2-(1-Oxo-4-methylpentyl)-3,5,6-trihydroxy-4,6-bis(3-methyl-2-butenyl)-2,4-cyclohexadien-1-one

Details

• Internal ID: 750812fb-f35b-4621-8cc9-5d6d814dc612
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Acyloins
• IUPAC Name: 3,5,6-trihydroxy-4,6-bis(3-methylbut-2-enyl)-2-(4-methylpentanoyl)cyclohexa-2,4-dien-1-one
• SMILES (Canonical): CC(C)CCC(=O)C1=C(C(=C(C(C1=O)(CC=C(C)C)O)O)CC=C(C)C)O
• SMILES (Isomeric): CC(C)CCC(=O)C1=C(C(=C(C(C1=O)(CC=C(C)C)O)O)CC=C(C)C)O
• InChI: InChI=1S/C22H32O5/c1-13(2)7-9-16-19(24)18(17(23)10-8-14(3)4)21(26)22(27,20(16)25)12-11-15(5)6/h7,11,14,24-25,27H,8-10,12H2,1-6H3
• InChI Key: OIXWZZRPUMLSMY-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₃₂O₅
• Molecular Weight: 376.50 g/mol
• Exact Mass: 376.22497412 g/mol
• Topological Polar Surface Area (TPSA): 94.80 Ų
• XlogP: 4.50
• Atomic LogP (AlogP): 4.64
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 8

Synonyms

• Prehumulone/Adprehumulone
• DTXSID201318224
• 2-(1-Oxo-4-methylpentyl)-3,5,6-trihydroxy-4,6-bis(3-methyl-2-butenyl)-2,4-cyclohexadien-1-one
• 4-(1-Oxo-4-methylpentyl)-3,5,6-trihydroxy-2,6-bis(3-methyl-2-butenyl)-2,4-cyclohexadien-1-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9367	93.67%
Caco-2	+	0.5556	55.56%
Blood Brain Barrier	+	0.6250	62.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.7907	79.07%
OATP2B1 inhibitior	-	0.5712	57.12%
OATP1B1 inhibitior	+	0.8700	87.00%
OATP1B3 inhibitior	+	0.9149	91.49%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	-	0.5487	54.87%
P-glycoprotein inhibitior	-	0.7303	73.03%
P-glycoprotein substrate	-	0.6269	62.69%
CYP3A4 substrate	+	0.5470	54.70%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8815	88.15%
CYP3A4 inhibition	-	0.8222	82.22%
CYP2C9 inhibition	-	0.8065	80.65%
CYP2C19 inhibition	-	0.7669	76.69%
CYP2D6 inhibition	-	0.9067	90.67%
CYP1A2 inhibition	-	0.9140	91.40%
CYP2C8 inhibition	-	0.9147	91.47%
CYP inhibitory promiscuity	-	0.9560	95.60%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.7022	70.22%
Eye corrosion	-	0.9861	98.61%
Eye irritation	-	0.6139	61.39%
Skin irritation	-	0.5520	55.20%
Skin corrosion	-	0.9205	92.05%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6545	65.45%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	+	0.6554	65.54%
skin sensitisation	-	0.5766	57.66%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.7222	72.22%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.7502	75.02%
Acute Oral Toxicity (c)	III	0.4453	44.53%
Estrogen receptor binding	+	0.5577	55.77%
Androgen receptor binding	-	0.4947	49.47%
Thyroid receptor binding	-	0.5056	50.56%
Glucocorticoid receptor binding	+	0.6751	67.51%
Aromatase binding	+	0.6013	60.13%
PPAR gamma	+	0.8367	83.67%
Honey bee toxicity	-	0.8411	84.11%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.9559	95.59%

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	96.11%	91.11%
CHEMBL2581	P07339	Cathepsin D	95.54%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	92.64%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.55%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.08%	94.45%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	85.27%	89.34%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.99%	85.14%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	82.91%	96.90%
CHEMBL3401	O75469	Pregnane X receptor	82.65%	94.73%
CHEMBL340	P08684	Cytochrome P450 3A4	80.71%	91.19%

Plants that contains it

• Humulus lupulus

Cross-Links

• PubChem: 90473758
• NPASS: NPC65990
• LOTUS: LTS0252750
• wikiData: Q104250638