Vaccaroside E

Details

• Internal ID: d1543ee0-24ae-4018-a303-8a3b8da63a9c
• 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,8R,8aR,12aS,14aR,14bR)-8a-[(2S,3R,4S,5S,6R)-5-acetyloxy-4-[(2S,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3-[(2S,3R,4S,5R,6S)-3,4-dihydroxy-6-methyl-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-6-methyloxan-2-yl]oxycarbonyl-4-formyl-8-hydroxy-4,6a,6b,11,11,14b-hexamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4-dihydroxy-5-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxane-2-carboxylic acid
• SMILES (Canonical): CC1C(C(C(C(O1)OC2C(C(C(OC2OC(=O)C34CCC(CC3C5=CCC6C7(CCC(C(C7CCC6(C5(CC4O)C)C)(C)C=O)OC8C(C(C(C(O8)C(=O)O)O)O)OC9C(C(C(C(O9)CO)O)O)O)C)(C)C)C)OC(=O)C)OC1C(C(C(O1)CO)O)O)O)O)OC1C(C(C(CO1)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]2OC(=O)[C@]34CCC(C[C@H]3C5=CC[C@@H]6[C@]7(CC[C@@H]([C@@]([C@@H]7CC[C@]6([C@@]5(C[C@H]4O)C)C)(C)C=O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)C(=O)O)O)O)O[C@H]9[C@@H]([C@H]([C@H]([C@H](O9)CO)O)O)O)C)(C)C)C)OC(=O)C)O[C@H]1[C@H]([C@@H]([C@H](O1)CO)O)O)O)O)O[C@H]1[C@@H]([C@H]([C@@H](CO1)O)O)O
• InChI: InChI=1S/C66H102O33/c1-24-47(94-54-43(80)36(73)29(71)22-87-54)42(79)46(83)55(88-24)98-52-51(97-56-44(81)38(75)31(21-68)92-56)48(90-26(3)70)25(2)89-59(52)99-60(86)66-17-16-61(4,5)18-28(66)27-10-11-33-62(6)14-13-35(63(7,23-69)32(62)12-15-64(33,8)65(27,9)19-34(66)72)93-58-50(41(78)40(77)49(95-58)53(84)85)96-57-45(82)39(76)37(74)30(20-67)91-57/h10,23-25,28-52,54-59,67-68,71-83H,11-22H2,1-9H3,(H,84,85)/t24-,25+,28-,29+,30+,31+,32+,33+,34+,35-,36-,37-,38+,39-,40-,41-,42-,43+,44-,45+,46+,47-,48-,49-,50+,51-,52+,54-,55-,56-,57-,58+,59-,62-,63-,64+,65+,66+/m0/s1
• InChI Key: BRAWHUQNAZTSAF-OTXRANDRSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₆₆H₁₀₂O₃₃
• Molecular Weight: 1423.50 g/mol
• Exact Mass: 1422.6303357 g/mol
• Topological Polar Surface Area (TPSA): 512.00 Ų
• XlogP: -1.80
• Atomic LogP (AlogP): -4.24
• H-Bond Acceptor: 32
• H-Bond Donor: 16
• Rotatable Bonds: 17

Synonyms

• 211508-49-5
• AKOS040763703

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8427	84.27%
Caco-2	-	0.8630	86.30%
Blood Brain Barrier	-	0.5000	50.00%
Human oral bioavailability	-	0.8000	80.00%
Subcellular localzation	Mitochondria	0.8733	87.33%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	-	0.3529	35.29%
OATP1B3 inhibitior	+	0.8381	83.81%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	+	0.9767	97.67%
P-glycoprotein inhibitior	+	0.7437	74.37%
P-glycoprotein substrate	+	0.6025	60.25%
CYP3A4 substrate	+	0.7447	74.47%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8774	87.74%
CYP3A4 inhibition	-	0.8187	81.87%
CYP2C9 inhibition	-	0.8372	83.72%
CYP2C19 inhibition	-	0.9259	92.59%
CYP2D6 inhibition	-	0.9408	94.08%
CYP1A2 inhibition	-	0.9133	91.33%
CYP2C8 inhibition	+	0.7828	78.28%
CYP inhibitory promiscuity	-	0.9476	94.76%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4689	46.89%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.8968	89.68%
Skin irritation	+	0.5000	50.00%
Skin corrosion	-	0.9368	93.68%
Ames mutagenesis	-	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7755	77.55%
Micronuclear	-	0.7900	79.00%
Hepatotoxicity	-	0.8750	87.50%
skin sensitisation	-	0.9098	90.98%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.8814	88.14%
Acute Oral Toxicity (c)	III	0.6742	67.42%
Estrogen receptor binding	+	0.6452	64.52%
Androgen receptor binding	+	0.7554	75.54%
Thyroid receptor binding	+	0.7043	70.43%
Glucocorticoid receptor binding	+	0.8168	81.68%
Aromatase binding	+	0.6988	69.88%
PPAR gamma	+	0.8354	83.54%
Honey bee toxicity	-	0.6421	64.21%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.9692	96.92%

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	97.90%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.50%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.17%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.09%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.27%	95.56%
CHEMBL3714130	P46095	G-protein coupled receptor 6	91.93%	97.36%
CHEMBL2716	Q8WUI4	Histone deacetylase 7	91.38%	89.44%
CHEMBL2581	P07339	Cathepsin D	90.88%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.30%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.78%	100.00%
CHEMBL5028	O14672	ADAM10	87.07%	97.50%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	85.69%	86.92%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.91%	97.09%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	84.27%	93.00%
CHEMBL1937	Q92769	Histone deacetylase 2	83.35%	94.75%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	83.15%	96.77%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.89%	95.89%
CHEMBL4187	Q99250	Sodium channel protein type II alpha subunit	82.31%	95.50%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	81.56%	89.67%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	80.73%	95.50%

Plants that contains it

• Vaccaria hispanica

Cross-Links

• PubChem: 102316455
• NPASS: NPC192411