(2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-2-[[(3S,5R,8R,9R,10R,12R,13S,14R,17S)-17-[(2S,5S)-5-hydroperoxy-6-methyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxyhept-6-en-2-yl]-12-hydroxy-4,4,8,10,14,17-hexamethyl-1,2,3,5,6,7,9,11,12,13,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: db099d75-2d8d-4c4f-a7ec-adaf8d9a4497
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Triterpenoids
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5S,6R)-2-[[(3S,5R,8R,9R,10R,12R,13S,14R,17S)-17-[(2S,5S)-5-hydroperoxy-6-methyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxan-2-yl]oxyhept-6-en-2-yl]-12-hydroxy-4,4,8,10,14,17-hexamethyl-1,2,3,5,6,7,9,11,12,13,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC(=C)C(CCC(C)(C1(CCC2(C1C(CC3C2(CCC4C3(CCC(C4(C)C)OC5C(C(C(C(O5)CO)O)O)OC6C(C(C(C(O6)CO)O)O)O)C)C)O)C)C)OC7C(C(C(C(O7)COC8C(C(C(CO8)O)O)O)O)O)O)OO
• SMILES (Isomeric): CC(=C)[C@H](CC[C@@](C)([C@]1(CC[C@@]2([C@@H]1[C@@H](C[C@H]3[C@]2(CC[C@@H]4[C@@]3(CC[C@@H](C4(C)C)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C)C)O)C)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO[C@H]8[C@@H]([C@H]([C@@H](CO8)O)O)O)O)O)O)OO
• InChI: InChI=1S/C54H92O24/c1-23(2)26(78-69)10-15-54(9,77-47-42(68)38(64)36(62)29(74-47)22-71-45-40(66)33(59)25(58)21-70-45)53(8)17-16-52(7)44(53)24(57)18-31-50(5)13-12-32(49(3,4)30(50)11-14-51(31,52)6)75-48-43(39(65)35(61)28(20-56)73-48)76-46-41(67)37(63)34(60)27(19-55)72-46/h24-48,55-69H,1,10-22H2,2-9H3/t24-,25-,26+,27-,28-,29-,30+,31-,32+,33+,34-,35-,36-,37+,38+,39+,40-,41-,42-,43-,44+,45+,46+,47+,48+,50+,51-,52-,53+,54+/m1/s1
• InChI Key: QKWHKGKNAQTSDU-ORTMGCNBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₄H₉₂O₂₄
• Molecular Weight: 1125.30 g/mol
• Exact Mass: 1124.59785380 g/mol
• Topological Polar Surface Area (TPSA): 387.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): -1.71
• H-Bond Acceptor: 24
• H-Bond Donor: 15
• Rotatable Bonds: 17

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6460	64.60%
Caco-2	-	0.8998	89.98%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.6310	63.10%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8139	81.39%
OATP1B3 inhibitior	+	0.8680	86.80%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	+	0.7858	78.58%
P-glycoprotein inhibitior	+	0.7488	74.88%
P-glycoprotein substrate	+	0.6080	60.80%
CYP3A4 substrate	+	0.7534	75.34%
CYP2C9 substrate	-	0.8022	80.22%
CYP2D6 substrate	-	0.8291	82.91%
CYP3A4 inhibition	-	0.9197	91.97%
CYP2C9 inhibition	-	0.8097	80.97%
CYP2C19 inhibition	-	0.8275	82.75%
CYP2D6 inhibition	-	0.9237	92.37%
CYP1A2 inhibition	-	0.8448	84.48%
CYP2C8 inhibition	+	0.7403	74.03%
CYP inhibitory promiscuity	-	0.9323	93.23%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.6397	63.97%
Eye corrosion	-	0.9851	98.51%
Eye irritation	-	0.9002	90.02%
Skin irritation	-	0.6258	62.58%
Skin corrosion	-	0.9264	92.64%
Ames mutagenesis	-	0.6015	60.15%
Human Ether-a-go-go-Related Gene inhibition	+	0.8350	83.50%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.5854	58.54%
skin sensitisation	-	0.8607	86.07%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	-	0.7631	76.31%
Acute Oral Toxicity (c)	III	0.4437	44.37%
Estrogen receptor binding	+	0.7647	76.47%
Androgen receptor binding	+	0.7527	75.27%
Thyroid receptor binding	+	0.5467	54.67%
Glucocorticoid receptor binding	+	0.7151	71.51%
Aromatase binding	+	0.6455	64.55%
PPAR gamma	+	0.7847	78.47%
Honey bee toxicity	-	0.5555	55.55%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9636	96.36%

