NAV

5'-{[4-(aminooxy)butyl](methyl)amino}-5'-deoxy-8-ethenyladenosine

Identification

Generic Name
5'-{[4-(aminooxy)butyl](methyl)amino}-5'-deoxy-8-ethenyladenosine
DrugBank Accession Number
DB08163
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 393.4408
Monoisotopic: 393.212452387
Chemical Formula
C17H27N7O4
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
US-adenosylmethionine decarboxylase proenzymeNot 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 5'-deoxyribonucleosides. These are nucleosides in which the oxygen atom at the 5'position of the ribose moiety has been replaced by another atom. The nucleobases here are limited to purine, pyrimidine, and pyridine derivatives.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
5'-deoxyribonucleosides
Sub Class
Not Available
Direct Parent
5'-deoxyribonucleosides
Alternative Parents
Glycosylamines / 6-aminopurines / Pentoses / Aminopyrimidines and derivatives / Imidolactams / N-substituted imidazoles / Heteroaromatic compounds / Tetrahydrofurans / Trialkylamines / 1,2-diols
show 6 more
Substituents
1,2-diol / 5'-deoxyribonucleoside / 6-aminopurine / Alcohol / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Glycosyl compound
show 23 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
XUKYGMIDWKBMIW-IWCJZZDYSA-N
InChI
InChI=1S/C17H27N7O4/c1-3-11-22-12-15(18)20-9-21-16(12)24(11)17-14(26)13(25)10(28-17)8-23(2)6-4-5-7-27-19/h3,9-10,13-14,17,25-26H,1,4-8,19H2,2H3,(H2,18,20,21)/t10-,13-,14-,17-/m1/s1
IUPAC Name
(2R,3R,4S,5R)-2-(6-amino-8-ethenyl-9H-purin-9-yl)-5-({[4-(aminooxy)butyl](methyl)amino}methyl)oxolane-3,4-diol
SMILES
[H][C@]1(CN(C)CCCCON)O[C@@]([H])(N2C(C=C)=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])O

References

General References
Not Available
PubChem Compound
25181315
PubChem Substance
99444634
ChemSpider
25060153
ZINC
ZINC000053683388
PDBe Ligand
M8E
PDB Entries
3dz6

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 Solubility2.68 mg/mLALOGPS
logP-0.11ALOGPS
logP-0.38Chemaxon
logS-2.2ALOGPS
pKa (Strongest Acidic)12.47Chemaxon
pKa (Strongest Basic)8.54Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count10Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area157.8 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity103.88 m3·mol-1Chemaxon
Polarizability41.47 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9685
Blood Brain Barrier+0.5535
Caco-2 permeable-0.6327
P-glycoprotein substrateSubstrate0.8436
P-glycoprotein inhibitor INon-inhibitor0.6587
P-glycoprotein inhibitor IINon-inhibitor0.9349
Renal organic cation transporterNon-inhibitor0.8769
CYP450 2C9 substrateNon-substrate0.8937
CYP450 2D6 substrateNon-substrate0.7917
CYP450 3A4 substrateSubstrate0.6467
CYP450 1A2 substrateNon-inhibitor0.8138
CYP450 2C9 inhibitorNon-inhibitor0.7884
CYP450 2D6 inhibitorNon-inhibitor0.8529
CYP450 2C19 inhibitorNon-inhibitor0.7749
CYP450 3A4 inhibitorNon-inhibitor0.7958
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9326
Ames testNon AMES toxic0.5
CarcinogenicityNon-carcinogens0.875
BiodegradationNot ready biodegradable0.996
Rat acute toxicity2.5135 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8684
hERG inhibition (predictor II)Non-inhibitor0.5765
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/MSsplash10-0006-0009000000-9c5d817578f64138c4a9
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0349000000-6b38b57c6c830123bc73
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ikc-2379000000-4f925b531cf5f830c4ef
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03dr-0946000000-d0d21d680f109b90935d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0k92-9442000000-9b0a057f92d15ebc5933
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0r0s-0911000000-b7138d49b97499f40811
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]-186.49327
predicted
DeepCCS 1.0 (2019)
[M+H]+188.88884
predicted
DeepCCS 1.0 (2019)
[M+Na]+195.25185
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. S-adenosylmethionine decarboxylase proenzyme
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Putrescine binding
Specific Function
Essential for biosynthesis of the polyamines spermidine and spermine. Promotes maintenance and self-renewal of embryonic stem cells, by maintaining spermine levels (By similarity).
Gene Name
AMD1
Uniprot ID
P17707
Uniprot Name
S-adenosylmethionine decarboxylase proenzyme
Molecular Weight
38339.335 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 September 15, 2010 21:29 / Updated at June 12, 2020 16:52