Aesculioside IIa

Details

• Internal ID: 44b2fb86-4a1c-48a6-aa51-dd3dca261fb8
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,7R,8S,8aR,9R,10R,12aS,14aR,14bR)-7,8,9-trihydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-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-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxy-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid
• SMILES (Canonical): CC=C(C)C(=O)OC1C(C2(C(CC1(C)C)C3=CCC4C5(CCC(C(C5CCC4(C3(C(C2O)O)C)C)(C)C)OC6C(C(C(C(O6)C(=O)O)O)OC7C(C(C(O7)CO)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](CC1(C)C)C3=CC[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3([C@H]([C@H]2O)O)C)C)(C)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)C(=O)O)O)O[C@H]7[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)CO)O
• InChI: InChI=1S/C52H82O22/c1-10-21(2)43(67)74-41-40(64)52(20-55)23(17-47(41,3)4)22-11-12-27-49(7)15-14-28(48(5,6)26(49)13-16-50(27,8)51(22,9)38(62)39(52)63)70-46-37(73-45-33(60)31(58)29(56)24(18-53)68-45)35(34(61)36(72-46)42(65)66)71-44-32(59)30(57)25(19-54)69-44/h10-11,23-41,44-46,53-64H,12-20H2,1-9H3,(H,65,66)/b21-10-/t23-,24+,25-,26-,27+,28-,29-,30-,31-,32+,33+,34-,35-,36-,37+,38-,39+,40-,41-,44-,45-,46+,49-,50+,51-,52-/m0/s1
• InChI Key: OSURIFGREXTNLJ-VZNPLFSISA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₂H₈₂O₂₂
• Molecular Weight: 1059.20 g/mol
• Exact Mass: 1058.52977424 g/mol
• Topological Polar Surface Area (TPSA): 362.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): -1.25
• H-Bond Acceptor: 21
• H-Bond Donor: 13
• Rotatable Bonds: 12

Synonyms

• RefChem:109965
• 886840-38-6
• (2S,3S,4S,5R,6R)-6-(((3S,4aR,6aR,6bS,7R,8S,8aR,9R,10R,12aS,14aR,14bR)-7,8,9-trihydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-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-((2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl)oxy-3-hydroxy-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxyoxane-2-carboxylic acid
• (2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,7R,8S,8aR,9R,10R,12aS,14aR,14bR)-7,8,9-trihydroxy-8a-(hydroxymethyl)-4,4,6a,6b,11,11,14b-heptamethyl-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-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxy-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid
• CHEMBL1094691
• BDBM50317532

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8106	81.06%
Caco-2	-	0.8766	87.66%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.8938	89.38%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7733	77.33%
OATP1B3 inhibitior	-	0.2400	24.00%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	+	0.5250	52.50%
BSEP inhibitior	+	0.9197	91.97%
P-glycoprotein inhibitior	+	0.7476	74.76%
P-glycoprotein substrate	-	0.5651	56.51%
CYP3A4 substrate	+	0.7323	73.23%
CYP2C9 substrate	-	0.8018	80.18%
CYP2D6 substrate	-	0.8966	89.66%
CYP3A4 inhibition	-	0.8885	88.85%
CYP2C9 inhibition	-	0.8346	83.46%
CYP2C19 inhibition	-	0.9134	91.34%
CYP2D6 inhibition	-	0.9416	94.16%
CYP1A2 inhibition	-	0.8884	88.84%
CYP2C8 inhibition	+	0.7607	76.07%
CYP inhibitory promiscuity	-	0.9147	91.47%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4933	49.33%
Eye corrosion	-	0.9887	98.87%
Eye irritation	-	0.9006	90.06%
Skin irritation	-	0.5513	55.13%
Skin corrosion	-	0.9369	93.69%
Ames mutagenesis	-	0.8178	81.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.7644	76.44%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.8183	81.83%
skin sensitisation	-	0.9110	91.10%
Respiratory toxicity	-	0.5889	58.89%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.6167	61.67%
Acute Oral Toxicity (c)	III	0.7300	73.00%
Estrogen receptor binding	+	0.7835	78.35%
Androgen receptor binding	+	0.7603	76.03%
Thyroid receptor binding	+	0.5258	52.58%
Glucocorticoid receptor binding	+	0.7754	77.54%
Aromatase binding	+	0.6427	64.27%
PPAR gamma	+	0.8129	81.29%
Honey bee toxicity	-	0.6602	66.02%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9795	97.95%

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	98.17%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.73%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.17%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	92.17%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.10%	95.56%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	88.83%	93.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.29%	95.89%
CHEMBL2581	P07339	Cathepsin D	87.43%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.96%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.77%	99.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.40%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.56%	97.09%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.26%	94.33%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.98%	96.21%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.75%	95.50%
CHEMBL5255	O00206	Toll-like receptor 4	82.47%	92.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.40%	89.00%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	82.17%	91.07%
CHEMBL4227	P25090	Lipoxin A4 receptor	82.13%	100.00%

Plants that contains it

• Aesculus pavia

Cross-Links

• PubChem: 46888259
• LOTUS: LTS0036722
• wikiData: Q105199333