[(1R,4S)-4-[(2S,4aR,8aS)-2-[(2R)-5-bromo-2,6,6-trimethyloxan-2-yl]-4a-methyl-3,4,6,7,8,8a-hexahydro-2H-pyrano[3,2-b]pyran-6-yl]-4-hydroxy-1-[(2R,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]pentyl] acetate

Details

• Internal ID: fc62667f-9d66-44d5-8d58-939f30da87b6
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: [(1R,4S)-4-[(2S,4aR,8aS)-2-[(2R)-5-bromo-2,6,6-trimethyloxan-2-yl]-4a-methyl-3,4,6,7,8,8a-hexahydro-2H-pyrano[3,2-b]pyran-6-yl]-4-hydroxy-1-[(2R,5R)-5-(2-hydroxypropan-2-yl)-2-methyloxolan-2-yl]pentyl] acetate
• SMILES (Canonical): CC(=O)OC(CCC(C)(C1CCC2C(O1)(CCC(O2)C3(CCC(C(O3)(C)C)Br)C)C)O)C4(CCC(O4)C(C)(C)O)C
• SMILES (Isomeric): CC(=O)O[C@H](CC[C@@](C)(C1CC[C@H]2[C@](O1)(CC[C@H](O2)[C@]3(CCC(C(O3)(C)C)Br)C)C)O)[C@]4(CC[C@@H](O4)C(C)(C)O)C
• InChI: InChI=1S/C32H55BrO8/c1-20(34)37-25(31(8)18-14-22(39-31)27(2,3)35)13-16-29(6,36)23-10-11-24-30(7,40-23)19-15-26(38-24)32(9)17-12-21(33)28(4,5)41-32/h21-26,35-36H,10-19H2,1-9H3/t21?,22-,23?,24+,25-,26+,29+,30-,31-,32-/m1/s1
• InChI Key: IXKSFJQVWRDNPC-GOMKVAPCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₅₅BrO₈
• Molecular Weight: 647.70 g/mol
• Exact Mass: 646.30803 g/mol
• Topological Polar Surface Area (TPSA): 104.00 Ų
• XlogP: 4.20
• Atomic LogP (AlogP): 5.75
• H-Bond Acceptor: 8
• H-Bond Donor: 2
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9741	97.41%
Caco-2	-	0.7755	77.55%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7717	77.17%
OATP2B1 inhibitior	-	0.5706	57.06%
OATP1B1 inhibitior	+	0.8829	88.29%
OATP1B3 inhibitior	+	0.8653	86.53%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7037	70.37%
BSEP inhibitior	+	0.8015	80.15%
P-glycoprotein inhibitior	+	0.7248	72.48%
P-glycoprotein substrate	-	0.5241	52.41%
CYP3A4 substrate	+	0.7125	71.25%
CYP2C9 substrate	-	0.8004	80.04%
CYP2D6 substrate	-	0.8433	84.33%
CYP3A4 inhibition	-	0.7032	70.32%
CYP2C9 inhibition	-	0.6688	66.88%
CYP2C19 inhibition	-	0.8295	82.95%
CYP2D6 inhibition	-	0.9079	90.79%
CYP1A2 inhibition	-	0.8684	86.84%
CYP2C8 inhibition	+	0.4745	47.45%
CYP inhibitory promiscuity	-	0.7351	73.51%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8610	86.10%
Carcinogenicity (trinary)	Non-required	0.5268	52.68%
Eye corrosion	-	0.9854	98.54%
Eye irritation	-	0.9195	91.95%
Skin irritation	-	0.6946	69.46%
Skin corrosion	-	0.9306	93.06%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4345	43.45%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.6500	65.00%
skin sensitisation	-	0.8316	83.16%
Respiratory toxicity	-	0.5333	53.33%
Reproductive toxicity	+	0.7111	71.11%
Mitochondrial toxicity	+	0.7500	75.00%
Nephrotoxicity	+	0.7167	71.67%
Acute Oral Toxicity (c)	III	0.4462	44.62%
Estrogen receptor binding	+	0.6871	68.71%
Androgen receptor binding	+	0.6064	60.64%
Thyroid receptor binding	+	0.5188	51.88%
Glucocorticoid receptor binding	+	0.6881	68.81%
Aromatase binding	+	0.7019	70.19%
PPAR gamma	+	0.5992	59.92%
Honey bee toxicity	-	0.7306	73.06%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	+	0.9895	98.95%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL218	P21554	Cannabinoid CB1 receptor	97.41%	96.61%
CHEMBL253	P34972	Cannabinoid CB2 receptor	97.27%	97.25%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.90%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.68%	91.11%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	94.13%	96.95%
CHEMBL284	P27487	Dipeptidyl peptidase IV	93.83%	95.69%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.78%	97.09%
CHEMBL2581	P07339	Cathepsin D	90.68%	98.95%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	89.02%	97.21%
CHEMBL4227	P25090	Lipoxin A4 receptor	88.20%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.62%	94.45%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	86.69%	92.29%
CHEMBL340	P08684	Cytochrome P450 3A4	86.64%	91.19%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.76%	89.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	85.71%	96.77%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	85.57%	89.05%
CHEMBL3922	P50579	Methionine aminopeptidase 2	84.86%	97.28%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	84.32%	95.71%
CHEMBL3401	O75469	Pregnane X receptor	84.24%	94.73%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.05%	92.62%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	83.81%	85.14%
CHEMBL204	P00734	Thrombin	83.79%	96.01%
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	83.55%	92.78%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	83.49%	93.04%
CHEMBL237	P41145	Kappa opioid receptor	83.33%	98.10%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.09%	97.14%
CHEMBL3437	Q16853	Amine oxidase, copper containing	83.05%	94.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.50%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.29%	86.33%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.05%	93.56%
CHEMBL2094135	Q96BI3	Gamma-secretase	82.02%	98.05%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.78%	95.50%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.69%	95.89%
CHEMBL2413	P32246	C-C chemokine receptor type 1	80.22%	89.50%
CHEMBL1795139	Q8IU80	Transmembrane protease serine 6	80.07%	98.33%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 162861146
• LOTUS: LTS0261381
• wikiData: Q105122232