(2S,3S,4S,5R,6R)-6-[[(3S,4S,4aR,6aR,6bS,8aR,11S,12aS,14aR,14bR)-11-carboxy-4-(hydroxymethyl)-4,6a,6b,8a,11,14b-hexamethyl-9-oxo-2,3,4a,5,6,7,8,10,12,12a,14,14a-dodecahydro-1H-picen-3-yl]oxy]-5-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxyoxane-2-carboxylic acid

Details

• Internal ID: 5035747e-a0be-49f3-bfe1-bc09716b6d55
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2S,3S,4S,5R,6R)-6-[[(3S,4S,4aR,6aR,6bS,8aR,11S,12aS,14aR,14bR)-11-carboxy-4-(hydroxymethyl)-4,6a,6b,8a,11,14b-hexamethyl-9-oxo-2,3,4a,5,6,7,8,10,12,12a,14,14a-dodecahydro-1H-picen-3-yl]oxy]-5-[(2S,3R,4S,5R,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxyoxane-2-carboxylic acid
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC3C(C(C(OC3OC4CCC5(C(C4(C)CO)CCC6(C5CC=C7C6(CCC8(C7CC(CC8=O)(C)C(=O)O)C)C)C)C)C(=O)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]([C@H](O[C@H]3O[C@H]4CC[C@]5([C@H]([C@@]4(C)CO)CC[C@@]6([C@@H]5CC=C7[C@]6(CC[C@@]8([C@H]7C[C@](CC8=O)(C)C(=O)O)C)C)C)C)C(=O)O)O)O)CO)O)O)O)O)O
• InChI: InChI=1S/C48H74O20/c1-20-28(52)30(54)34(58)39(63-20)67-36-31(55)29(53)23(18-49)64-40(36)68-37-33(57)32(56)35(38(59)60)66-41(37)65-27-11-12-45(4)24(46(27,5)19-50)10-13-48(7)25(45)9-8-21-22-16-43(2,42(61)62)17-26(51)44(22,3)14-15-47(21,48)6/h8,20,22-25,27-37,39-41,49-50,52-58H,9-19H2,1-7H3,(H,59,60)(H,61,62)/t20-,22-,23+,24+,25+,27-,28-,29-,30+,31-,32-,33-,34+,35-,36+,37+,39-,40-,41+,43-,44+,45-,46+,47+,48+/m0/s1
• InChI Key: JSLMCQLSDGMMRX-UEMPELRYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₈H₇₄O₂₀
• Molecular Weight: 971.10 g/mol
• Exact Mass: 970.47734475 g/mol
• Topological Polar Surface Area (TPSA): 329.00 Ų
• XlogP: 0.60
• Atomic LogP (AlogP): -0.02
• H-Bond Acceptor: 18
• H-Bond Donor: 11
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6512	65.12%
Caco-2	-	0.8971	89.71%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.8681	86.81%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8232	82.32%
OATP1B3 inhibitior	-	0.3733	37.33%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	+	0.5452	54.52%
BSEP inhibitior	+	0.7519	75.19%
P-glycoprotein inhibitior	+	0.7509	75.09%
P-glycoprotein substrate	-	0.5777	57.77%
CYP3A4 substrate	+	0.7287	72.87%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8837	88.37%
CYP3A4 inhibition	-	0.9116	91.16%
CYP2C9 inhibition	-	0.9240	92.40%
CYP2C19 inhibition	-	0.9287	92.87%
CYP2D6 inhibition	-	0.9557	95.57%
CYP1A2 inhibition	-	0.8761	87.61%
CYP2C8 inhibition	+	0.7542	75.42%
CYP inhibitory promiscuity	-	0.9598	95.98%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6152	61.52%
Eye corrosion	-	0.9897	98.97%
Eye irritation	-	0.9047	90.47%
Skin irritation	-	0.5790	57.90%
Skin corrosion	-	0.9471	94.71%
Ames mutagenesis	-	0.8200	82.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7250	72.50%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.9261	92.61%
Respiratory toxicity	-	0.6222	62.22%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	-	0.5500	55.00%
Nephrotoxicity	-	0.6343	63.43%
Acute Oral Toxicity (c)	III	0.6932	69.32%
Estrogen receptor binding	+	0.7750	77.50%
Androgen receptor binding	+	0.7340	73.40%
Thyroid receptor binding	-	0.5715	57.15%
Glucocorticoid receptor binding	+	0.7131	71.31%
Aromatase binding	+	0.5996	59.96%
PPAR gamma	+	0.7894	78.94%
Honey bee toxicity	-	0.7024	70.24%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6500	65.00%
Fish aquatic toxicity	+	0.9625	96.25%

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	97.85%	91.11%
CHEMBL3714130	P46095	G-protein coupled receptor 6	95.30%	97.36%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.79%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.53%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.31%	89.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	87.10%	97.09%
CHEMBL1937	Q92769	Histone deacetylase 2	86.66%	94.75%
CHEMBL221	P23219	Cyclooxygenase-1	86.03%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.80%	96.09%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	84.78%	93.04%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	84.06%	93.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	83.56%	99.17%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.10%	99.23%
CHEMBL2581	P07339	Cathepsin D	81.97%	98.95%
CHEMBL5255	O00206	Toll-like receptor 4	80.47%	92.50%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.34%	94.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.28%	100.00%

Plants that contains it

• Melilotus officinalis
• Melilotus officinalis

Cross-Links

• PubChem: 10557876
• NPASS: NPC295622
• LOTUS: LTS0169517
• wikiData: Q105134447