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Lipoteichoic Acid

PubChem CID
137349712
Structure
Lipoteichoic Acid_small.png
Molecular Formula
Synonyms
  • Lipoteichoic acid
  • 56411-57-5
  • [(2S)-1-[(2S,3R,4S,5R,6R)-4-[(2S,3R,4S,5R,6R)-3-acetamido-5-amino-4-hydroxy-6-methyloxan-2-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-heptanoyloxypropan-2-yl] (E)-pentadec-7-enoate
  • Teichoic acid I
  • LTA-1
Molecular Weight
775.0 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2019-03-12
  • Modify:
    2025-01-18
Description
Lipoteichoic acid has been reported in Streptococcus pyogenes with data available.
Lipoteichoic Acid is a biologically active lipopolysaccharide-type component of the Gram-negative bacterial cell wall. Lipoteichoic acid (LTA) may bind to cell surfaces non-specifically, through interactions with phospholipids, or specifically, through interactions with CD14 or toll-like receptors (TLR), and then be internalized. Binding to TLR2 may activate the NFkappaB pathway, mitogen-activated protein kinase (MAPK) signaling pathways and phosphoinositide 3-kinase (PI3K) activity. This can result in increased expression of pro-inflammatory cytokines and both pro- and anti-apoptotic genes and may stimulate expression of the immunosuppressive receptor programmed cell death protein 1 (PD-1; PDCD1; CD279). Increased expression of PD-1 promotes binding to its ligands, programmed cell death-1 ligand 1 (PD-L1) or 2 (PD-L2), which stimulates production of the anti-inflammatory cytokine interleukin-10 (IL-10) and leads to inhibition of CD4-positive T-cell proliferation and activity. Additionally, LTA also may induce cancer cell proliferation in certain susceptible tumor cells while having an inhibitory effect on proliferation of other cancer cells. Lastly, LTA levels in patient samples may also be correlated with inflammatory damage during acute bacterial infections.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Lipoteichoic Acid.png

1.2 3D Status

Conformer generation is disallowed since too many atoms, too flexible

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(2S)-1-[(2S,3R,4S,5R,6R)-4-[(2S,3R,4S,5R,6R)-3-acetamido-5-amino-4-hydroxy-6-methyloxan-2-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-heptanoyloxypropan-2-yl] (E)-pentadec-7-enoate
Computed by LexiChem 2.6.6 (PubChem release 2019.06.18)

2.1.2 InChI

InChI=1S/C39H70N2O13/c1-5-7-9-11-12-13-14-15-16-17-18-20-22-31(45)52-28(24-49-30(44)21-19-10-8-6-2)25-50-39-36(48)37(34(46)29(23-42)53-39)54-38-33(41-27(4)43)35(47)32(40)26(3)51-38/h14-15,26,28-29,32-39,42,46-48H,5-13,16-25,40H2,1-4H3,(H,41,43)/b15-14+/t26-,28-,29-,32+,33-,34-,35+,36-,37+,38+,39+/m1/s1
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

2.1.3 InChIKey

PANDRCFROUDETH-YLSOAJEOSA-N
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

2.1.4 SMILES

CCCCCCC/C=C/CCCCCC(=O)O[C@@H](CO[C@@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O[C@H]2[C@@H]([C@H]([C@H]([C@H](O2)C)N)O)NC(=O)C)O)COC(=O)CCCCCC
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C39H70N2O13
Computed by PubChem 2.1 (PubChem release 2019.06.18)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 NCI Thesaurus Code

2.3.3 Wikidata

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • lipoteichoic acid
  • LTA-1
  • LTA-2
  • teichoic acid I

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
775.0 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
4.7
Reference
Computed by XLogP3 3.0 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Donor Count
Property Value
6
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Acceptor Count
Property Value
14
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Rotatable Bond Count
Property Value
29
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Exact Mass
Property Value
774.48779029 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
774.48779029 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
226 Ų
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Heavy Atom Count
Property Value
54
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
1080
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
11
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2019.01.04)

5 Chemical Vendors

6 Associated Disorders and Diseases

7 Literature

7.1 Consolidated References

7.2 NLM Curated PubMed Citations

7.3 Chemical Co-Occurrences in Literature

7.4 Chemical-Gene Co-Occurrences in Literature

7.5 Chemical-Disease Co-Occurrences in Literature

8 Interactions and Pathways

8.1 Protein Bound 3D Structures

8.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

8.2 Chemical-Target Interactions

9 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

10 Classification

10.1 MeSH Tree

10.2 LOTUS Tree

10.3 MolGenie Organic Chemistry Ontology

11 Information Sources

  1. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  2. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  3. Therapeutic Target Database (TTD)
  4. LOTUS - the natural products occurrence database
    LICENSE
    The code for LOTUS is released under the GNU General Public License v3.0.
    https://lotus.nprod.net/
  5. NCI Thesaurus (NCIt)
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  6. Protein Data Bank in Europe (PDBe)
  7. Wikidata
  8. PubChem
  9. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  10. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
CONTENTS