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Record Information
Version2.0
Created at2022-09-07 07:19:26 UTC
Updated at2022-09-07 07:19:26 UTC
NP-MRD IDNP0246018
Secondary Accession NumbersNone
Natural Product Identification
Common Namelegionaminic acid
DescriptionLegionaminic acid, also known as legionaminate or 5,7-diacnh-tdna, belongs to the class of organic compounds known as pyranoid amino acids and derivatives. Pyranoid amino acids and derivatives are compounds containing a (hydro)pyran ring bearing unprotected amino and carboxylic acid functionalities. legionaminic acid is found in Tannerella forsythia. legionaminic acid was first documented in 2021 (PMID: 34519150). Based on a literature review a small amount of articles have been published on legionaminic acid (PMID: 35420827) (PMID: 34782242) (PMID: 33150386) (PMID: 32886756).
Structure
Thumb
Synonyms
ValueSource
(6S)-5-Amino-6-[(1R,2R)-1-amino-2-hydroxypropyl]-3,5-dideoxy-alpha-L-threo-hex-2-ulopyranosonateChEBI
(6S)-5-Amino-6-[(1R,2R)-1-amino-2-hydroxypropyl]-3,5-dideoxy-a-L-threo-hex-2-ulopyranosonateGenerator
(6S)-5-Amino-6-[(1R,2R)-1-amino-2-hydroxypropyl]-3,5-dideoxy-a-L-threo-hex-2-ulopyranosonic acidGenerator
(6S)-5-Amino-6-[(1R,2R)-1-amino-2-hydroxypropyl]-3,5-dideoxy-alpha-L-threo-hex-2-ulopyranosonic acidGenerator
(6S)-5-Amino-6-[(1R,2R)-1-amino-2-hydroxypropyl]-3,5-dideoxy-α-L-threo-hex-2-ulopyranosonateGenerator
(6S)-5-Amino-6-[(1R,2R)-1-amino-2-hydroxypropyl]-3,5-dideoxy-α-L-threo-hex-2-ulopyranosonic acidGenerator
LegionaminateGenerator
5,7-DiAcNH-tdnaMeSH
5,7-Diacetamido-8-O-acetyl-3,5,7,9-tetradeoxy-glycero-talo-nonulosonic acidMeSH
Chemical FormulaC9H18N2O6
Average Mass250.2510 Da
Monoisotopic Mass250.11649 Da
IUPAC Name(2S,4S,5R,6S)-5-amino-6-[(1R,2R)-1-amino-2-hydroxypropyl]-2,4-dihydroxyoxane-2-carboxylic acid
Traditional Name(2S,4S,5R,6S)-5-amino-6-[(1R,2R)-1-amino-2-hydroxypropyl]-2,4-dihydroxyoxane-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
C[C@@H](O)[C@@H](N)[C@@H]1O[C@@](O)(C[C@H](O)[C@H]1N)C(O)=O
InChI Identifier
InChI=1S/C9H18N2O6/c1-3(12)5(10)7-6(11)4(13)2-9(16,17-7)8(14)15/h3-7,12-13,16H,2,10-11H2,1H3,(H,14,15)/t3-,4+,5-,6-,7+,9+/m1/s1
InChI KeyZFZFJUIKYIVPNP-OWTNSLFHSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Tannerella forsythiaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyranoid amino acids and derivatives. Pyranoid amino acids and derivatives are compounds containing a (hydro)pyran ring bearing unprotected amino and carboxylic acid functionalities.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentPyranoid amino acids and derivatives
Alternative Parents
Substituents
  • Pyranoid amino acid
  • C-glucuronide
  • Delta amino acid or derivatives
  • C-glycosyl compound
  • Glycosyl compound
  • Amino saccharide
  • Alpha-hydroxy acid
  • Hydroxy acid
  • Oxane
  • Pyran
  • 1,2-aminoalcohol
  • Amino acid or derivatives
  • Amino acid
  • Hemiacetal
  • Secondary alcohol
  • Oxacycle
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organoheterocyclic compound
  • Primary aliphatic amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Alcohol
  • Organonitrogen compound
  • Primary amine
  • Amine
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
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)2.89ChemAxon
pKa (Strongest Basic)8.59ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area159.26 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity54.45 m³·mol⁻¹ChemAxon
Polarizability23.25 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID28533261
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound70678967
PDB IDNot Available
ChEBI ID68676
Good Scents IDNot Available
References
General References
  1. Siyabalapitiya Arachchige S, Crich D: Syntheses of Legionaminic Acid, Pseudaminic Acid, Acetaminic Acid, 8-epi-Acetaminic Acid, and 8-epi-Legionaminic Acid Glycosyl Donors from N-Acetylneuraminic Acid by Side Chain Exchange. Org Lett. 2022 Apr 29;24(16):2998-3002. doi: 10.1021/acs.orglett.2c00894. Epub 2022 Apr 14. [PubMed:35420827 ]
  2. Kint N, Unay J, Viollier PH: Specificity and modularity of flagellin nonulosonic acid glycosyltransferases. Trends Microbiol. 2022 Feb;30(2):109-111. doi: 10.1016/j.tim.2021.10.005. Epub 2021 Nov 13. [PubMed:34782242 ]
  3. Meng X, Boons GJ, Wosten MMSM, Wennekes T: Metabolic Labeling of Legionaminic Acid in Flagellin Glycosylation of Campylobacter jejuni Identifies Maf4 as a Putative Legionaminyl Transferase. Angew Chem Int Ed Engl. 2021 Nov 15;60(47):24811-24816. doi: 10.1002/anie.202107181. Epub 2021 Oct 27. [PubMed:34519150 ]
  4. Silva L, Grosso F, Rodrigues C, Ksiezarek M, Ramos H, Peixe L: The success of particular Acinetobacter baumannii clones: accumulating resistance and virulence inside a sugary shield. J Antimicrob Chemother. 2021 Jan 19;76(2):305-311. doi: 10.1093/jac/dkaa453. [PubMed:33150386 ]
  5. Khairnar A, Sunsunwal S, Babu P, Ramya TNC: Novel serine/threonine-O-glycosylation with N-acetylneuraminic acid and 3-deoxy-D-manno-octulosonic acid by bacterial flagellin glycosyltransferases. Glycobiology. 2021 Apr 1;31(3):288-306. doi: 10.1093/glycob/cwaa084. [PubMed:32886756 ]
  6. LOTUS database [Link]