Escin Ivc

Details

• Internal ID: 75d936b8-957a-4c0b-b0e3-84457d688192
• 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)-8a-(acetyloxymethyl)-8,10-dihydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-9-[(E)-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(C(CC2C1(C(CC3(C2=CCC4C3(CCC5C4(CCC(C5(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)C)C)O)COC(=O)C)(C)C)O
• SMILES (Isomeric): C/C=C(\C)/C(=O)O[C@H]1[C@@H](C(C[C@@H]2[C@]1([C@@H](C[C@@]3(C2=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)O)COC(=O)C)(C)C)O
• InChI: InChI=1S/C55H86O24/c1-10-23(2)46(71)79-44-43(68)50(4,5)17-26-25-11-12-30-51(6)15-14-32(52(7,21-58)29(51)13-16-53(30,8)54(25,9)18-31(60)55(26,44)22-72-24(3)59)75-49-41(77-48-38(66)36(64)34(62)28(20-57)74-48)39(67)40(42(78-49)45(69)70)76-47-37(65)35(63)33(61)27(19-56)73-47/h10-11,26-44,47-49,56-58,60-68H,12-22H2,1-9H3,(H,69,70)/b23-10+/t26-,27+,28+,29+,30+,31+,32-,33+,34+,35-,36-,37+,38+,39-,40-,41+,42-,43-,44-,47-,48-,49+,51-,52+,53+,54+,55-/m0/s1
• InChI Key: OBXUDMQHAYRBBM-IVKVKCDBSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₅H₈₆O₂₄
• Molecular Weight: 1131.30 g/mol
• Exact Mass: 1130.55090361 g/mol
• Topological Polar Surface Area (TPSA): 388.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): -1.32
• H-Bond Acceptor: 23
• H-Bond Donor: 13
• Rotatable Bonds: 14

Synonyms

• isoescine IVc
• CHEMBL502797
• SCHEMBL5608832
• 2-Butenoic acid, 2-methyl-, (3.beta.,4.beta.,16.alpha.,21.beta.,22.alpha.)-28-(acetyloxy)-3-[[O-.beta.-D-glucopyranosyl-(1->2)-O-[.beta.-D-glucopyranosyl-(1->4)]-.beta.-D-glucopyranuronosyl]oxy]-16,21,23-trihydroxyolean-12-en-22-yl ester, (2E)-
• 22alpha-tigloyl-28-acetylprotoaescigenin-3beta-O-[beta-D-glucopyranosyl (1-2)][beta-D-glucopyranosyl (1-4)]-beta-D-glucopyranosiduronic acid

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7601	76.01%
Caco-2	-	0.8705	87.05%
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	+	0.8004	80.04%
OATP1B3 inhibitior	-	0.4610	46.10%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5026	50.26%
BSEP inhibitior	+	0.9433	94.33%
P-glycoprotein inhibitior	+	0.7469	74.69%
P-glycoprotein substrate	+	0.5245	52.45%
CYP3A4 substrate	+	0.7387	73.87%
CYP2C9 substrate	-	0.7978	79.78%
CYP2D6 substrate	-	0.8976	89.76%
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	+	0.7847	78.47%
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	-	0.8991	89.91%
Skin irritation	-	0.5876	58.76%
Skin corrosion	-	0.9441	94.41%
Ames mutagenesis	-	0.7478	74.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.7449	74.49%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.7000	70.00%
skin sensitisation	-	0.9013	90.13%
Respiratory toxicity	-	0.6444	64.44%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	+	0.6394	63.94%
Acute Oral Toxicity (c)	III	0.8023	80.23%
Estrogen receptor binding	+	0.7453	74.53%
Androgen receptor binding	+	0.7573	75.73%
Thyroid receptor binding	+	0.5941	59.41%
Glucocorticoid receptor binding	+	0.7794	77.94%
Aromatase binding	+	0.6433	64.33%
PPAR gamma	+	0.8055	80.55%
Honey bee toxicity	-	0.6543	65.43%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5900	59.00%
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	95.96%	91.11%
CHEMBL2782	P35610	Acyl coenzyme A:cholesterol acyltransferase 1	95.56%	91.65%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.35%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.11%	94.45%
CHEMBL3714130	P46095	G-protein coupled receptor 6	92.29%	97.36%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.84%	86.33%
CHEMBL253	P34972	Cannabinoid CB2 receptor	90.42%	97.25%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.16%	95.89%
CHEMBL221	P23219	Cyclooxygenase-1	89.55%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.52%	95.56%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.95%	91.07%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	86.26%	94.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.79%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.32%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.61%	100.00%
CHEMBL5028	O14672	ADAM10	84.10%	97.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.52%	99.17%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	83.16%	93.00%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.42%	94.62%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.70%	95.50%
CHEMBL1937	Q92769	Histone deacetylase 2	81.33%	94.75%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.81%	95.50%
CHEMBL5255	O00206	Toll-like receptor 4	80.25%	92.50%

Plants that contains it

• Aesculus chinensis

Cross-Links

• PubChem: 6476034
• NPASS: NPC269484
• LOTUS: LTS0093712
• wikiData: Q105189208