3,5-Dihydroxy-4,6,6-tris(3-methylbut-2-enyl)-2-propanoylcyclohexa-2,4-dien-1-one

Details

• Internal ID: b13b207c-266f-41e4-8db9-61f2294121b6
• Taxonomy: Organic acids and derivatives > Vinylogous acids
• IUPAC Name: 3,5-dihydroxy-4,6,6-tris(3-methylbut-2-enyl)-2-propanoylcyclohexa-2,4-dien-1-one
• SMILES (Canonical): CCC(=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(=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/C24H34O4/c1-8-19(25)20-21(26)18(10-9-15(2)3)22(27)24(23(20)28,13-11-16(4)5)14-12-17(6)7/h9,11-12,26-27H,8,10,13-14H2,1-7H3
• InChI Key: VCANATCEXUMEMT-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₄H₃₄O₄
• Molecular Weight: 386.50 g/mol
• Exact Mass: 386.24570956 g/mol
• Topological Polar Surface Area (TPSA): 74.60 Ų
• XlogP: 5.90
• Atomic LogP (AlogP): 6.23
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9784	97.84%
Caco-2	+	0.7101	71.01%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.8392	83.92%
OATP2B1 inhibitior	-	0.7114	71.14%
OATP1B1 inhibitior	+	0.8676	86.76%
OATP1B3 inhibitior	+	0.9409	94.09%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.5919	59.19%
P-glycoprotein inhibitior	-	0.7182	71.82%
P-glycoprotein substrate	-	0.7688	76.88%
CYP3A4 substrate	-	0.5055	50.55%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8705	87.05%
CYP3A4 inhibition	-	0.7743	77.43%
CYP2C9 inhibition	-	0.7453	74.53%
CYP2C19 inhibition	-	0.6429	64.29%
CYP2D6 inhibition	-	0.8731	87.31%
CYP1A2 inhibition	-	0.9153	91.53%
CYP2C8 inhibition	-	0.8721	87.21%
CYP inhibitory promiscuity	-	0.7432	74.32%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.8348	83.48%
Carcinogenicity (trinary)	Non-required	0.6741	67.41%
Eye corrosion	-	0.9751	97.51%
Eye irritation	-	0.4788	47.88%
Skin irritation	-	0.6116	61.16%
Skin corrosion	-	0.9123	91.23%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4869	48.69%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	+	0.5802	58.02%
skin sensitisation	+	0.5215	52.15%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	+	0.6707	67.07%
Acute Oral Toxicity (c)	II	0.6009	60.09%
Estrogen receptor binding	+	0.7275	72.75%
Androgen receptor binding	+	0.5423	54.23%
Thyroid receptor binding	-	0.5309	53.09%
Glucocorticoid receptor binding	+	0.7186	71.86%
Aromatase binding	+	0.5982	59.82%
PPAR gamma	+	0.8958	89.58%
Honey bee toxicity	-	0.8901	89.01%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.7000	70.00%
Fish aquatic toxicity	+	0.9769	97.69%

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	95.29%	83.82%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.18%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	91.06%	90.17%
CHEMBL2581	P07339	Cathepsin D	90.83%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.92%	96.09%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	86.18%	89.34%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.93%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	82.52%	94.73%

Plants that contains it

• Humulus lupulus

Cross-Links

• PubChem: 101705386
• LOTUS: LTS0051805
• wikiData: Q104250629