(2E,6E)-2,6-bis(4-hydroxy-3-methoxybenzylidene)cyclohexanone

Details

• Internal ID: 237963f5-2cab-4f7f-87d3-7097dd1c2dec
• Taxonomy: Phenylpropanoids and polyketides > Diarylheptanoids > Linear diarylheptanoids
• IUPAC Name: (2E,6E)-2,6-bis[(4-hydroxy-3-methoxyphenyl)methylidene]cyclohexan-1-one
• SMILES (Canonical): COC1=C(C=CC(=C1)C=C2CCCC(=CC3=CC(=C(C=C3)O)OC)C2=O)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)/C=C\2/C(=O)/C(=C/C3=CC(=C(C=C3)O)OC)/CCC2)O
• InChI: InChI=1S/C22H22O5/c1-26-20-12-14(6-8-18(20)23)10-16-4-3-5-17(22(16)25)11-15-7-9-19(24)21(13-15)27-2/h6-13,23-24H,3-5H2,1-2H3/b16-10+,17-11+
• InChI Key: DHKKONBXGAAFTB-OTYYAQKOSA-N
• Popularity: 31 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₂₂O₅
• Molecular Weight: 366.40 g/mol
• Exact Mass: 366.14672380 g/mol
• Topological Polar Surface Area (TPSA): 76.00 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 4.34
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

• Cyqualon
• Divanil
• Curcumoid
• Cycvalon
• Divanon
• Flavugal
• Tsikvalon
• VANILONE
• Divanillalcyclohexanone
• 2,6-Divanillylidenecyclohexanone
• 579-23-7
• Beveno
• 2,6-Divanillidenecyclohexanone
• Cyclovalonum [INN-Latin]
• Ciclovalona [INN-Spanish]
• 2,6-Bis(4-hydroxy-3-methoxybenzylidene)cyclohexanone
• Cyclovalon
• CHEMBL17205
• (2E,6E)-2,6-bis(4-hydroxy-3-methoxybenzylidene)cyclohexanone
• Cyclohexanone, 2,6-vanillylidene-
• C22H22O5
• EINECS 209-438-9
• Cyclovalone [INN]
• NSC 26727
• BRN 2019082
• AI3-26016
• Ciclovalona
• Cyclovalonum
• Vanidene
• DVC
• Cyclohexanone, 2,6-bis((4-hydroxy-3-methoxyphenyl)methylene)-
• SMR000554641
• UNII-6M4YJ3FA16
• 2,6-Bis((4-hydroxy-3-methoxyphenyl)methylene)cyclohexanone
• 2,6-Bis[(4-hydroxy-3-methoxyphenyl)methylene]cyclohexanone
• Cyclohexanone, 2,6-bis[(4-hydroxy-3-methoxyphenyl)methylene]-
• Cyclohexanone, 2,6-divanillylidene-
• NCGC00164486-01
• 4-08-00-03586 (Beilstein Handbook Reference)
• (2E,6E)-2,6-bis[(4-hydroxy-3-methoxyphenyl)methylidene]cyclohexan-1-one
• MLS000881144
• MLS000881192
• MLS001194951
• SCHEMBL554417
• Cyclohexanone,6-vanillylidene-
• Cyclohexanone,6-divanillylidene-
• cid_1550234
• HMS642D03
• CHEBI:135543
• GT-18
• HMS2865P11
• NSC26727
• BDBM50067033
• NSC652893
• AKOS001571214
• NSC-652893
• NCGC00164486-02
• NCGC00164486-03
• LS-57369
• WLN: L6YVYTJ AU1R DQ CO1& CU1R DQ CO1
• 2,6-Bis-(4-hydroxy-3-methoxy-benzylidene)-cyclohexanone
• 2,6-Bis[(E)-3-methoxy-4-hydroxybenzylidene]cyclohexanone
• Cyclohexanone,6-bis[(4-hydroxy-3-methoxyphenyl)methylene]-
• 2,6-bis((3-methoxy-4-hydroxyphenyl)methylene)-cyclohexanone
• 2,6-Bis((4-hydroxy-3-methoxyphenyl)methylene)cyclohexan-1-one
• (2E,6E)-2,6-bis[(4-hydroxy-3-methoxy-phenyl)methylene]cyclohexanone
• 2,6-Bis-[1-(4-hydroxy-3-methoxy-phenyl)-meth-(E)-ylidene]-cyclohexanone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9905	99.05%
Caco-2	-	0.5218	52.18%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	+	0.6714	67.14%
Subcellular localzation	Mitochondria	0.9050	90.50%
OATP2B1 inhibitior	-	0.7073	70.73%
OATP1B1 inhibitior	+	0.9517	95.17%
OATP1B3 inhibitior	+	0.9574	95.74%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.8377	83.77%
P-glycoprotein inhibitior	+	0.8127	81.27%
P-glycoprotein substrate	-	0.9885	98.85%
CYP3A4 substrate	-	0.5901	59.01%
CYP2C9 substrate	-	0.5948	59.48%
CYP2D6 substrate	-	0.6870	68.70%
CYP3A4 inhibition	-	0.7056	70.56%
CYP2C9 inhibition	+	0.6170	61.70%
CYP2C19 inhibition	+	0.8440	84.40%
CYP2D6 inhibition	-	0.8079	80.79%
CYP1A2 inhibition	+	0.8935	89.35%
CYP2C8 inhibition	-	0.7754	77.54%
CYP inhibitory promiscuity	+	0.7329	73.29%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7125	71.25%
Carcinogenicity (trinary)	Non-required	0.6755	67.55%
Eye corrosion	-	0.9789	97.89%
Eye irritation	-	0.6979	69.79%
Skin irritation	-	0.7533	75.33%
Skin corrosion	-	0.9701	97.01%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6774	67.74%
Micronuclear	-	0.5300	53.00%
Hepatotoxicity	+	0.5212	52.12%
skin sensitisation	-	0.7216	72.16%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	-	0.7125	71.25%
Nephrotoxicity	-	0.6494	64.94%
Acute Oral Toxicity (c)	III	0.5614	56.14%
Estrogen receptor binding	+	0.9156	91.56%
Androgen receptor binding	+	0.7986	79.86%
Thyroid receptor binding	+	0.7223	72.23%
Glucocorticoid receptor binding	+	0.7032	70.32%
Aromatase binding	+	0.5659	56.59%
PPAR gamma	+	0.8708	87.08%
Honey bee toxicity	-	0.9376	93.76%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9909	99.09%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293266	Q9HC29	Nucleotide-binding oligomerization domain-containing protein 2	9950 nM	EC50	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	98.02%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.92%	91.11%
CHEMBL1929	P47989	Xanthine dehydrogenase	93.49%	96.12%
CHEMBL1951	P21397	Monoamine oxidase A	93.33%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.34%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.83%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.57%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.43%	89.00%
CHEMBL4208	P20618	Proteasome component C5	85.17%	90.00%
CHEMBL2581	P07339	Cathepsin D	85.04%	98.95%
CHEMBL2535	P11166	Glucose transporter	84.51%	98.75%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.59%	92.94%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.05%	95.89%
CHEMBL3194	P02766	Transthyretin	81.59%	90.71%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.52%	90.71%

Plants that contains it

• Curcuma longa

Cross-Links

• PubChem: 1550234
• NPASS: NPC276014
• ChEMBL: CHEMBL17205