Senegin III

Details

• Internal ID: 457b6eb5-f3e7-4002-9f1d-dff119855a55
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Terpene glycosides > Triterpene glycosides > Triterpene saponins
• IUPAC Name: (2S,3R,4S,4aR,6aR,6bR,8aS,12aS,14aR,14bR)-8a-[(2S,3R,4S,5S,6R)-3-[(2S,3R,4S,5R,6S)-5-[(2S,3R,4R,5R)-3,4-dihydroxy-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-3,4-dihydroxy-6-methyloxan-2-yl]oxy-5-[(E)-3-(4-methoxyphenyl)prop-2-enoyl]oxy-6-methyl-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-2-yl]oxycarbonyl-2-hydroxy-6b-(hydroxymethyl)-4,6a,11,11,14b-pentamethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicene-4-carboxylic acid
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(OC(C2OC3C(C(C(C(O3)C)OC4C(C(C(CO4)OC5C(C(C(C(O5)CO)O)O)O)O)O)O)O)OC(=O)C67CCC(CC6C8=CCC9C(C8(CC7)CO)(CCC1C9(CC(C(C1(C)C(=O)O)OC1C(C(C(C(O1)CO)O)O)O)O)C)C)(C)C)C)OC(=O)C=CC1=CC=C(C=C1)OC)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](O[C@H]([C@@H]2O[C@H]3[C@@H]([C@@H]([C@H]([C@@H](O3)C)O[C@H]4[C@@H]([C@H]([C@@H](CO4)O[C@H]5[C@@H]([C@H]([C@H]([C@H](O5)CO)O)O)O)O)O)O)O)OC(=O)[C@@]67CC[C@@]8(C(=CC[C@H]9[C@]8(CC[C@@H]1[C@@]9(C[C@@H]([C@@H]([C@@]1(C)C(=O)O)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)O)C)C)[C@@H]6CC(CC7)(C)C)CO)C)OC(=O)/C=C/C1=CC=C(C=C1)OC)O)O)O
• InChI: InChI=1S/C75H112O35/c1-30-44(81)48(85)53(90)63(99-30)107-59-58(105-43(80)17-12-33-10-13-34(97-9)14-11-33)32(3)101-67(60(59)108-64-56(93)51(88)57(31(2)100-64)106-62-52(89)47(84)40(28-98-62)104-65-54(91)49(86)45(82)38(26-76)102-65)110-69(96)74-21-20-70(4,5)24-36(74)35-15-16-41-71(6)25-37(79)61(109-66-55(92)50(87)46(83)39(27-77)103-66)73(8,68(94)95)42(71)18-19-72(41,7)75(35,29-78)23-22-74/h10-15,17,30-32,36-42,44-67,76-79,81-93H,16,18-29H2,1-9H3,(H,94,95)/b17-12+/t30-,31-,32+,36-,37-,38+,39+,40+,41+,42+,44-,45-,46+,47-,48+,49-,50-,51-,52+,53+,54+,55+,56+,57-,58-,59-,60+,61-,62-,63-,64-,65-,66-,67-,71+,72+,73-,74-,75-/m0/s1
• InChI Key: QSTBHNPMHXYCII-KJCIHCEPSA-N
• Popularity: 9 references in papers

Physical and Chemical Properties

• Molecular Formula: C₇₅H₁₁₂O₃₅
• Molecular Weight: 1573.70 g/mol
• Exact Mass: 1572.6984152 g/mol
• Topological Polar Surface Area (TPSA): 545.00 Ų
• XlogP: -1.80
• Atomic LogP (AlogP): -3.38
• H-Bond Acceptor: 34
• H-Bond Donor: 18
• Rotatable Bonds: 20

