(4aS,5R,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2R,3R,4S,5S,6R)-3-[(2S,3R,4S,5R,6R)-4-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxy-4a-(hydroxymethyl)-2,2,6a,6b,9,9,12a-heptamethyl-4,5,6,6a,7,8,8a,10,11,12,13,14b-dodecahydro-1H-picen-3-one

Details

• Internal ID: a40a27fd-f625-4c6b-9132-47d8aece504e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (4aS,5R,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-[(2R,3R,4S,5S,6R)-3-[(2S,3R,4S,5R,6R)-4-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-hydroxy-4a-(hydroxymethyl)-2,2,6a,6b,9,9,12a-heptamethyl-4,5,6,6a,7,8,8a,10,11,12,13,14b-dodecahydro-1H-picen-3-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3C(C(OC(C3O)OC4C(C(C(OC4OC5CCC6(C(C5(C)C)CCC7(C6CC=C8C7(CC(C9(C8CC(C(=O)C9)(C)C)CO)O)C)C)C)CO)O)O)CO)O)CO)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@H]([C@H](O[C@H]2O[C@H]3[C@@H]([C@H](O[C@H]([C@@H]3O)O[C@@H]4[C@H]([C@@H]([C@H](O[C@H]4O[C@H]5CC[C@]6([C@H](C5(C)C)CC[C@@]7([C@@H]6CC=C8[C@]7(C[C@H]([C@@]9([C@H]8CC(C(=O)C9)(C)C)CO)O)C)C)C)CO)O)O)CO)O)CO)O)O)O)O)O
• InChI: InChI=1S/C54H88O23/c1-22-33(61)37(65)40(68)45(70-22)76-44-39(67)35(63)26(19-56)73-48(44)75-42-36(64)27(20-57)71-46(41(42)69)77-43-38(66)34(62)25(18-55)72-47(43)74-32-12-13-51(6)28(50(32,4)5)11-14-52(7)29(51)10-9-23-24-15-49(2,3)30(59)17-54(24,21-58)31(60)16-53(23,52)8/h9,22,24-29,31-48,55-58,60-69H,10-21H2,1-8H3/t22-,24-,25+,26+,27+,28-,29+,31+,32-,33-,34+,35-,36+,37+,38-,39-,40+,41+,42-,43+,44+,45-,46-,47-,48-,51-,52+,53+,54+/m0/s1
• InChI Key: NXCHWALJUPRHLI-ZOCBMCFTSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₄H₈₈O₂₃
• Molecular Weight: 1105.30 g/mol
• Exact Mass: 1104.57163905 g/mol
• Topological Polar Surface Area (TPSA): 374.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -2.38
• H-Bond Acceptor: 23
• H-Bond Donor: 14
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7891	78.91%
Caco-2	-	0.8825	88.25%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.8567	85.67%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7556	75.56%
OATP1B3 inhibitior	-	0.5700	57.00%
MATE1 inhibitior	-	0.9812	98.12%
OCT2 inhibitior	-	0.6276	62.76%
BSEP inhibitior	+	0.9170	91.70%
P-glycoprotein inhibitior	+	0.7457	74.57%
P-glycoprotein substrate	-	0.6390	63.90%
CYP3A4 substrate	+	0.7310	73.10%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8581	85.81%
CYP3A4 inhibition	-	0.9300	93.00%
CYP2C9 inhibition	-	0.8838	88.38%
CYP2C19 inhibition	-	0.9101	91.01%
CYP2D6 inhibition	-	0.9422	94.22%
CYP1A2 inhibition	-	0.8933	89.33%
CYP2C8 inhibition	+	0.6999	69.99%
CYP inhibitory promiscuity	-	0.9668	96.68%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6254	62.54%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9019	90.19%
Skin irritation	-	0.6103	61.03%
Skin corrosion	-	0.9480	94.80%
Ames mutagenesis	-	0.7524	75.24%
Human Ether-a-go-go-Related Gene inhibition	+	0.8004	80.04%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.7848	78.48%
skin sensitisation	-	0.8917	89.17%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	-	0.7625	76.25%
Nephrotoxicity	-	0.8272	82.72%
Acute Oral Toxicity (c)	III	0.7945	79.45%
Estrogen receptor binding	+	0.8060	80.60%
Androgen receptor binding	+	0.7454	74.54%
Thyroid receptor binding	+	0.5282	52.82%
Glucocorticoid receptor binding	+	0.7329	73.29%
Aromatase binding	+	0.6455	64.55%
PPAR gamma	+	0.8046	80.46%
Honey bee toxicity	-	0.6588	65.88%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5350	53.50%
Fish aquatic toxicity	+	0.9411	94.11%

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	96.63%	91.11%
CHEMBL1937	Q92769	Histone deacetylase 2	93.41%	94.75%
CHEMBL3714130	P46095	G-protein coupled receptor 6	93.26%	97.36%
CHEMBL1293249	Q13887	Kruppel-like factor 5	92.57%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.38%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.26%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	89.24%	97.09%
CHEMBL218	P21554	Cannabinoid CB1 receptor	89.22%	96.61%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.99%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.08%	100.00%
CHEMBL2581	P07339	Cathepsin D	85.43%	98.95%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.06%	97.25%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.93%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.21%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.05%	89.00%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	81.30%	97.33%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	81.25%	96.21%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.56%	92.94%
CHEMBL221	P23219	Cyclooxygenase-1	80.53%	90.17%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.24%	93.04%

Plants that contains it

• Berneuxia thibetica

Cross-Links

• PubChem: 102438571
• LOTUS: LTS0147208
• wikiData: Q105186932