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TD-1607   Click here for help

GtoPdb Ligand ID: 14440

Compound class: Synthetic organic
Comment: TD-1607 is from a series of glycopeptide-cephalosporin heterodimer antibacterial compounds, disclosed in a 2005 patent [2] and designed to treat serious infections caused by Gram-positive bacteria.
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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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 46
Hydrogen bond donors 24
Rotatable bonds 36
Topological polar surface area 803.84
Molecular weight 2169.48
XLogP -4.5
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(=C(CNCCNC(=O)CCCCC(=O)NCC%10=CC=[N+](C=C%10)CC%11=C(C(=O)[O-])N%12C(=O)[C@H]([C@H]%12SC%11)NC(=O)/C(=N/OC)/C%13=C(Cl)SC(=N%13)N)C(=C9C%14=CC(=CC=C%14O)[C@H](C(=O)N8)NC(=O)[C@@H]4NC(=O)[C@H](CC(=O)N)NC1=O)O)O)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=C9[C@H](NC(=O)[C@H]([C@@H](C%10=CC(=C(O4)C=C%10)Cl)O)NC7=O)C(=O)O)O)CNCCNC(=O)CCCCC(=O)NCC%11=CC=[N+](C=C%11)CC%12=C(N%13[C@@H]([C@@H](C%13=O)NC(=O)/C(=N/OC)/C%14=C(SC(=N%14)N)Cl)SC%12)C(=O)[O-])O)CC(=O)N)NC(=O)[C@@H](CC(C)C)NC)O)Cl)CO)O)O)(C)N)O
InChI InChI=1S/C95H109Cl3N18O31S2/c1-37(2)23-50(102-5)82(129)110-69-73(123)41-12-15-54(48(96)25-41)143-56-27-43-28-57(78(56)147-93-79(77(127)76(126)58(35-117)145-93)146-62-31-95(4,101)80(128)38(3)142-62)144-55-16-13-42(26-49(55)97)74(124)70-88(135)109-66(91(137)138)46-29-53(119)47(75(125)63(46)45-24-40(11-14-52(45)118)64(84(131)111-70)108-85(132)65(43)107-83(130)51(30-59(99)120)106-87(69)134)33-103-19-20-104-60(121)9-7-8-10-61(122)105-32-39-17-21-115(22-18-39)34-44-36-148-90-71(89(136)116(90)72(44)92(139)140)112-86(133)68(114-141-6)67-81(98)149-94(100)113-67/h11-18,21-22,24-29,37-38,50-51,58,62,64-66,69-71,73-74,76-77,79-80,90,93,102-103,117,123-124,126-128H,7-10,19-20,23,30-36,101H2,1-6H3,(H17-,99,100,104,105,106,107,108,109,110,111,112,113,114,118,119,120,121,122,125,129,130,131,132,133,134,135,137,138,139,140)/t38-,50+,51-,58+,62-,64+,65+,66-,69+,70-,71+,73+,74+,76+,77-,79+,80+,90+,93-,95-/m0/s1
InChI Key WZCNRUDMIDKOGG-VJPNADEXSA-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/)
Bioactivity Comments
The MIC90 for antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA) isolates is 0.008-0.06 μg/ml [3]