[(3S,3aR,4R,5S,6R,7aS)-6-[(4R,5R,5aR,9aS)-4-acetyloxy-5,9a-dimethyl-2,7-dioxo-4,5a,6,9-tetrahydro-3H-pyrano[3,4-b]oxepin-5-yl]-5-formyloxy-3-(furan-3-yl)-7a-hydroxy-3a-methyl-7-methylidene-1-oxo-3,4,5,6-tetrahydro-2H-inden-4-yl] 2-hydroxy-3-methylpentanoate

Details

• Internal ID: b848c9e2-04cb-462c-97f8-525f061d306a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: [(3S,3aR,4R,5S,6R,7aS)-6-[(4R,5R,5aR,9aS)-4-acetyloxy-5,9a-dimethyl-2,7-dioxo-4,5a,6,9-tetrahydro-3H-pyrano[3,4-b]oxepin-5-yl]-5-formyloxy-3-(furan-3-yl)-7a-hydroxy-3a-methyl-7-methylidene-1-oxo-3,4,5,6-tetrahydro-2H-inden-4-yl] 2-hydroxy-3-methylpentanoate
• SMILES (Canonical): CCC(C)C(C(=O)OC1C(C(C(=C)C2(C1(C(CC2=O)C3=COC=C3)C)O)C4(C5CC(=O)OCC5(OC(=O)CC4OC(=O)C)C)C)OC=O)O
• SMILES (Isomeric): CCC(C)C(C(=O)O[C@H]1[C@H]([C@@H](C(=C)[C@@]2([C@@]1([C@@H](CC2=O)C3=COC=C3)C)O)[C@@]4([C@H]5CC(=O)OC[C@]5(OC(=O)C[C@H]4OC(=O)C)C)C)OC=O)O
• InChI: InChI=1S/C35H44O14/c1-8-17(2)28(41)31(42)48-30-29(46-16-36)27(18(3)35(43)23(38)11-21(34(30,35)7)20-9-10-44-14-20)33(6)22-12-25(39)45-15-32(22,5)49-26(40)13-24(33)47-19(4)37/h9-10,14,16-17,21-22,24,27-30,41,43H,3,8,11-13,15H2,1-2,4-7H3/t17?,21-,22-,24+,27+,28?,29-,30-,32+,33+,34+,35+/m0/s1
• InChI Key: FEQMUAOUKSLIFS-OJYVKABBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₄₄O₁₄
• Molecular Weight: 688.70 g/mol
• Exact Mass: 688.27310607 g/mol
• Topological Polar Surface Area (TPSA): 202.00 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.33
• H-Bond Acceptor: 14
• H-Bond Donor: 2
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9837	98.37%
Caco-2	-	0.8266	82.66%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7583	75.83%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	-	0.5000	50.00%
OATP1B3 inhibitior	+	0.8593	85.93%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8864	88.64%
BSEP inhibitior	+	0.9563	95.63%
P-glycoprotein inhibitior	+	0.8032	80.32%
P-glycoprotein substrate	+	0.7091	70.91%
CYP3A4 substrate	+	0.7080	70.80%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8461	84.61%
CYP3A4 inhibition	+	0.5229	52.29%
CYP2C9 inhibition	-	0.6947	69.47%
CYP2C19 inhibition	-	0.7442	74.42%
CYP2D6 inhibition	-	0.9487	94.87%
CYP1A2 inhibition	-	0.8142	81.42%
CYP2C8 inhibition	+	0.7974	79.74%
CYP inhibitory promiscuity	-	0.5877	58.77%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5902	59.02%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9092	90.92%
Skin irritation	-	0.6034	60.34%
Skin corrosion	-	0.9401	94.01%
Ames mutagenesis	-	0.6237	62.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.3951	39.51%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	+	0.5650	56.50%
skin sensitisation	-	0.8670	86.70%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	-	0.6378	63.78%
Acute Oral Toxicity (c)	I	0.4976	49.76%
Estrogen receptor binding	+	0.7711	77.11%
Androgen receptor binding	+	0.7560	75.60%
Thyroid receptor binding	+	0.5603	56.03%
Glucocorticoid receptor binding	+	0.7846	78.46%
Aromatase binding	+	0.6464	64.64%
PPAR gamma	+	0.7338	73.38%
Honey bee toxicity	-	0.6997	69.97%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5200	52.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	98.86%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.29%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.31%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.12%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.21%	86.33%
CHEMBL3524	P56524	Histone deacetylase 4	91.94%	92.97%
CHEMBL221	P23219	Cyclooxygenase-1	89.92%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.86%	95.56%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	89.76%	95.50%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.10%	85.14%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	88.31%	89.34%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.85%	97.25%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.04%	95.89%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	85.81%	98.75%
CHEMBL2413	P32246	C-C chemokine receptor type 1	85.75%	89.50%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.65%	96.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	84.98%	91.24%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.58%	99.23%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.24%	92.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.64%	89.00%
CHEMBL2996	Q05655	Protein kinase C delta	82.60%	97.79%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.80%	100.00%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.76%	93.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.90%	94.00%
CHEMBL340	P08684	Cytochrome P450 3A4	80.56%	91.19%
CHEMBL2096618	P11274	Bcr/Abl fusion protein	80.07%	85.83%

Plants that contains it

• Trichilia emetica

Cross-Links

• PubChem: 21600056
• LOTUS: LTS0236367
• wikiData: Q104994130