5'-S-[2-(decylamino)ethyl]-5'-thioadenosine

Identification

Generic Name
5'-S-[2-(decylamino)ethyl]-5'-thioadenosine
DrugBank Accession Number
DB07413
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 466.641
Monoisotopic: 466.272609802
Chemical Formula
C22H38N6O3S
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UHydroxymycolate synthase MmaA4Not AvailableMycobacterium tuberculosis
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'-deoxy-5'-thionucleosides. These are 5'-deoxyribonucleosides in which the ribose is thio-substituted at the 5'position by a S-alkyl group.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
5'-deoxyribonucleosides
Sub Class
5'-deoxy-5'-thionucleosides
Direct Parent
5'-deoxy-5'-thionucleosides
Alternative Parents
Glycosylamines / 6-aminopurines / Pentoses / Aminopyrimidines and derivatives / Imidolactams / N-substituted imidazoles / Tetrahydrofurans / Heteroaromatic compounds / 1,2-diols / Secondary alcohols
show 8 more
Substituents
1,2-diol / 5'-deoxy-5'-thionucleoside / 6-aminopurine / Alcohol / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Dialkylthioether
show 27 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
CJIJFWHOTNCRDA-WGQQHEPDSA-N
InChI
InChI=1S/C22H38N6O3S/c1-2-3-4-5-6-7-8-9-10-24-11-12-32-13-16-18(29)19(30)22(31-16)28-15-27-17-20(23)25-14-26-21(17)28/h14-16,18-19,22,24,29-30H,2-13H2,1H3,(H2,23,25,26)/t16-,18-,19-,22-/m1/s1
IUPAC Name
(2R,3R,4S,5S)-2-(6-amino-9H-purin-9-yl)-5-({[2-(decylamino)ethyl]sulfanyl}methyl)oxolane-3,4-diol
SMILES
[H][C@]1(CSCCNCCCCCCCCCC)O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])O

References

General References
Not Available
PubChem Compound
12000133
PubChem Substance
99443884
ChemSpider
10172600
ZINC
ZINC000053683035
PDBe Ligand
B32

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 Solubility0.0385 mg/mLALOGPS
logP2.44ALOGPS
logP2.76Chemaxon
logS-4.1ALOGPS
pKa (Strongest Acidic)12.47Chemaxon
pKa (Strongest Basic)10.16Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area131.34 Å2Chemaxon
Rotatable Bond Count15Chemaxon
Refractivity128.44 m3·mol-1Chemaxon
Polarizability54.6 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier-0.5578
Caco-2 permeable-0.7021
P-glycoprotein substrateSubstrate0.8074
P-glycoprotein inhibitor INon-inhibitor0.9006
P-glycoprotein inhibitor IINon-inhibitor0.9856
Renal organic cation transporterNon-inhibitor0.9081
CYP450 2C9 substrateNon-substrate0.8697
CYP450 2D6 substrateNon-substrate0.7749
CYP450 3A4 substrateNon-substrate0.5
CYP450 1A2 substrateNon-inhibitor0.8589
CYP450 2C9 inhibitorNon-inhibitor0.8665
CYP450 2D6 inhibitorNon-inhibitor0.8693
CYP450 2C19 inhibitorNon-inhibitor0.8513
CYP450 3A4 inhibitorNon-inhibitor0.9009
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9175
Ames testNon AMES toxic0.5554
CarcinogenicityNon-carcinogens0.8294
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5847 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9187
hERG inhibition (predictor II)Non-inhibitor0.7135
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/MSsplash10-014i-0010900000-782acb56c18d5e2d589d
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0400900000-f48dafbbc84da42d9824
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00kr-2980500000-f42fd36532c15f40c9fb
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00m0-0980300000-bbb08b6d0d21af4fee96
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0avl-8930000000-26c83d30e335b3c21adb
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-3910000000-fab4faed45cb7b0f8859
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]-205.13586
predicted
DeepCCS 1.0 (2019)
[M+H]+208.39595
predicted
DeepCCS 1.0 (2019)
[M+Na]+215.8932
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Mycobacterium tuberculosis
Pharmacological action
Unknown
General Function
S-adenosylmethionine-dependent methyltransferase activity
Specific Function
Involved in the biosynthesis of hydroxymycolate, a common precursor of oxygenated mycolic acids (methoxy-mycolate and keto-mycolate). Probably transfers a methyl group from the S-adenosylmethionine...
Gene Name
mmaA4
Uniprot ID
Q79FX8
Uniprot Name
Hydroxymycolate synthase MmaA4
Molecular Weight
34670.13 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 21:21 / Updated at June 12, 2020 16:52