Withanoside VI

Details

• Internal ID: a42a85fa-f2e5-42c9-95d4-bbfe515c00ea
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives > Withanolide glycosides and derivatives
• IUPAC Name: (2R)-2-[(1R)-1-hydroxy-1-[(1S,3R,8S,9S,10R,13S,14S,17S)-1-hydroxy-10,13-dimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl]-4,5-dimethyl-2,3-dihydropyran-6-one
• SMILES (Canonical): CC1=C(C(=O)OC(C1)C(C)(C2CCC3C2(CCC4C3CC=C5C4(C(CC(C5)OC6C(C(C(C(O6)COC7C(C(C(C(O7)CO)O)O)O)O)O)O)O)C)C)O)C
• SMILES (Isomeric): CC1=C(C(=O)O[C@H](C1)[C@@](C)([C@H]2CC[C@@H]3[C@@]2(CC[C@H]4[C@H]3CC=C5[C@@]4([C@H](C[C@@H](C5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)O)O)O)O)C)C)O)C
• InChI: InChI=1S/C40H62O15/c1-17-12-28(55-35(49)18(17)2)40(5,50)26-9-8-22-21-7-6-19-13-20(14-27(42)39(19,4)23(21)10-11-38(22,26)3)52-37-34(48)32(46)30(44)25(54-37)16-51-36-33(47)31(45)29(43)24(15-41)53-36/h6,20-34,36-37,41-48,50H,7-16H2,1-5H3/t20-,21+,22+,23+,24-,25-,26+,27+,28-,29-,30-,31+,32+,33-,34-,36-,37-,38+,39+,40-/m1/s1
• InChI Key: MKCYAASFWFGIJK-BWBMWEGTSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₆₂O₁₅
• Molecular Weight: 782.90 g/mol
• Exact Mass: 782.40887127 g/mol
• Topological Polar Surface Area (TPSA): 245.00 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): -0.05
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 8

Synonyms

• Withanoside vi, (-)-
• UNII-25Q6Y8Y108
• 25Q6Y8Y108
• Ergosta-5,24-dien-26-oic acid, 3-((6-o-beta-D-glucopyranosyl-beta-D-glucopyranosyl)oxy)-1,20,22-trihydroxy-, sigma-lactone, (1alpha,3beta,22R)-
• 362472-82-0
• SCHEMBL16365857
• Q27253989
• ERGOSTA-5,24-DIEN-26-OIC ACID, 3-((6-O-.BETA.-D-GLUCOPYRANOSYL-.BETA.-D-GLUCOPYRANOSYL)OXY)-1,20,22-TRIHYDROXY-, .SIGMA.-LACTONE, (1.ALPHA.,3.BETA.,22R)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7838	78.38%
Caco-2	-	0.8872	88.72%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7714	77.14%
Subcellular localzation	Mitochondria	0.8076	80.76%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8647	86.47%
OATP1B3 inhibitior	-	0.2313	23.13%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6776	67.76%
BSEP inhibitior	+	0.6896	68.96%
P-glycoprotein inhibitior	+	0.7188	71.88%
P-glycoprotein substrate	+	0.5322	53.22%
CYP3A4 substrate	+	0.7626	76.26%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8896	88.96%
CYP3A4 inhibition	-	0.9495	94.95%
CYP2C9 inhibition	-	0.9335	93.35%
CYP2C19 inhibition	-	0.9392	93.92%
CYP2D6 inhibition	-	0.9467	94.67%
CYP1A2 inhibition	-	0.9243	92.43%
CYP2C8 inhibition	+	0.6835	68.35%
CYP inhibitory promiscuity	-	0.9590	95.90%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6109	61.09%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.9170	91.70%
Skin irritation	+	0.5259	52.59%
Skin corrosion	-	0.9457	94.57%
Ames mutagenesis	-	0.7200	72.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8002	80.02%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.6923	69.23%
skin sensitisation	-	0.9254	92.54%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.5576	55.76%
Acute Oral Toxicity (c)	III	0.4565	45.65%
Estrogen receptor binding	+	0.8398	83.98%
Androgen receptor binding	+	0.7570	75.70%
Thyroid receptor binding	-	0.5874	58.74%
Glucocorticoid receptor binding	+	0.6445	64.45%
Aromatase binding	+	0.6676	66.76%
PPAR gamma	+	0.7558	75.58%
Honey bee toxicity	-	0.7241	72.41%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	+	0.9296	92.96%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.57%	97.25%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.06%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.10%	97.09%
CHEMBL1937	Q92769	Histone deacetylase 2	94.20%	94.75%
CHEMBL1871	P10275	Androgen Receptor	93.39%	96.43%
CHEMBL1994	P08235	Mineralocorticoid receptor	92.80%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.40%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.79%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.59%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.33%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.16%	89.00%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	90.20%	97.33%
CHEMBL3401	O75469	Pregnane X receptor	89.69%	94.73%
CHEMBL226	P30542	Adenosine A1 receptor	88.77%	95.93%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.64%	94.00%
CHEMBL5103	Q969S8	Histone deacetylase 10	88.50%	90.08%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	87.35%	95.89%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	86.77%	93.04%
CHEMBL5028	O14672	ADAM10	84.62%	97.50%
CHEMBL5255	O00206	Toll-like receptor 4	84.55%	92.50%
CHEMBL2581	P07339	Cathepsin D	84.00%	98.95%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.73%	99.23%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.73%	96.95%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.47%	97.14%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.13%	93.56%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.81%	95.89%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.02%	96.90%

Plants that contains it

• Withania somnifera

Cross-Links

• PubChem: 91827019
• LOTUS: LTS0216606
• wikiData: Q27253989