Adenosine-5'-Monophosphate Glucopyranosyl-Monophosphate Ester
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Identification
- Generic Name
- Adenosine-5'-Monophosphate Glucopyranosyl-Monophosphate Ester
- DrugBank Accession Number
- DB01774
- Background
Serves as the glycosyl donor for formation of bacterial glycogen, amylose in green algae, and amylopectin in higher plants. [PubChem]
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 589.3417
Monoisotopic: 589.082238179 - Chemical Formula
- C16H25N5O15P2
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UADP-L-glycero-D-manno-heptose-6-epimerase Not Available Escherichia coli (strain K12) - 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- 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 nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group.
- Kingdom
- Organic compounds
- Super Class
- Nucleosides, nucleotides, and analogues
- Class
- Purine nucleotides
- Sub Class
- Purine nucleotide sugars
- Direct Parent
- Purine nucleotide sugars
- Alternative Parents
- Purine ribonucleoside diphosphates / Purine ribonucleoside monophosphates / Pentose phosphates / Glycosylamines / 6-aminopurines / Organic pyrophosphates / Monosaccharide phosphates / Aminopyrimidines and derivatives / Monoalkyl phosphates / Oxanes show 13 more
- Substituents
- 6-aminopurine / Alcohol / Alkyl phosphate / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Glycosyl compound / Heteroaromatic compound show 33 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- alpha-D-glucoside, ADP-aldose (CHEBI:15751)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- Not Available
- CAS number
- Not Available
- InChI Key
- WFPZSXYXPSUOPY-ROYWQJLOSA-N
- InChI
- InChI=1S/C16H25N5O15P2/c17-13-7-14(19-3-18-13)21(4-20-7)15-11(26)9(24)6(33-15)2-32-37(28,29)36-38(30,31)35-16-12(27)10(25)8(23)5(1-22)34-16/h3-6,8-12,15-16,22-27H,1-2H2,(H,28,29)(H,30,31)(H2,17,18,19)/t5-,6-,8-,9-,10+,11-,12-,15-,16-/m1/s1
- IUPAC Name
- {[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[hydroxy({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphoryl]oxy})phosphinic acid
- SMILES
- NC1=C2N=CN([C@@H]3O[C@H](CO[P@](O)(=O)O[P@](O)(=O)O[C@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)[C@@H](O)[C@H]3O)C2=NC=N1
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0006557
- KEGG Compound
- C00498
- PubChem Compound
- 16500
- PubChem Substance
- 46506026
- ChemSpider
- 15642
- ChEBI
- 15751
- ChEMBL
- CHEMBL227552
- ZINC
- ZINC000008216005
- PDBe Ligand
- ADQ
- PDB Entries
- 1eq2 / 1yp4 / 2h39 / 3rt7 / 5k41 / 6men
Clinical Trials
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
Property Value Source Water Solubility 4.84 mg/mL ALOGPS logP -1.8 ALOGPS logP -6.9 Chemaxon logS -2.1 ALOGPS pKa (Strongest Acidic) 1.73 Chemaxon pKa (Strongest Basic) 4.93 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 16 Chemaxon Hydrogen Donor Count 9 Chemaxon Polar Surface Area 311.75 Å2 Chemaxon Rotatable Bond Count 9 Chemaxon Refractivity 117.09 m3·mol-1 Chemaxon Polarizability 49.4 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption - 0.8973 Blood Brain Barrier + 0.7713 Caco-2 permeable - 0.7464 P-glycoprotein substrate Non-substrate 0.6498 P-glycoprotein inhibitor I Non-inhibitor 0.8689 P-glycoprotein inhibitor II Non-inhibitor 0.9765 Renal organic cation transporter Non-inhibitor 0.9459 CYP450 2C9 substrate Non-substrate 0.842 CYP450 2D6 substrate Non-substrate 0.834 CYP450 3A4 substrate Non-substrate 0.5493 CYP450 1A2 substrate Non-inhibitor 0.8609 CYP450 2C9 inhibitor Non-inhibitor 0.9041 CYP450 2D6 inhibitor Non-inhibitor 0.8877 CYP450 2C19 inhibitor Non-inhibitor 0.8975 CYP450 3A4 inhibitor Non-inhibitor 0.7237 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.871 Ames test Non AMES toxic 0.8572 Carcinogenicity Non-carcinogens 0.9059 Biodegradation Not ready biodegradable 0.9798 Rat acute toxicity 3.0945 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9601 hERG inhibition (predictor II) Non-inhibitor 0.6225
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 242.3293899 predictedDarkChem Lite v0.1.0 [M-H]- 222.3170899 predictedDarkChem Lite v0.1.0 [M-H]- 194.65622 predictedDeepCCS 1.0 (2019) [M+H]+ 243.5152899 predictedDarkChem Lite v0.1.0 [M+H]+ 220.7975899 predictedDarkChem Lite v0.1.0 [M+H]+ 196.4811 predictedDeepCCS 1.0 (2019) [M+Na]+ 242.4116899 predictedDarkChem Lite v0.1.0 [M+Na]+ 220.6856899 predictedDarkChem Lite v0.1.0 [M+Na]+ 202.08687 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Escherichia coli (strain K12)
- Pharmacological action
- Unknown
- General Function
- Nadp+ binding
- Specific Function
- Catalyzes the interconversion between ADP-D-glycero-beta-D-manno-heptose and ADP-L-glycero-beta-D-manno-heptose via an epimerization at carbon 6 of the heptose.
- Gene Name
- hldD
- Uniprot ID
- P67910
- Uniprot Name
- ADP-L-glycero-D-manno-heptose-6-epimerase
- Molecular Weight
- 34892.905 Da
References
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52