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

Details

• Internal ID: 822d846b-09af-4351-91ec-6d1749c26f26
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: [(2R,3R)-3-[2-[(2R,3S)-3-[(E,5R)-5-hydroxy-4,8-dimethyl-7-methylidenenon-3-enyl]-3-methyloxiran-2-yl]ethyl]-3-methyloxiran-2-yl]methyl acetate
• SMILES (Canonical): CC(C)C(=C)CC(C(=CCCC1(C(O1)CCC2(C(O2)COC(=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@@]2([C@H](O2)COC(=O)C)C)C)/C)O
• InChI: InChI=1S/C23H38O5/c1-15(2)17(4)13-19(25)16(3)9-8-11-22(6)20(27-22)10-12-23(7)21(28-23)14-26-18(5)24/h9,15,19-21,25H,4,8,10-14H2,1-3,5-7H3/b16-9+/t19-,20-,21-,22+,23-/m1/s1
• InChI Key: DGPJCQKLZRTTKI-JKNJWTPCSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₃H₃₈O₅
• Molecular Weight: 394.50 g/mol
• Exact Mass: 394.27192431 g/mol
• Topological Polar Surface Area (TPSA): 71.60 Ų
• XlogP: 4.30
• Atomic LogP (AlogP): 4.33
• H-Bond Acceptor: 5
• 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	+	0.9134	91.34%
Caco-2	-	0.5887	58.87%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7645	76.45%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9000	90.00%
OATP1B3 inhibitior	+	0.9233	92.33%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	+	0.8303	83.03%
P-glycoprotein inhibitior	-	0.5318	53.18%
P-glycoprotein substrate	-	0.7390	73.90%
CYP3A4 substrate	+	0.6274	62.74%
CYP2C9 substrate	-	0.8032	80.32%
CYP2D6 substrate	-	0.8620	86.20%
CYP3A4 inhibition	-	0.7094	70.94%
CYP2C9 inhibition	-	0.6448	64.48%
CYP2C19 inhibition	-	0.7093	70.93%
CYP2D6 inhibition	-	0.9299	92.99%
CYP1A2 inhibition	-	0.6782	67.82%
CYP2C8 inhibition	-	0.6915	69.15%
CYP inhibitory promiscuity	-	0.9178	91.78%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8028	80.28%
Carcinogenicity (trinary)	Non-required	0.6485	64.85%
Eye corrosion	-	0.9706	97.06%
Eye irritation	-	0.8867	88.67%
Skin irritation	-	0.5361	53.61%
Skin corrosion	-	0.9495	94.95%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4914	49.14%
Micronuclear	-	0.5900	59.00%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.6176	61.76%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	-	0.5556	55.56%
Mitochondrial toxicity	-	0.6125	61.25%
Nephrotoxicity	+	0.7493	74.93%
Acute Oral Toxicity (c)	III	0.6245	62.45%
Estrogen receptor binding	+	0.7572	75.72%
Androgen receptor binding	-	0.5886	58.86%
Thyroid receptor binding	+	0.6433	64.33%
Glucocorticoid receptor binding	+	0.7043	70.43%
Aromatase binding	+	0.6700	67.00%
PPAR gamma	+	0.6373	63.73%
Honey bee toxicity	-	0.7210	72.10%
Biodegradation	-	0.5250	52.50%
Crustacea aquatic toxicity	-	0.8100	81.00%
Fish aquatic toxicity	+	0.9707	97.07%

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	98.53%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.65%	96.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.46%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.32%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.82%	94.45%
CHEMBL240	Q12809	HERG	91.55%	89.76%
CHEMBL2581	P07339	Cathepsin D	90.96%	98.95%
CHEMBL340	P08684	Cytochrome P450 3A4	88.64%	91.19%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	88.20%	98.75%
CHEMBL3401	O75469	Pregnane X receptor	87.40%	94.73%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	86.36%	92.62%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	85.69%	96.47%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.79%	97.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.55%	96.77%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.12%	99.17%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.57%	96.95%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.97%	94.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.90%	89.00%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	81.80%	82.50%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	81.73%	94.80%
CHEMBL5103	Q969S8	Histone deacetylase 10	81.34%	90.08%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.24%	95.89%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.17%	95.50%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	80.58%	92.32%

Plants that contains it

• Heliopsis helianthoides

Cross-Links

• PubChem: 162858017
• LOTUS: LTS0138535
• wikiData: Q104978980