(2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5R,6R)-3-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-2-[[(3S,5R,9R,10R,13S,14S,17S)-17-[(2S,3S,5R)-2-ethoxy-5-(2-methylprop-1-enyl)oxolan-3-yl]-4,4,10,13,14-pentamethyl-2,3,5,6,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-6-methyloxane-3,4,5-triol

Details

• Internal ID: 7a622e22-e37f-456d-b277-d5c3dfd58fca
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5R,6R)-3-[(2S,3R,4R,5S,6S)-3,5-dihydroxy-6-methyl-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-2-[[(3S,5R,9R,10R,13S,14S,17S)-17-[(2S,3S,5R)-2-ethoxy-5-(2-methylprop-1-enyl)oxolan-3-yl]-4,4,10,13,14-pentamethyl-2,3,5,6,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-5-hydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-6-methyloxane-3,4,5-triol
• SMILES (Canonical): CCOC1C(CC(O1)C=C(C)C)C2CCC3(C2(CCC4C3=CCC5C4(CCC(C5(C)C)OC6C(C(C(C(O6)CO)O)OC7C(C(C(C(O7)C)O)O)O)OC8C(C(C(C(O8)C)O)OC9C(C(C(CO9)O)O)O)O)C)C)C
• SMILES (Isomeric): CCO[C@@H]1[C@@H](C[C@@H](O1)C=C(C)C)[C@@H]2CC[C@]3([C@]2(CC[C@H]4C3=CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O[C@H]7[C@@H]([C@@H]([C@H]([C@@H](O7)C)O)O)O)O[C@H]8[C@@H]([C@@H]([C@H]([C@@H](O8)C)O)O[C@H]9[C@@H]([C@H]([C@@H](CO9)O)O)O)O)C)C)C
• InChI: InChI=1S/C55H90O20/c1-11-66-47-28(21-27(70-47)20-24(2)3)29-14-18-55(10)31-12-13-34-52(6,7)35(16-17-53(34,8)30(31)15-19-54(29,55)9)72-51-46(45(39(61)33(22-56)71-51)74-49-42(64)40(62)36(58)25(4)68-49)75-50-43(65)44(37(59)26(5)69-50)73-48-41(63)38(60)32(57)23-67-48/h12,20,25-30,32-51,56-65H,11,13-19,21-23H2,1-10H3/t25-,26-,27-,28-,29-,30-,32+,33+,34-,35-,36-,37-,38-,39+,40+,41+,42+,43+,44+,45-,46+,47-,48-,49-,50-,51-,53+,54-,55+/m0/s1
• InChI Key: DFPAGEXHKVXDKM-LADHQGJMSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₅H₉₀O₂₀
• Molecular Weight: 1071.30 g/mol
• Exact Mass: 1070.60254526 g/mol
• Topological Polar Surface Area (TPSA): 295.00 Ų
• XlogP: 2.80
• Atomic LogP (AlogP): 1.68
• H-Bond Acceptor: 20
• H-Bond Donor: 10
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9053	90.53%
Caco-2	-	0.8834	88.34%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.7735	77.35%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8098	80.98%
OATP1B3 inhibitior	+	0.8951	89.51%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.9406	94.06%
P-glycoprotein inhibitior	+	0.7482	74.82%
P-glycoprotein substrate	+	0.6239	62.39%
CYP3A4 substrate	+	0.7501	75.01%
CYP2C9 substrate	-	0.8025	80.25%
CYP2D6 substrate	-	0.8264	82.64%
CYP3A4 inhibition	-	0.7647	76.47%
CYP2C9 inhibition	-	0.8364	83.64%
CYP2C19 inhibition	-	0.8814	88.14%
CYP2D6 inhibition	-	0.9185	91.85%
CYP1A2 inhibition	-	0.9025	90.25%
CYP2C8 inhibition	+	0.8129	81.29%
CYP inhibitory promiscuity	-	0.8277	82.77%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5120	51.20%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.9034	90.34%
Skin irritation	-	0.5791	57.91%
Skin corrosion	-	0.9382	93.82%
Ames mutagenesis	-	0.7454	74.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.8270	82.70%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.8500	85.00%
skin sensitisation	-	0.9023	90.23%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.8492	84.92%
Acute Oral Toxicity (c)	I	0.4294	42.94%
Estrogen receptor binding	+	0.8183	81.83%
Androgen receptor binding	+	0.7515	75.15%
Thyroid receptor binding	+	0.5382	53.82%
Glucocorticoid receptor binding	+	0.7573	75.73%
Aromatase binding	+	0.6387	63.87%
PPAR gamma	+	0.8030	80.30%
Honey bee toxicity	-	0.5624	56.24%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9661	96.61%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.86%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.46%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	94.46%	95.93%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.74%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.48%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	92.78%	97.25%
CHEMBL1994	P08235	Mineralocorticoid receptor	92.13%	100.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	91.65%	97.36%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	91.55%	96.77%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.63%	92.94%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.13%	89.00%
CHEMBL218	P21554	Cannabinoid CB1 receptor	87.49%	96.61%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.75%	95.56%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.73%	95.50%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.56%	96.21%
CHEMBL1937	Q92769	Histone deacetylase 2	82.32%	94.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.46%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.25%	95.89%

Plants that contains it

• Sapindus mukorossi

Cross-Links

• PubChem: 162881123
• LOTUS: LTS0164778
• wikiData: Q104978136