[(1R,2R,4S,5S,9R,10R,13S,14S,15S,17R)-15-[(1R)-1-acetyloxy-2-methoxy-2-oxoethyl]-9-(furan-3-yl)-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.02,4.04,13.05,10]octadecan-17-yl] (E)-2-methylbut-2-enoate

Details

• Internal ID: 1aa49022-fd1e-4564-9e4c-444e6c94c616
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: [(1R,2R,4S,5S,9R,10R,13S,14S,15S,17R)-15-[(1R)-1-acetyloxy-2-methoxy-2-oxoethyl]-9-(furan-3-yl)-10,14,16,16-tetramethyl-7,18-dioxo-3,8-dioxapentacyclo[12.3.1.02,4.04,13.05,10]octadecan-17-yl] (E)-2-methylbut-2-enoate
• SMILES (Canonical): CC=C(C)C(=O)OC1C2C3C4(O3)C(CCC5(C4CC(=O)OC5C6=COC=C6)C)C(C2=O)(C(C1(C)C)C(C(=O)OC)OC(=O)C)C
• SMILES (Isomeric): C/C=C(\C)/C(=O)O[C@@H]1[C@@H]2[C@@H]3[C@@]4(O3)[C@@H](CC[C@@]5([C@@H]4CC(=O)O[C@H]5C6=COC=C6)C)[C@@](C2=O)([C@H](C1(C)C)[C@H](C(=O)OC)OC(=O)C)C
• InChI: InChI=1S/C34H42O11/c1-9-16(2)29(38)44-27-22-25(37)33(7,24(31(27,4)5)23(30(39)40-8)42-17(3)35)19-10-12-32(6)20(34(19)28(22)45-34)14-21(36)43-26(32)18-11-13-41-15-18/h9,11,13,15,19-20,22-24,26-28H,10,12,14H2,1-8H3/b16-9+/t19-,20-,22+,23+,24-,26-,27+,28+,32+,33+,34+/m0/s1
• InChI Key: YXZMPGCTSCKFQC-BYWHQJFMSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₄₂O₁₁
• Molecular Weight: 626.70 g/mol
• Exact Mass: 626.27271215 g/mol
• Topological Polar Surface Area (TPSA): 148.00 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 4.28
• H-Bond Acceptor: 11
• 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	+	0.9878	98.78%
Caco-2	-	0.7935	79.35%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.7634	76.34%
OATP2B1 inhibitior	-	0.5705	57.05%
OATP1B1 inhibitior	-	0.3382	33.82%
OATP1B3 inhibitior	+	0.9544	95.44%
MATE1 inhibitior	-	0.7600	76.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.9803	98.03%
P-glycoprotein inhibitior	+	0.8696	86.96%
P-glycoprotein substrate	+	0.6243	62.43%
CYP3A4 substrate	+	0.7280	72.80%
CYP2C9 substrate	-	0.8455	84.55%
CYP2D6 substrate	-	0.8849	88.49%
CYP3A4 inhibition	+	0.8274	82.74%
CYP2C9 inhibition	-	0.7886	78.86%
CYP2C19 inhibition	-	0.7452	74.52%
CYP2D6 inhibition	-	0.9164	91.64%
CYP1A2 inhibition	-	0.7366	73.66%
CYP2C8 inhibition	+	0.7196	71.96%
CYP inhibitory promiscuity	-	0.7755	77.55%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5310	53.10%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.8787	87.87%
Skin irritation	-	0.7050	70.50%
Skin corrosion	-	0.9187	91.87%
Ames mutagenesis	-	0.6578	65.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.7185	71.85%
Micronuclear	-	0.5400	54.00%
Hepatotoxicity	+	0.5625	56.25%
skin sensitisation	-	0.8097	80.97%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	+	0.8350	83.50%
Acute Oral Toxicity (c)	I	0.3213	32.13%
Estrogen receptor binding	+	0.8147	81.47%
Androgen receptor binding	+	0.7269	72.69%
Thyroid receptor binding	+	0.6270	62.70%
Glucocorticoid receptor binding	+	0.8186	81.86%
Aromatase binding	+	0.6762	67.62%
PPAR gamma	+	0.7857	78.57%
Honey bee toxicity	-	0.6328	63.28%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.6400	64.00%
Fish aquatic toxicity	+	0.9955	99.55%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	99.05%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.03%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	98.05%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.10%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.72%	89.00%
CHEMBL2581	P07339	Cathepsin D	88.57%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.46%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	88.28%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.34%	86.33%
CHEMBL340	P08684	Cytochrome P450 3A4	87.26%	91.19%
CHEMBL2996	Q05655	Protein kinase C delta	87.14%	97.79%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.59%	97.09%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.14%	92.62%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.93%	93.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.49%	100.00%
CHEMBL299	P17252	Protein kinase C alpha	82.50%	98.03%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.75%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.03%	95.56%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.91%	97.14%
CHEMBL2535	P11166	Glucose transporter	80.75%	98.75%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.64%	100.00%

Plants that contains it

• Swietenia mahagoni

Cross-Links

• PubChem: 163006355
• LOTUS: LTS0107425
• wikiData: Q105368328