NAV

4-CDP-2-C-methyl-D-erythritol 2-phosphate

Identification

Generic Name
4-CDP-2-C-methyl-D-erythritol 2-phosphate
DrugBank Accession Number
DB01859
Background

Not Available

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 601.2874
Monoisotopic: 601.047505957
Chemical Formula
C14H26N3O17P3
Synonyms
  • 2-Phospho-4-(cytidine 5'-diphospho)-2-C-methyl-D-erythritol
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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
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

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 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
Alcohol / Alkyl phosphate / Amine / Aminopyrimidine / Aromatic heteromonocyclic compound / Azacycle / Glycosyl compound / Heteroaromatic compound / Hydrocarbon derivative / Hydropyrimidine
show 26 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
alditol 4-phosphate, tetritol phosphate, nucleotide-alditol (CHEBI:16840)
Affected organisms
Not Available

Chemical Identifiers

UNII
Not Available
CAS number
263016-95-1
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
C[C@@](CO)(OP(O)(O)=O)[C@H](O)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N1C=CC(N)=NC1=O

References

General References
Not Available
KEGG Compound
C11436
PubChem Compound
443200
PubChem Substance
46506614
ChemSpider
391472
BindingDB
31908
ChEBI
16840
ChEMBL
CHEMBL1236081
ZINC
ZINC000008419062
PDBe Ligand
SUD
PDB Entries
1u43

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
logP-4.1Chemaxon
pKa (Strongest Acidic)1.06Chemaxon
pKa (Strongest Basic)3.56Chemaxon
Physiological Charge-4Chemaxon
Hydrogen Acceptor Count16Chemaxon
Hydrogen Donor Count10Chemaxon
Polar Surface Area318.88 Å2Chemaxon
Rotatable Bond Count13Chemaxon
Refractivity125.91 m3·mol-1Chemaxon
Polarizability48.76 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/MSsplash10-0f80-0000930000-d8d24d758263b40a57ad
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004j-9000000000-486e9f24efe98587efa5
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0una-9137310000-b1893cca1e1a9015b9e1
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fb9-9112483000-5558fb863c332ac81fb9
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-007o-3925200000-b5ed3ba1626cba443e2d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9141220000-da06b750df04d55ba2ee
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-240.907196
predicted
DarkChem Lite v0.1.0
[M-H]-191.21686
predicted
DeepCCS 1.0 (2019)
[M+H]+240.508696
predicted
DarkChem Lite v0.1.0
[M+H]+193.11232
predicted
DeepCCS 1.0 (2019)
[M+Na]+240.283296
predicted
DarkChem Lite v0.1.0
[M+Na]+199.26936
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. 2-C-methyl-D-erythritol 2,4-cyclodiphosphate synthase
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. [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