(4S)-1-[(2R,3R)-3-[(E)-5-hydroxy-3-(hydroxymethyl)pent-3-enyl]-2-methyloxiran-2-yl]-4,8-dimethyl-7-methylidenenonan-5-one

Details

• Internal ID: 1111dff0-d2ed-4867-9f52-f61d44e8a170
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: (4S)-1-[(2R,3R)-3-[(E)-5-hydroxy-3-(hydroxymethyl)pent-3-enyl]-2-methyloxiran-2-yl]-4,8-dimethyl-7-methylidenenonan-5-one
• SMILES (Canonical): CC(C)C(=C)CC(=O)C(C)CCCC1(C(O1)CCC(=CCO)CO)C
• SMILES (Isomeric): C[C@@H](CCC[C@@]1([C@H](O1)CC/C(=C\CO)/CO)C)C(=O)CC(=C)C(C)C
• InChI: InChI=1S/C21H36O4/c1-15(2)17(4)13-19(24)16(3)7-6-11-21(5)20(25-21)9-8-18(14-23)10-12-22/h10,15-16,20,22-23H,4,6-9,11-14H2,1-3,5H3/b18-10+/t16-,20+,21+/m0/s1
• InChI Key: LECHPDAMCTWYFO-LVDTUCNRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₃₆O₄
• Molecular Weight: 352.50 g/mol
• Exact Mass: 352.26135963 g/mol
• Topological Polar Surface Area (TPSA): 70.10 Ų
• XlogP: 3.40
• Atomic LogP (AlogP): 3.81
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9231	92.31%
Caco-2	-	0.5394	53.94%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7316	73.16%
OATP2B1 inhibitior	-	0.8566	85.66%
OATP1B1 inhibitior	+	0.8935	89.35%
OATP1B3 inhibitior	+	0.9243	92.43%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	+	0.5183	51.83%
BSEP inhibitior	+	0.6866	68.66%
P-glycoprotein inhibitior	-	0.6835	68.35%
P-glycoprotein substrate	-	0.5289	52.89%
CYP3A4 substrate	+	0.6260	62.60%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8192	81.92%
CYP3A4 inhibition	-	0.5200	52.00%
CYP2C9 inhibition	-	0.7059	70.59%
CYP2C19 inhibition	-	0.7318	73.18%
CYP2D6 inhibition	-	0.9035	90.35%
CYP1A2 inhibition	-	0.7320	73.20%
CYP2C8 inhibition	-	0.7785	77.85%
CYP inhibitory promiscuity	-	0.8528	85.28%
UGT catelyzed	-	0.8000	80.00%
Carcinogenicity (binary)	-	0.8328	83.28%
Carcinogenicity (trinary)	Non-required	0.6479	64.79%
Eye corrosion	-	0.9638	96.38%
Eye irritation	-	0.8878	88.78%
Skin irritation	-	0.7146	71.46%
Skin corrosion	-	0.9495	94.95%
Ames mutagenesis	-	0.5400	54.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4413	44.13%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.5843	58.43%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	-	0.6556	65.56%
Mitochondrial toxicity	-	0.5375	53.75%
Nephrotoxicity	+	0.5436	54.36%
Acute Oral Toxicity (c)	III	0.6118	61.18%
Estrogen receptor binding	+	0.5277	52.77%
Androgen receptor binding	-	0.4853	48.53%
Thyroid receptor binding	+	0.6636	66.36%
Glucocorticoid receptor binding	+	0.6156	61.56%
Aromatase binding	-	0.5589	55.89%
PPAR gamma	-	0.5113	51.13%
Honey bee toxicity	-	0.8302	83.02%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.8100	81.00%
Fish aquatic toxicity	+	0.9586	95.86%

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	97.20%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.76%	96.09%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	95.75%	96.47%
CHEMBL218	P21554	Cannabinoid CB1 receptor	95.44%	96.61%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.02%	94.45%
CHEMBL340	P08684	Cytochrome P450 3A4	91.39%	91.19%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	90.70%	91.24%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	90.11%	98.75%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	89.95%	92.88%
CHEMBL3267	P48736	PI3-kinase p110-gamma subunit	88.32%	95.71%
CHEMBL3359	P21462	Formyl peptide receptor 1	88.02%	93.56%
CHEMBL230	P35354	Cyclooxygenase-2	87.29%	89.63%
CHEMBL2094135	Q96BI3	Gamma-secretase	86.57%	98.05%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.49%	99.17%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.21%	95.50%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.12%	97.25%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	85.89%	97.29%
CHEMBL2581	P07339	Cathepsin D	85.85%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	85.20%	94.73%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.52%	94.33%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.29%	96.77%
CHEMBL2514	O95665	Neurotensin receptor 2	81.40%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.76%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.22%	95.89%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	80.01%	98.33%

Plants that contains it

• Montanoa tomentosa

Cross-Links

• PubChem: 163029608
• LOTUS: LTS0040829
• wikiData: Q105150497