)Ethyl)Amide

Identification

Generic Name
(2s,3r)-3-Amino-2-Hydroxy-5-(Ethylsulfanyl)Pentanoyl-((S)-(-)-(1-Naphthyl)Ethyl)Amide
DrugBank Accession Number
DB04108
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 346.487
Monoisotopic: 346.171498776
Chemical Formula
C19H26N2O2S
Synonyms
Not Available
Poor quality drug data slowing you down?
Unlock 38% more drug discovery time and eliminate decision-making doubts with this one-stop guide to quality drug data.
Download eBook
Poor quality drug data slowing you down?
Download eBook

Pharmacology

Indication

Not Available

Reduce drug development failure rates
Build, train, & validate machine-learning models
with evidence-based and structured datasets.
See how
Build, train, & validate predictive machine-learning models with structured datasets.
See how
Contraindications & Blackbox Warnings
Prevent Adverse Drug Events Today
Tap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.
Learn more
Avoid life-threatening adverse drug events with our Clinical API
Learn more
Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UMethionine aminopeptidase 2Not 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
Improve decision support & research outcomes
With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!
See the data
Improve decision support & research outcomes with our structured adverse effects data.
See a data sample
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 beta amino acids and derivatives. These are amino acids having a (-NH2) group attached to the beta carbon atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Beta amino acids and derivatives
Alternative Parents
Naphthalenes / N-acyl amines / Monosaccharides / Secondary carboxylic acid amides / Secondary alcohols / Sulfenyl compounds / Dialkylthioethers / Organopnictogen compounds / Organic oxides / Monoalkylamines
show 2 more
Substituents
Alcohol / Amine / Aromatic homopolycyclic compound / Benzenoid / Beta amino acid or derivatives / Carbonyl group / Carboxamide group / Dialkylthioether / Fatty acyl / Fatty amide
show 17 more
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
AIIOXZPEXXZCML-KKXDTOCCSA-N
InChI
InChI=1S/C19H26N2O2S/c1-3-24-12-11-17(20)18(22)19(23)21-13(2)15-10-6-8-14-7-4-5-9-16(14)15/h4-10,13,17-18,22H,3,11-12,20H2,1-2H3,(H,21,23)/t13-,17-,18-/m0/s1
IUPAC Name
(2S,3S)-3-amino-5-(ethylsulfanyl)-2-hydroxy-N-[(1S)-1-(naphthalen-1-yl)ethyl]pentanamide
SMILES
[H][C@](N)(CCSCC)[C@]([H])(O)C(=O)N[C@@]([H])(C)C1=C2C=CC=CC2=CC=C1

References

General References
Not Available
PubChem Compound
5287684
PubChem Substance
46508224
ChemSpider
4450002
ZINC
ZINC000012504146
PDBe Ligand
AO1
PDB Entries
1r5g

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 Solubility0.00918 mg/mLALOGPS
logP2.55ALOGPS
logP2.24Chemaxon
logS-4.6ALOGPS
pKa (Strongest Acidic)12.57Chemaxon
pKa (Strongest Basic)8.75Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area75.35 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity100.55 m3·mol-1Chemaxon
Polarizability38.96 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9961
Blood Brain Barrier+0.6308
Caco-2 permeable-0.622
P-glycoprotein substrateSubstrate0.788
P-glycoprotein inhibitor INon-inhibitor0.8056
P-glycoprotein inhibitor IINon-inhibitor0.841
Renal organic cation transporterNon-inhibitor0.8616
CYP450 2C9 substrateNon-substrate0.7859
CYP450 2D6 substrateNon-substrate0.6918
CYP450 3A4 substrateNon-substrate0.5
CYP450 1A2 substrateInhibitor0.5101
CYP450 2C9 inhibitorNon-inhibitor0.8022
CYP450 2D6 inhibitorNon-inhibitor0.6743
CYP450 2C19 inhibitorNon-inhibitor0.6996
CYP450 3A4 inhibitorNon-inhibitor0.6842
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5773
Ames testNon AMES toxic0.6518
CarcinogenicityNon-carcinogens0.8803
BiodegradationNot ready biodegradable0.9876
Rat acute toxicity2.3330 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9917
hERG inhibition (predictor II)Inhibitor0.7547
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-MSsplash10-0a6s-9822000000-f25dc7f66dbe64102675
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00kk-0889000000-878a6b9311f2ea96d9ce
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03dj-6904000000-aa8821a06b70d2789534
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-9200000000-adc00a4d49365703a108
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0l4j-3964000000-510eca61c2c3cadd5bf7
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-9100000000-f20f25da3656f37b9109
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0aor-2900000000-97c2e5505117ce0a5078
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]-187.52196
predicted
DeepCCS 1.0 (2019)
[M+H]+189.91753
predicted
DeepCCS 1.0 (2019)
[M+Na]+196.0796
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
Learn more
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
Learn more
Details1. Methionine aminopeptidase 2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Poly(a) rna binding
Specific Function
Cotranslationally removes the N-terminal methionine from nascent proteins. The N-terminal methionine is often cleaved when the second residue in the primary sequence is small and uncharged (Met-Ala...
Gene Name
METAP2
Uniprot ID
P50579
Uniprot Name
Methionine aminopeptidase 2
Molecular Weight
52891.145 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