(2S,3S,4S,5R,6R)-6-[(2S,4S,5S,6S)-2-[[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-2,3,4a,5,6,7,8,9,10,12,12a,14a-dodecahydro-1H-picen-3-yl]oxy]-6-carboxy-4,5-dihydroxyoxan-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid

Details

• Internal ID: fceba3dc-f3c1-4de3-92ec-0d1a96e1409a
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2S,3S,4S,5R,6R)-6-[(2S,4S,5S,6S)-2-[[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-11-carboxy-4,4,6a,6b,8a,11,14b-heptamethyl-14-oxo-2,3,4a,5,6,7,8,9,10,12,12a,14a-dodecahydro-1H-picen-3-yl]oxy]-6-carboxy-4,5-dihydroxyoxan-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• SMILES (Canonical): CC1(C2CCC3(C(C2(CCC1OC4C(C(C(C(O4)C(=O)O)O)O)OC5C(C(C(C(O5)C(=O)O)O)O)O)C)C(=O)C=C6C3(CCC7(C6CC(CC7)(C)C(=O)O)C)C)C)C
• SMILES (Isomeric): C[C@]12CC[C@](C[C@H]1C3=CC(=O)[C@@H]4[C@]5(CC[C@@H](C([C@@H]5CC[C@]4([C@@]3(CC2)C)C)(C)C)O[C@@H]6C([C@H]([C@@H]([C@H](O6)C(=O)O)O)O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)C(=O)O)O)O)O)C)(C)C(=O)O
• InChI: InChI=1S/C42H62O16/c1-37(2)21-8-11-42(7)31(20(43)16-18-19-17-39(4,36(53)54)13-12-38(19,3)14-15-41(18,42)6)40(21,5)10-9-22(37)55-35-30(26(47)25(46)29(57-35)33(51)52)58-34-27(48)23(44)24(45)28(56-34)32(49)50/h16,19,21-31,34-35,44-48H,8-15,17H2,1-7H3,(H,49,50)(H,51,52)(H,53,54)/t19-,21-,22-,23-,24-,25-,26-,27+,28-,29-,30?,31+,34-,35-,38+,39-,40-,41+,42+/m0/s1
• InChI Key: LPLVUJXQOOQHMX-YFINQFFOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₆₂O₁₆
• Molecular Weight: 822.90 g/mol
• Exact Mass: 822.40378589 g/mol
• Topological Polar Surface Area (TPSA): 267.00 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 2.25
• H-Bond Acceptor: 13
• H-Bond Donor: 8
• Rotatable Bonds: 7

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8728	87.28%
Caco-2	-	0.8793	87.93%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8383	83.83%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	-	0.4761	47.61%
OATP1B3 inhibitior	-	0.3963	39.63%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	+	0.6929	69.29%
BSEP inhibitior	+	0.6059	60.59%
P-glycoprotein inhibitior	+	0.7608	76.08%
P-glycoprotein substrate	-	0.7951	79.51%
CYP3A4 substrate	+	0.7215	72.15%
CYP2C9 substrate	-	0.7908	79.08%
CYP2D6 substrate	-	0.8981	89.81%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.8692	86.92%
CYP2C19 inhibition	-	0.9112	91.12%
CYP2D6 inhibition	-	0.9423	94.23%
CYP1A2 inhibition	-	0.8358	83.58%
CYP2C8 inhibition	+	0.6827	68.27%
CYP inhibitory promiscuity	-	0.9568	95.68%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6106	61.06%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9082	90.82%
Skin irritation	-	0.5295	52.95%
Skin corrosion	-	0.9236	92.36%
Ames mutagenesis	-	0.9000	90.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4544	45.44%
Micronuclear	-	0.7000	70.00%
Hepatotoxicity	+	0.6908	69.08%
skin sensitisation	-	0.8115	81.15%
Respiratory toxicity	+	0.6111	61.11%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	+	0.4867	48.67%
Acute Oral Toxicity (c)	IV	0.6130	61.30%
Estrogen receptor binding	+	0.7736	77.36%
Androgen receptor binding	+	0.7324	73.24%
Thyroid receptor binding	-	0.8319	83.19%
Glucocorticoid receptor binding	+	0.7152	71.52%
Aromatase binding	+	0.6753	67.53%
PPAR gamma	+	0.7700	77.00%
Honey bee toxicity	-	0.7043	70.43%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9886	98.86%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4235	P28845	11-beta-hydroxysteroid dehydrogenase 1	6 nM	IC50	via Super-PRED
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	0.4 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	95.50%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.87%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.08%	94.45%
CHEMBL221	P23219	Cyclooxygenase-1	91.01%	90.17%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.76%	97.36%
CHEMBL1951	P21397	Monoamine oxidase A	90.37%	91.49%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.94%	95.89%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.22%	96.09%
CHEMBL2581	P07339	Cathepsin D	87.28%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.35%	99.23%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	84.00%	93.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.34%	97.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.48%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.60%	86.33%
CHEMBL5255	O00206	Toll-like receptor 4	81.43%	92.50%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.36%	92.94%

Plants that contains it

• Abrus precatorius
• Glycyrrhiza glabra
• Glycyrrhiza inflata
• Glycyrrhiza uralensis
• Rheum officinale
• Rheum palmatum
• Rheum tanguticum

Cross-Links

• PubChem: 46878350
• NPASS: NPC308597