(2S,3R,4S,5R)-2-[(2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5R,6R)-2-[[(3S,4aR,6aR,6bS,8R,8aS,12aS,14R,14aR,14bS)-8-hydroxy-8a-(hydroxymethyl)-14-methoxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-4,5-dihydroxy-6-methyloxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol

Details

• Internal ID: 5fbdfa49-e915-4f3c-ac59-82efa9fb651c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2S,3R,4S,5R)-2-[(2S,3R,4S,5S,6R)-2-[(2R,3R,4S,5R,6R)-2-[[(3S,4aR,6aR,6bS,8R,8aS,12aS,14R,14aR,14bS)-8-hydroxy-8a-(hydroxymethyl)-14-methoxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-4,5-dihydroxy-6-methyloxan-3-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol
• SMILES (Canonical): CC1C(C(C(C(O1)OC2CCC3(C(C2(C)C)CCC4(C3C(C=C5C4(CC(C6(C5CC(CC6)(C)C)CO)O)C)OC)C)C)OC7C(C(C(C(O7)CO)O)O)OC8C(C(C(CO8)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](C2(C)C)CC[C@@]4([C@@H]3[C@@H](C=C5[C@]4(C[C@H]([C@@]6([C@H]5CC(CC6)(C)C)CO)O)C)OC)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](CO8)O)O)O)O)O
• InChI: InChI=1S/C48H80O17/c1-22-31(53)34(56)37(65-42-38(35(57)33(55)27(19-49)62-42)64-40-36(58)32(54)25(51)20-60-40)41(61-22)63-30-11-12-45(6)28(44(30,4)5)10-13-46(7)39(45)26(59-9)16-23-24-17-43(2,3)14-15-48(24,21-50)29(52)18-47(23,46)8/h16,22,24-42,49-58H,10-15,17-21H2,1-9H3/t22-,24+,25-,26-,27-,28+,29-,30+,31+,32+,33-,34+,35+,36-,37-,38-,39-,40+,41+,42+,45+,46-,47-,48-/m1/s1
• InChI Key: GHGSMSLFPHINJZ-XVFMJRNASA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₈₀O₁₇
• Molecular Weight: 929.10 g/mol
• Exact Mass: 928.53955108 g/mol
• Topological Polar Surface Area (TPSA): 267.00 Ų
• XlogP: 2.20
• Atomic LogP (AlogP): 0.88
• H-Bond Acceptor: 17
• H-Bond Donor: 10
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6944	69.44%
Caco-2	-	0.8966	89.66%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7695	76.95%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7314	73.14%
OATP1B3 inhibitior	-	0.3159	31.59%
MATE1 inhibitior	-	0.9612	96.12%
OCT2 inhibitior	-	0.6000	60.00%
BSEP inhibitior	-	0.4693	46.93%
P-glycoprotein inhibitior	+	0.7530	75.30%
P-glycoprotein substrate	-	0.5663	56.63%
CYP3A4 substrate	+	0.7420	74.20%
CYP2C9 substrate	-	0.8037	80.37%
CYP2D6 substrate	-	0.8331	83.31%
CYP3A4 inhibition	-	0.9419	94.19%
CYP2C9 inhibition	-	0.8766	87.66%
CYP2C19 inhibition	-	0.8778	87.78%
CYP2D6 inhibition	-	0.9383	93.83%
CYP1A2 inhibition	-	0.8917	89.17%
CYP2C8 inhibition	+	0.6419	64.19%
CYP inhibitory promiscuity	-	0.9651	96.51%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6205	62.05%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9065	90.65%
Skin irritation	-	0.6726	67.26%
Skin corrosion	-	0.9465	94.65%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7528	75.28%
Micronuclear	-	0.8400	84.00%
Hepatotoxicity	-	0.7677	76.77%
skin sensitisation	-	0.8831	88.31%
Respiratory toxicity	-	0.5000	50.00%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	-	0.7625	76.25%
Nephrotoxicity	-	0.9547	95.47%
Acute Oral Toxicity (c)	III	0.6850	68.50%
Estrogen receptor binding	+	0.7907	79.07%
Androgen receptor binding	+	0.7281	72.81%
Thyroid receptor binding	-	0.5581	55.81%
Glucocorticoid receptor binding	+	0.6679	66.79%
Aromatase binding	+	0.6544	65.44%
PPAR gamma	+	0.7782	77.82%
Honey bee toxicity	-	0.6155	61.55%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.8511	85.11%

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	98.24%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.25%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.70%	97.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.75%	97.36%
CHEMBL1937	Q92769	Histone deacetylase 2	88.93%	94.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.24%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.84%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.82%	94.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.22%	86.92%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.04%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.79%	95.89%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.88%	96.61%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.89%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.84%	92.94%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.59%	89.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.67%	95.50%
CHEMBL2243	O00519	Anandamide amidohydrolase	80.95%	97.53%
CHEMBL226	P30542	Adenosine A1 receptor	80.40%	95.93%

Plants that contains it

• Bupleurum rotundifolium

Cross-Links

• PubChem: 16097919
• LOTUS: LTS0128761
• wikiData: Q105008522