NAV

Guanosine-5'-Diphosphate-Rhamnose

Identification

Generic Name
Guanosine-5'-Diphosphate-Rhamnose
DrugBank Accession Number
DB02547
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 589.3417
Monoisotopic: 589.082238179
Chemical Formula
C16H25N5O15P2
Synonyms
Not Available
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
UGDP-mannose 4,6 dehydrataseNot 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 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-oxopurines / Hypoxanthines / Monosaccharide phosphates / Organic pyrophosphates / Monoalkyl phosphates / Aminopyrimidines and derivatives
show 14 more
Substituents
6-oxopurine / Alcohol / Alkyl phosphate / Amine / Aminopyrimidine / Aromatic heteropolycyclic compound / Azacycle / Azole / Glycosyl compound / Heteroaromatic compound
show 34 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
GDP-sugar (CHEBI:17661)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
Not Available
InChI Key
LQEBEXMHBLQMDB-GDJBGNAASA-N
InChI
InChI=1S/C16H25N5O15P2/c1-4-7(22)9(24)11(26)15(33-4)35-38(30,31)36-37(28,29)32-2-5-8(23)10(25)14(34-5)21-3-18-6-12(21)19-16(17)20-13(6)27/h3-5,7-11,14-15,22-26H,2H2,1H3,(H,28,29)(H,30,31)(H3,17,19,20,27)/t4-,5-,7-,8-,9+,10-,11+,14-,15-/m1/s1
IUPAC Name
{[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-3H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[hydroxy({[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy})phosphoryl]oxy})phosphinic acid
SMILES
C[C@H]1O[C@H](OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)N2C=NC3=C2NC(N)=NC3=O)[C@@H](O)[C@@H](O)[C@@H]1O

References

General References
Not Available
Human Metabolome Database
HMDB0001499
KEGG Compound
C03117
PubChem Compound
439912
PubChem Substance
46504876
ChemSpider
388945
ChEBI
17661
ChEMBL
CHEMBL1233001
ZINC
ZINC000008218184
PDBe Ligand
GDR
PDB Entries
1n7g / 7kf3

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 Solubility6.96 mg/mLALOGPS
logP-1.5ALOGPS
logP-3.9Chemaxon
logS-1.9ALOGPS
pKa (Strongest Acidic)1.65Chemaxon
pKa (Strongest Basic)2.46Chemaxon
Physiological Charge-2Chemaxon
Hydrogen Acceptor Count16Chemaxon
Hydrogen Donor Count9Chemaxon
Polar Surface Area307.2 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity116.53 m3·mol-1Chemaxon
Polarizability48.95 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption-0.7577
Blood Brain Barrier+0.5801
Caco-2 permeable-0.7522
P-glycoprotein substrateNon-substrate0.5057
P-glycoprotein inhibitor INon-inhibitor0.8905
P-glycoprotein inhibitor IINon-inhibitor0.9874
Renal organic cation transporterNon-inhibitor0.9482
CYP450 2C9 substrateNon-substrate0.7607
CYP450 2D6 substrateNon-substrate0.8395
CYP450 3A4 substrateNon-substrate0.5052
CYP450 1A2 substrateNon-inhibitor0.8041
CYP450 2C9 inhibitorNon-inhibitor0.9007
CYP450 2D6 inhibitorNon-inhibitor0.8608
CYP450 2C19 inhibitorNon-inhibitor0.9024
CYP450 3A4 inhibitorNon-inhibitor0.865
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9336
Ames testNon AMES toxic0.874
CarcinogenicityNon-carcinogens0.9059
BiodegradationNot ready biodegradable0.9822
Rat acute toxicity2.8046 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9811
hERG inhibition (predictor II)Non-inhibitor0.7144
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-MSsplash10-05bf-6985780000-f2b6a0fdececb1ffd409
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0000090000-fabd530c6140b0e9a046
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-0000090000-8d473cf4e0b6285c7e70
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-052f-6333960000-91bc61ee1dd32ef6e827
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-03e9-5303690000-1180921d927c17f80ae9
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0007-8986510000-5d8c21c94dbaa30d211d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0kos-1501950000-176d19996be44a636728
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-235.4019899
predicted
DarkChem Lite v0.1.0
[M-H]-199.95972
predicted
DeepCCS 1.0 (2019)
[M+H]+234.9293899
predicted
DarkChem Lite v0.1.0
[M+H]+202.35582
predicted
DeepCCS 1.0 (2019)
[M+Na]+234.2116899
predicted
DarkChem Lite v0.1.0
[M+Na]+208.26845
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. GDP-mannose 4,6 dehydratase
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Nadp+ binding
Specific Function
Catalyzes the conversion of GDP-D-mannose to GDP-4-dehydro-6-deoxy-D-mannose.
Gene Name
GMDS
Uniprot ID
O60547
Uniprot Name
GDP-mannose 4,6 dehydratase
Molecular Weight
41949.445 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 01, 2020 13:43