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606-59-7

606-59-7 structure
606-59-7 structure
  • Name: Cinnabarinic acid
  • Chemical Name: Cinnabarinic Acid
  • CAS Number: 606-59-7
  • Molecular Formula: C14H8N2O6
  • Molecular Weight: 300.223
  • Catalog: Signaling Pathways Apoptosis Apoptosis
  • Create Date: 2018-04-30 08:00:00
  • Modify Date: 2024-01-02 20:43:30
  • Cinnabarinic acid is a specific orthosteric agonist of mGlu4 by interacting with residues of the glutamate binding pocket of mGlu4, has no activity at other mGlu receptors. Cinnabarinic acid is an endogenous metabolite of the kynurenine pathway of tryptophan. Cinnabarinic acid induces cell apoptosis[1].
Name Cinnabarinic Acid
Synonyms 2-amino-3-oxophenoxazine-1,9-dicarboxylic acid
2-Amino-3-oxo-3H-phenoxazine-1,9-dicarboxylic acid
3H-Phenoxazine-1,9-dicarboxylic acid, 2-amino-3-oxo-
Description Cinnabarinic acid is a specific orthosteric agonist of mGlu4 by interacting with residues of the glutamate binding pocket of mGlu4, has no activity at other mGlu receptors. Cinnabarinic acid is an endogenous metabolite of the kynurenine pathway of tryptophan. Cinnabarinic acid induces cell apoptosis[1].
Related Catalog
Target

mGluR4
In Vitro Cinnabarinic acid (0-100 μM) does not activate mGlu1, mGlu2, mGlu5, mGlu6, mGlu7, and mGlu8 receptors as shown by measurements of [3H]InsP formation. In contrast, cinnabarinic acid acts as a partial agonist of mGlu4 receptors by increasing [3H]InsP formation by approximately 35% at 100 μM, which is 5-fold less efficacious than ACPT-I in activating mGlu4 receptors in HEK293 cells transiently transfected with rat mGlu1, -2, -4, -5, -6, -7, or -8 receptors[1]. Cinnabarinic acid (0-100 μM) reduces cAMP formation in a concentration-dependent manner with an excellent potency and efficacy. At 30 μM, cinnabarinic acid is effective at 30 μM, and substantially inhibits cAMP formation in cultured cerebellar granule cells[1].
References

[1]. F Fazio, et al. Cinnabarinic acid, an endogenous metabolite of the kynurenine pathway, activates type 4 metabotropic glutamate receptors.Mol Pharmacol. 2012 May;81(5):643-56.

[2]. Martina Ulivieri, et al. The Trace Kynurenine, Cinnabarinic Acid, Displays Potent Antipsychotic-Like Activity in Mice and Its Levels Are Reduced in the Prefrontal Cortex of Individuals Affected by Schizophrenia. Schizophr Bull. 2020 Jun 7;sbaa074.

[3]. Francesco Fazio, et al. Cinnabarinic acid and xanthurenic acid: Two kynurenine metabolites that interact with metabotropic glutamate receptors. Neuropharmacology. 2017 Jan;112(Pt B):365-372.
Density 1.8±0.1 g/cm3
Boiling Point 536.8±50.0 °C at 760 mmHg
Melting Point >300ºC
Molecular Formula C14H8N2O6
Molecular Weight 300.223
Flash Point 278.4±30.1 °C
Exact Mass 300.038239
PSA 143.72000
LogP -0.13
Vapour Pressure 0.0±1.5 mmHg at 25°C
Index of Refraction 1.780
RIDADR NONH for all modes of transport
50425-08-6 structure

50425-08-6

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606-59-7 structure

606-59-7
Literature: Korshunova, Z. I.; Popova, E. B.; Glibin, E. N.; Ginzburg, O. F. Journal of Organic Chemistry USSR (English Translation), 1991 , vol. 27, # 2.2 p. 314 - 319 Zhurnal Organicheskoi Khimii, 1991 , vol. 27, # 2 p. 369 - 376
137152-34-2 structure

137152-34-2

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606-59-7 structure

606-59-7

137179-11-4 structure

137179-11-4
137179-13-6 structure

137179-13-6
Literature: Korshunova, Z. I.; Popova, E. B.; Glibin, E. N.; Ginzburg, O. F. Journal of Organic Chemistry USSR (English Translation), 1991 , vol. 27, # 2.2 p. 314 - 319 Zhurnal Organicheskoi Khimii, 1991 , vol. 27, # 2 p. 369 - 376
548-93-6 structure

548-93-6

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606-59-7 structure

606-59-7

112817-49-9 structure

112817-49-9
Literature: Manthey, Michael K.; Pyne, Stephen G.; Truscott, Roger J. W. Journal of Organic Chemistry, 1988 , vol. 53, # 7 p. 1486 - 1488
602-00-6 structure

602-00-6
83748-53-2 structure

83748-53-2

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606-59-7

137152-36-4 structure

137152-36-4
Detail
Literature: Korshunova, Z. I.; Popova, E. B.; Glibin, E. N.; Ginzburg, O. F. Journal of Organic Chemistry USSR (English Translation), 1991 , vol. 27, # 2.2 p. 314 - 319 Zhurnal Organicheskoi Khimii, 1991 , vol. 27, # 2 p. 369 - 376
71489-74-2 structure

71489-74-2
83748-53-2 structure

83748-53-2

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606-59-7 structure

606-59-7

137152-37-5 structure

137152-37-5
Detail
Literature: Korshunova, Z. I.; Popova, E. B.; Glibin, E. N.; Ginzburg, O. F. Journal of Organic Chemistry USSR (English Translation), 1991 , vol. 27, # 2.2 p. 314 - 319 Zhurnal Organicheskoi Khimii, 1991 , vol. 27, # 2 p. 369 - 376
602-00-6 structure

602-00-6

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606-59-7 structure

606-59-7
Literature: Butenandt et al. Justus Liebigs Annalen der Chemie, 1957 , vol. 602, p. 72,79
548-93-6 structure

548-93-6

~%

96464-02-7 structure

96464-02-7
606-59-7 structure

606-59-7

112817-49-9 structure

112817-49-9
Detail
Literature: Hick, Larry A.; Manthey, Michael K.; Truscott, Roger J. W. Journal of Heterocyclic Chemistry, 1991 , vol. 28, # 4 p. 1157 - 1160
548-93-6 structure

548-93-6

~38%

606-59-7 structure

606-59-7
Literature: Pasceri, Raffaele; Siegel, David; Ross, David; Moody, Christopher J. Journal of Medicinal Chemistry, 2013 , vol. 56, # 8 p. 3310 - 3317
602-00-6 structure

602-00-6
137152-34-2 structure

137152-34-2

~%

606-59-7 structure

606-59-7

137179-11-4 structure

137179-11-4
Detail
Literature: Korshunova, Z. I.; Popova, E. B.; Glibin, E. N.; Ginzburg, O. F. Journal of Organic Chemistry USSR (English Translation), 1991 , vol. 27, # 2.2 p. 314 - 319 Zhurnal Organicheskoi Khimii, 1991 , vol. 27, # 2 p. 369 - 376

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title: CAS No. 606-59-7 | Chemsrc address: https://www.chemsrc.com/en/baike/1107203.html

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