(2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8R,8aS,9R,10R,12aS,14aR,14bR)-10-[(2R,3S)-2,3-dimethyloxirane-2-carbonyl]oxy-8-hydroxy-4,4,6a,6b,8a,11,11,14b-octamethyl-9-[(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,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid

Details

• Internal ID: bbe7e114-d48b-428b-a122-b95e4e0b758e
• 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,8R,8aS,9R,10R,12aS,14aR,14bR)-10-[(2R,3S)-2,3-dimethyloxirane-2-carbonyl]oxy-8-hydroxy-4,4,6a,6b,8a,11,11,14b-octamethyl-9-[(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,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid
• SMILES (Canonical): CC=C(C)C(=O)OC1C(C(CC2C1(C(CC3(C2=CCC4C3(CCC5C4(CCC(C5(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)C)C)O)C)(C)C)OC(=O)C9(C(O9)C)C
• 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](C5(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)C)C)O)C)(C)C)OC(=O)[C@]9([C@@H](O9)C)C
• InChI: InChI=1S/C57H88O22/c1-13-24(2)46(69)77-44-43(78-50(70)57(12)25(3)79-57)51(4,5)20-27-26-14-15-31-53(8)18-17-33(52(6,7)30(53)16-19-54(31,9)55(26,10)21-32(60)56(27,44)11)73-49-42(76-48-38(65)36(63)34(61)28(22-58)71-48)40(39(66)41(75-49)45(67)68)74-47-37(64)35(62)29(23-59)72-47/h13-14,25,27-44,47-49,58-66H,15-23H2,1-12H3,(H,67,68)/b24-13-/t25-,27-,28+,29-,30-,31+,32+,33-,34+,35-,36-,37+,38+,39-,40-,41-,42+,43-,44-,47-,48-,49+,53-,54+,55+,56-,57+/m0/s1
• InChI Key: YAHCESMXDBXUAC-VILTVYJDSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₇H₈₈O₂₂
• Molecular Weight: 1125.30 g/mol
• Exact Mass: 1124.57672443 g/mol
• Topological Polar Surface Area (TPSA): 340.00 Ų
• XlogP: 4.00
• Atomic LogP (AlogP): 1.53
• H-Bond Acceptor: 21
• H-Bond Donor: 10
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8437	84.37%
Caco-2	-	0.8667	86.67%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.8286	82.86%
Subcellular localzation	Mitochondria	0.8482	84.82%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7531	75.31%
OATP1B3 inhibitior	+	0.8844	88.44%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	+	0.9531	95.31%
P-glycoprotein inhibitior	+	0.7474	74.74%
P-glycoprotein substrate	+	0.5091	50.91%
CYP3A4 substrate	+	0.7396	73.96%
CYP2C9 substrate	-	0.8054	80.54%
CYP2D6 substrate	-	0.8910	89.10%
CYP3A4 inhibition	-	0.7646	76.46%
CYP2C9 inhibition	-	0.7646	76.46%
CYP2C19 inhibition	-	0.8952	89.52%
CYP2D6 inhibition	-	0.9282	92.82%
CYP1A2 inhibition	-	0.8828	88.28%
CYP2C8 inhibition	+	0.7758	77.58%
CYP inhibitory promiscuity	-	0.9422	94.22%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4922	49.22%
Eye corrosion	-	0.9871	98.71%
Eye irritation	-	0.8986	89.86%
Skin irritation	-	0.5551	55.51%
Skin corrosion	-	0.9310	93.10%
Ames mutagenesis	-	0.7842	78.42%
Human Ether-a-go-go-Related Gene inhibition	+	0.7185	71.85%
Micronuclear	-	0.6800	68.00%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.8886	88.86%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.5875	58.75%
Nephrotoxicity	-	0.8281	82.81%
Acute Oral Toxicity (c)	III	0.5480	54.80%
Estrogen receptor binding	+	0.7199	71.99%
Androgen receptor binding	+	0.7559	75.59%
Thyroid receptor binding	+	0.6342	63.42%
Glucocorticoid receptor binding	+	0.7995	79.95%
Aromatase binding	+	0.6499	64.99%
PPAR gamma	+	0.8135	81.35%
Honey bee toxicity	-	0.6366	63.66%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5355	53.55%
Fish aquatic toxicity	+	0.9694	96.94%

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	96.47%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.29%	96.09%
CHEMBL2581	P07339	Cathepsin D	90.51%	98.95%
CHEMBL221	P23219	Cyclooxygenase-1	90.14%	90.17%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	89.20%	93.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.98%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.66%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.62%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	86.48%	93.56%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.94%	95.56%
CHEMBL5255	O00206	Toll-like receptor 4	85.92%	92.50%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.81%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.52%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.10%	86.33%
CHEMBL1937	Q92769	Histone deacetylase 2	84.42%	94.75%
CHEMBL4227	P25090	Lipoxin A4 receptor	83.70%	100.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.50%	89.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.11%	96.21%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.20%	95.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	82.00%	94.33%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.52%	97.14%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.31%	95.50%
CHEMBL3714130	P46095	G-protein coupled receptor 6	80.70%	97.36%

Plants that contains it

• Dodonaea viscosa

Cross-Links

• PubChem: 163062513
• LOTUS: LTS0271462
• wikiData: Q105345394