CAY10581 is an enzyme indoleamine 2,3-dioxygenase (IDO) has been implicated in mediating pathological immunosuppression associated with certain diseases, including cancer. Several naphthoquinones inhibit IDO in cells and in vitro, but at low (μM) potency. Importantly, naphthoquinones reduce tumor growth in wild type mice but not in IDO-deficient mice. CAY10581 is a naphthoquinone derivative that potently inhibits IDO (IC50 = 55 nM). It is a more potent inhibitor of IDO than 1-methyl-d-tryptophan (1MT) or annulin B. CAY10581 acts as a reversible uncompetitive inhibitor of IDO and demonstrates minimal impact on cell viability at 100 μM after 24 hours.
| Canonical Smiles | CC1(C(C(C2=C(O1)C(=O)C3=CC=CC=C3C2=O)NCC4=CC=CC=C4)O)C |
|---|---|
| IUPAC Name | (3S,4S)-4-(benzylamino)-3-hydroxy-2,2-dimethyl-3,4-dihydrobenzo[g]chromene-5,10-dione |
| InChIKey | WKHJQIQDQXGUOD-UWJYYQICSA-N |
| INCHI | 1S/C22H21NO4/c1-22(2)21(26)17(23-12-13-8-4-3-5-9-13)16-18(24)14-10-6-7-11-15(14)19(25)20(16)27-22/h3-11,17,21,23,26H,12H2,1-2H3/t17-,21-/m0/s1 |
| Isomeric SMILES | CC1([C@H]([C@H](C2=C(O1)C(=O)C3=CC=CC=C3C2=O)NCC4=CC=CC=C4)O)C |
| Molecular Weight | 363.41 |
| Reaxy-Rn | 25694395 |
| Reaxys-RN_link_address | https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=25694395&ln= |
Comprehensive hazard, handling, storage, and regulatory compliance document.
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View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Organoheterocyclic compounds |
| Class | Naphthopyrans |
| Subclass | Naphthopyranones |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Naphthopyranones |
| Alternative Parents | Naphthoquinones Quinones Phenylmethylamines Benzylamines Aryl ketones Pyranones and derivatives Aralkylamines Vinylogous esters Secondary alcohols Oxacyclic compounds Dialkylamines Organic oxides Hydrocarbon derivatives |
| Molecular Framework | Aromatic heteropolycyclic compounds |
| Substituents | Naphthopyranone - Naphthoquinone - Naphthalene - Benzylamine - Phenylmethylamine - Quinone - Aryl ketone - Pyranone - Aralkylamine - Pyran - Benzenoid - Monocyclic benzene moiety - Vinylogous ester - Secondary alcohol - Ketone - Secondary amine - Oxacycle - Secondary aliphatic amine - Amine - Organic oxide - Organic oxygen compound - Hydrocarbon derivative - Organonitrogen compound - Organic nitrogen compound - Organooxygen compound - Alcohol - Aromatic heteropolycyclic compound |
| Description | This compound belongs to the class of organic compounds known as naphthopyranones. These are compounds containing a naphthopyran skeleton where a ring carbon bears a carboxylic acid group. Naphthtopyran is made up of the pyran ring fused to a naphthalene ring system. |
| External Descriptors | Not available |
| Solubility | Soluble in DMSO (~3 mg/ml), DMF (~10 mg/ml), and 1:9 DMF:PBS (pH 7.2) (~0.1 mg/ml). |
|---|---|
| Refractive Index | n20D1.65 (Predicted) |
| Molecular Weight | 363.400 g/mol |
| XLogP3 | 2.300 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 3 |
| Exact Mass | 363.147 Da |
| Monoisotopic Mass | 363.147 Da |
| Topological Polar Surface Area | 75.600 Ų |
| Heavy Atom Count | 27 |
| Formal Charge | 0 |
| Complexity | 647.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 2 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 0 |
| Covalently-Bonded Unit Count | 1 |
