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8-Bromo-Adenosine-5'-Monophosphate

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Identification

Generic Name
8-Bromo-Adenosine-5'-Monophosphate
DrugBank Accession Number
DB03349
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 426.117
Monoisotopic: 424.973596954
Chemical Formula
C10H13BrN5O7P
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
A3',5'-cyclic-AMP phosphodiesterase 4B
inhibitor
Humans
UAdenosine 5'-monophosphoramidase HINT1Not AvailableHumans
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 monophosphates. These are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Purine nucleotides
Sub Class
Purine ribonucleotides
Direct Parent
Purine ribonucleoside monophosphates
Alternative Parents
Pentose phosphates / Glycosylamines / 6-aminopurines / Monosaccharide phosphates / Monoalkyl phosphates / Aminopyrimidines and derivatives / N-substituted imidazoles / Imidolactams / Aryl bromides / Heteroaromatic compounds
show 10 more
Substituents
1,2-diol / 6-aminopurine / Alcohol / Alkyl phosphate / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Aryl bromide / Aryl halide / Azacycle
show 33 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
DNPIJKNXFSPNNY-UUOKFMHZSA-N
InChI
InChI=1S/C10H13BrN5O7P/c11-10-15-4-7(12)13-2-14-8(4)16(10)9-6(18)5(17)3(23-9)1-22-24(19,20)21/h2-3,5-6,9,17-18H,1H2,(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}phosphonic acid
SMILES
[H][C@]1(COP(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
168120
PubChem Substance
46506327
ChemSpider
147060
BindingDB
50222467
ChEMBL
CHEMBL1230617
ZINC
ZINC000013527361
PDBe Ligand
8BR
PDB Entries
1ro9 / 5o0j / 5rhn / 7d7u

Clinical Trials

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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 Solubility3.26 mg/mLALOGPS
logP-2.5ALOGPS
logP-2.9Chemaxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.22Chemaxon
pKa (Strongest Basic)2.89Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count10Chemaxon
Hydrogen Donor Count5Chemaxon
Polar Surface Area186.07 Å2Chemaxon
Rotatable Bond Count4Chemaxon
Refractivity81.69 m3·mol-1Chemaxon
Polarizability33.01 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.7031
Blood Brain Barrier+0.8779
Caco-2 permeable-0.7019
P-glycoprotein substrateNon-substrate0.6684
P-glycoprotein inhibitor INon-inhibitor0.8871
P-glycoprotein inhibitor IINon-inhibitor0.967
Renal organic cation transporterNon-inhibitor0.9392
CYP450 2C9 substrateNon-substrate0.8688
CYP450 2D6 substrateNon-substrate0.8245
CYP450 3A4 substrateNon-substrate0.5322
CYP450 1A2 substrateNon-inhibitor0.7295
CYP450 2C9 inhibitorNon-inhibitor0.896
CYP450 2D6 inhibitorNon-inhibitor0.8551
CYP450 2C19 inhibitorNon-inhibitor0.8784
CYP450 3A4 inhibitorNon-inhibitor0.8434
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8818
Ames testNon AMES toxic0.7931
CarcinogenicityNon-carcinogens0.8993
BiodegradationNot ready biodegradable0.9953
Rat acute toxicity2.2506 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9839
hERG inhibition (predictor II)Non-inhibitor0.7778
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/MSsplash10-004i-0009800000-d89f5655f7eeefffb1fa
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000300000-4f2ee4c58252dd7e8409
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03fr-0299000000-7b16651fc5310ff33bf3
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000100000-f0c268320fd7244fe8de
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-1920000000-b8ff8f2b4354e9d4ff50
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9110000000-399d210e301d8c708dc9
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]-163.38744
predicted
DeepCCS 1.0 (2019)
[M+H]+165.783
predicted
DeepCCS 1.0 (2019)
[M+Na]+171.69554
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. 3',5'-cyclic-AMP phosphodiesterase 4B
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes (PubMed:15260978). May be involved in mediating central nervous system effects of therapeutic agents ranging from antidepressants to antiasthmatic and anti-inflammatory agents
Specific Function
3',5'-cyclic-amp phosphodiesterase activity
Gene Name
PDE4B
Uniprot ID
Q07343
Uniprot Name
3',5'-cyclic-AMP phosphodiesterase 4B
Molecular Weight
83342.695 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]
  3. Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Details2. Adenosine 5'-monophosphoramidase HINT1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Exhibits adenosine 5'-monophosphoramidase activity, hydrolyzing purine nucleotide phosphoramidates with a single phosphate group such as adenosine 5'monophosphoramidate (AMP-NH2) to yield AMP and NH2 (PubMed:15703176, PubMed:16835243, PubMed:17217311, PubMed:17337452, PubMed:22329685, PubMed:23614568, PubMed:28691797, PubMed:29787766, PubMed:31990367). Hydrolyzes adenosine 5'monophosphomorpholidate (AMP-morpholidate) and guanosine 5'monophosphomorpholidate (GMP-morpholidate) (PubMed:15703176, PubMed:16835243). Hydrolyzes lysyl-AMP (AMP-N-epsilon-(N-alpha-acetyl lysine methyl ester)) generated by lysine tRNA ligase, as well as Met-AMP, His-AMP and Asp-AMP, lysyl-GMP (GMP-N-epsilon-(N-alpha-acetyl lysine methyl ester)) and AMP-N-alanine methyl ester (PubMed:15703176, PubMed:17337452, PubMed:22329685). Hydrolyzes 3-indolepropionic acyl-adenylate, tryptamine adenosine phosphoramidate monoester and other fluorogenic purine nucleoside tryptamine phosphoramidates in vitro (PubMed:17217311, PubMed:17337452, PubMed:23614568, PubMed:28691797, PubMed:29787766, PubMed:31990367). Can also convert adenosine 5'-O-phosphorothioate and guanosine 5'-O-phosphorothioate to the corresponding nucleoside 5'-O-phosphates with concomitant release of hydrogen sulfide (PubMed:30772266). In addition, functions as scaffolding protein that modulates transcriptional activation by the LEF1/TCF1-CTNNB1 complex and by the complex formed with MITF and CTNNB1 (PubMed:16014379, PubMed:22647378). Modulates p53/TP53 levels and p53/TP53-mediated apoptosis (PubMed:16835243). Modulates proteasomal degradation of target proteins by the SCF (SKP2-CUL1-F-box protein) E3 ubiquitin-protein ligase complex (PubMed:19112177). Also exhibits SUMO-specific isopeptidase activity, deconjugating SUMO1 from RGS17 (PubMed:31088288). Deconjugates SUMO1 from RANGAP1 (By similarity)
Specific Function
Adenosine 5'-monophosphoramidase activity
Gene Name
HINT1
Uniprot ID
P49773
Uniprot Name
Adenosine 5'-monophosphoramidase HINT1
Molecular Weight
13801.815 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]
  3. 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 June 13, 2005 13:24 / Updated at August 26, 2024 19:22