[(3S,3Ar,4R,5R,6R,7aS)-6-[(2S,3R,4R,5S)-5-acetyloxy-2-(acetyloxymethyl)-3-(2-methoxy-2-oxoethyl)-2,4-dimethyl-7-oxooxepan-4-yl]-5-formyloxy-3-(furan-3-yl)-7a-hydroxy-3a-methyl-7-methylidene-1-oxo-3,4,5,6-tetrahydro-2H-inden-4-yl] (2R,3R)-2-hydroxy-3-methylpentanoate

Details

• Internal ID: 41bb12cc-14f0-4d50-a331-afdf733748c9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: [(3S,3aR,4R,5R,6R,7aS)-6-[(2S,3R,4R,5S)-5-acetyloxy-2-(acetyloxymethyl)-3-(2-methoxy-2-oxoethyl)-2,4-dimethyl-7-oxooxepan-4-yl]-5-formyloxy-3-(furan-3-yl)-7a-hydroxy-3a-methyl-7-methylidene-1-oxo-3,4,5,6-tetrahydro-2H-inden-4-yl] (2R,3R)-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(C(CC(=O)OC(C4CC(=O)OC)(C)COC(=O)C)OC(=O)C)C)OC=O)O
• SMILES (Isomeric): CC[C@@H](C)[C@H](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](CC(=O)O[C@]([C@@H]4CC(=O)OC)(C)COC(=O)C)OC(=O)C)C)OC=O)O
• InChI: InChI=1S/C38H50O16/c1-10-19(2)31(45)34(46)53-33-32(51-18-39)30(20(3)38(47)26(42)13-24(37(33,38)8)23-11-12-49-16-23)36(7)25(14-28(43)48-9)35(6,17-50-21(4)40)54-29(44)15-27(36)52-22(5)41/h11-12,16,18-19,24-25,27,30-33,45,47H,3,10,13-15,17H2,1-2,4-9H3/t19-,24+,25+,27+,30-,31-,32-,33+,35-,36-,37-,38-/m1/s1
• InChI Key: LRLMYQFHTXHFRH-HEPLJILTSA-N
• Popularity: 9 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₅₀O₁₆
• Molecular Weight: 762.80 g/mol
• Exact Mass: 762.30988550 g/mol
• Topological Polar Surface Area (TPSA): 229.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.51
• H-Bond Acceptor: 16
• 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	+	0.9882	98.82%
Caco-2	-	0.8418	84.18%
Blood Brain Barrier	+	0.7000	70.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.7154	71.54%
OATP2B1 inhibitior	-	0.8600	86.00%
OATP1B1 inhibitior	-	0.6551	65.51%
OATP1B3 inhibitior	+	0.9391	93.91%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9364	93.64%
BSEP inhibitior	+	0.9811	98.11%
P-glycoprotein inhibitior	+	0.8137	81.37%
P-glycoprotein substrate	+	0.7441	74.41%
CYP3A4 substrate	+	0.7164	71.64%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8461	84.61%
CYP3A4 inhibition	+	0.5985	59.85%
CYP2C9 inhibition	-	0.6572	65.72%
CYP2C19 inhibition	-	0.7525	75.25%
CYP2D6 inhibition	-	0.9469	94.69%
CYP1A2 inhibition	-	0.7482	74.82%
CYP2C8 inhibition	+	0.8039	80.39%
CYP inhibitory promiscuity	-	0.7120	71.20%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.5508	55.08%
Eye corrosion	-	0.9882	98.82%
Eye irritation	-	0.9083	90.83%
Skin irritation	-	0.6793	67.93%
Skin corrosion	-	0.9440	94.40%
Ames mutagenesis	-	0.5037	50.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.6486	64.86%
Micronuclear	-	0.6200	62.00%
Hepatotoxicity	+	0.6151	61.51%
skin sensitisation	-	0.8527	85.27%
Respiratory toxicity	+	0.7222	72.22%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.4733	47.33%
Acute Oral Toxicity (c)	II	0.3518	35.18%
Estrogen receptor binding	+	0.7743	77.43%
Androgen receptor binding	+	0.7616	76.16%
Thyroid receptor binding	+	0.5839	58.39%
Glucocorticoid receptor binding	+	0.7907	79.07%
Aromatase binding	+	0.6448	64.48%
PPAR gamma	+	0.7714	77.14%
Honey bee toxicity	-	0.7024	70.24%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5400	54.00%
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
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	99.04%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.44%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.74%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.36%	94.45%
CHEMBL2581	P07339	Cathepsin D	97.22%	98.95%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	91.59%	95.50%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.71%	86.33%
CHEMBL3524	P56524	Histone deacetylase 4	88.97%	92.97%
CHEMBL221	P23219	Cyclooxygenase-1	88.69%	90.17%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	88.68%	96.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.60%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	85.08%	92.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	84.19%	94.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.17%	95.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.92%	97.25%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	83.29%	91.24%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.21%	97.14%
CHEMBL340	P08684	Cytochrome P450 3A4	82.86%	91.19%
CHEMBL4208	P20618	Proteasome component C5	82.82%	90.00%
CHEMBL3430907	Q96GD4	Aurora kinase B/Inner centromere protein	82.53%	97.50%
CHEMBL2996	Q05655	Protein kinase C delta	81.91%	97.79%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.78%	95.71%
CHEMBL2964	P36507	Dual specificity mitogen-activated protein kinase kinase 2	81.63%	80.00%
CHEMBL5028	O14672	ADAM10	81.56%	97.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.25%	100.00%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.93%	89.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.56%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.26%	89.00%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	80.05%	85.30%

Plants that contains it

• Nymania capensis

Cross-Links

• PubChem: 24772559
• LOTUS: LTS0045479
• wikiData: Q105156198