Adenosine Phosphonoacetic Acid

Identification

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Name
Adenosine Phosphonoacetic Acid
Accession Number
DB02607  (EXPT02938)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
UNII
Not Available
CAS number
Not Available
Weight
Average: 389.2579
Monoisotopic: 389.073649025
Chemical Formula
C12H16N5O8P
InChI Key
KJNLSEOJEFDELT-JJNLEZRASA-N
InChI
InChI=1S/C12H16N5O8P/c13-10-7-11(15-3-14-10)17(4-16-7)12-9(20)8(19)5(25-12)1-24-6(18)2-26(21,22)23/h3-5,8-9,12,19-20H,1-2H2,(H2,13,14,15)(H2,21,22,23)/t5-,8-,9-,12-/m1/s1
IUPAC Name
(2-{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}-2-oxoethyl)phosphonic acid
SMILES
[H][C@]1(COC(=O)CP(O)(O)=O)O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UNucleoside diphosphate kinase ANot 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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
448505
PubChem Substance
46507434
ChemSpider
395282
ChEMBL
CHEMBL1236003
HET
SON
PDB Entries
1s5z

Clinical Trials

Clinical Trials
Not Available

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 Solubility2.97 mg/mLALOGPS
logP-2.6ALOGPS
logP-6.1ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.64ChemAxon
pKa (Strongest Basic)4.99ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area203.14 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity83.34 m3·mol-1ChemAxon
Polarizability33.92 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.8743
Blood Brain Barrier+0.8029
Caco-2 permeable-0.7651
P-glycoprotein substrateNon-substrate0.5149
P-glycoprotein inhibitor INon-inhibitor0.8958
P-glycoprotein inhibitor IINon-inhibitor0.989
Renal organic cation transporterNon-inhibitor0.9676
CYP450 2C9 substrateNon-substrate0.8575
CYP450 2D6 substrateNon-substrate0.8378
CYP450 3A4 substrateNon-substrate0.5691
CYP450 1A2 substrateNon-inhibitor0.8772
CYP450 2C9 inhibitorNon-inhibitor0.9213
CYP450 2D6 inhibitorNon-inhibitor0.894
CYP450 2C19 inhibitorNon-inhibitor0.9105
CYP450 3A4 inhibitorNon-inhibitor0.8893
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9684
Ames testNon AMES toxic0.8198
CarcinogenicityNon-carcinogens0.8983
BiodegradationNot ready biodegradable0.9619
Rat acute toxicity2.6707 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.983
hERG inhibition (predictor II)Non-inhibitor0.7923
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/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as purine nucleosides. These are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Purine nucleosides
Sub Class
Not Available
Direct Parent
Purine nucleosides
Alternative Parents
Glycosylamines / Pentoses / 6-aminopurines / Aminopyrimidines and derivatives / N-substituted imidazoles / Imidolactams / Tetrahydrofurans / Organic phosphonic acids / Heteroaromatic compounds / Secondary alcohols
show 12 more
Substituents
Purine nucleoside / Glycosyl compound / N-glycosyl compound / 6-aminopurine / Pentose monosaccharide / Purine / Imidazopyrimidine / Aminopyrimidine / Monosaccharide / Imidolactam
show 30 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Ribosomal small subunit binding
Specific Function
Major role in the synthesis of nucleoside triphosphates other than ATP. The ATP gamma phosphate is transferred to the NDP beta phosphate via a ping-pong mechanism, using a phosphorylated active-sit...
Gene Name
NME1
Uniprot ID
P15531
Uniprot Name
Nucleoside diphosphate kinase A
Molecular Weight
17148.635 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. [PubMed:17139284]
  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. [PubMed:17016423]
  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. [PubMed:10592235]

Drug created on June 13, 2005 07:24 / Updated on June 04, 2019 05:37