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XAC-X-BY630   Click here for help

GtoPdb Ligand ID: 3279

Synonyms: compound 14 [PMID: 20105183] | XAC-BY630
 Ligand is labelled
Compound class: Synthetic organic
Comment: XAC-X-BY630 is a fluorescent adenosine A1 receptor (antagonist) probe [1].
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 16
Hydrogen bond donors 4
Rotatable bonds 26
Topological polar surface area 196.07
Molecular weight 973.9
XLogP 6.35
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 CCCN1C2=C(C(=O)N(CCC)C1=O)NC(=N2)C3=CC=C(C=C3)OCC(=O)NCCNC(=O)CCCCCNC(=O)COC4=CC=C(C=CC5=CC=C6C=C7C=CC(=[N]7[B+3]([F-])([F-])[N-]56)C8=CC=CS8)C=C4
Isomeric SMILES O=C(NCCNC(=O)CCCCCNC(=O)COC1=CC=C(C=C1)C=CC2=CC=C3C=C4C=CC(C=5SC=CC5)=[N]4[B+3]([F-])([F-])[N-]23)COC=6C=CC(=CC6)C7=NC8=C(N7)C(=O)N(C(=O)N8CCC)CCC
InChI InChI=1S/C50H54BF2N9O7S/c1-3-28-59-48-46(49(66)60(29-4-2)50(59)67)57-47(58-48)35-14-22-40(23-15-35)69-33-45(65)56-27-26-55-43(63)10-6-5-7-25-54-44(64)32-68-39-20-12-34(13-21-39)11-16-36-17-18-37-31-38-19-24-41(42-9-8-30-70-42)62(38)51(52,53)61(36)37/h8-9,11-24,30-31H,3-7,10,25-29,32-33H2,1-2H3,(H,54,64)(H,55,63)(H,56,65)(H,57,58)
InChI Key KISAJDBDJSTRDP-UHFFFAOYSA-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. Baker JG, Middleton R, Adams L, May LT, Briddon SJ, Kellam B, Hill SJ. (2010)
Influence of fluorophore and linker composition on the pharmacology of fluorescent adenosine A1 receptor ligands.
Br J Pharmacol, 159 (4): 772-86. [PMID:20105183]