Synonyms

• Senegin III
• 35906-36-6
• Sinegin 3
• Onjisaponin B; Senegin III
• SCHEMBL4097653
• CHEBI:66469
• CHEBI:177680
• HY-N2099
• AKOS030530165
• AC-35037
• MS-32199
• CS-0018620
• C17760
• Q27135064
• 2beta-Hydroxy-3beta-(beta-D-glucopyranosyloxy)-27-hydroxy-28-[2-O-[4-O-(4-O-beta-D-galactopyranosyl-beta-D-xylopyranosyl)-6-deoxy-alpha-L-mannopyranosyl]-3-O-alpha-L-rhamnopyranosyl-4-O-(4-methoxystyrylcarbonyl)-6-deoxy-beta-D-galactopyranosyloxy]-28-oxooleana-12-ene-23-oic acid
• 3-O-beta-D-glucopyranosylpresenegenin-28-O-[2-[beta-D-galactopyranosyl(1->4)-beta-D-xylopyranosyl(1->4)-alpha-L-rhamnopyranosyl]]-3-(alpha-L-rhamnopyranosyl)-4-[4'-methoxycinnamoyl]-beta-D-fucopyranoside
• 6-deoxy-alpha-L-mannopyranosyl-(1->3)-[beta-D-galactopyranosyl-(1->4)-beta-D-xylopyranosyl-(1->4)-6-deoxy-alpha-L-mannopyranosyl-(1->2)]-6-deoxy-1-O-[(2beta,3beta)-3-(beta-D-glucopyranosyloxy)-2,23,27-trihydroxy-23,28-dioxoolean-12-en-28-yl]-4-O-[3-(4-methoxyphenyl)prop-2-enoyl]-beta-D-galactopyranose

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8498	84.98%
Caco-2	-	0.8587	85.87%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7899	78.99%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.7945	79.45%
OATP1B3 inhibitior	-	0.2743	27.43%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.6750	67.50%
BSEP inhibitior	+	0.9625	96.25%
P-glycoprotein inhibitior	+	0.7426	74.26%
P-glycoprotein substrate	+	0.7278	72.78%
CYP3A4 substrate	+	0.7478	74.78%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8706	87.06%
CYP3A4 inhibition	-	0.7267	72.67%
CYP2C9 inhibition	-	0.8290	82.90%
CYP2C19 inhibition	-	0.8146	81.46%
CYP2D6 inhibition	-	0.9263	92.63%
CYP1A2 inhibition	-	0.7939	79.39%
CYP2C8 inhibition	+	0.8241	82.41%
CYP inhibitory promiscuity	-	0.9582	95.82%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.5897	58.97%
Eye corrosion	-	0.9895	98.95%
Eye irritation	-	0.8960	89.60%
Skin irritation	-	0.6958	69.58%
Skin corrosion	-	0.9434	94.34%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7523	75.23%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.7675	76.75%
skin sensitisation	-	0.8854	88.54%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	-	0.5625	56.25%
Nephrotoxicity	-	0.8842	88.42%
Acute Oral Toxicity (c)	III	0.5833	58.33%
Estrogen receptor binding	+	0.5654	56.54%
Androgen receptor binding	+	0.7643	76.43%
Thyroid receptor binding	+	0.7436	74.36%
Glucocorticoid receptor binding	+	0.8202	82.02%
Aromatase binding	+	0.7528	75.28%
PPAR gamma	+	0.8202	82.02%
Honey bee toxicity	-	0.6264	62.64%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.5300	53.00%
Fish aquatic toxicity	+	0.9767	97.67%

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	99.86%	91.11%
CHEMBL221	P23219	Cyclooxygenase-1	97.98%	90.17%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.84%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.17%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.88%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.94%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.23%	96.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	93.67%	97.36%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.52%	94.45%
CHEMBL4302	P08183	P-glycoprotein 1	92.28%	92.98%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	88.68%	91.07%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.50%	89.00%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	87.02%	97.33%
CHEMBL5028	O14672	ADAM10	85.74%	97.50%
CHEMBL4208	P20618	Proteasome component C5	85.10%	90.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	84.89%	86.92%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	84.50%	92.62%
CHEMBL2581	P07339	Cathepsin D	84.31%	98.95%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	83.91%	95.17%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.24%	95.89%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	82.97%	93.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.79%	99.17%
CHEMBL2243	O00519	Anandamide amidohydrolase	82.10%	97.53%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.77%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.92%	100.00%
CHEMBL340	P08684	Cytochrome P450 3A4	80.38%	91.19%

Plants that contains it

• Foeniculum vulgare
• Polygala fallax
• Polygala senega
• Polygala sibirica
• Polygala tenuifolia

Cross-Links

• PubChem: 21669942
• NPASS: NPC151110
• LOTUS: LTS0049590
• wikiData: Q104248945