NAV

(3R,4S)-1-[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-[(butylsulfanyl)methyl]pyrrolidin-3-ol

Identification

Generic Name
(3R,4S)-1-[(4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl)methyl]-4-[(butylsulfanyl)methyl]pyrrolidin-3-ol
DrugBank Accession Number
DB07463
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 335.468
Monoisotopic: 335.177981137
Chemical Formula
C16H25N5OS
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
U5'-methylthioadenosine/S-adenosylhomocysteine nucleosidaseNot AvailableVibrio cholerae serotype O1 (strain ATCC 39315 / El Tor Inaba N16961)
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 pyrrolopyrimidines. These are compounds containing a pyrrolopyrimidine moiety, which consists of a pyrrole ring fused to a pyrimidine. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyrrolopyrimidines
Sub Class
Not Available
Direct Parent
Pyrrolopyrimidines
Alternative Parents
Aralkylamines / Aminopyrimidines and derivatives / Substituted pyrroles / N-alkylpyrrolidines / Imidolactams / Heteroaromatic compounds / Trialkylamines / Secondary alcohols / 1,2-aminoalcohols / Sulfenyl compounds
show 5 more
Substituents
1,2-aminoalcohol / Alcohol / Amine / Aminopyrimidine / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle / Dialkylthioether / Heteroaromatic compound / Hydrocarbon derivative
show 19 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
LTSUEVPGSXUJHT-OLZOCXBDSA-N
InChI
InChI=1S/C16H25N5OS/c1-2-3-4-23-9-12-7-21(8-13(12)22)6-11-5-18-15-14(11)19-10-20-16(15)17/h5,10,12-13,18,22H,2-4,6-9H2,1H3,(H2,17,19,20)/t12-,13+/m1/s1
IUPAC Name
(3R,4S)-1-({4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl}methyl)-4-[(butylsulfanyl)methyl]pyrrolidin-3-ol
SMILES
[H][C@]1(O)CN(CC2=CNC3=C2N=CN=C3N)C[C@]1([H])CSCCCC

References

General References
Not Available
PubChem Compound
11393519
PubChem Substance
99443934
ChemSpider
9568421
BindingDB
36436
ChEMBL
CHEMBL1231347
ZINC
ZINC000013648011
PDBe Ligand
BIG
PDB Entries
3dp9 / 4f3c / 4ffs / 4wkc / 5tc5 / 6ayr

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 Solubility0.0861 mg/mLALOGPS
logP1.67ALOGPS
logP1.66Chemaxon
logS-3.6ALOGPS
pKa (Strongest Acidic)13.47Chemaxon
pKa (Strongest Basic)8.37Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area91.06 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity96.44 m3·mol-1Chemaxon
Polarizability37.74 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.997
Blood Brain Barrier+0.63
Caco-2 permeable-0.6034
P-glycoprotein substrateSubstrate0.8295
P-glycoprotein inhibitor INon-inhibitor0.8971
P-glycoprotein inhibitor IINon-inhibitor0.9341
Renal organic cation transporterNon-inhibitor0.8069
CYP450 2C9 substrateNon-substrate0.8472
CYP450 2D6 substrateNon-substrate0.7284
CYP450 3A4 substrateNon-substrate0.6066
CYP450 1A2 substrateNon-inhibitor0.7613
CYP450 2C9 inhibitorNon-inhibitor0.879
CYP450 2D6 inhibitorNon-inhibitor0.849
CYP450 2C19 inhibitorNon-inhibitor0.8453
CYP450 3A4 inhibitorNon-inhibitor0.9172
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9092
Ames testNon AMES toxic0.6149
CarcinogenicityNon-carcinogens0.923
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5934 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.5292
hERG inhibition (predictor II)Non-inhibitor0.6261
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/MSsplash10-000i-0039000000-cddabf79bae5f42b8036
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0109000000-f8c621d18ced3d8ce4b8
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-00nr-0196000000-ab1467529aa175e5fa94
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0gx0-1096000000-ace1a15489a9e3754ffd
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000j-2961000000-5e5a375eee17ed9c2abd
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-8491000000-ac22db3f0b50bf63e26f
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]-176.38693
predicted
DeepCCS 1.0 (2019)
[M+H]+178.90694
predicted
DeepCCS 1.0 (2019)
[M+Na]+186.14442
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. 5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase
Kind
Protein
Organism
Vibrio cholerae serotype O1 (strain ATCC 39315 / El Tor Inaba N16961)
Pharmacological action
Unknown
General Function
Methylthioadenosine nucleosidase activity
Specific Function
Catalyzes the irreversible cleavage of the glycosidic bond in both 5'-methylthioadenosine (MTA) and S-adenosylhomocysteine (SAH/AdoHcy) to adenine and the corresponding thioribose, 5'-methylthiorib...
Gene Name
mtnN
Uniprot ID
Q9KPI8
Uniprot Name
5'-methylthioadenosine/S-adenosylhomocysteine nucleosidase
Molecular Weight
24525.01 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 21:22 / Updated at June 12, 2020 16:52