[(5R,7R,8S,9S,10R,11S,12R,13S,17R)-7-acetyloxy-12-hydroxy-17-[(2R)-2-hydroxy-5-oxo-2H-furan-3-yl]-4,4,8,10,13-pentamethyl-3-oxo-5,6,7,9,11,12,16,17-octahydrocyclopenta[a]phenanthren-11-yl] 2-hydroxy-2-methylpropanoate

Details

• Internal ID: bfb5ffa0-fe57-458f-acb2-533cfadc9c1a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: [(5R,7R,8S,9S,10R,11S,12R,13S,17R)-7-acetyloxy-12-hydroxy-17-[(2R)-2-hydroxy-5-oxo-2H-furan-3-yl]-4,4,8,10,13-pentamethyl-3-oxo-5,6,7,9,11,12,16,17-octahydrocyclopenta[a]phenanthren-11-yl] 2-hydroxy-2-methylpropanoate
• SMILES (Canonical): CC(=O)OC1CC2C(C(=O)C=CC2(C3C1(C4=CCC(C4(C(C3OC(=O)C(C)(C)O)O)C)C5=CC(=O)OC5O)C)C)(C)C
• SMILES (Isomeric): CC(=O)O[C@@H]1C[C@@H]2[C@@](C=CC(=O)C2(C)C)([C@H]3[C@]1(C4=CC[C@H]([C@@]4([C@H]([C@H]3OC(=O)C(C)(C)O)O)C)C5=CC(=O)O[C@H]5O)C)C
• InChI: InChI=1S/C32H42O10/c1-15(33)40-21-14-19-28(2,3)20(34)11-12-30(19,6)24-23(42-27(38)29(4,5)39)25(36)31(7)17(9-10-18(31)32(21,24)8)16-13-22(35)41-26(16)37/h10-13,17,19,21,23-26,36-37,39H,9,14H2,1-8H3/t17-,19-,21+,23-,24-,25-,26+,30+,31-,32-/m0/s1
• InChI Key: PIWZQVRGLJAFQQ-MMYSUKNVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₂O₁₀
• Molecular Weight: 586.70 g/mol
• Exact Mass: 586.27779753 g/mol
• Topological Polar Surface Area (TPSA): 157.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 2.54
• H-Bond Acceptor: 10
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9875	98.75%
Caco-2	-	0.7850	78.50%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.7798	77.98%
OATP2B1 inhibitior	-	0.7175	71.75%
OATP1B1 inhibitior	+	0.7673	76.73%
OATP1B3 inhibitior	+	0.8282	82.82%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.9583	95.83%
P-glycoprotein inhibitior	+	0.7621	76.21%
P-glycoprotein substrate	+	0.5942	59.42%
CYP3A4 substrate	+	0.7214	72.14%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8992	89.92%
CYP3A4 inhibition	-	0.7213	72.13%
CYP2C9 inhibition	-	0.7188	71.88%
CYP2C19 inhibition	-	0.8299	82.99%
CYP2D6 inhibition	-	0.9185	91.85%
CYP1A2 inhibition	-	0.7804	78.04%
CYP2C8 inhibition	+	0.5334	53.34%
CYP inhibitory promiscuity	-	0.5741	57.41%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Danger	0.4903	49.03%
Eye corrosion	-	0.9870	98.70%
Eye irritation	-	0.9081	90.81%
Skin irritation	-	0.5785	57.85%
Skin corrosion	-	0.9071	90.71%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5407	54.07%
Micronuclear	-	0.5700	57.00%
Hepatotoxicity	-	0.5250	52.50%
skin sensitisation	-	0.7689	76.89%
Respiratory toxicity	+	0.5667	56.67%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.6261	62.61%
Acute Oral Toxicity (c)	III	0.4124	41.24%
Estrogen receptor binding	+	0.7615	76.15%
Androgen receptor binding	+	0.6888	68.88%
Thyroid receptor binding	+	0.6038	60.38%
Glucocorticoid receptor binding	+	0.7328	73.28%
Aromatase binding	+	0.6738	67.38%
PPAR gamma	+	0.7106	71.06%
Honey bee toxicity	-	0.7008	70.08%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9827	98.27%

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	97.66%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.72%	94.45%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.08%	85.14%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.54%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.70%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.07%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.05%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.49%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.61%	99.23%
CHEMBL340	P08684	Cytochrome P450 3A4	87.43%	91.19%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.75%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.59%	95.56%
CHEMBL259	P32245	Melanocortin receptor 4	83.96%	95.38%
CHEMBL2581	P07339	Cathepsin D	83.60%	98.95%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	81.25%	91.07%

Plants that contains it

• Azadirachta indica

Cross-Links

• PubChem: 163026908
• LOTUS: LTS0133343
• wikiData: Q105209771