(2R,alphaS)-alpha-[3-[(2R,4aalpha,8abeta)-6beta-[(2S,5R)-5-Bromo-2,6,6-trimethyltetrahydro-2H-pyran-2-yl]octahydro-8a-methylpyrano[3,2-b]pyran-2beta-yl]-3-butenyl]tetrahydro-alpha',alpha',2-trimethyl-2beta,5alpha-furandimethanol diacetate

Details

• Internal ID: 9792b261-1931-4af0-adc9-03bec91c27ee
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: [(1S)-4-[(2R,4aS,6R,8aR)-2-[(2S,5R)-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]-1-[(2R,5R)-5-(2-acetyloxypropan-2-yl)-2-methyloxolan-2-yl]pent-4-enyl] acetate
• SMILES (Canonical): CC(=O)OC(CCC(=C)C1CCC2C(O1)(CCC(O2)C3(CCC(C(O3)(C)C)Br)C)C)C4(CCC(O4)C(C)(C)OC(=O)C)C
• SMILES (Isomeric): CC(=O)O[C@@H](CCC(=C)[C@H]1CC[C@@H]2[C@@](O1)(CC[C@@H](O2)[C@@]3(CC[C@H](C(O3)(C)C)Br)C)C)[C@]4(CC[C@@H](O4)C(C)(C)OC(=O)C)C
• InChI: InChI=1S/C34H55BrO8/c1-21(11-13-27(38-22(2)36)33(9)19-16-26(42-33)31(6,7)40-23(3)37)24-12-14-28-32(8,41-24)20-17-29(39-28)34(10)18-15-25(35)30(4,5)43-34/h24-29H,1,11-20H2,2-10H3/t24-,25-,26-,27+,28-,29-,32+,33-,34+/m1/s1
• InChI Key: KLHKXTGRUQGLFW-MMNZDONDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₅₅BrO₈
• Molecular Weight: 671.70 g/mol
• Exact Mass: 670.30803 g/mol
• Topological Polar Surface Area (TPSA): 89.50 Ų
• XlogP: 6.00
• Atomic LogP (AlogP): 7.13
• H-Bond Acceptor: 8
• H-Bond Donor: 0
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9867	98.67%
Caco-2	-	0.7991	79.91%
Blood Brain Barrier	+	0.8500	85.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7244	72.44%
OATP2B1 inhibitior	-	0.7142	71.42%
OATP1B1 inhibitior	+	0.8720	87.20%
OATP1B3 inhibitior	-	0.3084	30.84%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8855	88.55%
P-glycoprotein inhibitior	+	0.7701	77.01%
P-glycoprotein substrate	+	0.5253	52.53%
CYP3A4 substrate	+	0.7154	71.54%
CYP2C9 substrate	-	0.7977	79.77%
CYP2D6 substrate	-	0.8447	84.47%
CYP3A4 inhibition	+	0.5338	53.38%
CYP2C9 inhibition	-	0.5945	59.45%
CYP2C19 inhibition	-	0.7680	76.80%
CYP2D6 inhibition	-	0.9085	90.85%
CYP1A2 inhibition	-	0.7886	78.86%
CYP2C8 inhibition	+	0.5797	57.97%
CYP inhibitory promiscuity	-	0.5297	52.97%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.8410	84.10%
Carcinogenicity (trinary)	Non-required	0.5352	53.52%
Eye corrosion	-	0.9819	98.19%
Eye irritation	-	0.9092	90.92%
Skin irritation	-	0.6996	69.96%
Skin corrosion	-	0.9172	91.72%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5148	51.48%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	+	0.5303	53.03%
skin sensitisation	-	0.7770	77.70%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	+	0.7923	79.23%
Acute Oral Toxicity (c)	III	0.5726	57.26%
Estrogen receptor binding	+	0.7087	70.87%
Androgen receptor binding	+	0.6569	65.69%
Thyroid receptor binding	-	0.4900	49.00%
Glucocorticoid receptor binding	+	0.7772	77.72%
Aromatase binding	+	0.7141	71.41%
PPAR gamma	+	0.6349	63.49%
Honey bee toxicity	-	0.7451	74.51%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	1.0000	100.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL240	Q12809	HERG	98.24%	89.76%
CHEMBL218	P21554	Cannabinoid CB1 receptor	97.24%	96.61%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.17%	96.09%
CHEMBL233	P35372	Mu opioid receptor	96.41%	97.93%
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.25%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.71%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.35%	98.95%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	91.93%	89.05%
CHEMBL340	P08684	Cytochrome P450 3A4	90.58%	91.19%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	89.43%	96.95%
CHEMBL4227	P25090	Lipoxin A4 receptor	87.61%	100.00%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	87.37%	97.21%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	87.00%	97.14%
CHEMBL2094135	Q96BI3	Gamma-secretase	86.14%	98.05%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.83%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.38%	94.45%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.02%	93.56%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	84.42%	95.71%
CHEMBL3976	Q9UHL4	Dipeptidyl peptidase II	84.10%	92.29%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.00%	92.62%
CHEMBL5255	O00206	Toll-like receptor 4	83.50%	92.50%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	83.06%	82.69%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.86%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.86%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.74%	89.00%
CHEMBL3437	Q16853	Amine oxidase, copper containing	82.06%	94.00%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.65%	100.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.60%	95.50%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.09%	96.77%
CHEMBL1293249	Q13887	Kruppel-like factor 5	80.55%	86.33%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.51%	91.07%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.33%	95.89%

Plants that contains it

• Anethum graveolens
• Cymbidium aloifolium
• Delphinium dictyocarpum
• Ladeania juncea
• Ligularia atroviolacea
• Scutellaria glabra
• Trifolium pannonicum

Cross-Links

• PubChem: 23425821
• NPASS: NPC3149