[(2S,3R,3aR,4S,5R,7aR)-3-acetyl-2-[(Z)-2-methylbut-2-enoyl]oxy-7-methylidene-4-propan-2-yl-1,2,3,3a,4,5,6,7a-octahydroinden-5-yl] (2S,3S)-2,3-dimethyloxirane-2-carboxylate

Details

• Internal ID: 5b600efd-8c0c-438a-a909-0f21be38e8b6
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids
• IUPAC Name: [(2S,3R,3aR,4S,5R,7aR)-3-acetyl-2-[(Z)-2-methylbut-2-enoyl]oxy-7-methylidene-4-propan-2-yl-1,2,3,3a,4,5,6,7a-octahydroinden-5-yl] (2S,3S)-2,3-dimethyloxirane-2-carboxylate
• SMILES (Canonical): CC=C(C)C(=O)OC1CC2C(C1C(=O)C)C(C(CC2=C)OC(=O)C3(C(O3)C)C)C(C)C
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@H]1C[C@@H]2[C@@H]([C@H]1C(=O)C)[C@@H]([C@@H](CC2=C)OC(=O)[C@@]3([C@@H](O3)C)C)C(C)C
• InChI: InChI=1S/C25H36O6/c1-9-13(4)23(27)29-19-11-17-14(5)10-18(30-24(28)25(8)16(7)31-25)20(12(2)3)22(17)21(19)15(6)26/h9,12,16-22H,5,10-11H2,1-4,6-8H3/b13-9-/t16-,17-,18+,19-,20+,21-,22+,25-/m0/s1
• InChI Key: MUOZMUCRIJJEQD-ZGVHUTQJSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₅H₃₆O₆
• Molecular Weight: 432.50 g/mol
• Exact Mass: 432.25118886 g/mol
• Topological Polar Surface Area (TPSA): 82.20 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 4.03
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9805	98.05%
Caco-2	+	0.4909	49.09%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.6701	67.01%
OATP2B1 inhibitior	-	0.8602	86.02%
OATP1B1 inhibitior	+	0.8627	86.27%
OATP1B3 inhibitior	+	0.9194	91.94%
MATE1 inhibitior	-	0.6400	64.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.5000	50.00%
P-glycoprotein inhibitior	+	0.6634	66.34%
P-glycoprotein substrate	+	0.5197	51.97%
CYP3A4 substrate	+	0.6631	66.31%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8961	89.61%
CYP3A4 inhibition	-	0.5284	52.84%
CYP2C9 inhibition	-	0.8557	85.57%
CYP2C19 inhibition	-	0.7217	72.17%
CYP2D6 inhibition	-	0.9540	95.40%
CYP1A2 inhibition	-	0.7581	75.81%
CYP2C8 inhibition	-	0.6961	69.61%
CYP inhibitory promiscuity	-	0.8111	81.11%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8943	89.43%
Carcinogenicity (trinary)	Non-required	0.5390	53.90%
Eye corrosion	-	0.9617	96.17%
Eye irritation	-	0.9263	92.63%
Skin irritation	-	0.6493	64.93%
Skin corrosion	-	0.9284	92.84%
Ames mutagenesis	+	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6113	61.13%
Micronuclear	+	0.5100	51.00%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	+	0.5000	50.00%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	+	0.4789	47.89%
Acute Oral Toxicity (c)	III	0.4381	43.81%
Estrogen receptor binding	+	0.7654	76.54%
Androgen receptor binding	+	0.6020	60.20%
Thyroid receptor binding	+	0.6235	62.35%
Glucocorticoid receptor binding	+	0.7266	72.66%
Aromatase binding	+	0.7004	70.04%
PPAR gamma	+	0.6241	62.41%
Honey bee toxicity	-	0.5410	54.10%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5455	54.55%
Fish aquatic toxicity	+	0.9840	98.40%

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	97.28%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.96%	96.09%
CHEMBL340	P08684	Cytochrome P450 3A4	93.51%	91.19%
CHEMBL2581	P07339	Cathepsin D	89.82%	98.95%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	89.35%	85.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.99%	97.25%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.75%	97.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.56%	94.45%
CHEMBL3359	P21462	Formyl peptide receptor 1	86.22%	93.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	85.78%	99.17%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	85.42%	91.24%
CHEMBL4227	P25090	Lipoxin A4 receptor	84.65%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.42%	95.56%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.31%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.74%	89.00%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	83.36%	92.29%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.25%	96.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	82.37%	97.09%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	81.76%	82.50%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	81.72%	98.75%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	81.48%	96.47%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	81.36%	100.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.99%	89.50%
CHEMBL2179	P04062	Beta-glucocerebrosidase	80.56%	85.31%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	80.43%	97.53%

Plants that contains it

• Robinsonecio gerberifolius

Cross-Links

• PubChem: 21626057
• LOTUS: LTS0045556
• wikiData: Q105172606