3beta-[2-O,4-O-Di(beta-D-glucopyranosyl)-beta-D-glucopyranuronosyloxy]oleana-12-ene-16alpha,21beta,22alpha,24,28-pentol 21-[(Z)-2-methyl-2-butenoate]

Details

• Internal ID: 8d6c4c4f-383d-426b-add3-e8a3e1749cde
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2S,3S,4S,5R,6R)-6-[[(3S,4S,4aR,6aR,6bS,8R,8aR,9R,10R,12aS,14aR,14bR)-8,9-dihydroxy-4,8a-bis(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-10-[(Z)-2-methylbut-2-enoyl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-4-hydroxy-3,5-bis[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy]oxane-2-carboxylic acid
• SMILES (Canonical): CC=C(C)C(=O)OC1C(C2(C(CC1(C)C)C3=CCC4C5(CCC(C(C5CCC4(C3(CC2O)C)C)(C)CO)OC6C(C(C(C(O6)C(=O)O)OC7C(C(C(C(O7)CO)O)O)O)O)OC8C(C(C(C(O8)CO)O)O)O)C)CO)O
• SMILES (Isomeric): C/C=C(/C)\C(=O)O[C@H]1[C@@H]([C@@]2([C@@H](C[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H]([C@]5(C)CO)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)C(=O)O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)C)C)[C@@H]2CC1(C)C)C)O)CO)O
• InChI: InChI=1S/C53H84O23/c1-9-22(2)44(69)76-42-41(66)53(21-57)24(16-48(42,3)4)23-10-11-28-49(5)14-13-30(50(6,20-56)27(49)12-15-51(28,7)52(23,8)17-29(53)58)72-47-39(74-46-36(64)34(62)32(60)26(19-55)71-46)37(65)38(40(75-47)43(67)68)73-45-35(63)33(61)31(59)25(18-54)70-45/h9-10,24-42,45-47,54-66H,11-21H2,1-8H3,(H,67,68)/b22-9-/t24-,25+,26+,27+,28+,29+,30-,31+,32+,33-,34-,35+,36+,37-,38-,39+,40-,41-,42-,45-,46-,47+,49-,50+,51+,52+,53-/m0/s1
• InChI Key: VCTRQTABKHTJAO-NZMKYMEGSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₃H₈₄O₂₃
• Molecular Weight: 1089.20 g/mol
• Exact Mass: 1088.54033892 g/mol
• Topological Polar Surface Area (TPSA): 382.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): -1.89
• H-Bond Acceptor: 22
• H-Bond Donor: 14
• Rotatable Bonds: 13

Synonyms

• 3beta-[2-O,4-O-Di(beta-D-glucopyranosyl)-beta-D-glucopyranuronosyloxy]oleana-12-ene-16alpha,21beta,22alpha,24,28-pentol 21-[(Z)-2-methyl-2-butenoate]

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7601	76.01%
Caco-2	-	0.8759	87.59%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.8703	87.03%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8093	80.93%
OATP1B3 inhibitior	-	0.4610	46.10%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5026	50.26%
BSEP inhibitior	+	0.9071	90.71%
P-glycoprotein inhibitior	+	0.7480	74.80%
P-glycoprotein substrate	-	0.5164	51.64%
CYP3A4 substrate	+	0.7357	73.57%
CYP2C9 substrate	-	0.8018	80.18%
CYP2D6 substrate	-	0.8966	89.66%
CYP3A4 inhibition	-	0.8310	83.10%
CYP2C9 inhibition	-	0.8704	87.04%
CYP2C19 inhibition	-	0.9216	92.16%
CYP2D6 inhibition	-	0.9491	94.91%
CYP1A2 inhibition	-	0.9009	90.09%
CYP2C8 inhibition	+	0.7717	77.17%
CYP inhibitory promiscuity	-	0.9733	97.33%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6024	60.24%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9004	90.04%
Skin irritation	-	0.5876	58.76%
Skin corrosion	-	0.9441	94.41%
Ames mutagenesis	-	0.7978	79.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.7622	76.22%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.7750	77.50%
skin sensitisation	-	0.9013	90.13%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	+	0.7358	73.58%
Acute Oral Toxicity (c)	III	0.8023	80.23%
Estrogen receptor binding	+	0.7731	77.31%
Androgen receptor binding	+	0.7550	75.50%
Thyroid receptor binding	+	0.5583	55.83%
Glucocorticoid receptor binding	+	0.7668	76.68%
Aromatase binding	+	0.6384	63.84%
PPAR gamma	+	0.8050	80.50%
Honey bee toxicity	-	0.6522	65.22%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9585	95.85%

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	97.00%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.17%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.76%	94.45%
CHEMBL3714130	P46095	G-protein coupled receptor 6	91.54%	97.36%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.23%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.79%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.46%	86.33%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.44%	91.07%
CHEMBL221	P23219	Cyclooxygenase-1	86.63%	90.17%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	85.81%	93.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.09%	89.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.83%	94.33%
CHEMBL1937	Q92769	Histone deacetylase 2	84.52%	94.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.25%	99.17%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	84.06%	95.50%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.00%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.91%	97.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	83.40%	97.25%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.99%	100.00%
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	82.87%	91.65%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.50%	95.50%
CHEMBL5255	O00206	Toll-like receptor 4	81.35%	92.50%
CHEMBL5028	O14672	ADAM10	80.45%	97.50%

Plants that contains it

• Aesculus chinensis

Cross-Links

• PubChem: 10606149
• NPASS: NPC115656
• LOTUS: LTS0255249
• wikiData: Q105283944