(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-6-[(2R,3R,4S,5S,6R)-2-[[(3S,4R,4aR,6aR,6bS,8aS,14aR,14bS)-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,14a-dodecahydropicen-3-yl]oxy]-5-hydroxy-6-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-4-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: da7a8d4a-c468-4ed7-b22a-26ac98a51383
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6S)-6-[(2R,3R,4S,5S,6R)-2-[[(3S,4R,4aR,6aR,6bS,8aS,14aR,14bS)-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,14a-dodecahydropicen-3-yl]oxy]-5-hydroxy-6-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-4-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): CC1C(C(C(C(O1)OC2CCC3(C(C2(C)CO)CCC4(C3C=CC5=C6CC(CCC6(CCC54C)CO)(C)C)C)C)OC7C(C(C(C(O7)CO)O)O)O)OC8C(C(C(C(O8)CO)OC9C(C(C(C(O9)CO)O)O)O)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)O[C@H]2CC[C@]3([C@H]([C@]2(C)CO)CC[C@@]4([C@@H]3C=CC5=C6CC(CC[C@@]6(CC[C@]54C)CO)(C)C)C)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)O)O)O
• InChI: InChI=1S/C54H88O22/c1-24-33(60)43(75-47-41(68)38(65)42(29(21-57)72-47)74-45-39(66)36(63)34(61)27(19-55)70-45)44(76-46-40(67)37(64)35(62)28(20-56)71-46)48(69-24)73-32-11-12-50(4)30(51(32,5)22-58)10-13-53(7)31(50)9-8-25-26-18-49(2,3)14-16-54(26,23-59)17-15-52(25,53)6/h8-9,24,27-48,55-68H,10-23H2,1-7H3/t24-,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: CNBUEKQQBLCIHJ-URADCOCDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₄H₈₈O₂₂
• Molecular Weight: 1089.30 g/mol
• Exact Mass: 1088.57672443 g/mol
• Topological Polar Surface Area (TPSA): 357.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -1.64
• H-Bond Acceptor: 22
• H-Bond Donor: 14
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6624	66.24%
Caco-2	-	0.8818	88.18%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.8215	82.15%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8558	85.58%
OATP1B3 inhibitior	-	0.4699	46.99%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.5000	50.00%
BSEP inhibitior	+	0.8510	85.10%
P-glycoprotein inhibitior	+	0.7450	74.50%
P-glycoprotein substrate	+	0.5080	50.80%
CYP3A4 substrate	+	0.7225	72.25%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8401	84.01%
CYP3A4 inhibition	-	0.9574	95.74%
CYP2C9 inhibition	-	0.8723	87.23%
CYP2C19 inhibition	-	0.8879	88.79%
CYP2D6 inhibition	-	0.9407	94.07%
CYP1A2 inhibition	-	0.8680	86.80%
CYP2C8 inhibition	+	0.6787	67.87%
CYP inhibitory promiscuity	-	0.9298	92.98%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6302	63.02%
Eye corrosion	-	0.9888	98.88%
Eye irritation	-	0.9020	90.20%
Skin irritation	-	0.6831	68.31%
Skin corrosion	-	0.9498	94.98%
Ames mutagenesis	-	0.7608	76.08%
Human Ether-a-go-go-Related Gene inhibition	+	0.7534	75.34%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.5177	51.77%
skin sensitisation	-	0.8935	89.35%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8556	85.56%
Mitochondrial toxicity	-	0.8125	81.25%
Nephrotoxicity	-	0.7433	74.33%
Acute Oral Toxicity (c)	III	0.7395	73.95%
Estrogen receptor binding	+	0.7947	79.47%
Androgen receptor binding	+	0.7472	74.72%
Thyroid receptor binding	+	0.5333	53.33%
Glucocorticoid receptor binding	+	0.6906	69.06%
Aromatase binding	+	0.6302	63.02%
PPAR gamma	+	0.7864	78.64%
Honey bee toxicity	-	0.6831	68.31%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.6000	60.00%
Fish aquatic toxicity	+	0.9438	94.38%

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	98.60%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.35%	96.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	95.17%	97.36%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.03%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.80%	86.33%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.60%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.93%	100.00%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.84%	92.94%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.31%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.20%	94.45%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	85.11%	95.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.85%	95.56%
CHEMBL1937	Q92769	Histone deacetylase 2	83.00%	94.75%
CHEMBL2581	P07339	Cathepsin D	82.76%	98.95%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.38%	93.04%
CHEMBL226	P30542	Adenosine A1 receptor	81.15%	95.93%
CHEMBL2842	P42345	Serine/threonine-protein kinase mTOR	80.96%	92.78%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.88%	91.07%

Plants that contains it

• Verbascum songaricum

Cross-Links

• PubChem: 101681777
• LOTUS: LTS0165291
• wikiData: Q104965587