2-O-methyl 4a-O-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2S,4aR,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-[(2S,3R,4S,5R)-4-[(2S,3R,4S,5R)-3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl]oxy-3,5-dihydroxyoxan-2-yl]oxy-9-(hydroxymethyl)-2,6a,6b,9,12a-pentamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-2,4a-dicarboxylate

Details

• Internal ID: 90f0f90a-ff58-41ef-a223-d29c98dcc053
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: 2-O-methyl 4a-O-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (2S,4aR,6aR,6aS,6bR,8aR,9R,10S,12aR,14bS)-10-[(2S,3R,4S,5R)-4-[(2S,3R,4S,5R)-3-[(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-4,5-dihydroxyoxan-2-yl]oxy-3,5-dihydroxyoxan-2-yl]oxy-9-(hydroxymethyl)-2,6a,6b,9,12a-pentamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-2,4a-dicarboxylate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3C(C(COC3OC4C(COC(C4O)OC5CCC6(C(C5(C)CO)CCC7(C6CC=C8C7(CCC9(C8CC(CC9)(C)C(=O)OC)C(=O)OC1C(C(C(C(O1)CO)O)O)O)C)C)C)O)O)O)CO)O)O)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2O[C@@H]3[C@H]([C@@H](CO[C@H]3O[C@H]4[C@@H](CO[C@H]([C@@H]4O)O[C@H]5CC[C@]6([C@H]([C@]5(C)CO)CC[C@@]7([C@@H]6CC=C8[C@]7(CC[C@@]9([C@H]8C[C@@](CC9)(C)C(=O)OC)C(=O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)C)C)C)O)O)O)CO)O)O)O)O)O
• InChI: InChI=1S/C59H94O28/c1-24-34(65)38(69)41(72)48(80-24)85-46-40(71)37(68)30(20-61)82-51(46)86-45-35(66)27(63)21-79-50(45)84-44-28(64)22-78-47(43(44)74)83-33-11-12-55(3)31(56(33,4)23-62)10-13-58(6)32(55)9-8-25-26-18-54(2,52(75)77-7)14-16-59(26,17-15-57(25,58)5)53(76)87-49-42(73)39(70)36(67)29(19-60)81-49/h8,24,26-51,60-74H,9-23H2,1-7H3/t24-,26-,27+,28+,29+,30+,31+,32+,33-,34-,35-,36+,37+,38+,39-,40-,41+,42+,43+,44-,45+,46+,47-,48-,49-,50-,51-,54-,55-,56-,57+,58+,59-/m0/s1
• InChI Key: NBNAOSJJHSGRFO-QBGVXYMISA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₉H₉₄O₂₈
• Molecular Weight: 1251.40 g/mol
• Exact Mass: 1250.59316234 g/mol
• Topological Polar Surface Area (TPSA): 439.00 Ų
• XlogP: -2.60
• Atomic LogP (AlogP): -3.78
• H-Bond Acceptor: 28
• H-Bond Donor: 15
• Rotatable Bonds: 14

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6877	68.77%
Caco-2	-	0.8701	87.01%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.8112	81.12%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8272	82.72%
OATP1B3 inhibitior	-	0.2293	22.93%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.5771	57.71%
BSEP inhibitior	+	0.9408	94.08%
P-glycoprotein inhibitior	+	0.7442	74.42%
P-glycoprotein substrate	+	0.5401	54.01%
CYP3A4 substrate	+	0.7455	74.55%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8587	85.87%
CYP3A4 inhibition	-	0.8833	88.33%
CYP2C9 inhibition	-	0.9285	92.85%
CYP2C19 inhibition	-	0.9205	92.05%
CYP2D6 inhibition	-	0.9538	95.38%
CYP1A2 inhibition	-	0.9078	90.78%
CYP2C8 inhibition	+	0.7646	76.46%
CYP inhibitory promiscuity	-	0.9806	98.06%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5987	59.87%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.8982	89.82%
Skin irritation	-	0.5824	58.24%
Skin corrosion	-	0.9452	94.52%
Ames mutagenesis	-	0.6900	69.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8068	80.68%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.8500	85.00%
skin sensitisation	-	0.9182	91.82%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.7507	75.07%
Acute Oral Toxicity (c)	III	0.6557	65.57%
Estrogen receptor binding	+	0.7414	74.14%
Androgen receptor binding	+	0.7501	75.01%
Thyroid receptor binding	+	0.6469	64.69%
Glucocorticoid receptor binding	+	0.7824	78.24%
Aromatase binding	+	0.6462	64.62%
PPAR gamma	+	0.8054	80.54%
Honey bee toxicity	-	0.6538	65.38%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.8974	89.74%

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	99.14%	91.11%
CHEMBL3714130	P46095	G-protein coupled receptor 6	97.44%	97.36%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.01%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.19%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.19%	94.45%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	87.00%	91.07%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	86.36%	95.50%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	86.14%	94.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.99%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.75%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.73%	86.33%
CHEMBL2581	P07339	Cathepsin D	84.99%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.81%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.71%	99.17%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.84%	96.77%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	81.80%	91.24%
CHEMBL5028	O14672	ADAM10	81.17%	97.50%
CHEMBL5255	O00206	Toll-like receptor 4	80.53%	92.50%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	80.51%	95.17%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.48%	96.90%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.41%	95.89%

Plants that contains it

• Phytolacca americana

Cross-Links

• PubChem: 44448291
• LOTUS: LTS0245053
• wikiData: Q105176848