beta-D-Glucopyranosiduronic acid, (3beta)-28-(beta-D-glucopyranosyloxy)-28-oxo-30-noroleana-12,20(29)-dien-3-yl 3-O-((1S,2S)-2-carboxy-1-(carboxymethoxy)-2-hydroxyethyl)-

Details

• Internal ID: 45cb26ef-c77c-4682-bea4-a064195b968c
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Diterpene glycosides
• IUPAC Name: (2S,3S,4S,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aS,12aR,14aR,14bR)-4,4,6a,6b,14b-pentamethyl-11-methylidene-8a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-4-[(2R)-2-carboxy-1-(carboxymethoxy)-2-hydroxyethoxy]-3,5-dihydroxyoxane-2-carboxylic acid
• SMILES (Canonical): CC1(C2CCC3(C(C2(CCC1OC4C(C(C(C(O4)C(=O)O)O)OC(C(C(=O)O)O)OCC(=O)O)O)C)CC=C5C3(CCC6(C5CC(=C)CC6)C(=O)OC7C(C(C(C(O7)CO)O)O)O)C)C)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(=C)CC5)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)C(=O)O)O)OC([C@H](C(=O)O)O)OCC(=O)O)O
• InChI: InChI=1S/C46H68O20/c1-20-9-14-46(41(60)66-39-30(52)29(51)28(50)23(18-47)62-39)16-15-44(5)21(22(46)17-20)7-8-25-43(4)12-11-26(42(2,3)24(43)10-13-45(25,44)6)63-40-32(54)34(31(53)35(65-40)37(58)59)64-38(33(55)36(56)57)61-19-27(48)49/h7,22-26,28-35,38-40,47,50-55H,1,8-19H2,2-6H3,(H,48,49)(H,56,57)(H,58,59)/t22-,23-,24+,25-,26+,28-,29+,30-,31+,32-,33+,34+,35+,38?,39+,40-,43+,44-,45-,46+/m1/s1
• InChI Key: JFNPDXITRQKPBX-ATJIJZBGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₆H₆₈O₂₀
• Molecular Weight: 941.00 g/mol
• Exact Mass: 940.43039455 g/mol
• Topological Polar Surface Area (TPSA): 326.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 0.84
• H-Bond Acceptor: 17
• H-Bond Donor: 10
• Rotatable Bonds: 13

Synonyms

• 178535-52-9
• beta-D-Glucopyranosiduronic acid, (3beta)-28-(beta-D-glucopyranosyloxy)-28-oxo-30-noroleana-12,20(29)-dien-3-yl 3-O-((1S,2S)-2-carboxy-1-(carboxymethoxy)-2-hydroxyethyl)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7412	74.12%
Caco-2	-	0.8710	87.10%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.8514	85.14%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7680	76.80%
OATP1B3 inhibitior	-	0.4149	41.49%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.5276	52.76%
BSEP inhibitior	+	0.7322	73.22%
P-glycoprotein inhibitior	+	0.7494	74.94%
P-glycoprotein substrate	+	0.5212	52.12%
CYP3A4 substrate	+	0.7343	73.43%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8745	87.45%
CYP3A4 inhibition	-	0.7385	73.85%
CYP2C9 inhibition	-	0.8388	83.88%
CYP2C19 inhibition	-	0.8911	89.11%
CYP2D6 inhibition	-	0.9464	94.64%
CYP1A2 inhibition	-	0.8860	88.60%
CYP2C8 inhibition	+	0.7938	79.38%
CYP inhibitory promiscuity	-	0.9736	97.36%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6233	62.33%
Eye corrosion	-	0.9881	98.81%
Eye irritation	-	0.9020	90.20%
Skin irritation	-	0.5687	56.87%
Skin corrosion	-	0.9385	93.85%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7042	70.42%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.8197	81.97%
skin sensitisation	-	0.8870	88.70%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	-	0.5875	58.75%
Nephrotoxicity	-	0.9275	92.75%
Acute Oral Toxicity (c)	III	0.8004	80.04%
Estrogen receptor binding	+	0.7660	76.60%
Androgen receptor binding	+	0.7510	75.10%
Thyroid receptor binding	-	0.5373	53.73%
Glucocorticoid receptor binding	+	0.7039	70.39%
Aromatase binding	+	0.5842	58.42%
PPAR gamma	+	0.7744	77.44%
Honey bee toxicity	-	0.6427	64.27%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9787	97.87%

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	98.20%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.05%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.63%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.00%	94.45%
CHEMBL237	P41145	Kappa opioid receptor	92.62%	98.10%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.40%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.29%	95.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.24%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.46%	99.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	85.81%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.24%	86.33%
CHEMBL4227	P25090	Lipoxin A4 receptor	85.23%	100.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	84.46%	100.00%
CHEMBL5028	O14672	ADAM10	83.92%	97.50%
CHEMBL340	P08684	Cytochrome P450 3A4	83.62%	91.19%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.62%	93.56%
CHEMBL5255	O00206	Toll-like receptor 4	82.22%	92.50%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.17%	89.00%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	81.16%	95.50%

Plants that contains it

• Beta vulgaris

Cross-Links

• PubChem: 132472065
• LOTUS: LTS0245130
• wikiData: Q105126780