[(1S,2S,3R,4R,5S)-5-ethenyl-3-hydroxy-4-(3-hydroxyprop-1-en-2-yl)-2-(3-methoxy-3-oxoprop-1-en-2-yl)-5-methylcyclohexyl] (Z)-4-acetyloxy-2-(hydroxymethyl)but-2-enoate

Details

• Internal ID: 981eefc6-e5a6-4dc0-a6c0-960151ce501d
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Elemane sesquiterpenoids
• IUPAC Name: [(1S,2S,3R,4R,5S)-5-ethenyl-3-hydroxy-4-(3-hydroxyprop-1-en-2-yl)-2-(3-methoxy-3-oxoprop-1-en-2-yl)-5-methylcyclohexyl] (Z)-4-acetyloxy-2-(hydroxymethyl)but-2-enoate
• SMILES (Canonical): CC(=O)OCC=C(CO)C(=O)OC1CC(C(C(C1C(=C)C(=O)OC)O)C(=C)CO)(C)C=C
• SMILES (Isomeric): CC(=O)OC/C=C(/CO)\C(=O)O[C@H]1C[C@@]([C@@H]([C@H]([C@@H]1C(=C)C(=O)OC)O)C(=C)CO)(C)C=C
• InChI: InChI=1S/C23H32O9/c1-7-23(5)10-17(32-22(29)16(12-25)8-9-31-15(4)26)18(14(3)21(28)30-6)20(27)19(23)13(2)11-24/h7-8,17-20,24-25,27H,1-3,9-12H2,4-6H3/b16-8-/t17-,18+,19+,20-,23+/m0/s1
• InChI Key: IWDKJDOUWOTZPS-UPUSNDMNSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₂O₉
• Molecular Weight: 452.50 g/mol
• Exact Mass: 452.20463259 g/mol
• Topological Polar Surface Area (TPSA): 140.00 Ų
• XlogP: 1.20
• Atomic LogP (AlogP): 0.85
• H-Bond Acceptor: 9
• H-Bond Donor: 3
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9087	90.87%
Caco-2	-	0.8116	81.16%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.8637	86.37%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9101	91.01%
OATP1B3 inhibitior	+	0.9044	90.44%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.8343	83.43%
BSEP inhibitior	+	0.6458	64.58%
P-glycoprotein inhibitior	-	0.4731	47.31%
P-glycoprotein substrate	+	0.5217	52.17%
CYP3A4 substrate	+	0.6793	67.93%
CYP2C9 substrate	-	0.7952	79.52%
CYP2D6 substrate	-	0.9058	90.58%
CYP3A4 inhibition	-	0.6240	62.40%
CYP2C9 inhibition	-	0.8801	88.01%
CYP2C19 inhibition	-	0.7727	77.27%
CYP2D6 inhibition	-	0.9177	91.77%
CYP1A2 inhibition	-	0.7892	78.92%
CYP2C8 inhibition	-	0.6294	62.94%
CYP inhibitory promiscuity	-	0.9441	94.41%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.7583	75.83%
Carcinogenicity (trinary)	Non-required	0.6642	66.42%
Eye corrosion	-	0.9830	98.30%
Eye irritation	-	0.9233	92.33%
Skin irritation	-	0.7312	73.12%
Skin corrosion	-	0.9789	97.89%
Ames mutagenesis	-	0.5444	54.44%
Human Ether-a-go-go-Related Gene inhibition	-	0.6477	64.77%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	+	0.5231	52.31%
skin sensitisation	-	0.7727	77.27%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	-	0.6500	65.00%
Nephrotoxicity	+	0.8764	87.64%
Acute Oral Toxicity (c)	III	0.5638	56.38%
Estrogen receptor binding	+	0.6631	66.31%
Androgen receptor binding	+	0.6092	60.92%
Thyroid receptor binding	+	0.5186	51.86%
Glucocorticoid receptor binding	+	0.6878	68.78%
Aromatase binding	+	0.6213	62.13%
PPAR gamma	-	0.5428	54.28%
Honey bee toxicity	-	0.5486	54.86%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9884	98.84%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.73%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.48%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.83%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	92.13%	91.19%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	90.55%	95.71%
CHEMBL221	P23219	Cyclooxygenase-1	90.46%	90.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.71%	85.14%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	88.32%	91.24%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	85.79%	94.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.31%	100.00%
CHEMBL5028	O14672	ADAM10	83.67%	97.50%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.62%	95.50%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.55%	96.77%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.41%	91.07%
CHEMBL3437	Q16853	Amine oxidase, copper containing	83.20%	94.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.92%	96.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	81.57%	89.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.32%	99.17%
CHEMBL4005	P42336	PI3-kinase p110-alpha subunit	81.05%	97.47%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	80.10%	91.03%

Plants that contains it

• Centaurea aspera

Cross-Links

• PubChem: 97301589
• LOTUS: LTS0224898
• wikiData: Q105121514