Np mrd loader

Record Information
Version2.0
Created at2024-09-11 23:14:16 UTC
Updated at2024-09-11 23:14:17 UTC
NP-MRD IDNP0339723
Secondary Accession NumbersNone
Natural Product Identification
Common NameCMP-3-deoxy-D-manno-octulosonate
Description CMP-3-deoxy-D-manno-octulosonate was first documented in 1985 (PMID: 2997221). Based on a literature review a significant number of articles have been published on CMP-3-deoxy-D-manno-octulosonate (PMID: 8699165) (PMID: 7543480) (PMID: 2162683) (PMID: 2834331) (PMID: 2833499) (PMID: 3023327).
Structure
Thumb
Synonyms
ValueSource
CMP-3-Deoxy-D-manno-octulosonic acidGenerator
Chemical FormulaC17H24N3O15P
Average Mass541.3600 Da
Monoisotopic Mass541.09560 Da
IUPAC Name2-[({[5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(oxido)phosphoryl)oxy]-6-(1,2-dihydroxyethyl)-4,5-dihydroxyoxane-2-carboxylate
Traditional Name2-({[5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(oxido)phosphoryl}oxy)-6-(1,2-dihydroxyethyl)-4,5-dihydroxyoxane-2-carboxylate
CAS Registry NumberNot Available
SMILES
NC1=NC(=O)N(C=C1)C1OC(COP([O-])(=O)OC2(CC(O)C(O)C(O2)C(O)CO)C([O-])=O)C(O)C1O
InChI Identifier
InChI=1/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)/p-2
InChI KeyYWWJKULNWGRYAS-UHFFFAOYNA-L
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
ClassificationNot classified
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-4.8ChemAxon
pKa (Strongest Acidic)1.4ChemAxon
pKa (Strongest Basic)4.14ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count15ChemAxon
Hydrogen Donor Count7ChemAxon
Polar Surface Area297.25 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity118.07 m³·mol⁻¹ChemAxon
Polarizability46.15 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Pilot-Matias TJ, Muerhoff AS, Simons JN, Leary TP, Buijk SL, Chalmers ML, Erker JC, Dawson GJ, Desai SM, Mushahwar IK: Identification of antigenic regions in the GB hepatitis viruses GBV-A, GBV-B, and GBV-C. J Med Virol. 1996 Apr;48(4):329-38. doi: 10.1002/(SICI)1096-9071(199604)48:4<329::AID-JMV6>3.0.CO;2-9. [PubMed:8699165 ]
  2. Strohmaier H, Remler P, Renner W, Hogenauer G: Expression of genes kdsA and kdsB involved in 3-deoxy-D-manno-octulosonic acid metabolism and biosynthesis of enterobacterial lipopolysaccharide is growth phase regulated primarily at the transcriptional level in Escherichia coli K-12. J Bacteriol. 1995 Aug;177(15):4488-500. doi: 10.1128/jb.177.15.4488-4500.1995. [PubMed:7543480 ]
  3. Bolling TJ, Mandecki W: An Escherichia coli expression vector for high-level production of heterologous proteins in fusion with CMP-KDO synthetase. Biotechniques. 1990 May;8(5):488-92. [PubMed:2162683 ]
  4. Goldman RC, Doran CC, Capobianco JO: Analysis of lipopolysaccharide biosynthesis in Salmonella typhimurium and Escherichia coli by using agents which specifically block incorporation of 3-deoxy-D-manno-octulosonate. J Bacteriol. 1988 May;170(5):2185-91. doi: 10.1128/jb.170.5.2185-2191.1988. [PubMed:2834331 ]
  5. Goldman RC, Doran CC, Kadam SK, Capobianco JO: Lipid A precursor from Pseudomonas aeruginosa is completely acylated prior to addition of 3-deoxy-D-manno-octulosonate. J Biol Chem. 1988 Apr 15;263(11):5217-23. [PubMed:2833499 ]
  6. Goldman RC, Bolling TJ, Kohlbrenner WE, Kim Y, Fox JL: Primary structure of CTP:CMP-3-deoxy-D-manno-octulosonate cytidylyltransferase (CMP-KDO synthetase) from Escherichia coli. J Biol Chem. 1986 Dec 5;261(34):15831-5. [PubMed:3023327 ]
  7. Kohlbrenner WE, Fesik SW: Determination of the anomeric specificity of the Escherichia coli CTP:CMP-3-deoxy-D-manno-octulosonate cytidylyltransferase by 13C NMR spectroscopy. J Biol Chem. 1985 Nov 25;260(27):14695-700. [PubMed:2997221 ]