(2S,3S,4S,5R,6R)-6-[[(3S,4S,4aR,6aR,6bS,8aR,12aS,14aR,14bR)-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-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)-4,5-dihydroxy-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: ea88d2cf-fa1b-470a-b3b8-fa802ff1dee5
• 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,12aS,14aR,14bR)-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-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)-4,5-dihydroxy-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(COC2OC3C(C(C(OC3OC4CCC5(C(C4(C)CO)CCC6(C5CC=C7C6(CCC8(C7CC(CC8=O)(C)C)C)C)C)C)C(=O)O)O)O)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](CO[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]7CC(CC8=O)(C)C)C)C)C)C)C(=O)O)O)O)O)O)O)O)O
• InChI: InChI=1S/C47H74O17/c1-21-29(51)31(53)34(56)39(60-21)63-36-30(52)24(49)19-59-40(36)64-37-33(55)32(54)35(38(57)58)62-41(37)61-28-12-13-44(5)25(45(28,6)20-48)11-14-47(8)26(44)10-9-22-23-17-42(2,3)18-27(50)43(23,4)15-16-46(22,47)7/h9,21,23-26,28-37,39-41,48-49,51-56H,10-20H2,1-8H3,(H,57,58)/t21-,23-,24+,25+,26+,28-,29-,30-,31+,32-,33-,34+,35-,36+,37+,39-,40-,41+,43+,44-,45+,46+,47+/m0/s1
• InChI Key: ZNWGBWWXJAYIOM-HMAPMRIXSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₇H₇₄O₁₇
• Molecular Weight: 911.10 g/mol
• Exact Mass: 910.49260089 g/mol
• Topological Polar Surface Area (TPSA): 272.00 Ų
• XlogP: 2.10
• Atomic LogP (AlogP): 1.55
• H-Bond Acceptor: 16
• H-Bond Donor: 9
• Rotatable Bonds: 8

Synonyms

• 136033-54-0
• Wistaria-saponin D
• (2S,3S,4S,5R,6R)-6-[[(3S,4S,4aR,6aR,6bS,8aR,12aS,14aR,14bR)-4-(hydroxymethyl)-4,6a,6b,8a,11,11,14b-heptamethyl-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)-4,5-dihydroxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxyoxane-2-carboxylic acid
• beta-D-Glucopyranosiduronic acid, (3-beta,4beta)-23-hydroxy-22-oxoolean-12-en-3-yl O-6-deoxy-alpha-L-mannopyranosyl-(1-2)-O-beta-D-xylopyranosyl-(1-2)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7601	76.01%
Caco-2	-	0.9048	90.48%
Blood Brain Barrier	-	0.5250	52.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8703	87.03%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8502	85.02%
OATP1B3 inhibitior	-	0.4610	46.10%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.5026	50.26%
BSEP inhibitior	+	0.8815	88.15%
P-glycoprotein inhibitior	+	0.7565	75.65%
P-glycoprotein substrate	-	0.5355	53.55%
CYP3A4 substrate	+	0.7328	73.28%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8837	88.37%
CYP3A4 inhibition	-	0.8310	83.10%
CYP2C9 inhibition	-	0.8704	87.04%
CYP2C19 inhibition	-	0.9216	92.16%
CYP2D6 inhibition	-	0.9491	94.91%
CYP1A2 inhibition	-	0.9009	90.09%
CYP2C8 inhibition	+	0.7502	75.02%
CYP inhibitory promiscuity	-	0.9733	97.33%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6024	60.24%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9081	90.81%
Skin irritation	-	0.5876	58.76%
Skin corrosion	-	0.9441	94.41%
Ames mutagenesis	-	0.6700	67.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7225	72.25%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.8250	82.50%
skin sensitisation	-	0.9013	90.13%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	-	0.6250	62.50%
Nephrotoxicity	-	0.8065	80.65%
Acute Oral Toxicity (c)	III	0.8023	80.23%
Estrogen receptor binding	+	0.7905	79.05%
Androgen receptor binding	+	0.7327	73.27%
Thyroid receptor binding	-	0.6094	60.94%
Glucocorticoid receptor binding	+	0.6900	69.00%
Aromatase binding	+	0.6383	63.83%
PPAR gamma	+	0.7915	79.15%
Honey bee toxicity	-	0.7218	72.18%
Biodegradation	-	0.6750	67.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9585	95.85%

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	97.25%	91.11%
CHEMBL3714130	P46095	G-protein coupled receptor 6	94.24%	97.36%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.79%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.10%	86.33%
CHEMBL2581	P07339	Cathepsin D	88.38%	98.95%
CHEMBL1937	Q92769	Histone deacetylase 2	88.19%	94.75%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.63%	89.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.56%	96.77%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.00%	96.09%
CHEMBL221	P23219	Cyclooxygenase-1	85.92%	90.17%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.16%	91.07%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	84.75%	93.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.15%	97.09%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.70%	99.23%
CHEMBL1994	P08235	Mineralocorticoid receptor	81.71%	100.00%
CHEMBL4829	O00763	Acetyl-CoA carboxylase 2	80.91%	98.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.80%	92.62%
CHEMBL5028	O14672	ADAM10	80.42%	97.50%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.31%	99.17%

Plants that contains it

• Melilotus officinalis
• Melilotus officinalis
• Wisteria brachybotrys

Cross-Links

• PubChem: 160022
• NPASS: NPC92684
• LOTUS: LTS0189413
• wikiData: Q105380271