fospropofol   Click here for help

GtoPdb Ligand ID: 7475

Synonyms: Lusedra®
Approved drug
fospropofol is an approved drug (FDA (2008))
Compound class: Synthetic organic
Comment: Fospropofol is a prodrug which undergoes hepatic conversion to the active moeity, propofol.
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 CDK toolkit. 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 4
Hydrogen bond donors 2
Rotatable bonds 6
Topological polar surface area 85.8
Molecular weight 288.11
XLogP 2.52
No. Lipinski's rules broken 0
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.

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Canonical SMILES CC(c1cccc(c1OCOP(=O)(O)O)C(C)C)C
Isomeric SMILES CC(c1cccc(c1OCOP(=O)(O)O)C(C)C)C
InChI InChI=1S/C13H21O5P/c1-9(2)11-6-5-7-12(10(3)4)13(11)17-8-18-19(14,15)16/h5-7,9-10H,8H2,1-4H3,(H2,14,15,16)
InChI Key QVNNONOFASOXQV-UHFFFAOYSA-N
References
1. Bennett DJ, Anderson A, Buchanan K, Byford A, Cooke A, Gemmell DK, Hamilton NM, Maidment MS, McPhail P, Stevenson DF et al.. (2003)
Novel water soluble 2,6-dimethoxyphenyl ester derivatives with intravenous anaesthetic activity.
Bioorg Med Chem Lett, 13 (12): 1971-5. [PMID:12781176]
2. Cooke A, Anderson A, Buchanan K, Byford A, Gemmell D, Hamilton N, McPhail P, Miller S, Sundaram H, Vijn P. (2001)
Water-soluble propofol analogues with intravenous anaesthetic activity.
Bioorg Med Chem Lett, 11 (7): 927-30. [PMID:11294393]
3. Haeseler G, Karst M, Foadi N, Gudehus S, Roeder A, Hecker H, Dengler R, Leuwer M. (2008)
High-affinity blockade of voltage-operated skeletal muscle and neuronal sodium channels by halogenated propofol analogues.
Br J Pharmacol, 155 (2): 265-75. [PMID:18574460]
4. Haeseler G, Leuwer M. (2003)
High-affinity block of voltage-operated rat IIA neuronal sodium channels by 2,6 di-tert-butylphenol, a propofol analogue.
Eur J Anaesthesiol, 20 (3): 220-4. [PMID:12650493]
5. Krasowski MD, Hong X, Hopfinger AJ, Harrison NL. (2002)
4D-QSAR analysis of a set of propofol analogues: mapping binding sites for an anesthetic phenol on the GABA(A) receptor.
J Med Chem, 45 (15): 3210-21. [PMID:12109905]
6. Trapani G, Latrofa A, Franco M, Altomare C, Sanna E, Usala M, Biggio G, Liso G. (1998)
Propofol analogues. Synthesis, relationships between structure and affinity at GABAA receptor in rat brain, and differential electrophysiological profile at recombinant human GABAA receptors.
J Med Chem, 41 (11): 1846-54. [PMID:9599235]
7. Yip GM, Chen ZW, Edge CJ, Smith EH, Dickinson R, Hohenester E, Townsend RR, Fuchs K, Sieghart W, Evers AS et al.. (2013)
A propofol binding site on mammalian GABAA receptors identified by photolabeling.
Nat Chem Biol, 9 (11): 715-20. [PMID:24056400]