[(1S,2R,4S,7R,10S,11R)-11-hydroxy-4,6,6,10-tetramethyl-5-oxo-2-tricyclo[5.3.1.04,11]undecanyl] (Z)-2-methylbut-2-enoate

Details

• Internal ID: 3d027997-b6db-4df5-ae5e-dbe6dcde6779
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: [(1S,2R,4S,7R,10S,11R)-11-hydroxy-4,6,6,10-tetramethyl-5-oxo-2-tricyclo[5.3.1.04,11]undecanyl] (Z)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1CC2(C(=O)C(C3C2(C1C(CC3)C)O)(C)C)C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@@H]1C[C@@]2(C(=O)C([C@@H]3[C@]2([C@H]1[C@H](CC3)C)O)(C)C)C
• InChI: InChI=1S/C20H30O4/c1-7-11(2)16(21)24-13-10-19(6)17(22)18(4,5)14-9-8-12(3)15(13)20(14,19)23/h7,12-15,23H,8-10H2,1-6H3/b11-7-/t12-,13+,14+,15-,19+,20+/m0/s1
• InChI Key: MDGMPVBQCKPVIQ-JETVGVLUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₃₀O₄
• Molecular Weight: 334.40 g/mol
• Exact Mass: 334.21440943 g/mol
• Topological Polar Surface Area (TPSA): 63.60 Ų
• XlogP: 3.50
• Atomic LogP (AlogP): 3.28
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9907	99.07%
Caco-2	+	0.7508	75.08%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.8435	84.35%
OATP2B1 inhibitior	-	0.8635	86.35%
OATP1B1 inhibitior	+	0.8978	89.78%
OATP1B3 inhibitior	-	0.3530	35.30%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.6571	65.71%
BSEP inhibitior	-	0.6890	68.90%
P-glycoprotein inhibitior	-	0.7283	72.83%
P-glycoprotein substrate	-	0.7476	74.76%
CYP3A4 substrate	+	0.6391	63.91%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9011	90.11%
CYP3A4 inhibition	-	0.9019	90.19%
CYP2C9 inhibition	-	0.7608	76.08%
CYP2C19 inhibition	-	0.8526	85.26%
CYP2D6 inhibition	-	0.9561	95.61%
CYP1A2 inhibition	-	0.5644	56.44%
CYP2C8 inhibition	-	0.8115	81.15%
CYP inhibitory promiscuity	-	0.9348	93.48%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5614	56.14%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9328	93.28%
Skin irritation	+	0.6535	65.35%
Skin corrosion	-	0.9246	92.46%
Ames mutagenesis	-	0.6937	69.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.7600	76.00%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	+	0.6502	65.02%
skin sensitisation	-	0.6039	60.39%
Respiratory toxicity	-	0.5556	55.56%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	+	0.4905	49.05%
Acute Oral Toxicity (c)	III	0.3352	33.52%
Estrogen receptor binding	+	0.8228	82.28%
Androgen receptor binding	+	0.6575	65.75%
Thyroid receptor binding	+	0.7891	78.91%
Glucocorticoid receptor binding	-	0.4803	48.03%
Aromatase binding	+	0.6078	60.78%
PPAR gamma	+	0.6102	61.02%
Honey bee toxicity	-	0.7830	78.30%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5600	56.00%
Fish aquatic toxicity	+	0.9916	99.16%

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	96.25%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.60%	96.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.01%	92.94%
CHEMBL340	P08684	Cytochrome P450 3A4	89.96%	91.19%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.86%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.27%	95.56%
CHEMBL2581	P07339	Cathepsin D	86.72%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.55%	86.33%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.32%	93.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.45%	95.89%

Plants that contains it

• Senecio coronatus
• Ursinia nana

Cross-Links

• PubChem: 163042966
• LOTUS: LTS0253730
• wikiData: Q105161702