(4R)-4-[(1S,3R,6S,8R,11S,12S,15R,16R)-6-hydroxy-7,7,12,16-tetramethyl-15-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]oxolan-2-one

Details

• Internal ID: a937eeb5-35c4-4f39-8b17-6221cbe13c69
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids > Limonoids
• IUPAC Name: (4R)-4-[(1S,3R,6S,8R,11S,12S,15R,16R)-6-hydroxy-7,7,12,16-tetramethyl-15-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]oxolan-2-one
• SMILES (Canonical): CC1(C2CCC3C4(CCC(C4(CCC35C2(C5)CCC1O)C)C6CC(=O)OC6)C)C
• SMILES (Isomeric): C[C@]12CC[C@@]34C[C@@]35CC[C@@H](C([C@@H]5CC[C@H]4[C@@]1(CC[C@@H]2[C@H]6CC(=O)OC6)C)(C)C)O
• InChI: InChI=1S/C26H40O3/c1-22(2)18-5-6-19-24(4)9-7-17(16-13-21(28)29-14-16)23(24,3)11-12-26(19)15-25(18,26)10-8-20(22)27/h16-20,27H,5-15H2,1-4H3/t16-,17+,18-,19-,20-,23+,24-,25+,26-/m0/s1
• InChI Key: SPPZJSWPWQTMPS-VUGRUASXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₄₀O₃
• Molecular Weight: 400.60 g/mol
• Exact Mass: 400.29774513 g/mol
• Topological Polar Surface Area (TPSA): 46.50 Ų
• XlogP: 6.30
• Atomic LogP (AlogP): 5.35
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9945	99.45%
Caco-2	-	0.5215	52.15%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.8212	82.12%
OATP2B1 inhibitior	-	0.7136	71.36%
OATP1B1 inhibitior	+	0.8760	87.60%
OATP1B3 inhibitior	+	0.9103	91.03%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.5250	52.50%
BSEP inhibitior	+	0.6323	63.23%
P-glycoprotein inhibitior	-	0.7727	77.27%
P-glycoprotein substrate	-	0.7976	79.76%
CYP3A4 substrate	+	0.6518	65.18%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8149	81.49%
CYP3A4 inhibition	-	0.6813	68.13%
CYP2C9 inhibition	-	0.5945	59.45%
CYP2C19 inhibition	-	0.7048	70.48%
CYP2D6 inhibition	-	0.9485	94.85%
CYP1A2 inhibition	-	0.8441	84.41%
CYP2C8 inhibition	-	0.7408	74.08%
CYP inhibitory promiscuity	-	0.9305	93.05%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6362	63.62%
Eye corrosion	-	0.9876	98.76%
Eye irritation	-	0.9044	90.44%
Skin irritation	-	0.6694	66.94%
Skin corrosion	-	0.9338	93.38%
Ames mutagenesis	-	0.6400	64.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4756	47.56%
Micronuclear	-	0.8200	82.00%
Hepatotoxicity	-	0.6751	67.51%
skin sensitisation	-	0.8316	83.16%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.7667	76.67%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.6146	61.46%
Acute Oral Toxicity (c)	III	0.4407	44.07%
Estrogen receptor binding	+	0.7962	79.62%
Androgen receptor binding	+	0.7632	76.32%
Thyroid receptor binding	+	0.6281	62.81%
Glucocorticoid receptor binding	+	0.7845	78.45%
Aromatase binding	+	0.7530	75.30%
PPAR gamma	+	0.5174	51.74%
Honey bee toxicity	-	0.7331	73.31%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9784	97.84%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.75%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	92.29%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	89.43%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	88.36%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.44%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.69%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.43%	89.00%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.01%	96.95%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.74%	93.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.54%	94.45%

Plants that contains it

• Monocyclanthus vignei

Cross-Links

• PubChem: 71664703
• LOTUS: LTS0264347
• wikiData: Q105257521