(4R)-3,4,5-Trihydroxy-4,6-bis(3-methyl-2-butenyl)-2-(2-methylpropanoyl)-2,5-cyclohexadien-1-one

Details

• Internal ID: 57be843d-d298-46ae-bac9-88aedf16f459
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Acyloins
• IUPAC Name: (6R)-3,5,6-trihydroxy-4,6-bis(3-methylbut-2-enyl)-2-(2-methylpropanoyl)cyclohexa-2,4-dien-1-one
• SMILES (Canonical): CC(C)C(=O)C1=C(C(=C(C(C1=O)(CC=C(C)C)O)O)CC=C(C)C)O
• SMILES (Isomeric): CC(C)C(=O)C1=C(C(=C([C@@](C1=O)(CC=C(C)C)O)O)CC=C(C)C)O
• InChI: InChI=1S/C20H28O5/c1-11(2)7-8-14-17(22)15(16(21)13(5)6)19(24)20(25,18(14)23)10-9-12(3)4/h7,9,13,22-23,25H,8,10H2,1-6H3/t20-/m1/s1
• InChI Key: DRSITEVYZGOOQG-HXUWFJFHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₅
• Molecular Weight: 348.40 g/mol
• Exact Mass: 348.19367399 g/mol
• Topological Polar Surface Area (TPSA): 94.80 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 3.86
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

• SCHEMBL818622
• (4R)-3,4,5-Trihydroxy-4,6-bis(3-methyl-2-butenyl)-2-(2-methylpropanoyl)-2,5-cyclohexadien-1-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9357	93.57%
Caco-2	+	0.5734	57.34%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7969	79.69%
OATP2B1 inhibitior	-	0.5663	56.63%
OATP1B1 inhibitior	+	0.8927	89.27%
OATP1B3 inhibitior	+	0.9428	94.28%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.7805	78.05%
P-glycoprotein inhibitior	-	0.8361	83.61%
P-glycoprotein substrate	-	0.7530	75.30%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8815	88.15%
CYP3A4 inhibition	-	0.9127	91.27%
CYP2C9 inhibition	-	0.8298	82.98%
CYP2C19 inhibition	-	0.7481	74.81%
CYP2D6 inhibition	-	0.8974	89.74%
CYP1A2 inhibition	-	0.9326	93.26%
CYP2C8 inhibition	-	0.9388	93.88%
CYP inhibitory promiscuity	-	0.9475	94.75%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Non-required	0.6930	69.30%
Eye corrosion	-	0.9832	98.32%
Eye irritation	+	0.5486	54.86%
Skin irritation	-	0.6099	60.99%
Skin corrosion	-	0.9104	91.04%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7217	72.17%
Micronuclear	-	0.6241	62.41%
Hepatotoxicity	+	0.6429	64.29%
skin sensitisation	-	0.5308	53.08%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.7775	77.75%
Acute Oral Toxicity (c)	III	0.4185	41.85%
Estrogen receptor binding	+	0.6864	68.64%
Androgen receptor binding	+	0.5327	53.27%
Thyroid receptor binding	-	0.5344	53.44%
Glucocorticoid receptor binding	+	0.7580	75.80%
Aromatase binding	-	0.5396	53.96%
PPAR gamma	+	0.7900	79.00%
Honey bee toxicity	-	0.8566	85.66%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.7300	73.00%
Fish aquatic toxicity	+	0.9438	94.38%

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	97.33%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.50%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.80%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.72%	96.09%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	86.50%	89.34%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.90%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	83.77%	94.73%
CHEMBL221	P23219	Cyclooxygenase-1	83.59%	90.17%
CHEMBL253	P34972	Cannabinoid CB2 receptor	80.51%	97.25%

Plants that contains it

• Humulus lupulus

Cross-Links

• PubChem: 25200458
• NPASS: NPC310767
• LOTUS: LTS0111546
• wikiData: Q104987607