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cefilavancin   Click here for help

GtoPdb Ligand ID: 14349

Synonyms: TD-1792
Compound class: Synthetic organic
Comment: Cefilavancin is the clinical lead from a series of glycopeptide-cephalosporin heterodimer antibacterial compounds, designed to treat serious infections caused by Gram-positive bacteria [2].
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Click here for structure editor
Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 41
Hydrogen bond donors 21
Rotatable bonds 27
Topological polar surface area 725.41
Molecular weight 1983.27
XLogP -3.9
No. Lipinski's rules broken 4

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CC(C)C[C@H](C(=O)N[C@@H]1[C@@H](C2=CC=C(C(=C2)Cl)OC3=CC4=CC(=C3O[C@H]5[C@@H]([C@H]([C@@H]([C@@H](CO)O5)O)O)O[C@H]6C[C@@](C)([C@@H]([C@H](C)O6)O)N)OC7=CC=C(C=C7Cl)[C@H]([C@H]8C(=O)N[C@@H](C9=CC(=CC(=C9C%10=CC(=CC=C%10O)[C@H](C(=O)N8)NC(=O)[C@@H]4NC(=O)[C@H](CC(=O)N)NC1=O)O)O)C(=O)NCCCO/N=C(/C%11=C(Cl)SC(=N%11)N)\C(=O)N[C@@H]%12C(=O)N%13C(=C(C[N+]%14=CC=CC=C%14)CS[C@H]%12%13)C(=O)[O-])O)O)NC
Isomeric SMILES C[C@H]1[C@H]([C@@](C[C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2OC3=C4C=C5C=C3OC6=C(C=C(C=C6)[C@H]([C@H](C(=O)N[C@H](C(=O)N[C@H]5C(=O)N[C@@H]7C8=CC(=C(C=C8)O)C9=C(C=C(C=C9O)O)[C@H](NC(=O)[C@H]([C@@H](C%10=CC(=C(O4)C=C%10)Cl)O)NC7=O)C(=O)NCCCO/N=C(/C%11=C(SC(=N%11)N)Cl)\C(=O)N[C@H]%12[C@@H]%13N(C%12=O)C(=C(CS%13)C[N+]%14=CC=CC=C%14)C(=O)[O-])CC(=O)N)NC(=O)[C@@H](CC(C)C)NC)O)Cl)CO)O)O)(C)N)O
InChI InChI=1S/C87H95Cl3N16O28S2/c1-33(2)20-45(94-5)74(117)100-62-66(112)36-11-14-49(43(88)22-36)130-51-24-38-25-52(70(51)134-85-71(69(115)68(114)53(31-107)132-85)133-55-29-87(4,93)72(116)34(3)129-55)131-50-15-12-37(23-44(50)89)67(113)63-81(124)99-59(42-26-40(108)27-48(110)56(42)41-21-35(10-13-47(41)109)57(77(120)101-63)98-78(121)58(38)97-75(118)46(28-54(91)111)96-80(62)123)76(119)95-16-9-19-128-104-61(60-73(90)136-86(92)103-60)79(122)102-64-82(125)106-65(84(126)127)39(32-135-83(64)106)30-105-17-7-6-8-18-105/h6-8,10-15,17-18,21-27,33-34,45-46,53,55,57-59,62-64,66-69,71-72,83,85,94,107,112-116H,9,16,19-20,28-32,93H2,1-5H3,(H15-,91,92,95,96,97,98,99,100,101,102,103,104,108,109,110,111,117,118,119,120,121,122,123,124,126,127)/t34-,45+,46-,53+,55-,57+,58+,59-,62+,63-,64+,66+,67+,68+,69-,71+,72+,83+,85-,87-/m0/s1
InChI Key OGUAFUAJSPORAH-KHCCTVBNSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
References
1. Blais J, Lewis SR, Krause KM, Benton BM. (2012)
Antistaphylococcal activity of TD-1792, a multivalent glycopeptide-cephalosporin antibiotic.
Antimicrob Agents Chemother, 56 (3): 1584-7. [PMID:22203585]
2. Long DD, Aggen JB, Chinn J, Choi SK, Christensen BG, Fatheree PR, Green D, Hegde SS, Judice JK, Kaniga K et al.. (2008)
Exploring the positional attachment of glycopeptide/beta-lactam heterodimers.
J Antibiot (Tokyo), 61 (10): 603-14. [PMID:19168974]