NAV

(2R,3R,4S,5R,6E)-3,4,5-Trihydroxy-N-[(3S,6R)-6-hydroxy-2-oxo-3-azepanyl]-2-methoxy-8,8-dimethyl-6-nonenamide

Identification

Generic Name
(2R,3R,4S,5R,6E)-3,4,5-Trihydroxy-N-[(3S,6R)-6-hydroxy-2-oxo-3-azepanyl]-2-methoxy-8,8-dimethyl-6-nonenamide
DrugBank Accession Number
DB03396
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 388.4559
Monoisotopic: 388.220951388
Chemical Formula
C18H32N2O7
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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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
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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
Caprolactams / Azepanes / N-acyl amines / Monosaccharides / Secondary carboxylic acid amides / Secondary alcohols / Polyols / Dialkyl ethers / Azacyclic compounds / Organopnictogen compounds
show 4 more
Substituents
Alcohol / Aliphatic heteromonocyclic compound / Azacycle / Azepane / Caprolactam / Carbonyl group / Carboxamide group / Dialkyl ether / Ether / Fatty acyl
show 16 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
FVBBTOIQETYGOA-SDNORSGYSA-N
InChI
InChI=1S/C18H32N2O7/c1-18(2,3)8-7-12(22)13(23)14(24)15(27-4)17(26)20-11-6-5-10(21)9-19-16(11)25/h7-8,10-15,21-24H,5-6,9H2,1-4H3,(H,19,25)(H,20,26)/b8-7+/t10-,11+,12-,13+,14-,15-/m1/s1
IUPAC Name
(2R,3R,4S,5R,6E)-3,4,5-trihydroxy-N-[(3S,6R)-6-hydroxy-2-oxoazepan-3-yl]-2-methoxy-8,8-dimethylnon-6-enamide
SMILES
[H]N([C@H]1CC[C@@H](O)CN([H])C1=O)C(=O)[C@H](OC)[C@H](O)[C@@H](O)[C@H](O)\C=C\C(C)(C)C

References

General References
Not Available
PubChem Compound
448235
PubChem Substance
46507692
ChemSpider
395101
ZINC
ZINC000005884811
PDBe Ligand
TDE
PDB Entries
1qzy

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 Solubility10.9 mg/mLALOGPS
logP-0.69ALOGPS
logP-1.6Chemaxon
logS-1.6ALOGPS
pKa (Strongest Acidic)12.15Chemaxon
pKa (Strongest Basic)-2.9Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count7Chemaxon
Hydrogen Donor Count6Chemaxon
Polar Surface Area148.35 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity97.96 m3·mol-1Chemaxon
Polarizability41.34 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.6486
Blood Brain Barrier-0.9032
Caco-2 permeable-0.6869
P-glycoprotein substrateSubstrate0.8376
P-glycoprotein inhibitor INon-inhibitor0.5078
P-glycoprotein inhibitor IINon-inhibitor0.8606
Renal organic cation transporterNon-inhibitor0.9427
CYP450 2C9 substrateNon-substrate0.8186
CYP450 2D6 substrateNon-substrate0.8143
CYP450 3A4 substrateSubstrate0.6398
CYP450 1A2 substrateNon-inhibitor0.9007
CYP450 2C9 inhibitorNon-inhibitor0.8979
CYP450 2D6 inhibitorNon-inhibitor0.9138
CYP450 2C19 inhibitorNon-inhibitor0.8953
CYP450 3A4 inhibitorNon-inhibitor0.9582
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9907
Ames testNon AMES toxic0.7862
CarcinogenicityNon-carcinogens0.9401
BiodegradationNot ready biodegradable0.9756
Rat acute toxicity2.4992 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9948
hERG inhibition (predictor II)Non-inhibitor0.8568
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/MSsplash10-010a-3598000000-77ca9cc1653b50d0d80e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-054x-0915000000-d4aeb97896d509ce8fff
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-006y-2921000000-cba2635d0f1ea3ef54d5
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-5792000000-c979888bea9a5dcabeda
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-006x-2900000000-518d84caa8064e918cfc
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0bvi-5911000000-96c904add7b11c423be5
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]-183.41982
predicted
DeepCCS 1.0 (2019)
[M+H]+185.2447
predicted
DeepCCS 1.0 (2019)
[M+Na]+191.03108
predicted
DeepCCS 1.0 (2019)

Targets

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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]

Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52