[(1S,2R,4S,7S,8S,11R,13S,15R,17S,19R)-13-acetyloxy-7-(furan-3-yl)-15-hydroxy-1,8,12,16,16-pentamethyl-5-oxo-3,6-dioxapentacyclo[9.8.0.02,4.02,8.012,17]nonadecan-19-yl] acetate

Details

• Internal ID: 1d03a657-a6ec-489d-9e49-7febf8452ffd
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: [(1S,2R,4S,7S,8S,11R,13S,15R,17S,19R)-13-acetyloxy-7-(furan-3-yl)-15-hydroxy-1,8,12,16,16-pentamethyl-5-oxo-3,6-dioxapentacyclo[9.8.0.02,4.02,8.012,17]nonadecan-19-yl] acetate
• SMILES (Canonical): CC(=O)OC1CC2C(C(CC(C2(C3C1(C45C(O4)C(=O)OC(C5(CC3)C)C6=COC=C6)C)C)OC(=O)C)O)(C)C
• SMILES (Isomeric): CC(=O)O[C@@H]1C[C@H]2C([C@@H](C[C@@H](C2([C@@H]3[C@@]1([C@]45[C@H](O4)C(=O)O[C@H]([C@@]5(CC3)C)C6=COC=C6)C)C)OC(=O)C)O)(C)C
• InChI: InChI=1S/C30H40O9/c1-15(31)36-21-13-20(33)26(3,4)19-12-22(37-16(2)32)29(7)18(28(19,21)6)8-10-27(5)23(17-9-11-35-14-17)38-25(34)24-30(27,29)39-24/h9,11,14,18-24,33H,8,10,12-13H2,1-7H3/t18-,19+,20-,21+,22-,23+,24-,27+,28?,29+,30-/m1/s1
• InChI Key: PDKGFQJSCXMICA-QPUIADIWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₀O₉
• Molecular Weight: 544.60 g/mol
• Exact Mass: 544.26723285 g/mol
• Topological Polar Surface Area (TPSA): 125.00 Ų
• XlogP: 3.90
• Atomic LogP (AlogP): 4.12
• H-Bond Acceptor: 9
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9584	95.84%
Caco-2	-	0.7416	74.16%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7181	71.81%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	-	0.6180	61.80%
OATP1B3 inhibitior	-	0.5698	56.98%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.8443	84.43%
P-glycoprotein inhibitior	+	0.7277	72.77%
P-glycoprotein substrate	-	0.6421	64.21%
CYP3A4 substrate	+	0.7016	70.16%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8241	82.41%
CYP3A4 inhibition	+	0.8073	80.73%
CYP2C9 inhibition	-	0.7880	78.80%
CYP2C19 inhibition	-	0.8008	80.08%
CYP2D6 inhibition	-	0.9301	93.01%
CYP1A2 inhibition	-	0.8351	83.51%
CYP2C8 inhibition	+	0.6686	66.86%
CYP inhibitory promiscuity	-	0.9495	94.95%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5251	52.51%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.8550	85.50%
Skin irritation	-	0.6612	66.12%
Skin corrosion	-	0.8686	86.86%
Ames mutagenesis	-	0.6919	69.19%
Human Ether-a-go-go-Related Gene inhibition	+	0.7703	77.03%
Micronuclear	-	0.6500	65.00%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.8531	85.31%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.5752	57.52%
Acute Oral Toxicity (c)	I	0.4459	44.59%
Estrogen receptor binding	+	0.8396	83.96%
Androgen receptor binding	+	0.7419	74.19%
Thyroid receptor binding	+	0.6257	62.57%
Glucocorticoid receptor binding	+	0.8208	82.08%
Aromatase binding	+	0.7912	79.12%
PPAR gamma	+	0.7178	71.78%
Honey bee toxicity	-	0.7230	72.30%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9664	96.64%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4040	P28482	MAP kinase ERK2	125.9 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.50%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.86%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.68%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.85%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.18%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.52%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.54%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.02%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.51%	100.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	85.33%	93.04%
CHEMBL2581	P07339	Cathepsin D	84.86%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.52%	99.23%
CHEMBL340	P08684	Cytochrome P450 3A4	83.48%	91.19%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.33%	95.89%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	81.73%	100.00%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	80.52%	81.11%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.37%	92.62%
CHEMBL1937	Q92769	Histone deacetylase 2	80.10%	94.75%

Plants that contains it

• Khaya anthotheca
• Khaya senegalensis
• Swietenia mahagoni

Cross-Links

• PubChem: 163191152
• LOTUS: LTS0017218
• wikiData: Q105206567