[(1S,2R,3S,5S,6S,8R,10S,11S,12R,14R,15S,16R,19S,21R)-6-(furan-3-yl)-3,12,16,19-tetrahydroxy-5,11,15-trimethyl-4-oxo-9,17-dioxahexacyclo[13.3.3.01,14.02,11.05,10.08,10]henicosan-21-yl] acetate

Details

• Internal ID: bc72cbb3-42be-4433-9c60-ac7795fea037
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: [(1S,2R,3S,5S,6S,8R,10S,11S,12R,14R,15S,16R,19S,21R)-6-(furan-3-yl)-3,12,16,19-tetrahydroxy-5,11,15-trimethyl-4-oxo-9,17-dioxahexacyclo[13.3.3.01,14.02,11.05,10.08,10]henicosan-21-yl] acetate
• SMILES (Canonical): CC(=O)OC1CC(C23COC(C1(C2CC(C4(C3C(C(=O)C5(C46C(O6)CC5C7=COC=C7)C)O)C)O)C)O)O
• SMILES (Isomeric): CC(=O)O[C@@H]1C[C@@H]([C@@]23CO[C@H]([C@]1([C@@H]2C[C@H]([C@@]4([C@@H]3[C@@H](C(=O)[C@@]5([C@]46[C@H](O6)C[C@H]5C7=COC=C7)C)O)C)O)C)O)O
• InChI: InChI=1S/C28H36O10/c1-12(29)37-18-9-17(31)27-11-36-23(34)24(18,2)15(27)8-16(30)26(4)21(27)20(32)22(33)25(3)14(13-5-6-35-10-13)7-19-28(25,26)38-19/h5-6,10,14-21,23,30-32,34H,7-9,11H2,1-4H3/t14-,15-,16+,17-,18+,19+,20-,21-,23+,24-,25+,26+,27+,28+/m0/s1
• InChI Key: NQVQTSVUXGDIAQ-UUUIWOIYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₆O₁₀
• Molecular Weight: 532.60 g/mol
• Exact Mass: 532.23084734 g/mol
• Topological Polar Surface Area (TPSA): 159.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): 0.90
• H-Bond Acceptor: 10
• H-Bond Donor: 4
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9542	95.42%
Caco-2	-	0.7849	78.49%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7945	79.45%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	-	0.3548	35.48%
OATP1B3 inhibitior	+	0.8518	85.18%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8864	88.64%
BSEP inhibitior	+	0.8810	88.10%
P-glycoprotein inhibitior	-	0.4568	45.68%
P-glycoprotein substrate	+	0.5890	58.90%
CYP3A4 substrate	+	0.7120	71.20%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8417	84.17%
CYP3A4 inhibition	-	0.6196	61.96%
CYP2C9 inhibition	-	0.8569	85.69%
CYP2C19 inhibition	-	0.8888	88.88%
CYP2D6 inhibition	-	0.9471	94.71%
CYP1A2 inhibition	-	0.8875	88.75%
CYP2C8 inhibition	+	0.6669	66.69%
CYP inhibitory promiscuity	-	0.9290	92.90%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5696	56.96%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.9178	91.78%
Skin irritation	-	0.7410	74.10%
Skin corrosion	-	0.9394	93.94%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7844	78.44%
Micronuclear	-	0.5100	51.00%
Hepatotoxicity	+	0.5677	56.77%
skin sensitisation	-	0.8858	88.58%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	+	0.5054	50.54%
Acute Oral Toxicity (c)	I	0.5895	58.95%
Estrogen receptor binding	+	0.8387	83.87%
Androgen receptor binding	+	0.7300	73.00%
Thyroid receptor binding	+	0.5531	55.31%
Glucocorticoid receptor binding	+	0.7737	77.37%
Aromatase binding	+	0.7771	77.71%
PPAR gamma	+	0.6955	69.55%
Honey bee toxicity	-	0.7150	71.50%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9705	97.05%

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	97.88%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.83%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.73%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.20%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.17%	89.00%
CHEMBL340	P08684	Cytochrome P450 3A4	89.12%	91.19%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.77%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.74%	95.56%
CHEMBL2581	P07339	Cathepsin D	86.89%	98.95%
CHEMBL3922	P50579	Methionine aminopeptidase 2	86.13%	97.28%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.72%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.24%	99.23%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	83.40%	91.07%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	82.58%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.40%	94.00%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	81.72%	100.00%

Plants that contains it

• Melia azedarach

Cross-Links

• PubChem: 101193721
• LOTUS: LTS0024100
• wikiData: Q104399985