NAV

[(2R,3S,4R,5R)-5-(4-acetonyl-3-carbamoyl-pyridin-1-ium-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methyl [[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl] phosphate

Identification

Generic Name
[(2R,3S,4R,5R)-5-(4-acetonyl-3-carbamoyl-pyridin-1-ium-1-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methyl [[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxy-tetrahydrofuran-2-yl]methoxy-hydroxy-phosphoryl] phosphate
DrugBank Accession Number
DB02732
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 719.4884
Monoisotopic: 719.135336381
Chemical Formula
C24H31N7O15P2
Synonyms
  • Nicotinamide adenine dinucleotide acetone adduct
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
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'->5')-dinucleotides. These are dinucleotides where the two bases are connected via a (5'->5')-phosphodiester linkage.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
(5'->5')-dinucleotides
Sub Class
Not Available
Direct Parent
(5'->5')-dinucleotides
Alternative Parents
Purine nucleotide sugars / Purine ribonucleoside diphosphates / Purine ribonucleoside monophosphates / Nicotinamide nucleotides / Pentose phosphates / Glycosylamines / Monosaccharide phosphates / 6-aminopurines / Organic pyrophosphates / Nicotinamides
show 19 more
Substituents
(5'->5')-dinucleotide / 6-aminopurine / Alcohol / Alkyl phosphate / Amine / Amino acid or derivatives / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole
show 45 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
SGHBFOOIAAJJMI-YDKVLQLQSA-N
InChI
InChI=1S/C24H31N7O15P2/c1-10(32)4-11-2-3-30(5-12(11)21(26)37)23-18(35)16(33)13(44-23)6-42-47(38,39)46-48(40,41)43-7-14-17(34)19(36)24(45-14)31-9-29-15-20(25)27-8-28-22(15)31/h2-3,5,8-9,13-14,16-19,23-24,33-36H,4,6-7H2,1H3,(H5-,25,26,27,28,37,38,39,40,41)/t13-,14-,16-,17-,18-,19-,23-,24-/m1/s1
IUPAC Name
1-[(2R,3R,4S,5R)-5-{[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl phosphonato)oxy]methyl}-3,4-dihydroxyoxolan-2-yl]-3-carbamoyl-4-(2-oxopropyl)-1lambda5-pyridin-1-ylium
SMILES
[H]N([H])C(=O)C1=C(CC(C)=O)C=C[N+](=C1)[C@@H]1O[C@H](COP([O-])(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C(N=CN=C23)N([H])[H])[C@@H](O)[C@H]1O

References

General References
Not Available
PubChem Compound
131704217
PubChem Substance
46507420
ChemSpider
4450943
PDBe Ligand
NAE
PDB Entries
1b15 / 3i3o

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 Solubility1.7 mg/mLALOGPS
logP-0.83ALOGPS
logP-10Chemaxon
logS-2.7ALOGPS
pKa (Strongest Acidic)1.85Chemaxon
pKa (Strongest Basic)4.93Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count16Chemaxon
Hydrogen Donor Count7Chemaxon
Polar Surface Area338.16 Å2Chemaxon
Rotatable Bond Count13Chemaxon
Refractivity155.73 m3·mol-1Chemaxon
Polarizability64.38 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.8623
Blood Brain Barrier+0.6392
Caco-2 permeable-0.7154
P-glycoprotein substrateSubstrate0.5287
P-glycoprotein inhibitor INon-inhibitor0.8663
P-glycoprotein inhibitor IINon-inhibitor0.9527
Renal organic cation transporterNon-inhibitor0.9518
CYP450 2C9 substrateNon-substrate0.801
CYP450 2D6 substrateNon-substrate0.8379
CYP450 3A4 substrateSubstrate0.5265
CYP450 1A2 substrateNon-inhibitor0.8832
CYP450 2C9 inhibitorNon-inhibitor0.8808
CYP450 2D6 inhibitorNon-inhibitor0.886
CYP450 2C19 inhibitorNon-inhibitor0.8682
CYP450 3A4 inhibitorNon-inhibitor0.8341
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8987
Ames testNon AMES toxic0.83
CarcinogenicityNon-carcinogens0.9016
BiodegradationNot ready biodegradable0.969
Rat acute toxicity2.5961 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9744
hERG inhibition (predictor II)Non-inhibitor0.6579
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-237.77237
predicted
DeepCCS 1.0 (2019)
[M+H]+239.49657
predicted
DeepCCS 1.0 (2019)
[M+Na]+245.82632
predicted
DeepCCS 1.0 (2019)

Drug created at June 13, 2005 13:24 / Updated at August 01, 2020 13:45