3beta-[(6-Deoxy-beta-D-glucopyranosyl)oxy]-27-norolean-13-en-28-oic acid beta-D-glucopyranosyl ester

Details

• Internal ID: 29b789dd-1c72-4649-a930-2c0f0198eb54
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Diterpene glycosides
• IUPAC Name: [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (4aS,6aR,6bR,8aR,10S,12aR,14bS)-2,2,6b,9,9,12a-hexamethyl-10-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-3,4,5,6,6a,7,8,8a,10,11,12,13,14,14b-tetradecahydro-1H-picene-4a-carboxylate
• SMILES (Canonical): CC1C(C(C(C(O1)OC2CCC3(C4CCC5=C(C4(CCC3C2(C)C)C)CCC6(C5CC(CC6)(C)C)C(=O)OC7C(C(C(C(O7)CO)O)O)O)C)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@H]2CC[C@@]3([C@H]4CCC5=C([C@@]4(CC[C@H]3C2(C)C)C)CC[C@@]6([C@H]5CC(CC6)(C)C)C(=O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)C)O)O)O
• InChI: InChI=1S/C41H66O12/c1-20-28(43)30(45)32(47)34(50-20)52-27-12-14-40(7)25(38(27,4)5)11-13-39(6)22-10-15-41(17-16-37(2,3)18-23(41)21(22)8-9-26(39)40)36(49)53-35-33(48)31(46)29(44)24(19-42)51-35/h20,23-35,42-48H,8-19H2,1-7H3/t20-,23+,24-,25+,26+,27+,28-,29-,30+,31+,32-,33-,34+,35+,39+,40+,41-/m1/s1
• InChI Key: CESLMJOIHBNCGO-MEYMADEWSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₁H₆₆O₁₂
• Molecular Weight: 751.00 g/mol
• Exact Mass: 750.45542754 g/mol
• Topological Polar Surface Area (TPSA): 196.00 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 3.10
• H-Bond Acceptor: 12
• H-Bond Donor: 7
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8210	82.10%
Caco-2	-	0.8734	87.34%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.8817	88.17%
OATP2B1 inhibitior	-	0.8683	86.83%
OATP1B1 inhibitior	+	0.7785	77.85%
OATP1B3 inhibitior	-	0.5767	57.67%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.5526	55.26%
BSEP inhibitior	-	0.6320	63.20%
P-glycoprotein inhibitior	+	0.7473	74.73%
P-glycoprotein substrate	-	0.7584	75.84%
CYP3A4 substrate	+	0.7121	71.21%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8587	85.87%
CYP3A4 inhibition	-	0.9299	92.99%
CYP2C9 inhibition	-	0.8494	84.94%
CYP2C19 inhibition	-	0.9071	90.71%
CYP2D6 inhibition	-	0.9413	94.13%
CYP1A2 inhibition	-	0.8344	83.44%
CYP2C8 inhibition	+	0.5563	55.63%
CYP inhibitory promiscuity	-	0.9187	91.87%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6503	65.03%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9119	91.19%
Skin irritation	-	0.5939	59.39%
Skin corrosion	-	0.9500	95.00%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6583	65.83%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.9021	90.21%
skin sensitisation	-	0.8962	89.62%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	-	0.7625	76.25%
Nephrotoxicity	-	0.9366	93.66%
Acute Oral Toxicity (c)	III	0.7830	78.30%
Estrogen receptor binding	+	0.6824	68.24%
Androgen receptor binding	+	0.7038	70.38%
Thyroid receptor binding	-	0.6102	61.02%
Glucocorticoid receptor binding	+	0.6189	61.89%
Aromatase binding	+	0.6479	64.79%
PPAR gamma	+	0.6708	67.08%
Honey bee toxicity	-	0.6900	69.00%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5655	56.55%
Fish aquatic toxicity	+	0.9684	96.84%

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	97.28%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.02%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.87%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	92.64%	95.93%
CHEMBL3714130	P46095	G-protein coupled receptor 6	92.15%	97.36%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.87%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.97%	86.33%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.13%	100.00%
CHEMBL2581	P07339	Cathepsin D	86.24%	98.95%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	85.22%	91.24%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.69%	94.45%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.24%	99.17%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	82.77%	89.05%
CHEMBL5255	O00206	Toll-like receptor 4	82.27%	92.50%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.30%	95.50%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.51%	95.83%

Plants that contains it

• Ageratina tomentella
• Caralluma stalagmifera
• Drymaria cordata
• Euthamia graminifolia
• Ficus nervosa
• Isertia haenkeana
• Prosopis cineraria
• Rubus xanthocarpus
• Uncaria hirsuta

Cross-Links

• PubChem: 21625902
• NPASS: NPC170707
• LOTUS: LTS0036897
• wikiData: Q104956017