[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-2,2,6a,6b,9,9,12a-heptamethyl-10-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate

Details

• Internal ID: e65e9269-a7af-4785-b6ca-33b96c7e1a36
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: [(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-2,2,6a,6b,9,9,12a-heptamethyl-10-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• SMILES (Canonical): CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)OC6C(C(C(C(O6)CO)O)O)O)C)C)C2C1)C)C(=O)OC7C(C(C(C(O7)CO)O)O)O)C
• SMILES (Isomeric): C[C@]12CC[C@@H](C([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(CC[C@@]5([C@H]4CC(CC5)(C)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C)C)(C)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O
• InChI: InChI=1S/C42H68O13/c1-37(2)14-16-42(36(51)55-35-33(50)31(48)29(46)24(20-44)53-35)17-15-40(6)21(22(42)18-37)8-9-26-39(5)12-11-27(38(3,4)25(39)10-13-41(26,40)7)54-34-32(49)30(47)28(45)23(19-43)52-34/h8,22-35,43-50H,9-20H2,1-7H3/t22-,23+,24+,25-,26+,27-,28+,29+,30-,31-,32+,33+,34-,35-,39-,40+,41+,42-/m0/s1
• InChI Key: LKYABSOYLMWGQR-WLMDKFIXSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₆₈O₁₃
• Molecular Weight: 781.00 g/mol
• Exact Mass: 780.46599222 g/mol
• Topological Polar Surface Area (TPSA): 216.00 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 2.32
• H-Bond Acceptor: 13
• H-Bond Donor: 8
• Rotatable Bonds: 6

Synonyms

• SCHEMBL3012957
• BDBM50235145

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7499	74.99%
Caco-2	-	0.8763	87.63%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.8758	87.58%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7137	71.37%
OATP1B3 inhibitior	-	0.5977	59.77%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.5776	57.76%
BSEP inhibitior	-	0.5106	51.06%
P-glycoprotein inhibitior	+	0.7502	75.02%
P-glycoprotein substrate	-	0.9242	92.42%
CYP3A4 substrate	+	0.7022	70.22%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8587	85.87%
CYP3A4 inhibition	-	0.9589	95.89%
CYP2C9 inhibition	-	0.8763	87.63%
CYP2C19 inhibition	-	0.9003	90.03%
CYP2D6 inhibition	-	0.9427	94.27%
CYP1A2 inhibition	-	0.8671	86.71%
CYP2C8 inhibition	+	0.5722	57.22%
CYP inhibitory promiscuity	-	0.9423	94.23%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6313	63.13%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.9106	91.06%
Skin irritation	-	0.6520	65.20%
Skin corrosion	-	0.9500	95.00%
Ames mutagenesis	-	0.8600	86.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6473	64.73%
Micronuclear	-	0.8700	87.00%
Hepatotoxicity	-	0.9822	98.22%
skin sensitisation	-	0.8940	89.40%
Respiratory toxicity	-	0.5222	52.22%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	-	0.7750	77.50%
Nephrotoxicity	-	0.8344	83.44%
Acute Oral Toxicity (c)	III	0.7822	78.22%
Estrogen receptor binding	+	0.6869	68.69%
Androgen receptor binding	+	0.7211	72.11%
Thyroid receptor binding	-	0.5861	58.61%
Glucocorticoid receptor binding	+	0.6271	62.71%
Aromatase binding	+	0.6175	61.75%
PPAR gamma	+	0.6992	69.92%
Honey bee toxicity	-	0.7421	74.21%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6205	62.05%
Fish aquatic toxicity	+	0.9603	96.03%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4081	P13726	Coagulation factor III	15.95 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.74%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.14%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.22%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.24%	94.45%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	87.60%	96.21%
CHEMBL2581	P07339	Cathepsin D	87.39%	98.95%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	86.03%	95.17%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.56%	100.00%
CHEMBL5255	O00206	Toll-like receptor 4	85.52%	92.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.47%	95.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.22%	96.77%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.06%	99.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.89%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.66%	89.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	80.58%	95.50%

Plants that contains it

• Amaranthus caudatus
• Bassia muricata
• Fadogia ancylantha
• Luffa aegyptiaca

Cross-Links

• PubChem: 13518132
• LOTUS: LTS0184214
• wikiData: Q105153345