Details of the Drug

General Information of Drug (ID: DMEMRW0)

Drug Name
Lipoteichoic acid
Synonyms Oncomycin; Lipoteichoic acid (cancer); Lipoteichoic acid (cancer), Lunamed; TLR-2 modulator (subcutaneous, solid tumor), LUNAMeD; Toll like receptor-2 modulator (subcutaneous, solid tumor), LUNAMeD
Indication
Disease Entry ICD 11 Status REF
Solid tumour/cancer 2A00-2F9Z Phase 1/2 [1]
Structure
3D MOL is unavailable 2D MOL
#Ro5 Violations (Lipinski): 4 Molecular Weight (mw) 775
Logarithm of the Partition Coefficient (xlogp) 4.7
Rotatable Bond Count (rotbonds) 29
Hydrogen Bond Donor Count (hbonddonor) 6
Hydrogen Bond Acceptor Count (hbondacc) 14
Chemical Identifiers
Formula
C39H70N2O13
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
Canonical 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
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
InChIKey
PANDRCFROUDETH-YLSOAJEOSA-N
Cross-matching ID
PubChem CID
137349712
CAS Number
56411-57-5
TTD ID
D00UVU

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Toll-like receptor 2 (TLR2) TTY7ZHS TLR2_HUMAN Modulator [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
C-C motif chemokine 2 (CCL2) OTAD2HEL CCL2_HUMAN Protein Interaction/Cellular Processes [3]
C-X-C chemokine receptor type 2 (CXCR2) OTISGW7L CXCR2_HUMAN Gene/Protein Processing [4]
Granulocyte-macrophage colony-stimulating factor (CSF2) OT1M7D28 CSF2_HUMAN Protein Interaction/Cellular Processes [3]
Interleukin-10 (IL10) OTIRFRXC IL10_HUMAN Gene/Protein Processing [5]
Interleukin-6 (IL6) OTUOSCCU IL6_HUMAN Gene/Protein Processing [6]
Interleukin-8 (CXCL8) OTS7T5VH IL8_HUMAN Protein Interaction/Cellular Processes [7]
Lactotransferrin (LTF) OT8JWCZ0 TRFL_HUMAN Protein Interaction/Cellular Processes [8]
Neutrophil elastase (ELANE) OTCOHLXR ELNE_HUMAN Protein Interaction/Cellular Processes [8]
Tumor necrosis factor (TNF) OT4IE164 TNFA_HUMAN Gene/Protein Processing [5]
Ubiquitin-like protein ISG15 (ISG15) OT53QQ7N ISG15_HUMAN Gene/Protein Processing [9]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Solid tumour/cancer
ICD Disease Classification 2A00-2F9Z
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Toll-like receptor 2 (TLR2) DTT TLR2 1.75E-01 -0.48 -0.45
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

References

1 Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800024869)
2 Lipoteichoic acid (LTA) of Streptococcus pneumoniae and Staphylococcus aureus activates immune cells via Toll-like receptor (TLR)-2, lipopolysaccha... J Biol Chem. 2003 May 2;278(18):15587-94.
3 Resveratrol attenuates the release of inflammatory cytokines from human bronchial smooth muscle cells exposed to lipoteichoic acid in chronic obstructive pulmonary disease. Basic Clin Pharmacol Toxicol. 2014 Feb;114(2):202-9. doi: 10.1111/bcpt.12129. Epub 2013 Sep 30.
4 Expression of the chemokine receptors CXCR1 and CXCR2 on granulocytes in human endotoxemia and tuberculosis: involvement of the p38 mitogen-activated protein kinase pathway. J Infect Dis. 2000 Sep;182(3):888-94. doi: 10.1086/315750. Epub 2000 Aug 17.
5 Sirolimus interferes with the innate response to bacterial products in human whole blood by attenuation of IL-10 production. Scand J Immunol. 2001 Feb;53(2):184-91. doi: 10.1046/j.1365-3083.2001.00862.x.
6 Intramuscular 17-hydroxyprogesterone caproate administration attenuates immunoresponsiveness of maternal peripheral blood mononuclear cells. Am J Obstet Gynecol. 2010 Dec;203(6):561.e1-5. doi: 10.1016/j.ajog.2010.07.016. Epub 2010 Sep 1.
7 Differences in lipopolysaccharide- and lipoteichoic acid-induced cytokine/chemokine expression. Intensive Care Med. 2012 Feb;38(2):324-32. doi: 10.1007/s00134-011-2444-5. Epub 2011 Dec 20.
8 Thalidomide inhibits granulocyte responses in healthy humans after ex vivo stimulation with bacterial antigens. Antimicrob Agents Chemother. 2001 May;45(5):1547-9. doi: 10.1128/AAC.45.5.1547-1549.2001.
9 An alternative model for type I interferon induction downstream of human TLR2. J Biol Chem. 2020 Oct 16;295(42):14325-14342. doi: 10.1074/jbc.RA120.015283. Epub 2020 Aug 12.