[(1R,3R,4aS,5S,6S,6aS,7R,10R,10aS,10bS)-1,6-diacetyloxy-3-ethenyl-5-hydroxy-7-(hydroxymethyl)-3,4a,7,10a-tetramethyl-2,5,6,6a,8,9,10,10b-octahydro-1H-benzo[f]chromen-10-yl] acetate

Details

• Internal ID: f37d4580-0956-4375-81ba-dce1fd49f0e9
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: [(1R,3R,4aS,5S,6S,6aS,7R,10R,10aS,10bS)-1,6-diacetyloxy-3-ethenyl-5-hydroxy-7-(hydroxymethyl)-3,4a,7,10a-tetramethyl-2,5,6,6a,8,9,10,10b-octahydro-1H-benzo[f]chromen-10-yl] acetate
• SMILES (Canonical): CC(=O)OC1CCC(C2C1(C3C(CC(OC3(C(C2OC(=O)C)O)C)(C)C=C)OC(=O)C)C)(C)CO
• SMILES (Isomeric): CC(=O)O[C@@H]1CC[C@@]([C@H]2[C@]1([C@H]3[C@@H](C[C@](O[C@@]3([C@H]([C@H]2OC(=O)C)O)C)(C)C=C)OC(=O)C)C)(C)CO
• InChI: InChI=1S/C26H40O9/c1-9-24(6)12-17(32-14(2)28)20-25(7)18(33-15(3)29)10-11-23(5,13-27)21(25)19(34-16(4)30)22(31)26(20,8)35-24/h9,17-22,27,31H,1,10-13H2,2-8H3/t17-,18-,19+,20-,21+,22+,23+,24+,25-,26+/m1/s1
• InChI Key: KNWFGKVPKAOCLQ-TTYBACRPSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₄₀O₉
• Molecular Weight: 496.60 g/mol
• Exact Mass: 496.26723285 g/mol
• Topological Polar Surface Area (TPSA): 129.00 Ų
• XlogP: 2.00
• Atomic LogP (AlogP): 2.31
• H-Bond Acceptor: 9
• H-Bond Donor: 2
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8399	83.99%
Caco-2	-	0.6606	66.06%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.7695	76.95%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8257	82.57%
OATP1B3 inhibitior	+	0.8802	88.02%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.6250	62.50%
BSEP inhibitior	-	0.4834	48.34%
P-glycoprotein inhibitior	+	0.6551	65.51%
P-glycoprotein substrate	-	0.7149	71.49%
CYP3A4 substrate	+	0.6780	67.80%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8528	85.28%
CYP3A4 inhibition	+	0.6389	63.89%
CYP2C9 inhibition	-	0.8721	87.21%
CYP2C19 inhibition	-	0.8578	85.78%
CYP2D6 inhibition	-	0.9620	96.20%
CYP1A2 inhibition	-	0.7635	76.35%
CYP2C8 inhibition	-	0.5876	58.76%
CYP inhibitory promiscuity	-	0.9031	90.31%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6973	69.73%
Eye corrosion	-	0.9890	98.90%
Eye irritation	-	0.9319	93.19%
Skin irritation	-	0.5918	59.18%
Skin corrosion	-	0.9371	93.71%
Ames mutagenesis	-	0.6570	65.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.3932	39.32%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.6169	61.69%
skin sensitisation	-	0.9277	92.77%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.7200	72.00%
Acute Oral Toxicity (c)	III	0.6748	67.48%
Estrogen receptor binding	+	0.8220	82.20%
Androgen receptor binding	+	0.5787	57.87%
Thyroid receptor binding	+	0.6068	60.68%
Glucocorticoid receptor binding	+	0.7221	72.21%
Aromatase binding	+	0.7544	75.44%
PPAR gamma	+	0.6548	65.48%
Honey bee toxicity	-	0.7645	76.45%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9667	96.67%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.90%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.09%	91.11%
CHEMBL340	P08684	Cytochrome P450 3A4	89.29%	91.19%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.04%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.31%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.53%	95.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.78%	95.89%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	84.71%	93.04%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.46%	97.09%
CHEMBL3922	P50579	Methionine aminopeptidase 2	84.14%	97.28%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.89%	95.89%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.81%	86.92%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.56%	97.25%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.82%	91.07%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.68%	92.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	80.65%	95.56%
CHEMBL5028	O14672	ADAM10	80.63%	97.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.56%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.25%	86.33%

Plants that contains it

• Ptychanthus striatus

Cross-Links

• PubChem: 163185353
• LOTUS: LTS0059531
• wikiData: Q105143621