Details of the Drug

General Information of Drug (ID: DM6QV8A)

• Drug Name: Beta-ionone
• Synonyms: BETA-IONONE; beta-Cyclocitrylideneacetone; beta-E-Ionone; trans-beta-Ionone; (3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one; (E)-4-(2,6,6-Trimethylcyclohex-1-en-1-yl)but-3-en-2-one; (E)-beta-Ionone; .beta.-Ionone; 14901-07-6; 3-Buten-2-one, 4-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (3E)-; 4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-3-buten-2-one; 4-(2,6,6-Trimethyl-1-cyclohexenyl)-3-buten-2-one; 4-(2,6,6-Trimethylcyclohex-1-en-1-yl)but-3-en-2-one; 79-77-6; NSC 402758; UNII-A7NRR1HLH6
• #Ro5 Violations (Lipinski): 0:
  Molecular Weight (mw); 192.3
  Logarithm of the Partition Coefficient (xlogp); 2.9
  Rotatable Bond Count (rotbonds); 2
  Hydrogen Bond Donor Count (hbonddonor); 0
  Hydrogen Bond Acceptor Count (hbondacc); 1
• Chemical Identifiers:
  Formula: C13H20O
  IUPAC Name: (E)-4-(2,6,6-trimethylcyclohexen-1-yl)but-3-en-2-one
  Canonical SMILES: CC1=C(C(CCC1)(C)C)C=CC(=O)C
  InChI: PSQYTAPXSHCGMF-BQYQJAHWSA-N
  InChIKey: 1S/C13H20O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h7-8H,5-6,9H2,1-4H3/b8-7+
• Cross-matching ID:
  PubChem CID: 638014
  ChEBI ID: CHEBI:32325
  CAS Number: 79-77-6
  INTEDE ID: DR2614

Molecular Interaction Atlas of This Drug

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 109B1 (cyp109)	DE06B47	U5U1Z3_BACIU	Substrate	[1], [2]
Cytochrome P450 101B1 (cyp101)	DEKYTSB	Q2G637_NOVAD	Substrate	[3], [4]
Cytochrome P450 101C1 (cyp101)	DEGJFHV	Q2G637_NOVAD	Substrate	[3], [5]

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Apoptosis regulator BAX (BAX)	OTAW0V4V	BAX_HUMAN	Gene/Protein Processing	[6]
Apoptosis regulator Bcl-2 (BCL2)	OT9DVHC0	BCL2_HUMAN	Gene/Protein Processing	[7]
Caspase-3 (CASP3)	OTIJRBE7	CASP3_HUMAN	Protein Interaction/Cellular Processes	[6]
Caspase-9 (CASP9)	OTD4RFFG	CASP9_HUMAN	Protein Interaction/Cellular Processes	[8]
Cyclin-dependent kinase 2 (CDK2)	OTB5DYYZ	CDK2_HUMAN	Gene/Protein Processing	[9]
Cyclin-dependent kinase 4 (CDK4)	OT7EP05T	CDK4_HUMAN	Gene/Protein Processing	[9]
G1/S-specific cyclin-D1 (CCND1)	OT8HPTKJ	CCND1_HUMAN	Gene/Protein Processing	[9]
Lamin-B1 (LMNB1)	OT100T3P	LMNB1_HUMAN	Post-Translational Modifications	[10]
Mitogen-activated protein kinase 1 (MAPK1)	OTH85PI5	MK01_HUMAN	Post-Translational Modifications	[11]
Mitogen-activated protein kinase 3 (MAPK3)	OTCYKGKO	MK03_HUMAN	Post-Translational Modifications	[11]

References

• [1] The crystal structure of the versatile cytochrome P450 enzyme CYP109B1 from Bacillus subtilis. Mol Biosyst. 2015 Mar;11(3):869-81.
• [2] The promises and risks of probiotic Bacillus species. Acta Biochim Pol. 2018 Dec 6;65(4):509-519.
• [3] Patients with primary biliary cirrhosis react against a ubiquitous xenobiotic-metabolizing bacterium. Hepatology. 2003 Nov;38(5):1250-7.
• [4] A cytochrome P450 class I electron transfer system from Novosphingobium aromaticivorans. Appl Microbiol Biotechnol. 2010 Mar;86(1):163-75.
• [5] Structural analysis of CYP101C1 from Novosphingobium aromaticivorans DSM12444. Chembiochem. 2011 Jan 3;12(1):88-99.
• [6] Beta-ionone-inhibited proliferation of breast cancer cells by inhibited COX-2 activity. Arch Toxicol. 2019 Oct;93(10):2993-3003.
• [7] Apoptosis initiation of -ionone in SGC-7901 gastric carcinoma cancer cells via a PI3K-AKT pathway. Arch Toxicol. 2013 Mar;87(3):481-90. doi: 10.1007/s00204-012-0962-8. Epub 2012 Oct 26.
• [8] -Ionone represses renal cell carcinoma progression through activating LKB1/AMPK-triggered autophagy. J Biochem Mol Toxicol. 2023 Jun;37(6):e23331. doi: 10.1002/jbt.23331. Epub 2023 Feb 26.
• [9] Geraniol and beta-ionone inhibit proliferation, cell cycle progression, and cyclin-dependent kinase 2 activity in MCF-7 breast cancer cells independent of effects on HMG-CoA reductase activity. Biochem Pharmacol. 2004 Nov 1;68(9):1739-47.
• [10] Apoptosis and cell-cycle arrest in human and murine tumor cells are initiated by isoprenoids. J Nutr. 1999 Apr;129(4):804-13. doi: 10.1093/jn/129.4.804.
• [11] Functional Characterization of the Odorant Receptor 51E2 in Human Melanocytes. J Biol Chem. 2016 Aug 19;291(34):17772-86. doi: 10.1074/jbc.M116.734517. Epub 2016 May 18.