(2R,3R,4R,5S,6S)-2-[[(2R,3S,4S,5R,6S)-6-[2-[3-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-12-hydroxy-4,4,8,14-tetramethyl-1,2,3,5,6,7,9,10,11,12,13,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-6-methylhept-5-en-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-methyloxane-3,4,5-triol

Details

• Internal ID: ca8b433f-a694-464a-9a4a-3d4528a25a00
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
• IUPAC Name: (2R,3R,4R,5S,6S)-2-[[(2R,3S,4S,5R,6S)-6-[2-[3-[(2R,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-12-hydroxy-4,4,8,14-tetramethyl-1,2,3,5,6,7,9,10,11,12,13,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-6-methylhept-5-en-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methoxy]-6-methyloxane-3,4,5-triol
• SMILES (Canonical): CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC(C)(CCC=C(C)C)C3CCC4(C3C(CC5C4(CCC6C5CCC(C6(C)C)OC7C(C(C(C(O7)CO)O)O)OC8C(C(C(C(O8)CO)O)O)O)C)O)C)O)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@H]([C@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC(C)(CCC=C(C)C)C3CCC4(C3C(CC5C4(CCC6C5CCC(C6(C)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)C)O)C)O)O)O)O)O)O
• InChI: InChI=1S/C53H90O22/c1-22(2)10-9-15-53(8,75-48-44(67)40(63)37(60)31(72-48)21-68-46-42(65)38(61)34(57)23(3)69-46)26-14-17-52(7)33(26)28(56)18-27-24-11-12-32(50(4,5)25(24)13-16-51(27,52)6)73-49-45(41(64)36(59)30(20-55)71-49)74-47-43(66)39(62)35(58)29(19-54)70-47/h10,23-49,54-67H,9,11-21H2,1-8H3/t23-,24?,25?,26?,27?,28?,29+,30+,31+,32?,33?,34+,35+,36+,37+,38+,39-,40-,41-,42+,43+,44+,45+,46+,47-,48-,49-,51?,52?,53?/m0/s1
• InChI Key: WIAADPBOLHIACB-RXDBHHMVSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₃H₉₀O₂₂
• Molecular Weight: 1079.30 g/mol
• Exact Mass: 1078.59237449 g/mol
• Topological Polar Surface Area (TPSA): 357.00 Ų
• XlogP: 0.40
• Atomic LogP (AlogP): -1.57
• H-Bond Acceptor: 22
• H-Bond Donor: 14
• Rotatable Bonds: 15

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6877	68.77%
Caco-2	-	0.9182	91.82%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.7251	72.51%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8146	81.46%
OATP1B3 inhibitior	+	0.8189	81.89%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	+	0.8741	87.41%
P-glycoprotein inhibitior	+	0.7499	74.99%
P-glycoprotein substrate	+	0.5056	50.56%
CYP3A4 substrate	+	0.7334	73.34%
CYP2C9 substrate	-	0.8025	80.25%
CYP2D6 substrate	-	0.8264	82.64%
CYP3A4 inhibition	-	0.9502	95.02%
CYP2C9 inhibition	-	0.8671	86.71%
CYP2C19 inhibition	-	0.9036	90.36%
CYP2D6 inhibition	-	0.9380	93.80%
CYP1A2 inhibition	-	0.9057	90.57%
CYP2C8 inhibition	+	0.7260	72.60%
CYP inhibitory promiscuity	-	0.9413	94.13%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6474	64.74%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9025	90.25%
Skin irritation	-	0.5956	59.56%
Skin corrosion	-	0.9488	94.88%
Ames mutagenesis	-	0.8154	81.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.8428	84.28%
Micronuclear	-	0.8800	88.00%
Hepatotoxicity	-	0.5718	57.18%
skin sensitisation	-	0.8991	89.91%
Respiratory toxicity	+	0.6556	65.56%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.7925	79.25%
Acute Oral Toxicity (c)	I	0.5677	56.77%
Estrogen receptor binding	+	0.8157	81.57%
Androgen receptor binding	+	0.7558	75.58%
Thyroid receptor binding	+	0.5358	53.58%
Glucocorticoid receptor binding	+	0.7338	73.38%
Aromatase binding	+	0.6469	64.69%
PPAR gamma	+	0.7993	79.93%
Honey bee toxicity	-	0.5373	53.73%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5300	53.00%
Fish aquatic toxicity	+	0.9172	91.72%

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	98.92%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.51%	91.11%
CHEMBL218	P21554	Cannabinoid CB1 receptor	96.74%	96.61%
CHEMBL3714130	P46095	G-protein coupled receptor 6	95.73%	97.36%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.16%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.96%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.43%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	93.93%	95.93%
CHEMBL1994	P08235	Mineralocorticoid receptor	91.39%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	89.40%	92.94%
CHEMBL259	P32245	Melanocortin receptor 4	89.11%	95.38%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.64%	89.00%
CHEMBL2996	Q05655	Protein kinase C delta	88.62%	97.79%
CHEMBL1937	Q92769	Histone deacetylase 2	87.69%	94.75%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	87.69%	95.50%
CHEMBL5888	Q99558	Mitogen-activated protein kinase kinase kinase 14	86.67%	100.00%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	85.33%	93.04%
CHEMBL2581	P07339	Cathepsin D	84.86%	98.95%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.10%	97.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.14%	95.89%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	82.35%	100.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.21%	100.00%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.00%	95.83%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	81.93%	96.90%
CHEMBL2243	O00519	Anandamide amidohydrolase	81.83%	97.53%
CHEMBL1951	P21397	Monoamine oxidase A	81.58%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.30%	94.45%
CHEMBL5028	O14672	ADAM10	80.11%	97.50%

Plants that contains it

• Gynostemma pentaphyllum

Cross-Links

• PubChem: 11968563
• NPASS: NPC81540