[(Z)-5-[(2R,3S)-3-[(E,5R)-5-hydroxy-4,8-dimethyl-7-methylidenenon-3-enyl]-3-methyloxiran-2-yl]-3-methylpent-2-enyl] acetate

Details

• Internal ID: 2d8ece45-10cb-4fc1-9849-030b9068e044
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: [(Z)-5-[(2R,3S)-3-[(E,5R)-5-hydroxy-4,8-dimethyl-7-methylidenenon-3-enyl]-3-methyloxiran-2-yl]-3-methylpent-2-enyl] acetate
• SMILES (Canonical): CC(C)C(=C)CC(C(=CCCC1(C(O1)CCC(=CCOC(=O)C)C)C)C)O
• SMILES (Isomeric): CC(C)C(=C)C[C@H](/C(=C/CC[C@]1([C@H](O1)CC/C(=C\COC(=O)C)/C)C)/C)O
• InChI: InChI=1S/C23H38O4/c1-16(2)19(5)15-21(25)18(4)9-8-13-23(7)22(27-23)11-10-17(3)12-14-26-20(6)24/h9,12,16,21-22,25H,5,8,10-11,13-15H2,1-4,6-7H3/b17-12-,18-9+/t21-,22-,23+/m1/s1
• InChI Key: FJKRTEHKFZYJAN-YQXSAZGWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₈O₄
• Molecular Weight: 378.50 g/mol
• Exact Mass: 378.27700969 g/mol
• Topological Polar Surface Area (TPSA): 59.10 Ų
• XlogP: 5.40
• Atomic LogP (AlogP): 5.12
• H-Bond Acceptor: 4
• H-Bond Donor: 1
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9487	94.87%
Caco-2	+	0.5218	52.18%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7815	78.15%
OATP2B1 inhibitior	-	0.8598	85.98%
OATP1B1 inhibitior	+	0.8957	89.57%
OATP1B3 inhibitior	+	0.9260	92.60%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5750	57.50%
BSEP inhibitior	+	0.8738	87.38%
P-glycoprotein inhibitior	-	0.5587	55.87%
P-glycoprotein substrate	-	0.6947	69.47%
CYP3A4 substrate	+	0.6363	63.63%
CYP2C9 substrate	-	0.8032	80.32%
CYP2D6 substrate	-	0.8620	86.20%
CYP3A4 inhibition	-	0.5438	54.38%
CYP2C9 inhibition	-	0.5977	59.77%
CYP2C19 inhibition	-	0.6657	66.57%
CYP2D6 inhibition	-	0.9208	92.08%
CYP1A2 inhibition	-	0.6084	60.84%
CYP2C8 inhibition	-	0.6372	63.72%
CYP inhibitory promiscuity	-	0.8552	85.52%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.7828	78.28%
Carcinogenicity (trinary)	Non-required	0.6714	67.14%
Eye corrosion	-	0.9633	96.33%
Eye irritation	-	0.8501	85.01%
Skin irritation	-	0.5495	54.95%
Skin corrosion	-	0.9584	95.84%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4698	46.98%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	+	0.5290	52.90%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	-	0.5778	57.78%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	+	0.7004	70.04%
Acute Oral Toxicity (c)	III	0.6812	68.12%
Estrogen receptor binding	+	0.5919	59.19%
Androgen receptor binding	-	0.6264	62.64%
Thyroid receptor binding	+	0.6589	65.89%
Glucocorticoid receptor binding	+	0.7065	70.65%
Aromatase binding	+	0.7131	71.31%
PPAR gamma	+	0.6942	69.42%
Honey bee toxicity	-	0.7298	72.98%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	-	0.8000	80.00%
Fish aquatic toxicity	+	0.9834	98.34%

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	98.35%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.07%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.91%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.60%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.74%	94.45%
CHEMBL240	Q12809	HERG	92.12%	89.76%
CHEMBL340	P08684	Cytochrome P450 3A4	90.08%	91.19%
CHEMBL3401	O75469	Pregnane X receptor	88.27%	94.73%
CHEMBL2581	P07339	Cathepsin D	87.98%	98.95%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	87.28%	92.62%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	84.94%	98.75%
CHEMBL1937	Q92769	Histone deacetylase 2	84.72%	94.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.56%	99.17%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	83.84%	95.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.34%	97.09%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	82.65%	95.71%
CHEMBL221	P23219	Cyclooxygenase-1	82.29%	90.17%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.68%	96.77%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	81.20%	82.50%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	81.11%	96.47%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	80.62%	91.24%
CHEMBL5103	Q969S8	Histone deacetylase 10	80.56%	90.08%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.30%	89.00%

Plants that contains it

• Heliopsis helianthoides

Cross-Links

• PubChem: 163022755
• LOTUS: LTS0225862
• wikiData: Q104996177