2-Acetyl-4-[(5-butanoyl-2,6-dihydroxy-3,3-dimethyl-4-oxocyclohexa-1,5-dien-1-yl)methyl]-3,5-dihydroxy-6,6-dimethylcyclohexa-2,4-dien-1-one

Details

• Internal ID: 23f566b1-216b-4494-9523-c7e738158c4a
• Taxonomy: Organic acids and derivatives > Vinylogous acids
• IUPAC Name: 2-acetyl-4-[(5-butanoyl-2,6-dihydroxy-3,3-dimethyl-4-oxocyclohexa-1,5-dien-1-yl)methyl]-3,5-dihydroxy-6,6-dimethylcyclohexa-2,4-dien-1-one
• SMILES (Canonical): CCCC(=O)C1=C(C(=C(C(C1=O)(C)C)O)CC2=C(C(C(=O)C(=C2O)C(=O)C)(C)C)O)O
• SMILES (Isomeric): CCCC(=O)C1=C(C(=C(C(C1=O)(C)C)O)CC2=C(C(C(=O)C(=C2O)C(=O)C)(C)C)O)O
• InChI: InChI=1S/C23H28O8/c1-7-8-13(25)15-17(27)12(19(29)23(5,6)21(15)31)9-11-16(26)14(10(2)24)20(30)22(3,4)18(11)28/h26-29H,7-9H2,1-6H3
• InChI Key: NXDMJEFAVIPWBQ-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₂₈O₈
• Molecular Weight: 432.50 g/mol
• Exact Mass: 432.17841785 g/mol
• Topological Polar Surface Area (TPSA): 149.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 3.80
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9669	96.69%
Caco-2	-	0.5587	55.87%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8150	81.50%
OATP2B1 inhibitior	-	0.7153	71.53%
OATP1B1 inhibitior	+	0.8151	81.51%
OATP1B3 inhibitior	+	0.9181	91.81%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	-	0.6219	62.19%
P-glycoprotein inhibitior	-	0.6664	66.64%
P-glycoprotein substrate	-	0.8349	83.49%
CYP3A4 substrate	+	0.5206	52.06%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8650	86.50%
CYP3A4 inhibition	-	0.6033	60.33%
CYP2C9 inhibition	-	0.6784	67.84%
CYP2C19 inhibition	-	0.7344	73.44%
CYP2D6 inhibition	-	0.8686	86.86%
CYP1A2 inhibition	-	0.9107	91.07%
CYP2C8 inhibition	-	0.8162	81.62%
CYP inhibitory promiscuity	-	0.5684	56.84%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8966	89.66%
Carcinogenicity (trinary)	Non-required	0.6238	62.38%
Eye corrosion	-	0.9863	98.63%
Eye irritation	+	0.5626	56.26%
Skin irritation	-	0.6383	63.83%
Skin corrosion	-	0.9228	92.28%
Ames mutagenesis	-	0.7500	75.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7220	72.20%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	+	0.6534	65.34%
skin sensitisation	-	0.5372	53.72%
Respiratory toxicity	-	0.6444	64.44%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.7011	70.11%
Acute Oral Toxicity (c)	III	0.5386	53.86%
Estrogen receptor binding	+	0.8096	80.96%
Androgen receptor binding	-	0.6716	67.16%
Thyroid receptor binding	+	0.5789	57.89%
Glucocorticoid receptor binding	+	0.6336	63.36%
Aromatase binding	+	0.5209	52.09%
PPAR gamma	+	0.6945	69.45%
Honey bee toxicity	-	0.9003	90.03%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9690	96.90%

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	94.60%	91.11%
CHEMBL2581	P07339	Cathepsin D	92.84%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.57%	96.09%
CHEMBL4040	P28482	MAP kinase ERK2	89.23%	83.82%
CHEMBL221	P23219	Cyclooxygenase-1	88.91%	90.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.49%	99.23%

Plants that contains it

• Dryopteris villarii

Cross-Links

• PubChem: 102317602
• LOTUS: LTS0067703
• wikiData: Q105187114