[(2R,3S,4S,5R,6R)-6-[[(1S,2R,3R,5S,8R,9S,10R,13R,14R,17S)-17-[(2R)-2,5-dihydroxy-6-methylhept-6-en-2-yl]-1,2-dihydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate

Details

• Internal ID: a49afdf0-c00e-4bef-b221-985492a3620a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: [(2R,3S,4S,5R,6R)-6-[[(1S,2R,3R,5S,8R,9S,10R,13R,14R,17S)-17-[(2R)-2,5-dihydroxy-6-methylhept-6-en-2-yl]-1,2-dihydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-3,4,5-trihydroxyoxan-2-yl]methyl acetate
• SMILES (Canonical): CC(=C)C(CCC(C)(C1CCC2(C1CCC3C2(CCC4C3(C(C(C(C4(C)C)OC5C(C(C(C(O5)COC(=O)C)O)O)O)O)O)C)C)C)O)O
• SMILES (Isomeric): CC(=C)C(CC[C@](C)([C@H]1CC[C@@]2([C@@H]1CC[C@H]3[C@]2(CC[C@@H]4[C@@]3([C@@H]([C@H]([C@@H](C4(C)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)COC(=O)C)O)O)O)O)O)C)C)C)O)O
• InChI: InChI=1S/C38H64O11/c1-19(2)23(40)13-17-37(8,46)22-12-15-35(6)21(22)10-11-26-36(35,7)16-14-25-34(4,5)32(30(44)31(45)38(25,26)9)49-33-29(43)28(42)27(41)24(48-33)18-47-20(3)39/h21-33,40-46H,1,10-18H2,2-9H3/t21-,22+,23?,24-,25+,26+,27-,28+,29-,30-,31-,32+,33+,35-,36-,37-,38+/m1/s1
• InChI Key: AKUSREPTEAYSBY-ZBZQTYFVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₆₄O₁₁
• Molecular Weight: 696.90 g/mol
• Exact Mass: 696.44486285 g/mol
• Topological Polar Surface Area (TPSA): 186.00 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 2.84
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8843	88.43%
Caco-2	-	0.8765	87.65%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7991	79.91%
OATP2B1 inhibitior	-	0.8654	86.54%
OATP1B1 inhibitior	+	0.8351	83.51%
OATP1B3 inhibitior	+	0.8467	84.67%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7818	78.18%
BSEP inhibitior	-	0.5841	58.41%
P-glycoprotein inhibitior	+	0.7666	76.66%
P-glycoprotein substrate	-	0.5597	55.97%
CYP3A4 substrate	+	0.7205	72.05%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8900	89.00%
CYP3A4 inhibition	-	0.8568	85.68%
CYP2C9 inhibition	-	0.7252	72.52%
CYP2C19 inhibition	-	0.7966	79.66%
CYP2D6 inhibition	-	0.9332	93.32%
CYP1A2 inhibition	-	0.7767	77.67%
CYP2C8 inhibition	+	0.6238	62.38%
CYP inhibitory promiscuity	-	0.9111	91.11%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.7225	72.25%
Eye corrosion	-	0.9908	99.08%
Eye irritation	-	0.9120	91.20%
Skin irritation	+	0.5495	54.95%
Skin corrosion	-	0.9409	94.09%
Ames mutagenesis	-	0.6537	65.37%
Human Ether-a-go-go-Related Gene inhibition	+	0.6605	66.05%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.6175	61.75%
skin sensitisation	-	0.8713	87.13%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.8444	84.44%
Mitochondrial toxicity	+	0.7375	73.75%
Nephrotoxicity	-	0.7308	73.08%
Acute Oral Toxicity (c)	III	0.4191	41.91%
Estrogen receptor binding	+	0.6896	68.96%
Androgen receptor binding	+	0.7422	74.22%
Thyroid receptor binding	-	0.6076	60.76%
Glucocorticoid receptor binding	+	0.6320	63.20%
Aromatase binding	+	0.6736	67.36%
PPAR gamma	+	0.6866	68.66%
Honey bee toxicity	-	0.6626	66.26%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.9890	98.90%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.85%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.93%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.54%	96.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	95.87%	96.61%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.50%	94.45%
CHEMBL2581	P07339	Cathepsin D	95.38%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.78%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.39%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.37%	85.14%
CHEMBL4227	P25090	Lipoxin A4 receptor	88.89%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.25%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.94%	100.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.36%	95.89%
CHEMBL2179	P04062	Beta-glucocerebrosidase	86.63%	85.31%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	85.98%	93.04%
CHEMBL3401	O75469	Pregnane X receptor	85.95%	94.73%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	84.11%	96.47%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.92%	97.14%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	82.80%	96.95%
CHEMBL5028	O14672	ADAM10	81.99%	97.50%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	81.78%	100.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.72%	95.71%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	81.01%	82.50%
CHEMBL3359	P21462	Formyl peptide receptor 1	80.73%	93.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.23%	99.17%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.02%	92.62%
CHEMBL340	P08684	Cytochrome P450 3A4	80.01%	91.19%

Plants that contains it

• Rhoiptelea chiliantha

Cross-Links

• PubChem: 10842401
• LOTUS: LTS0193109
• wikiData: Q104913862