(1S,2R,4aS,6aR,6bR,8aR,10S,12aR,12bR,14bS)-1,2,6b,9,9,12a-hexamethyl-10-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-4a-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)carbonyl)-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-6a-carboxylic acid

Details

• Internal ID: e6dc2843-da25-4cb2-8fb3-bb8c1ab2b202
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (1S,2R,4aS,6aR,6aR,6bR,8aR,10S,12aR,14bS)-1,2,6b,9,9,12a-hexamethyl-10-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4a-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxycarbonyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1H-picene-6a-carboxylic acid
• SMILES (Canonical): CC1CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)OC6C(C(C(C(O6)CO)O)O)O)C)C)C2C1C)C(=O)O)C(=O)OC7C(C(C(C(O7)CO)O)O)O
• SMILES (Isomeric): C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C)C)[C@@H]2[C@H]1C)C(=O)O)C(=O)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O
• InChI: InChI=1S/C42H66O15/c1-19-9-14-41(37(53)57-35-33(50)31(48)29(46)23(18-44)55-35)15-16-42(36(51)52)21(27(41)20(19)2)7-8-25-39(5)12-11-26(38(3,4)24(39)10-13-40(25,42)6)56-34-32(49)30(47)28(45)22(17-43)54-34/h7,19-20,22-35,43-50H,8-18H2,1-6H3,(H,51,52)/t19-,20+,22-,23-,24+,25-,26+,27+,28-,29-,30+,31+,32-,33-,34+,35+,39+,40-,41+,42-/m1/s1
• InChI Key: LDCLXZSKVDYDBF-DTJUAWDLSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₆₆O₁₅
• Molecular Weight: 811.00 g/mol
• Exact Mass: 810.44017139 g/mol
• Topological Polar Surface Area (TPSA): 253.00 Ų
• XlogP: 2.50
• Atomic LogP (AlogP): 1.24
• H-Bond Acceptor: 14
• H-Bond Donor: 9
• Rotatable Bonds: 7

Synonyms

• Zygophyloside E
• DTXSID601171323
• BDBM50317552
• 3-O-beta-D-Glucopyranosyl quinovic acid 28-beta-D-glucopyranosyl ester
• 3-O-beta-D-glucopyranosyl quinovic acid28-O-beta-D-glucopyranosyl ester
• (1S,2R,4aS,6aR,6bR,8aR,10S,12aR,12bR,14bS)-1,2,6b,9,9,12a-hexamethyl-10-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)-4a-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yloxy)carbonyl)-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-6a-carboxylic acid
• 104055-77-8

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7181	71.81%
Caco-2	-	0.8834	88.34%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8914	89.14%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7582	75.82%
OATP1B3 inhibitior	-	0.5187	51.87%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	+	0.5974	59.74%
BSEP inhibitior	+	0.6626	66.26%
P-glycoprotein inhibitior	+	0.7384	73.84%
P-glycoprotein substrate	-	0.7481	74.81%
CYP3A4 substrate	+	0.7098	70.98%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8776	87.76%
CYP3A4 inhibition	-	0.9061	90.61%
CYP2C9 inhibition	-	0.8653	86.53%
CYP2C19 inhibition	-	0.9130	91.30%
CYP2D6 inhibition	-	0.9498	94.98%
CYP1A2 inhibition	-	0.8749	87.49%
CYP2C8 inhibition	+	0.6855	68.55%
CYP inhibitory promiscuity	-	0.9549	95.49%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6115	61.15%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9115	91.15%
Skin irritation	-	0.6295	62.95%
Skin corrosion	-	0.9453	94.53%
Ames mutagenesis	-	0.7270	72.70%
Human Ether-a-go-go-Related Gene inhibition	-	0.4057	40.57%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.8334	83.34%
skin sensitisation	-	0.9028	90.28%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.8778	87.78%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	-	0.8472	84.72%
Acute Oral Toxicity (c)	III	0.7689	76.89%
Estrogen receptor binding	+	0.7682	76.82%
Androgen receptor binding	+	0.7375	73.75%
Thyroid receptor binding	-	0.6169	61.69%
Glucocorticoid receptor binding	+	0.6189	61.89%
Aromatase binding	+	0.5996	59.96%
PPAR gamma	+	0.7338	73.38%
Honey bee toxicity	-	0.7257	72.57%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.5905	59.05%
Fish aquatic toxicity	+	0.9722	97.22%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.41%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.27%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.97%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.03%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.79%	86.33%
CHEMBL3714130	P46095	G-protein coupled receptor 6	88.20%	97.36%
CHEMBL2581	P07339	Cathepsin D	86.90%	98.95%
CHEMBL5255	O00206	Toll-like receptor 4	83.92%	92.50%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	83.83%	94.45%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	82.59%	96.21%
CHEMBL5028	O14672	ADAM10	82.40%	97.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.86%	99.17%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.57%	93.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.28%	100.00%
CHEMBL221	P23219	Cyclooxygenase-1	80.38%	90.17%

Plants that contains it

• Cephalanthus occidentalis
• Guettarda platypoda
• Isertia haenkeana
• Mitragyna inermis
• Mussaenda pubescens
• Nauclea diderrichii
• Neolamarckia cadamba
• Neonauclea sessilifolia
• Tocoyena formosa
• Uncaria tomentosa
• Zygophyllum fabago

Cross-Links

• PubChem: 14194010
• NPASS: NPC30397
• LOTUS: LTS0265343
• wikiData: Q105150157