NAV

5'-O-(L-Serylsulfamoyl)adenosine

Identification

Generic Name
5'-O-(L-Serylsulfamoyl)adenosine
DrugBank Accession Number
DB03869
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 433.397
Monoisotopic: 433.101581309
Chemical Formula
C13H19N7O8S
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UThreonine--tRNA ligaseNot AvailableShigella flexneri
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 purine nucleosides. These are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Purine nucleosides
Sub Class
Not Available
Direct Parent
Purine nucleosides
Alternative Parents
Serine and derivatives / Glycosylamines / 6-aminopurines / Aminopyrimidines and derivatives / Imidolactams / Monosaccharides / N-substituted imidazoles / Tetrahydrofurans / Heteroaromatic compounds / Organic sulfuric acids and derivatives
show 9 more
Substituents
6-aminopurine / Alcohol / Alpha-amino acid or derivatives / Amine / Amino acid or derivatives / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Carbonyl group
show 28 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
HQXFJGONGJPTLZ-YTMOPEAISA-N
InChI
InChI=1S/C13H19N7O8S/c14-5(1-21)12(24)19-29(25,26)27-2-6-8(22)9(23)13(28-6)20-4-18-7-10(15)16-3-17-11(7)20/h3-6,8-9,13,21-23H,1-2,14H2,(H,19,24)(H2,15,16,17)/t5-,6+,8+,9+,13+/m0/s1
IUPAC Name
(2S)-2-amino-1-[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}sulfonyl)amino]-3-hydroxypropan-1-one
SMILES
[H]N([H])[C@@H](CO)C(=O)N([H])S(=O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=NC2=C(N=CN=C12)N([H])[H]

References

General References
Not Available
PubChem Compound
445736
PubChem Substance
46508279
ChemSpider
393288
BindingDB
50339906
ChEMBL
CHEMBL1163070
ZINC
ZINC000013542770
PDBe Ligand
SSA
PDB Entries
1fyf / 1set / 1tkg / 2cj9 / 2dq0 / 2dq3 / 2hl2 / 3hxw / 3hy1 / 3qo8 …
show 12 more

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 Solubility6.31 mg/mLALOGPS
logP-1.6ALOGPS
logP-4.9Chemaxon
logS-1.8ALOGPS
pKa (Strongest Acidic)2.69Chemaxon
pKa (Strongest Basic)6.22Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count13Chemaxon
Hydrogen Donor Count6Chemaxon
Polar Surface Area238.03 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity93.69 m3·mol-1Chemaxon
Polarizability40.55 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9576
Blood Brain Barrier+0.5369
Caco-2 permeable-0.6554
P-glycoprotein substrateNon-substrate0.6293
P-glycoprotein inhibitor INon-inhibitor0.816
P-glycoprotein inhibitor IINon-inhibitor0.9598
Renal organic cation transporterNon-inhibitor0.9483
CYP450 2C9 substrateNon-substrate0.8792
CYP450 2D6 substrateNon-substrate0.8026
CYP450 3A4 substrateNon-substrate0.5448
CYP450 1A2 substrateNon-inhibitor0.8027
CYP450 2C9 inhibitorNon-inhibitor0.8143
CYP450 2D6 inhibitorNon-inhibitor0.8709
CYP450 2C19 inhibitorNon-inhibitor0.8158
CYP450 3A4 inhibitorNon-inhibitor0.767
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9395
Ames testNon AMES toxic0.6434
CarcinogenicityNon-carcinogens0.5536
BiodegradationNot ready biodegradable0.9273
Rat acute toxicity2.5079 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9446
hERG inhibition (predictor II)Non-inhibitor0.6879
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/MSsplash10-001j-0019800000-48fe255e8889ee25bcd2
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000x-0109200000-d74ef4c92541a8ec7347
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-1930200000-d2a4b63eb377100bcc9b
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000x-9557300000-3a25821b00834926bf20
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-2910100000-c5c58f7586cf248e4b36
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0902100000-ce9b5b8a1ea6ee55c563
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]-174.21046
predicted
DeepCCS 1.0 (2019)
[M+H]+176.10979
predicted
DeepCCS 1.0 (2019)
[M+Na]+181.8502
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Threonine--tRNA ligase
Kind
Protein
Organism
Shigella flexneri
Pharmacological action
Unknown
General Function
Threonine-trna ligase activity
Specific Function
ThrS is also a translational repressor protein, it controls the translation of its own gene by binding to its mRNA.
Gene Name
thrS
Uniprot ID
P0A8M5
Uniprot Name
Threonine--tRNA ligase
Molecular Weight
74013.765 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