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	99.52%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.13%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.03%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.90%	96.09%
CHEMBL2996	Q05655	Protein kinase C delta	93.57%	97.79%
CHEMBL218	P21554	Cannabinoid CB1 receptor	93.27%	96.61%
CHEMBL1914	P06276	Butyrylcholinesterase	92.19%	95.00%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	91.78%	100.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	90.27%	82.69%
CHEMBL226	P30542	Adenosine A1 receptor	89.55%	95.93%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	89.47%	97.14%
CHEMBL233	P35372	Mu opioid receptor	89.38%	97.93%
CHEMBL237	P41145	Kappa opioid receptor	89.31%	98.10%
CHEMBL2581	P07339	Cathepsin D	88.83%	98.95%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	88.47%	95.50%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	88.36%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.98%	95.89%
CHEMBL6136	O60341	Lysine-specific histone demethylase 1	87.64%	95.58%
CHEMBL206	P03372	Estrogen receptor alpha	87.51%	97.64%
CHEMBL1937	Q92769	Histone deacetylase 2	87.07%	94.75%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	86.98%	92.86%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.62%	92.94%
CHEMBL1871	P10275	Androgen Receptor	86.20%	96.43%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	85.65%	93.04%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	85.56%	95.83%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.45%	94.45%
CHEMBL4581	P52732	Kinesin-like protein 1	85.06%	93.18%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.38%	100.00%
CHEMBL4105786	P41182	B-cell lymphoma 6 protein	84.04%	92.86%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	83.83%	91.03%
CHEMBL5255	O00206	Toll-like receptor 4	83.66%	92.50%
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	83.45%	92.78%
CHEMBL2534	O15530	3-phosphoinositide dependent protein kinase-1	83.42%	95.36%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	82.77%	89.05%
CHEMBL5103	Q969S8	Histone deacetylase 10	82.40%	90.08%
CHEMBL4618	P09960	Leukotriene A4 hydrolase	82.38%	97.86%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.09%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.09%	86.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.03%	92.62%
CHEMBL2360	P00492	Hypoxanthine-guanine phosphoribosyltransferase	82.00%	87.38%
CHEMBL2094135	Q96BI3	Gamma-secretase	81.97%	98.05%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.76%	97.36%
CHEMBL3892	Q99500	Sphingosine 1-phosphate receptor Edg-3	81.54%	97.29%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.52%	96.90%
CHEMBL259	P32245	Melanocortin receptor 4	81.31%	95.38%
CHEMBL344	Q99705	Melanin-concentrating hormone receptor 1	81.28%	92.50%
CHEMBL5524	Q99873	Protein-arginine N-methyltransferase 1	81.03%	96.67%
CHEMBL5028	O14672	ADAM10	80.74%	97.50%
CHEMBL3524	P56524	Histone deacetylase 4	80.40%	92.97%
CHEMBL3145	P42338	PI3-kinase p110-beta subunit	80.30%	98.75%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	80.21%	82.50%
CHEMBL1951	P21397	Monoamine oxidase A	80.02%	91.49%

Plants that contains it

• Panax notoginseng

Cross-Links

• PubChem: 162938238
• LOTUS: LTS0104349
• wikiData: Q105223370