4-Deoxycohumulone

Details

• Internal ID: 1889550f-7f6c-4477-98a8-7d1b41e71ad1
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Phenylketones > Alkyl-phenylketones
• IUPAC Name: 2-methyl-1-[2,4,6-trihydroxy-3,5-bis(3-methylbut-2-enyl)phenyl]propan-1-one
• SMILES (Canonical): CC(C)C(=O)C1=C(C(=C(C(=C1O)CC=C(C)C)O)CC=C(C)C)O
• SMILES (Isomeric): CC(C)C(=O)C1=C(C(=C(C(=C1O)CC=C(C)C)O)CC=C(C)C)O
• InChI: InChI=1S/C20H28O4/c1-11(2)7-9-14-18(22)15(10-8-12(3)4)20(24)16(19(14)23)17(21)13(5)6/h7-8,13,22-24H,9-10H2,1-6H3
• InChI Key: KKFIZYKKQLWBKH-UHFFFAOYSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₈O₄
• Molecular Weight: 332.40 g/mol
• Exact Mass: 332.19875937 g/mol
• Topological Polar Surface Area (TPSA): 77.80 Ų
• XlogP: 6.00
• Atomic LogP (AlogP): 4.66
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 6

Synonyms

• Desoxycohumulone
• 5880-42-2
• 3,5-Bis(3-methyl-2-butenyl)phlorisobutyrophenone
• diprenylphlorisobutyrophenone
• 2-methyl-1-[2,4,6-trihydroxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl]propan-1-one
• 2-methyl-1-[2,4,6-trihydroxy-3,5-bis(3-methylbut-2-enyl)phenyl]propan-1-one
• SCHEMBL24075655
• 3,5-diprenylphlorisobutyrophenone
• CHEBI:134353
• DTXSID001316660
• {3,5-bis(3-methyl-2-butenyl)-2,4,6-trihydroxyphenyl} (2-propyl) ketone
• 2',4',6'-Trihydroxy-2-methyl-3',5'-bis(3-methyl-2-butenyl)propiophenone, 8CI
• 2,4-Bis(3-methyl-2-butenyl)-6-(2-methyl-1-oxopropyl)-1,3,5-cyclohexanetrione, 9CI
• 2-methyl-1-[2,4,6-trihydroxy-3,5-bis(3-methyl-2-butenyl)phenyl]-1-propanone

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9944	99.44%
Caco-2	+	0.7151	71.51%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8206	82.06%
OATP2B1 inhibitior	-	0.5654	56.54%
OATP1B1 inhibitior	+	0.8133	81.33%
OATP1B3 inhibitior	+	0.9472	94.72%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	-	0.6599	65.99%
P-glycoprotein inhibitior	-	0.7638	76.38%
P-glycoprotein substrate	-	0.9256	92.56%
CYP3A4 substrate	-	0.6411	64.11%
CYP2C9 substrate	-	0.7891	78.91%
CYP2D6 substrate	-	0.8268	82.68%
CYP3A4 inhibition	+	0.5189	51.89%
CYP2C9 inhibition	+	0.8408	84.08%
CYP2C19 inhibition	+	0.8648	86.48%
CYP2D6 inhibition	-	0.7821	78.21%
CYP1A2 inhibition	+	0.8236	82.36%
CYP2C8 inhibition	-	0.9763	97.63%
CYP inhibitory promiscuity	+	0.7516	75.16%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7816	78.16%
Carcinogenicity (trinary)	Non-required	0.7821	78.21%
Eye corrosion	-	0.9490	94.90%
Eye irritation	+	0.7399	73.99%
Skin irritation	-	0.6249	62.49%
Skin corrosion	-	0.8879	88.79%
Ames mutagenesis	-	0.6500	65.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5000	50.00%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	+	0.7304	73.04%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	-	0.6679	66.79%
Acute Oral Toxicity (c)	III	0.6787	67.87%
Estrogen receptor binding	+	0.8481	84.81%
Androgen receptor binding	-	0.4920	49.20%
Thyroid receptor binding	+	0.6232	62.32%
Glucocorticoid receptor binding	+	0.8015	80.15%
Aromatase binding	-	0.5199	51.99%
PPAR gamma	+	0.8778	87.78%
Honey bee toxicity	-	0.9329	93.29%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.8500	85.00%
Fish aquatic toxicity	+	0.9963	99.63%

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	97.10%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.26%	98.95%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	90.01%	89.34%
CHEMBL3401	O75469	Pregnane X receptor	89.29%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.26%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.40%	96.09%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	84.64%	100.00%
CHEMBL221	P23219	Cyclooxygenase-1	84.18%	90.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.25%	85.14%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.36%	96.00%

Plants that contains it

• Alkanna cappadocica
• Artemisia rupestris subsp. rupestris
• Atalantia racemosa
• Buddleja cordata
• Crambe tatarica
• Diospyros eriantha
• Fritillaria monantha
• Hoffmannia strigillosa
• Humulus lupulus
• Millettia erythrocalyx
• Myrsine lancifolia
• Ononis vaginalis
• Pteris semipinnata
• Salvia hispanica
• Scorzonera pseudodivaricata
• Stenocereus griseus
• Syncarpia hillii

Cross-Links

• PubChem: 25203730
• NPASS: NPC103402
• LOTUS: LTS0229901
• wikiData: Q74417224