Vicanicin

Details

• Internal ID: ce922d01-1ef7-454e-9484-646c63b3f0d1
• Taxonomy: Phenylpropanoids and polyketides > Depsides and depsidones
• IUPAC Name: 2,8-dichloro-9-hydroxy-3-methoxy-1,4,7,10-tetramethylbenzo[b][1,4]benzodioxepin-6-one
• SMILES (Canonical): CC1=C2C(=C(C(=C1Cl)O)C)OC3=C(C(=C(C(=C3OC2=O)C)OC)Cl)C
• SMILES (Isomeric): CC1=C2C(=C(C(=C1Cl)O)C)OC3=C(C(=C(C(=C3OC2=O)C)OC)Cl)C
• InChI: InChI=1S/C18H16Cl2O5/c1-6-10-14(8(3)13(21)11(6)19)24-16-7(2)12(20)15(23-5)9(4)17(16)25-18(10)22/h21H,1-5H3
• InChI Key: DJIUVCGPONSSSV-UHFFFAOYSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₁₆Cl₂O₅
• Molecular Weight: 383.20 g/mol
• Exact Mass: 382.0374790 g/mol
• Topological Polar Surface Area (TPSA): 65.00 Ų
• XlogP: 5.30
• Atomic LogP (AlogP): 5.27
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

• 33211-22-2
• NSC 289106
• 11H-Dibenzo(b,e)(1,4)dioxepin-11-one, 2,7-dichloro-3-hydroxy-8-methoxy-1,4,6,9-tetramethyl-
• 2,8-dichloro-9-hydroxy-3-methoxy-1,4,7,10-tetramethylbenzo[b][1,4]benzodioxepin-6-one
• NSC-289106
• NSC289106
• FHW4YP3B2Z
• DTXSID50186863
• 2,7-Dichloro-3-hydroxy-8-methoxy-1,4,6,9-tetramethyl-11H-dibenzo[b,e][1,4]dioxepin-11-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9851	98.51%
Caco-2	+	0.7911	79.11%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.4620	46.20%
OATP2B1 inhibitior	-	0.8552	85.52%
OATP1B1 inhibitior	+	0.7129	71.29%
OATP1B3 inhibitior	-	0.4407	44.07%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.5391	53.91%
P-glycoprotein inhibitior	-	0.7558	75.58%
P-glycoprotein substrate	-	0.9639	96.39%
CYP3A4 substrate	+	0.5465	54.65%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	-	0.8539	85.39%
CYP3A4 inhibition	-	0.6252	62.52%
CYP2C9 inhibition	-	0.8520	85.20%
CYP2C19 inhibition	-	0.7357	73.57%
CYP2D6 inhibition	-	0.8821	88.21%
CYP1A2 inhibition	-	0.7543	75.43%
CYP2C8 inhibition	+	0.5321	53.21%
CYP inhibitory promiscuity	-	0.6537	65.37%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.7957	79.57%
Carcinogenicity (trinary)	Danger	0.6549	65.49%
Eye corrosion	-	0.9789	97.89%
Eye irritation	+	0.7853	78.53%
Skin irritation	-	0.6711	67.11%
Skin corrosion	-	0.9627	96.27%
Ames mutagenesis	-	0.5542	55.42%
Human Ether-a-go-go-Related Gene inhibition	-	0.6200	62.00%
Micronuclear	+	0.7348	73.48%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.8630	86.30%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.5738	57.38%
Acute Oral Toxicity (c)	II	0.4614	46.14%
Estrogen receptor binding	+	0.8271	82.71%
Androgen receptor binding	-	0.7305	73.05%
Thyroid receptor binding	+	0.6026	60.26%
Glucocorticoid receptor binding	+	0.7188	71.88%
Aromatase binding	+	0.5996	59.96%
PPAR gamma	+	0.6783	67.83%
Honey bee toxicity	-	0.9230	92.30%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9858	98.58%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.44%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.80%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.05%	94.00%
CHEMBL3401	O75469	Pregnane X receptor	92.93%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.96%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.99%	86.33%
CHEMBL2581	P07339	Cathepsin D	82.75%	98.95%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.75%	96.95%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 324269
• LOTUS: LTS0233044
• wikiData: Q75059743