8-Bromoadenosine-5'-Diphosphate

Identification

Generic Name
8-Bromoadenosine-5'-Diphosphate
DrugBank Accession Number
DB04554
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 506.097
Monoisotopic: 504.939927364
Chemical Formula
C10H14BrN5O10P2
Synonyms
Not Available

Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
US-adenosylmethionine synthaseNot 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 ribonucleoside diphosphates. These are purine ribobucleotides with diphosphate group linked to the ribose moiety.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Purine nucleotides
Sub Class
Purine ribonucleotides
Direct Parent
Purine ribonucleoside diphosphates
Alternative Parents
Purine ribonucleoside monophosphates / Pentose phosphates / Glycosylamines / 6-aminopurines / Monosaccharide phosphates / Organic pyrophosphates / Aminopyrimidines and derivatives / Monoalkyl phosphates / Aryl bromides / Imidolactams
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Substituents
1,2-diol / 6-aminopurine / Alcohol / Alkyl phosphate / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Aryl bromide / Aryl halide / Azacycle
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Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
KVVVTFSHHQCHNZ-UUOKFMHZSA-N
InChI
InChI=1S/C10H14BrN5O10P2/c11-10-15-4-7(12)13-2-14-8(4)16(10)9-6(18)5(17)3(25-9)1-24-28(22,23)26-27(19,20)21/h2-3,5-6,9,17-18H,1H2,(H,22,23)(H2,12,13,14)(H2,19,20,21)/t3-,5-,6-,9-/m1/s1
IUPAC Name
[({[(2R,3S,4R,5R)-5-(6-amino-8-bromo-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]phosphonic acid
SMILES
[H][C@]1(COP(O)(=O)OP(O)(O)=O)O[C@@]([H])(N2C(Br)=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])O

References

General References
Not Available
PubChem Compound
447236
PubChem Substance
46508153
ChemSpider
394387
ChEMBL
CHEMBL1230795
ZINC
ZINC000013548110
PDBe Ligand
ABP
PDB Entries
1mxc

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 Solubility2.76 mg/mLALOGPS
logP-1ALOGPS
logP-3Chemaxon
logS-2.3ALOGPS
pKa (Strongest Acidic)1.74Chemaxon
pKa (Strongest Basic)3.93Chemaxon
Physiological Charge-3Chemaxon
Hydrogen Acceptor Count12Chemaxon
Hydrogen Donor Count6Chemaxon
Polar Surface Area232.6 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity92.57 m3·mol-1Chemaxon
Polarizability37.74 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.9078
Blood Brain Barrier+0.8077
Caco-2 permeable-0.7096
P-glycoprotein substrateNon-substrate0.6499
P-glycoprotein inhibitor INon-inhibitor0.8794
P-glycoprotein inhibitor IINon-inhibitor0.956
Renal organic cation transporterNon-inhibitor0.9513
CYP450 2C9 substrateNon-substrate0.8597
CYP450 2D6 substrateNon-substrate0.8279
CYP450 3A4 substrateNon-substrate0.5566
CYP450 1A2 substrateNon-inhibitor0.7165
CYP450 2C9 inhibitorNon-inhibitor0.8994
CYP450 2D6 inhibitorNon-inhibitor0.8217
CYP450 2C19 inhibitorNon-inhibitor0.8891
CYP450 3A4 inhibitorNon-inhibitor0.882
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9162
Ames testNon AMES toxic0.8118
CarcinogenicityNon-carcinogens0.8894
BiodegradationNot ready biodegradable0.9918
Rat acute toxicity2.4905 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9817
hERG inhibition (predictor II)Non-inhibitor0.7331
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/MSsplash10-0a4i-0002090000-caac81ca7445348cf143
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ufr-8002090000-26c25df2971196158cd3
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03fr-0095200000-630b79159cebb1fcfbb2
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9002320000-38a300e99eb84635022e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-0090000000-2d32b87326b83f9194d2
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000200000-5b02563a86bfea3c5af2
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-162.01515
predicted
DeepCCS 1.0 (2019)
[M+H]+164.4107
predicted
DeepCCS 1.0 (2019)
[M+Na]+170.25558
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Shigella flexneri
Pharmacological action
Unknown
General Function
Methionine adenosyltransferase activity
Specific Function
Catalyzes the formation of S-adenosylmethionine from methionine and ATP. The overall synthetic reaction is composed of two sequential steps, AdoMet formation and the subsequent tripolyphosphate hyd...
Gene Name
metK
Uniprot ID
P0A820
Uniprot Name
S-adenosylmethionine synthase
Molecular Weight
41951.285 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