Lupulone

Details

• Internal ID: 360b8690-f2c8-4998-b9d8-1eaab2fd072f
• Taxonomy: Organic acids and derivatives > Vinylogous acids
• IUPAC Name: 3,5-dihydroxy-2-(3-methylbutanoyl)-4,6,6-tris(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-one
• SMILES (Canonical): CC(C)CC(=O)C1=C(C(=C(C(C1=O)(CC=C(C)C)CC=C(C)C)O)CC=C(C)C)O
• SMILES (Isomeric): CC(C)CC(=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/c1-16(2)9-10-20-23(28)22(21(27)15-19(7)8)25(30)26(24(20)29,13-11-17(3)4)14-12-18(5)6/h9,11-12,19,28-29H,10,13-15H2,1-8H3
• InChI Key: LSDULPZJLTZEFD-UHFFFAOYSA-N
• Popularity: 313 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: 6.70
• Atomic LogP (AlogP): 6.86
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 9

Synonyms

• Lupulon
• 468-28-0
• beta-Lupulic acid
• beta-Bitter acid
• B'' -Acid
• Lupolon
• B-Lupulic acid
• EINECS 207-405-3
• .beta.-Bitter acid
• .beta.-Lupulic acid
• 2,4-Cyclohexadien-1-one, 3,5-dihydroxy-4-isovaleryl-2,6,6-tris(3-methyl-2-butenyl)-
• 3,5-Dihydroxy-2,6,6-tris(3-methyl-2-butenyl)-4-(3-methyl-1-oxobutyl)-2,4-cyclohexadien-1-one
• UNII-B7425USG94
• 3,5-dihydroxy-2-(3-methylbutanoyl)-4,6,6-tris(3-methylbut-2-enyl)cyclohexa-2,4-dien-1-one
• CHEBI:6574
• 2,4-Cyclohexadien-1-one,3,5-dihydroxy-2,6,6-tris(3-methyl-2-buten-1-yl)-4-(3-methyl-1-oxobutyl)-
• B7425USG94
• 3,5-Dihydroxy-2,6,6-tris(3-methylbuten-2-yl)-4-(3-methyl-1-oxobutyl)cyclohexa-2,4-dien-1-one
• 3,5-Dihydroxy-2,6,6-tris(3-methyl-2-buten-1-yl)-4-(3-methyl-1-oxobutyl)-2,4-cyclohexadien-1-one
• hop beta-acid
• LUPULON [MI]
• 3,5-dihydroxy-2-(3-methylbutanoyl)-4,6,6-tris(3-methylbut-2-en-1-yl)cyclohexa-2,4-dien-1-one
• SCHEMBL819253
• CHEMBL480267
• SCHEMBL2431439
• GTPL12445
• DTXSID00875553
• AKOS015896772
• AKOS040744749
• 2,4-Cyclohexadien-1-one, 3,5-dihydroxy-2,6,6-tris(3-methyl-2-butenyl)-4-(3-methyl-1-oxobutyl)-
• 3,5-dihydroxy-2,6,6-tris(3-methylbut-2-enyl)-4-(3-methyl-1-oxobutyl)cyclohexa-2,4-dien-1-one
• LS-88211
• PD118550
• HY-124923
• CS-0089577
• FT-0650864
• Q27107249
• Q55939056
• 3,5-dihydroxy-2,6,6-tris(3-methylbut-2-enyl)-4-(3-methylbutanoyl)cyclohexa-2,4-dienone
• 3,5-Dihydroxy-4,4,6-tris(3-methyl-2-butenyl)-2-isovaleryl-2,5-cyclohexadien-1-one
• 4,6,6-Triprenyl-2-(1-oxo-3-methylbutyl)-3,5-dihydroxy-2,4-cyclohexadiene-1-one
• 3,5-Dihydroxy-4-(3-methylbutanoyl)-2,6,6-tris(3-methyl-2-butenyl)-2,4-cyclohexadien-1-one #

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9698	96.98%
Caco-2	+	0.6314	63.14%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8241	82.41%
OATP2B1 inhibitior	-	0.7136	71.36%
OATP1B1 inhibitior	+	0.8399	83.99%
OATP1B3 inhibitior	+	0.9210	92.10%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.6178	61.78%
P-glycoprotein inhibitior	-	0.7585	75.85%
P-glycoprotein substrate	-	0.7083	70.83%
CYP3A4 substrate	-	0.5000	50.00%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8758	87.58%
CYP3A4 inhibition	-	0.7903	79.03%
CYP2C9 inhibition	-	0.7931	79.31%
CYP2C19 inhibition	-	0.7099	70.99%
CYP2D6 inhibition	-	0.9018	90.18%
CYP1A2 inhibition	-	0.9125	91.25%
CYP2C8 inhibition	-	0.9199	91.99%
CYP inhibitory promiscuity	-	0.8297	82.97%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.8450	84.50%
Carcinogenicity (trinary)	Non-required	0.6579	65.79%
Eye corrosion	-	0.9764	97.64%
Eye irritation	-	0.5000	50.00%
Skin irritation	-	0.6153	61.53%
Skin corrosion	-	0.9259	92.59%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6324	63.24%
Micronuclear	-	0.7600	76.00%
Hepatotoxicity	+	0.7179	71.79%
skin sensitisation	+	0.5428	54.28%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.6667	66.67%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	+	0.7455	74.55%
Acute Oral Toxicity (c)	II	0.7129	71.29%
Estrogen receptor binding	+	0.6873	68.73%
Androgen receptor binding	+	0.5333	53.33%
Thyroid receptor binding	+	0.5232	52.32%
Glucocorticoid receptor binding	+	0.7636	76.36%
Aromatase binding	+	0.6564	65.64%
PPAR gamma	+	0.8733	87.33%
Honey bee toxicity	-	0.8428	84.28%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.7500	75.00%
Fish aquatic toxicity	+	0.9839	98.39%

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	95.96%	83.82%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.39%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.37%	91.11%
CHEMBL2581	P07339	Cathepsin D	94.99%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	90.30%	90.17%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	87.44%	89.34%
CHEMBL3401	O75469	Pregnane X receptor	85.85%	94.73%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.32%	96.09%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.46%	90.71%
CHEMBL3830	Q2M2I8	Adaptor-associated kinase	80.08%	83.10%

Plants that contains it

• Humulus lupulus

Cross-Links

• PubChem: 68051
• NPASS: NPC226867
• LOTUS: LTS0156659
• wikiData: Q27107249