[(3S)-2-(5-hydroxy-4-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)-6-methylhepta-1,5-dien-3-yl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: 06c9b6e3-4701-461b-a455-79fd3aa02304
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: [(3S)-2-(5-hydroxy-4-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)-6-methylhepta-1,5-dien-3-yl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC(CC=C(C)C)C(=C)C1=CC(=O)C(=C(C1=O)O)C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@@H](CC=C(C)C)C(=C)C1=CC(=O)C(=C(C1=O)O)C
• InChI: InChI=1S/C20H24O5/c1-7-12(4)20(24)25-17(9-8-11(2)3)13(5)15-10-16(21)14(6)18(22)19(15)23/h7-8,10,17,22H,5,9H2,1-4,6H3/b12-7-/t17-/m0/s1
• InChI Key: UKBQPCCZPZCSCR-PJCWUCBCSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₄O₅
• Molecular Weight: 344.40 g/mol
• Exact Mass: 344.16237386 g/mol
• Topological Polar Surface Area (TPSA): 80.70 Ų
• XlogP: 4.20
• Atomic LogP (AlogP): 3.69
• H-Bond Acceptor: 5
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9786	97.86%
Caco-2	+	0.6957	69.57%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8540	85.40%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8731	87.31%
OATP1B3 inhibitior	+	0.9183	91.83%
MATE1 inhibitior	-	0.6800	68.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	-	0.4731	47.31%
P-glycoprotein inhibitior	-	0.6322	63.22%
P-glycoprotein substrate	-	0.7920	79.20%
CYP3A4 substrate	+	0.5636	56.36%
CYP2C9 substrate	-	0.5868	58.68%
CYP2D6 substrate	-	0.8988	89.88%
CYP3A4 inhibition	-	0.8021	80.21%
CYP2C9 inhibition	-	0.8748	87.48%
CYP2C19 inhibition	-	0.7739	77.39%
CYP2D6 inhibition	-	0.8366	83.66%
CYP1A2 inhibition	-	0.9292	92.92%
CYP2C8 inhibition	-	0.7506	75.06%
CYP inhibitory promiscuity	-	0.9304	93.04%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.6920	69.20%
Carcinogenicity (trinary)	Non-required	0.7219	72.19%
Eye corrosion	-	0.9399	93.99%
Eye irritation	-	0.5866	58.66%
Skin irritation	-	0.6384	63.84%
Skin corrosion	-	0.9620	96.20%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7025	70.25%
Micronuclear	-	0.6541	65.41%
Hepatotoxicity	+	0.5155	51.55%
skin sensitisation	+	0.5670	56.70%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	-	0.5000	50.00%
Mitochondrial toxicity	-	0.8375	83.75%
Nephrotoxicity	+	0.5357	53.57%
Acute Oral Toxicity (c)	III	0.4018	40.18%
Estrogen receptor binding	+	0.5424	54.24%
Androgen receptor binding	+	0.6401	64.01%
Thyroid receptor binding	-	0.5097	50.97%
Glucocorticoid receptor binding	-	0.5208	52.08%
Aromatase binding	-	0.4887	48.87%
PPAR gamma	+	0.6647	66.47%
Honey bee toxicity	-	0.7350	73.50%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6800	68.00%
Fish aquatic toxicity	+	0.9817	98.17%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.89%	98.95%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	93.76%	97.21%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.98%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.86%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.65%	91.11%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	88.63%	96.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.00%	99.23%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.80%	99.17%
CHEMBL3401	O75469	Pregnane X receptor	83.16%	94.73%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	80.61%	96.00%
CHEMBL221	P23219	Cyclooxygenase-1	80.18%	90.17%

Plants that contains it

• Senecio rosmarinifolius

Cross-Links

• PubChem: 163048126
• LOTUS: LTS0193964
• wikiData: Q105274443