methyl 2-[(1S,3R,4R,5S,7S,8R,10R,11S,12S,13R)-4,5,11-triacetyloxy-13-[(2S)-2-hydroxy-5-oxo-2H-furan-4-yl]-6,6,8,12-tetramethyl-17-methylidene-9,15-dioxo-2,14-dioxatetracyclo[8.6.1.01,12.03,8]heptadecan-7-yl]acetate

Details

• Internal ID: 8319881d-e32d-435c-87db-db8073ef539e
• Taxonomy: Organic acids and derivatives > Carboxylic acids and derivatives > Hexacarboxylic acids and derivatives
• IUPAC Name: methyl 2-[(1S,3R,4R,5S,7S,8R,10R,11S,12S,13R)-4,5,11-triacetyloxy-13-[(2S)-2-hydroxy-5-oxo-2H-furan-4-yl]-6,6,8,12-tetramethyl-17-methylidene-9,15-dioxo-2,14-dioxatetracyclo[8.6.1.01,12.03,8]heptadecan-7-yl]acetate
• SMILES (Canonical): CC(=O)OC1C2C(C(C(C1OC(=O)C)(C)C)CC(=O)OC)(C(=O)C3C(C4(C(OC(=O)CC4(C3=C)O2)C5=CC(OC5=O)O)C)OC(=O)C)C
• SMILES (Isomeric): CC(=O)O[C@@H]1[C@H]2[C@@]([C@H](C([C@@H]1OC(=O)C)(C)C)CC(=O)OC)(C(=O)[C@H]3[C@@H]([C@]4([C@@H](OC(=O)C[C@@]4(C3=C)O2)C5=C[C@H](OC5=O)O)C)OC(=O)C)C
• InChI: InChI=1S/C33H40O15/c1-13-22-24(40)31(7)18(11-19(37)42-9)30(5,6)27(45-16(4)36)23(43-14(2)34)28(31)48-33(13)12-21(39)46-25(17-10-20(38)47-29(17)41)32(33,8)26(22)44-15(3)35/h10,18,20,22-23,25-28,38H,1,11-12H2,2-9H3/t18-,20-,22-,23-,25-,26-,27+,28-,31-,32+,33-/m0/s1
• InChI Key: AWCRMZMPNCVDTK-GLEGPAFTSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₀O₁₅
• Molecular Weight: 676.70 g/mol
• Exact Mass: 676.23672056 g/mol
• Topological Polar Surface Area (TPSA): 204.00 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): 1.02
• H-Bond Acceptor: 15
• H-Bond Donor: 1
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9815	98.15%
Caco-2	-	0.8285	82.85%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.7331	73.31%
OATP2B1 inhibitior	-	0.5733	57.33%
OATP1B1 inhibitior	+	0.6965	69.65%
OATP1B3 inhibitior	-	0.4251	42.51%
MATE1 inhibitior	-	0.7400	74.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.7383	73.83%
P-glycoprotein inhibitior	+	0.8256	82.56%
P-glycoprotein substrate	+	0.6099	60.99%
CYP3A4 substrate	+	0.7076	70.76%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8852	88.52%
CYP3A4 inhibition	+	0.5991	59.91%
CYP2C9 inhibition	-	0.8509	85.09%
CYP2C19 inhibition	-	0.7812	78.12%
CYP2D6 inhibition	-	0.9236	92.36%
CYP1A2 inhibition	-	0.9352	93.52%
CYP2C8 inhibition	+	0.6669	66.69%
CYP inhibitory promiscuity	-	0.7694	76.94%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4728	47.28%
Eye corrosion	-	0.9819	98.19%
Eye irritation	-	0.8944	89.44%
Skin irritation	-	0.6904	69.04%
Skin corrosion	-	0.9154	91.54%
Ames mutagenesis	-	0.6437	64.37%
Human Ether-a-go-go-Related Gene inhibition	-	0.4799	47.99%
Micronuclear	-	0.5841	58.41%
Hepatotoxicity	-	0.5558	55.58%
skin sensitisation	-	0.7371	73.71%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	+	0.7741	77.41%
Acute Oral Toxicity (c)	III	0.4670	46.70%
Estrogen receptor binding	+	0.7752	77.52%
Androgen receptor binding	+	0.7327	73.27%
Thyroid receptor binding	+	0.5912	59.12%
Glucocorticoid receptor binding	+	0.7334	73.34%
Aromatase binding	+	0.6772	67.72%
PPAR gamma	+	0.7507	75.07%
Honey bee toxicity	-	0.6209	62.09%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9578	95.78%

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	99.22%	91.11%
CHEMBL4040	P28482	MAP kinase ERK2	97.76%	83.82%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.48%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.66%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.21%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.97%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.78%	86.33%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.54%	91.07%
CHEMBL2581	P07339	Cathepsin D	87.50%	98.95%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	86.40%	95.17%
CHEMBL3401	O75469	Pregnane X receptor	84.69%	94.73%
CHEMBL2996	Q05655	Protein kinase C delta	84.63%	97.79%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.32%	92.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.09%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	83.74%	91.19%
CHEMBL3922	P50579	Methionine aminopeptidase 2	83.46%	97.28%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.42%	99.17%
CHEMBL5028	O14672	ADAM10	83.31%	97.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.15%	99.23%

Plants that contains it

• Cipadessa baccifera

Cross-Links

• PubChem: 122179345
• LOTUS: LTS0260178
• wikiData: Q104919952