Isoescine IVf

Details

• Internal ID: 235bf7ac-57be-400e-bb95-51901eb10971
• 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)-8,9,10-trihydroxy-4-(hydroxymethyl)-4,6a,6b,11,11,14b-hexamethyl-8a-[[(Z)-2-methylbut-2-enoyl]oxymethyl]-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)OCC12C(CC(C(C1O)O)(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
• SMILES (Isomeric): C/C=C(/C)\C(=O)OC[C@@]12[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]1CC([C@H]([C@@H]2O)O)(C)C)C)O
• InChI: InChI=1S/C53H84O23/c1-9-22(2)44(69)70-21-53-24(16-48(3,4)41(65)42(53)66)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)57)73-47-39(75-46-36(63)34(61)32(59)26(19-55)72-46)37(64)38(40(76-47)43(67)68)74-45-35(62)33(60)31(58)25(18-54)71-45/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: YLCOBYJIGZMEEB-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: -0.50
• Atomic LogP (AlogP): -1.89
• H-Bond Acceptor: 22
• H-Bond Donor: 14
• Rotatable Bonds: 13

Synonyms

• Isoescine IVf
• CHEMBL503158
• SCHEMBL5608569
• 2-Butenoic acid, 2-methyl-, (3.beta.,4.beta.,16.alpha.,21.beta.,22.alpha.)-3-[[O-.beta.-D-glucopyranosyl-(1->2)-O-[.beta.-D-glucopyranosyl-(1->4)]-.beta.-D-glucopyranuronosyl]oxy]-16,21,22,23-tetrahydroxyolean-12-en-28-yl ester, (2Z)-
• 28-angeloylprotoaescigenin-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	-	0.8768	87.68%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.8703	87.03%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8159	81.59%
OATP1B3 inhibitior	-	0.4610	46.10%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5026	50.26%
BSEP inhibitior	+	0.9307	93.07%
P-glycoprotein inhibitior	+	0.7476	74.76%
P-glycoprotein substrate	-	0.5146	51.46%
CYP3A4 substrate	+	0.7398	73.98%
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	+	0.7642	76.42%
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	-	0.9002	90.02%
Skin irritation	-	0.5876	58.76%
Skin corrosion	-	0.9441	94.41%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7372	73.72%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.7125	71.25%
skin sensitisation	-	0.9013	90.13%
Respiratory toxicity	-	0.6111	61.11%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	+	0.4873	48.73%
Acute Oral Toxicity (c)	III	0.8023	80.23%
Estrogen receptor binding	+	0.7803	78.03%
Androgen receptor binding	+	0.7600	76.00%
Thyroid receptor binding	+	0.5518	55.18%
Glucocorticoid receptor binding	+	0.7686	76.86%
Aromatase binding	+	0.6185	61.85%
PPAR gamma	+	0.8098	80.98%
Honey bee toxicity	-	0.6660	66.60%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
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	95.90%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.23%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.30%	94.45%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.62%	95.89%
CHEMBL221	P23219	Cyclooxygenase-1	89.37%	90.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.27%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.14%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.13%	99.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.04%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.79%	97.09%
CHEMBL5028	O14672	ADAM10	84.58%	97.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	84.13%	91.07%
CHEMBL226	P30542	Adenosine A1 receptor	82.80%	95.93%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.96%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	81.28%	97.25%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.00%	94.33%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.93%	97.36%
CHEMBL2243	O00519	Anandamide amidohydrolase	80.83%	97.53%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.55%	95.50%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	80.31%	93.00%
CHEMBL4227	P25090	Lipoxin A4 receptor	80.21%	100.00%
CHEMBL5255	O00206	Toll-like receptor 4	80.11%	92.50%

Plants that contains it

• Aesculus chinensis

Cross-Links

• PubChem: 6476037
• NPASS: NPC252657
• LOTUS: LTS0151155
• wikiData: Q105350063