{"id":"bdf7a90c-8219-5ae6-b4ed-fee1275aab87","stable_key":"3d41d18a-e13a-59a0-a081-55bfcdd43e55:ceylon-methoxy-heme","predicate":"increases","statement":"The methoxy analogue caused reported CYP2A6 heme loss of 48.5 ± 13.4% in the LC-MS/MS experiment.","claim_class":"mechanistic","status":"source_derived_draft","evidence_grade":"ungraded","direction":"context_dependent","is_public":true,"mechanism_event_id":"82d4573d-7fde-56da-9963-4bb4b11eee90","mechanism_event_label":"Heme damage was measured for the methoxy analogue; this number should not be attributed to cinnamaldehyde.","subject":{"id":"3b784ae4-53c7-5d28-a5ca-55e15189abd6","slug":"2-methoxycinnamaldehyde","display_name":"2-Methoxycinnamaldehyde","entity_type_key":"small_molecule"},"object":{"id":"02fe2d79-44e8-547f-a093-54bad26d7d48","slug":"cyp2a6-heme-loss","display_name":"CYP2A6 heme loss measured after methoxycinnamaldehyde exposure","entity_type_key":"cellular_process"},"evidence_count":1,"mechanism_event":{"id":"82d4573d-7fde-56da-9963-4bb4b11eee90","stable_key":"3d41d18a-e13a-59a0-a081-55bfcdd43e55:ceylon-methoxy-heme-event","event_type":"biochemical_relationship","label":"Heme damage was measured for the methoxy analogue; this number should not be attributed to cinnamaldehyde.","description":"The methoxy analogue caused reported CYP2A6 heme loss of 48.5 ± 13.4% in the LC-MS/MS experiment.","status":"provisional","compartment":null,"participants":[{"entity":{"id":"44b7b150-3615-5d52-9db8-beb212fc31eb","slug":"cyp2a6","display_name":"Human cytochrome P450 2A6 / CYP2A6","entity_type_key":"protein"},"role":"enzyme","stoichiometry":null,"state_label":"","sequence_order":0,"notes":""},{"entity":{"id":"3b784ae4-53c7-5d28-a5ca-55e15189abd6","slug":"2-methoxycinnamaldehyde","display_name":"2-Methoxycinnamaldehyde","entity_type_key":"small_molecule"},"role":"subject","stoichiometry":null,"state_label":"","sequence_order":1,"notes":""},{"entity":{"id":"02fe2d79-44e8-547f-a093-54bad26d7d48","slug":"cyp2a6-heme-loss","display_name":"CYP2A6 heme loss measured after methoxycinnamaldehyde exposure","entity_type_key":"cellular_process"},"role":"target","stoichiometry":null,"state_label":"","sequence_order":2,"notes":""}]},"contexts":[{"dimension":"evidence_span","value_text":"{\"source_cache\": \"artifacts/ceylon-research/32788161.abstract.txt\", \"locator\": \"Primary indexed abstract; zero-based, end-exclusive Unicode character offsets\", \"file_sha256\": \"431169f83241cb83b84dd81d84eb1db225735677cabf33f09af8b1e22dfe64f4\", \"start_char\": 0, \"end_char\": 2507, \"text_sha256\": \"431169f83241cb83b84dd81d84eb1db225735677cabf33f09af8b1e22dfe64f4\"}","comparator":null,"unit":null,"notes":"","entity":null},{"dimension":"experimental_model","value_text":"CYP2A6 mass spectrometry, time-dependent inhibition and numerical modeling","comparator":null,"unit":null,"notes":"","entity":null},{"dimension":"exposure","value_text":"Cinnamaldehyde and separately 2-methoxycinnamaldehyde; model exposure approximately 275 mg cinnamaldehyde","comparator":null,"unit":null,"notes":"","entity":null},{"dimension":"limitations","value_text":"Rat-scaled predicted human AUC is not observed AUC. Heme loss was specifically reported for the methoxy analogue; apoprotein adduction is a different endpoint from inhibition.","comparator":null,"unit":null,"notes":"","entity":null},{"dimension":"nutrient_topic","value_text":"Ceylon cinnamon research collection; topical membership is not evidence of a direct dietary effect.","comparator":null,"unit":null,"notes":"","entity":{"slug":"ceylon","display_name":"Ceylon cinnamon / Cinnamomum verum bark preparations","entity_type_key":"chemical_species"}},{"dimension":"organism","value_text":"Human CYP2A6; rat-scaled modeling parameters","comparator":null,"unit":null,"notes":"","entity":null},{"dimension":"plain_language","value_text":"Heme damage was measured for the methoxy analogue; this number should not be attributed to cinnamaldehyde.","comparator":null,"unit":null,"notes":"","entity":null},{"dimension":"primary_references","value_text":"[ceylon-p32788161] Mechanisms of Herb-Drug Interactions Involving Cinnamon and CYP2A6: Focus on Time-Dependent Inhibition by Cinnamaldehyde and 2-Methoxycinnamaldehyde. (2020). https://pubmed.ncbi.nlm.nih.gov/32788161/ DOI: 10.1124/dmd.120.000087","comparator":null,"unit":null,"notes":"","entity":null},{"dimension":"tissue_or_cell_type","value_text":"Enzyme apoprotein/heme; simulated drug exposure","comparator":null,"unit":null,"notes":"","entity":null}],"evidence":[{"id":"23a6340a-ee4f-53aa-9426-791f34fd4ae1","evidence_kind":"source_excerpt","locator":"Lines 779-790","start_line":779,"end_line":790,"excerpt":"### ceylon-methoxy-heme\nThe methoxy analogue caused reported CYP2A6 heme loss of 48.5 ± 13.4% in the LC-MS/MS experiment.\nCondition category: normal\nnutrient_topic: Ceylon cinnamon research collection; topical membership is not evidence of a direct dietary effect.\nplain_language: Heme damage was measured for the methoxy analogue; this number should not be attributed to cinnamaldehyde.\norganism: Human CYP2A6; rat-scaled modeling parameters\ntissue_or_cell_type: Enzyme apoprotein/heme; simulated drug exposure\nexperimental_model: CYP2A6 mass spectrometry, time-dependent inhibition and numerical modeling\nlimitations: Rat-scaled predicted human AUC is not observed AUC. Heme loss was specifically reported for the methoxy analogue; apoprotein adduction is a different endpoint from inhibition.\nexposure: Cinnamaldehyde and separately 2-methoxycinnamaldehyde; model exposure approximately 275 mg cinnamaldehyde\nevidence_span: {\"source_cache\": \"artifacts/ceylon-research/32788161.abstract.txt\", \"locator\": \"Primary indexed abstract; zero-based, end-exclusive Unicode character offsets\", \"file_sha256\": \"431169f83241cb83b84dd81d84eb1db225735677cabf33f09af8b1e22dfe64f4\", \"start_char\": 0, \"end_char\": 2507, \"text_sha256\": \"431169f83241cb83b84dd81d84eb1db225735677cabf33f09af8b1e22dfe64f4\"}\n[ceylon-p32788161] Mechanisms of Herb-Drug Interactions Involving Cinnamon and CYP2A6: Focus on Time-Dependent Inhibition by Cinnamaldehyde and 2-Methoxycinnamaldehyde. 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