AH10-7   Click here for help

GtoPdb Ligand ID: 9899

Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: AH10-7 is a sphinganine α-galactosylceramide (or galactosylsphingamide) that has been designed for the potential to activate CD1d-restricted invariant natural killer T (iNKT) cells as a mechanism to augment immune responses against cancer and infections [1]. It is an analogue of KRN7000 (PubChem CID 2826713, a.k.a. α-GalCer) that was originally developed for its potent immunomodulatory effects, and which was investigated as an immuno-oncology agent [3,7]. However, KRN7000 induces both Th1 and Th2 cytokine production, and produces a suboptimal immune response, which likely accounts for its apparent limited efficacy in clinical trials [5,8]. AH10-7 overcomes KRN7000's unpredictable effects by promoting a Th1-biased immune response, which suggests that it will elicit more favorable results against cancer and infection (whereas a Th2-biased response would likely be of more benefit against autoimmune diseases). Both KRN7000 and AH10-7 are ligands for the lipid-binding MHC class I-like protein CD1d. Recognition of lipid-based antigens presented by CD1d sets iNKT cells apart from conventional T cells.
Van Kaer and Wu (2018) have published a review of the therapeutic potential of iNKT cells in autoimmune conditions [6] and the application of unconventional T cells in immuno-oncology is reviewed by Godfrey et al. (2018) [2] and Krijgsman et al. (2018) [4].
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 9
Hydrogen bond donors 5
Rotatable bonds 50
Topological polar surface area 137.71
Molecular weight 971.82
XLogP 21.6
No. Lipinski's rules broken 2
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 CCCCCCCCCCCCCCCCCCCCCCCCCC(=O)NC(C(CCCCCCCCCCCCCCC)O)COC1OC(COC(=C)CCc2ccccc2)C(C(C1O)O)O
Isomeric SMILES CCCCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@H]([C@@H](CCCCCCCCCCCCCCC)O)CO[C@H]1O[C@H](COC(=C)CCc2ccccc2)[C@@H]([C@@H]([C@H]1O)O)O
InChI InChI=1S/C60H109NO8/c1-4-6-8-10-12-14-16-18-19-20-21-22-23-24-25-26-27-29-31-33-35-37-42-46-56(63)61-53(54(62)45-41-36-34-32-30-28-17-15-13-11-9-7-5-2)49-68-60-59(66)58(65)57(64)55(69-60)50-67-51(3)47-48-52-43-39-38-40-44-52/h38-40,43-44,53-55,57-60,62,64-66H,3-37,41-42,45-50H2,1-2H3,(H,61,63)/t53-,54+,55+,57-,58-,59+,60-/m0/s1
InChI Key AACQUTZHAXVZEB-MMSUBXCOSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
N-[(2S,3R)-3-hydroxy-1-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-{[(4-phenylbut-1-en-2-yl)oxy]methyl}oxan-2-yl]oxy}octadecan-2-yl]hexacosanamide
Database Links Click here for help
GtoPdb PubChem SID 363894193
PubChem CID 133081970
Search Google for chemical match using the InChIKey AACQUTZHAXVZEB-MMSUBXCOSA-N
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UniChem Compound Search for chemical match using the InChIKey AACQUTZHAXVZEB-MMSUBXCOSA-N
UniChem Connectivity Search for chemical match using the InChIKey AACQUTZHAXVZEB-MMSUBXCOSA-N