Adenosine-5'-Monophosphate Glucopyranosyl-Monophosphate Ester

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
TargetActionsOrganism
UADP-L-glycero-D-manno-heptose-6-epimeraseNot AvailableEscherichia 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
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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 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
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

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 Solubility4.84 mg/mLALOGPS
logP-1.8ALOGPS
logP-6.9Chemaxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.73Chemaxon
pKa (Strongest Basic)4.93Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count16Chemaxon
Hydrogen Donor Count9Chemaxon
Polar Surface Area311.75 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity117.09 m3·mol-1Chemaxon
Polarizability49.4 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.8973
Blood Brain Barrier+0.7713
Caco-2 permeable-0.7464
P-glycoprotein substrateNon-substrate0.6498
P-glycoprotein inhibitor INon-inhibitor0.8689
P-glycoprotein inhibitor IINon-inhibitor0.9765
Renal organic cation transporterNon-inhibitor0.9459
CYP450 2C9 substrateNon-substrate0.842
CYP450 2D6 substrateNon-substrate0.834
CYP450 3A4 substrateNon-substrate0.5493
CYP450 1A2 substrateNon-inhibitor0.8609
CYP450 2C9 inhibitorNon-inhibitor0.9041
CYP450 2D6 inhibitorNon-inhibitor0.8877
CYP450 2C19 inhibitorNon-inhibitor0.8975
CYP450 3A4 inhibitorNon-inhibitor0.7237
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.871
Ames testNon AMES toxic0.8572
CarcinogenicityNon-carcinogens0.9059
BiodegradationNot ready biodegradable0.9798
Rat acute toxicity3.0945 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9601
hERG inhibition (predictor II)Non-inhibitor0.6225
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 GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-05di-5941580000-aa3b11c510a971dd2bae
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0000090000-5ee0398c4b308dc72748
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0000090000-43db9f965faafdb11ab1
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0079-0000490000-8e050ad6024721364d7f
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0076-1323490000-653d915d7b4c51bc6abd
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000j-2934410000-605ff3a3aed595d7589e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4j-1922860000-f0e38b34eda3bacd44b8
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-242.3293899
predicted
DarkChem Lite v0.1.0
[M-H]-222.3170899
predicted
DarkChem Lite v0.1.0
[M-H]-194.65622
predicted
DeepCCS 1.0 (2019)
[M+H]+243.5152899
predicted
DarkChem Lite v0.1.0
[M+H]+220.7975899
predicted
DarkChem Lite v0.1.0
[M+H]+196.4811
predicted
DeepCCS 1.0 (2019)
[M+Na]+242.4116899
predicted
DarkChem Lite v0.1.0
[M+Na]+220.6856899
predicted
DarkChem Lite v0.1.0
[M+Na]+202.08687
predicted
DeepCCS 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
  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