Adlupulone

Details

• Internal ID: 90249e9a-2811-4439-8203-807793586fa2
• Taxonomy: Organic acids and derivatives > Vinylogous acids
• IUPAC Name: 3,5-dihydroxy-2-(2-methylbutanoyl)-4,6,6-tris(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-one
• SMILES (Canonical): CCC(C)C(=O)C1=C(C(=C(C(C1=O)(CC=C(C)C)CC=C(C)C)O)CC=C(C)C)O
• SMILES (Isomeric): CCC(C)C(=O)C1=C(C(=C(C(C1=O)(CC=C(C)C)CC=C(C)C)O)CC=C(C)C)O
• InChI: InChI=1S/C26H38O4/c1-9-19(8)22(27)21-23(28)20(11-10-16(2)3)24(29)26(25(21)30,14-12-17(4)5)15-13-18(6)7/h10,12-13,19,28-29H,9,11,14-15H2,1-8H3
• InChI Key: QXPOWGXRDUFAQW-UHFFFAOYSA-N
• Popularity: 10 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₈O₄
• Molecular Weight: 414.60 g/mol
• Exact Mass: 414.27700969 g/mol
• Topological Polar Surface Area (TPSA): 74.60 Ų
• XlogP: 6.90
• Atomic LogP (AlogP): 6.86
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 9

Synonyms

• O2S4D7K08Y
• 28374-71-2
• 31769-60-5
• UNII-O2S4D7K08Y
• 2,4-Cyclohexadien-1-one, 3,5-dihydroxy-4,6,6-tris(3-methyl-2-buten-1-yl)-2-(2-methyl-1-oxobutyl)-
• 35049-54-8
• 3,5-dihydroxy-2-(2-methylbutanoyl)-4,6,6-tris(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-one
• 4-Cyclohexene-1,3-dione, 5-hydroxy-2,2,6-tris(3-methyl-2-buten-1-yl)-4-(2-methyl-1-oxobutyl)-
• SCHEMBL817774
• CHEBI:136852
• DTXSID901318318
• Q27894794
• 3,5-Dihydroxy-4,4,6-tris(3-methyl-2-butenyl)-2-(2-methylbutyryl)-2,5-cyclohexadien-1-one
• 3,5-Dihydroxy-2,6,6-tris(3-methyl-2-butenyl)-4-(2-methyl-1-oxobutyl)-2,4-cyclohexadien-1-one
• 3,5-dihydroxy-2-(2-methylbutanoyl)-4,6,6-tris(3-methylbut-2-en-1-yl)cyclohexa-2,4-dien-1-one
• 468-26-8

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9888	98.88%
Caco-2	+	0.7273	72.73%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7759	77.59%
OATP2B1 inhibitior	-	0.7124	71.24%
OATP1B1 inhibitior	+	0.8192	81.92%
OATP1B3 inhibitior	+	0.9330	93.30%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.7854	78.54%
P-glycoprotein inhibitior	-	0.6895	68.95%
P-glycoprotein substrate	-	0.7022	70.22%
CYP3A4 substrate	-	0.5128	51.28%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8758	87.58%
CYP3A4 inhibition	-	0.7829	78.29%
CYP2C9 inhibition	-	0.6739	67.39%
CYP2C19 inhibition	-	0.7176	71.76%
CYP2D6 inhibition	-	0.8764	87.64%
CYP1A2 inhibition	-	0.8976	89.76%
CYP2C8 inhibition	-	0.9071	90.71%
CYP inhibitory promiscuity	-	0.7453	74.53%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.7923	79.23%
Carcinogenicity (trinary)	Non-required	0.6621	66.21%
Eye corrosion	-	0.9705	97.05%
Eye irritation	-	0.5928	59.28%
Skin irritation	-	0.6147	61.47%
Skin corrosion	-	0.9257	92.57%
Ames mutagenesis	-	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5745	57.45%
Micronuclear	-	0.7500	75.00%
Hepatotoxicity	+	0.5929	59.29%
skin sensitisation	+	0.5892	58.92%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.6222	62.22%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	+	0.5991	59.91%
Acute Oral Toxicity (c)	II	0.5022	50.22%
Estrogen receptor binding	+	0.7648	76.48%
Androgen receptor binding	+	0.5542	55.42%
Thyroid receptor binding	+	0.5319	53.19%
Glucocorticoid receptor binding	+	0.7517	75.17%
Aromatase binding	-	0.5114	51.14%
PPAR gamma	+	0.8592	85.92%
Honey bee toxicity	-	0.8939	89.39%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7700	77.00%
Fish aquatic toxicity	+	0.9942	99.42%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4040	P28482	MAP kinase ERK2	99.65%	83.82%
CHEMBL2581	P07339	Cathepsin D	96.05%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.24%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.37%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.08%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	90.48%	90.17%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	90.09%	89.34%
CHEMBL236	P41143	Delta opioid receptor	87.19%	99.35%
CHEMBL3401	O75469	Pregnane X receptor	84.48%	94.73%
CHEMBL3286	P00749	Urokinase-type plasminogen activator	84.06%	97.88%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	82.76%	100.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	82.64%	90.71%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.49%	85.14%

Plants that contains it

• Humulus lupulus

Cross-Links

• PubChem: 9909740
• NPASS: NPC2825
• LOTUS: LTS0193610
• wikiData: Q27894794