4-Diphosphocytidyl-2-C-Methyl-D-Erythritol 2-Phosphate

Identification

Name
4-Diphosphocytidyl-2-C-Methyl-D-Erythritol 2-Phosphate
Accession Number
DB01859  (EXPT02978)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
UNII
Not Available
CAS number
Not Available
Weight
Average: 601.2874
Monoisotopic: 601.047505957
Chemical Formula
C14H26N3O17P3
InChI Key
HTJXTKBIUVFUAR-XHIBXCGHSA-N
InChI
InChI=1S/C14H26N3O17P3/c1-14(6-18,33-35(23,24)25)8(19)5-31-37(28,29)34-36(26,27)30-4-7-10(20)11(21)12(32-7)17-3-2-9(15)16-13(17)22/h2-3,7-8,10-12,18-21H,4-6H2,1H3,(H,26,27)(H,28,29)(H2,15,16,22)(H2,23,24,25)/t7-,8-,10-,11-,12-,14+/m1/s1
IUPAC Name
{[(2S,3R)-4-({[({[(2R,3S,4R,5R)-3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-1,3-dihydroxy-2-methylbutan-2-yl]oxy}phosphonic acid
SMILES
[H][C@@](O)(COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=CC(=N)N=C2O)[C@]([H])(O)[C@]1([H])O)[C@](C)(CO)OP(O)(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
U2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthaseNot AvailableShigella flexneri
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
KEGG Compound
C11436
PubChem Compound
443200
PubChem Substance
46506614
ChemSpider
391472
BindingDB
31908
ChEBI
16840
ChEMBL
CHEMBL1236081
HET
SUD
PDB Entries
1u43

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 Solubility9.98 mg/mLALOGPS
logP-1.1ALOGPS
logP-5.5ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)1.05ChemAxon
pKa (Strongest Basic)1.85ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area318.88 Å2ChemAxon
Rotatable Bond Count13ChemAxon
Refractivity125.91 m3·mol-1ChemAxon
Polarizability48.74 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.5522
Blood Brain Barrier+0.7297
Caco-2 permeable-0.7119
P-glycoprotein substrateSubstrate0.581
P-glycoprotein inhibitor INon-inhibitor0.8798
P-glycoprotein inhibitor IINon-inhibitor0.9955
Renal organic cation transporterNon-inhibitor0.9749
CYP450 2C9 substrateNon-substrate0.6569
CYP450 2D6 substrateNon-substrate0.827
CYP450 3A4 substrateNon-substrate0.5665
CYP450 1A2 substrateNon-inhibitor0.8467
CYP450 2C9 inhibitorNon-inhibitor0.8595
CYP450 2D6 inhibitorNon-inhibitor0.8654
CYP450 2C19 inhibitorNon-inhibitor0.8345
CYP450 3A4 inhibitorNon-inhibitor0.9224
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9692
Ames testNon AMES toxic0.7169
CarcinogenicityNon-carcinogens0.8229
BiodegradationNot ready biodegradable0.9545
Rat acute toxicity2.3829 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9726
hERG inhibition (predictor II)Non-inhibitor0.7963
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/MSsplash10-03di-1900010000-23a4ee9860d27e357bb0
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-1900000000-ac2d62a2bad3cc2b9d09
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-03di-8910000000-9ba03b1df6c8e4cd78c6
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0w29-4901043000-b5fbdc577444608870da
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-056r-9707010000-50a4154a2160feaa8e43
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-06vi-8901000000-f3de08e80f369b37214b

Taxonomy

Description
This compound belongs to the class of organic compounds known as pyrimidine ribonucleoside diphosphates. These are pyrimidine ribonucleotides with diphosphate group linked to the ribose moiety.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Pyrimidine nucleotides
Sub Class
Pyrimidine ribonucleotides
Direct Parent
Pyrimidine ribonucleoside diphosphates
Alternative Parents
Pentose phosphates / Glycosylamines / Organic pyrophosphates / Monosaccharide phosphates / Pyrimidones / Aminopyrimidines and derivatives / Monoalkyl phosphates / Imidolactams / Hydropyrimidines / Tetrahydrofurans
show 9 more
Substituents
Pyrimidine ribonucleoside diphosphate / Pentose-5-phosphate / Pentose phosphate / Glycosyl compound / N-glycosyl compound / Pentose monosaccharide / Monosaccharide phosphate / Organic pyrophosphate / Aminopyrimidine / Pyrimidone
show 26 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
alditol 4-phosphate, tetritol phosphate, nucleotide-alditol (CHEBI:16840)

Targets

Kind
Protein
Organism
Shigella flexneri
Pharmacological action
Unknown
General Function
Metal ion binding
Specific Function
Involved in the biosynthesis of isopentenyl diphosphate (IPP) and dimethylallyl diphosphate (DMAPP), two major building blocks of isoprenoid compounds. Catalyzes the conversion of 4-diphosphocytidy...
Gene Name
ispF
Uniprot ID
P62619
Uniprot Name
2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase
Molecular Weight
16897.37 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]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 05:07