Adenylyl-(3'-5')-uridine 3'-monophosphate

Identification

Generic Name
Adenylyl-(3'-5')-uridine 3'-monophosphate
DrugBank Accession Number
DB01792
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 653.3872
Monoisotopic: 653.088386189
Chemical Formula
C19H25N7O15P2
Synonyms
  • Adenylyl-(3'-5')-3'-uridylic acid
  • Adenylyl-3'-5'-phospho-uridine-3'-monophosphate

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UDiphtheria toxinNot AvailableCorynephage omega
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
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as (3'->5')-dinucleotides. These are dinucleotides where the two bases are connected via a (3'->5')-phosphodiester linkage.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
(3'->5')-dinucleotides and analogues
Sub Class
(3'->5')-dinucleotides
Direct Parent
(3'->5')-dinucleotides
Alternative Parents
Pyrimidine ribonucleoside 3',5'-bisphosphates / Pentose phosphates / Ribonucleoside 3'-phosphates / Glycosylamines / Monosaccharide phosphates / 6-aminopurines / Monoalkyl phosphates / Dialkyl phosphates / Aminopyrimidines and derivatives / Pyrimidones
show 16 more
Substituents
(3'->5')-dinucleotide / 6-aminopurine / Alcohol / Alkyl phosphate / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Dialkyl phosphate
show 37 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
1985-21-3
InChI Key
FZCSEXOMUJFOHQ-KPKSGTNCSA-N
InChI
InChI=1S/C19H25N7O15P2/c20-15-10-16(22-5-21-15)26(6-23-10)18-11(29)13(7(3-27)38-18)41-43(35,36)37-4-8-14(40-42(32,33)34)12(30)17(39-8)25-2-1-9(28)24-19(25)31/h1-2,5-8,11-14,17-18,27,29-30H,3-4H2,(H,35,36)(H2,20,21,22)(H,24,28,31)(H2,32,33,34)/t7-,8-,11-,12-,13-,14-,17-,18-/m1/s1
IUPAC Name
{[(2R,3S,4R,5R)-2-{[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy}(hydroxy)phosphoryl)oxy]methyl}-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid
SMILES
NC1=NC=NC2=C1N=CN2[C@@H]1O[C@H](CO)[C@@H](OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2OP(O)(O)=O)N2C=CC(=O)NC2=O)[C@H]1O

References

General References
Not Available
PubChem Compound
164908
PubChem Substance
46508572
ChemSpider
144575
ZINC
ZINC000024469737
PDBe Ligand
APU
PDB Entries
1ddt / 1dtp / 1f0l / 1mdt / 8g0g

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
logP-6.4Chemaxon
pKa (Strongest Acidic)0.83Chemaxon
pKa (Strongest Basic)4.88Chemaxon
Physiological Charge-3Chemaxon
Hydrogen Acceptor Count16Chemaxon
Hydrogen Donor Count8Chemaxon
Polar Surface Area320.7 Å2Chemaxon
Rotatable Bond Count10Chemaxon
Refractivity133.73 m3·mol-1Chemaxon
Polarizability52.77 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.5765
Blood Brain Barrier+0.9409
Caco-2 permeable-0.7537
P-glycoprotein substrateNon-substrate0.5965
P-glycoprotein inhibitor INon-inhibitor0.8737
P-glycoprotein inhibitor IINon-inhibitor0.9515
Renal organic cation transporterNon-inhibitor0.9225
CYP450 2C9 substrateNon-substrate0.7501
CYP450 2D6 substrateNon-substrate0.842
CYP450 3A4 substrateNon-substrate0.5488
CYP450 1A2 substrateNon-inhibitor0.8704
CYP450 2C9 inhibitorNon-inhibitor0.8821
CYP450 2D6 inhibitorNon-inhibitor0.9017
CYP450 2C19 inhibitorNon-inhibitor0.8896
CYP450 3A4 inhibitorNon-inhibitor0.6969
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8719
Ames testNon AMES toxic0.8666
CarcinogenicityNon-carcinogens0.8548
BiodegradationNot ready biodegradable0.9803
Rat acute toxicity2.5366 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9665
hERG inhibition (predictor II)Non-inhibitor0.6867
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/MSsplash10-0udi-0000039000-367472d5cf4ae44ff522
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0000009000-b5e7a9bd857f7d298e87
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f79-0512019000-f744c952c680baef4d3c
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0zor-2001019000-6990a9404f7a43e9c88f
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01pc-0900001000-a014d2ffe20d5a84c9ca
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-03gl-8602259000-79a0c060ede35965b3e0
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-248.9903678
predicted
DarkChem Lite v0.1.0
[M-H]-204.26813
predicted
DeepCCS 1.0 (2019)
[M+H]+247.9173678
predicted
DarkChem Lite v0.1.0
[M+H]+206.16356
predicted
DeepCCS 1.0 (2019)
[M+Na]+247.3853678
predicted
DarkChem Lite v0.1.0
[M+Na]+211.94518
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Corynephage omega
Pharmacological action
Unknown
General Function
Nad+-diphthamide adp-ribosyltransferase activity
Specific Function
Diphtheria toxin, produced by a phage infecting Corynebacterium diphtheriae, is a proenzyme that, after activation, catalyzes the covalent attachment of the ADP ribose moiety of NAD to elongation f...
Gene Name
Not Available
Uniprot ID
P00587
Uniprot Name
Diphtheria toxin
Molecular Weight
60814.155 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