Cmp-2-Keto-3-Deoxy-Octulosonic Acid

Identification

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Name
Cmp-2-Keto-3-Deoxy-Octulosonic Acid
Accession Number
DB04482  (EXPT00957)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
Not Available
Categories
Not Available
UNII
Not Available
CAS number
Not Available
Weight
Average: 543.3732
Monoisotopic: 543.110153689
Chemical Formula
C17H26N3O15P
InChI Key
YWWJKULNWGRYAS-UOVSKDHASA-N
InChI
InChI=1S/C17H26N3O15P/c18-9-1-2-20(16(29)19-9)14-12(26)11(25)8(33-14)5-32-36(30,31)35-17(15(27)28)3-6(22)10(24)13(34-17)7(23)4-21/h1-2,6-8,10-14,21-26H,3-5H2,(H,27,28)(H,30,31)(H2,18,19,29)/t6-,7-,8-,10-,11-,12-,13-,14-,17-/m1/s1
IUPAC Name
(2R,4R,5R,6R)-2-[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]-6-[(1R)-1,2-dihydroxyethyl]-4,5-dihydroxyoxane-2-carboxylic acid
SMILES
NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](COP(O)(=O)O[C@]2(C[C@@H](O)[C@@H](O)[C@H](O2)[C@H](O)CO)C(O)=O)[C@@H](O)[C@H]1O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
U3-deoxy-manno-octulosonate cytidylyltransferaseNot AvailableHaemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
U3-deoxy-manno-octulosonate cytidylyltransferaseNot AvailableEscherichia coli
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
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

References

General References
Not Available
External Links
KEGG Compound
C04121
PubChem Compound
445888
PubChem Substance
46506999
ChemSpider
393385
ChEBI
86284
HET
CMK
PDB Entries
1gqc / 1vh3 / 3etn / 3k2v / 4o9k

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 Solubility49.6 mg/mLALOGPS
logP-2.8ALOGPS
logP-4.9ChemAxon
logS-1ALOGPS
pKa (Strongest Acidic)1.47ChemAxon
pKa (Strongest Basic)-0.77ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area291.59 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity108.36 m3·mol-1ChemAxon
Polarizability47.05 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.9056
Blood Brain Barrier+0.7173
Caco-2 permeable-0.7566
P-glycoprotein substrateNon-substrate0.6998
P-glycoprotein inhibitor INon-inhibitor0.8786
P-glycoprotein inhibitor IINon-inhibitor0.9721
Renal organic cation transporterNon-inhibitor0.9607
CYP450 2C9 substrateNon-substrate0.7458
CYP450 2D6 substrateNon-substrate0.8433
CYP450 3A4 substrateNon-substrate0.5749
CYP450 1A2 substrateNon-inhibitor0.8866
CYP450 2C9 inhibitorNon-inhibitor0.8788
CYP450 2D6 inhibitorNon-inhibitor0.871
CYP450 2C19 inhibitorNon-inhibitor0.8512
CYP450 3A4 inhibitorNon-inhibitor0.6584
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8911
Ames testNon AMES toxic0.8201
CarcinogenicityNon-carcinogens0.871
BiodegradationNot ready biodegradable0.833
Rat acute toxicity2.4753 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9798
hERG inhibition (predictor II)Non-inhibitor0.6191
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/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.
Kingdom
Organic compounds
Super Class
Nucleosides, nucleotides, and analogues
Class
Pyrimidine nucleotides
Sub Class
Pyrimidine nucleotide sugars
Direct Parent
Pyrimidine nucleotide sugars
Alternative Parents
Pyrimidine ribonucleoside monophosphates / Pentose phosphates / C-glucuronides / Glycosylamines / C-glycosyl compounds / Monosaccharide phosphates / Pyrimidones / Dialkyl phosphates / Aminopyrimidines and derivatives / Hydropyrimidines
show 17 more
Substituents
Pyrimidine nucleotide sugar / Pyrimidine ribonucleoside monophosphate / Pentose phosphate / Pentose-5-phosphate / C-glucuronide / C-glycosyl compound / Glycosyl compound / N-glycosyl compound / Monosaccharide phosphate / Aminopyrimidine
show 35 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
CMP-sugar (CHEBI:86284)

Targets

Kind
Protein
Organism
Haemophilus influenzae (strain ATCC 51907 / DSM 11121 / KW20 / Rd)
Pharmacological action
Unknown
General Function
3-deoxy-manno-octulosonate cytidylyltransferase activity
Specific Function
Activates KDO (a required 8-carbon sugar) for incorporation into bacterial lipopolysaccharide in Gram-negative bacteria.
Gene Name
kdsB
Uniprot ID
P44490
Uniprot Name
3-deoxy-manno-octulosonate cytidylyltransferase
Molecular Weight
28255.205 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]
Kind
Protein
Organism
Escherichia coli
Pharmacological action
Unknown
General Function
3-deoxy-manno-octulosonate cytidylyltransferase activity
Specific Function
Activates KDO (a required 8-carbon sugar) for incorporation into bacterial lipopolysaccharide in Gram-negative bacteria.
Gene Name
kpsU
Uniprot ID
P42216
Uniprot Name
3-deoxy-manno-octulosonate cytidylyltransferase
Molecular Weight
27158.885 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 January 02, 2020 05:28