NAV

GDP-alpha-D-mannuronic acid

Identification

Generic Name
GDP-alpha-D-mannuronic acid
DrugBank Accession Number
DB04023
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 619.3246
Monoisotopic: 619.056417359
Chemical Formula
C16H23N5O17P2
Synonyms
  • GDP-α-D-mannuronic acid
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UGDP-mannose 6-dehydrogenaseNot AvailablePseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
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 / Glucuronic acid derivatives / Glycosylamines / 6-oxopurines / Hypoxanthines / Monosaccharide phosphates / Organic pyrophosphates / Aminopyrimidines and derivatives
show 21 more
Substituents
6-oxopurine / Alcohol / Alkyl phosphate / Amine / Amino acid / Amino acid or derivatives / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole
show 44 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
GDP-D-mannuronic acid (CHEBI:85507)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
DNBSDUDYNPJVCN-ZXTXFPBHSA-N
InChI
InChI=1S/C16H23N5O17P2/c17-16-19-11-4(12(27)20-16)18-2-21(11)13-8(25)5(22)3(35-13)1-34-39(30,31)38-40(32,33)37-15-9(26)6(23)7(24)10(36-15)14(28)29/h2-3,5-10,13,15,22-26H,1H2,(H,28,29)(H,30,31)(H,32,33)(H3,17,19,20,27)/t3-,5-,6+,7+,8-,9+,10+,13-,15-/m1/s1
IUPAC Name
(2S,3S,4S,5S,6R)-6-({[({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
SMILES
NC1=NC2=C(N=CN2[C@@H]2O[C@H](COP(O)(=O)OP(O)(=O)O[C@H]3O[C@@H]([C@@H](O)[C@H](O)[C@@H]3O)C(O)=O)[C@@H](O)[C@H]2O)C(=O)N1

References

General References
Not Available
KEGG Compound
C00976
PubChem Compound
447152
PubChem Substance
46508808
ChemSpider
394330
ChEBI
85507
ZINC
ZINC000008216635
PDBe Ligand
GDX
PDB Entries
1mfz / 1muu / 1mv8 / 2bo8 / 2y4m

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 Solubility7.6 mg/mLALOGPS
logP-1.6ALOGPS
logP-5Chemaxon
logS-1.9ALOGPS
pKa (Strongest Acidic)1.72Chemaxon
pKa (Strongest Basic)-3.7Chemaxon
Physiological Charge-3Chemaxon
Hydrogen Acceptor Count17Chemaxon
Hydrogen Donor Count10Chemaxon
Polar Surface Area344.5 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity118.38 m3·mol-1Chemaxon
Polarizability49.01 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.8437
Blood Brain Barrier+0.7474
Caco-2 permeable-0.7522
P-glycoprotein substrateNon-substrate0.5889
P-glycoprotein inhibitor INon-inhibitor0.8987
P-glycoprotein inhibitor IINon-inhibitor0.9803
Renal organic cation transporterNon-inhibitor0.9425
CYP450 2C9 substrateNon-substrate0.82
CYP450 2D6 substrateNon-substrate0.8368
CYP450 3A4 substrateNon-substrate0.5336
CYP450 1A2 substrateNon-inhibitor0.8047
CYP450 2C9 inhibitorNon-inhibitor0.9074
CYP450 2D6 inhibitorNon-inhibitor0.8805
CYP450 2C19 inhibitorNon-inhibitor0.9016
CYP450 3A4 inhibitorNon-inhibitor0.863
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9461
Ames testNon AMES toxic0.8924
CarcinogenicityNon-carcinogens0.9132
BiodegradationNot ready biodegradable0.974
Rat acute toxicity2.8552 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9835
hERG inhibition (predictor II)Non-inhibitor0.7196
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/MSsplash10-00di-0100019000-268733a986f835ab7866
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0000019000-f9ea21ff5e36785c6121
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0911316000-8b78e9bf0345ec8c3e59
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-1030-2100395000-32ce16db6d0e8c53962d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0920310000-1792e20f74b0a321ff07
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ab9-2800952000-3be38563f8870ee85bd2
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-206.57938
predicted
DeepCCS 1.0 (2019)
[M+H]+208.4753
predicted
DeepCCS 1.0 (2019)
[M+Na]+214.59569
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. GDP-mannose 6-dehydrogenase
Kind
Protein
Organism
Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)
Pharmacological action
Unknown
General Function
Udp-glucose 6-dehydrogenase activity
Specific Function
Catalyzes the oxidation of guanosine diphospho-D-mannose (GDP-D-mannose) to GDP-D-mannuronic acid, a precursor for alginate polymerization. The alginate layer causes a mucoid phenotype and provides...
Gene Name
algD
Uniprot ID
P11759
Uniprot Name
GDP-mannose 6-dehydrogenase
Molecular Weight
47599.155 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