Withanoside X

Details

• Internal ID: 400225de-4f71-4468-b75c-70cd54156975
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives > Withanolide glycosides and derivatives
• IUPAC Name: (2R)-2-[(1S)-1-[(1S,3R,8S,9S,10R,13S,14S,17R)-1-hydroxy-10,13-dimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)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-methyl-5-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-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)CO)O)O)O)O)C)C)COC7C(C(C(C(O7)CO)O)O)O
• SMILES (Isomeric): CC1=C(C(=O)O[C@H](C1)[C@@H](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)O)O)O)O)C)C)CO[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O
• InChI: InChI=1S/C40H62O15/c1-17-11-26(53-36(50)22(17)16-51-37-34(48)32(46)30(44)27(14-41)54-37)18(2)23-7-8-24-21-6-5-19-12-20(52-38-35(49)33(47)31(45)28(15-42)55-38)13-29(43)40(19,4)25(21)9-10-39(23,24)3/h5,18,20-21,23-35,37-38,41-49H,6-16H2,1-4H3/t18-,20+,21-,23+,24-,25-,26+,27+,28+,29-,30+,31+,32-,33-,34+,35+,37+,38+,39+,40-/m0/s1
• InChI Key: LIUXGMCZRMPQQZ-IFUSOADVSA-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: 1.00
• Atomic LogP (AlogP): -0.19
• H-Bond Acceptor: 15
• H-Bond Donor: 9
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7838	78.38%
Caco-2	-	0.8801	88.01%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6714	67.14%
Subcellular localzation	Mitochondria	0.8076	80.76%
OATP2B1 inhibitior	-	0.8674	86.74%
OATP1B1 inhibitior	+	0.8513	85.13%
OATP1B3 inhibitior	-	0.2313	23.13%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.6776	67.76%
BSEP inhibitior	+	0.7320	73.20%
P-glycoprotein inhibitior	+	0.7378	73.78%
P-glycoprotein substrate	+	0.5810	58.10%
CYP3A4 substrate	+	0.7581	75.81%
CYP2C9 substrate	-	0.8046	80.46%
CYP2D6 substrate	-	0.8853	88.53%
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	+	0.6700	67.00%
CYP inhibitory promiscuity	-	0.9590	95.90%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6109	61.09%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.9163	91.63%
Skin irritation	+	0.5259	52.59%
Skin corrosion	-	0.9457	94.57%
Ames mutagenesis	-	0.7544	75.44%
Human Ether-a-go-go-Related Gene inhibition	+	0.7986	79.86%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.7231	72.31%
skin sensitisation	-	0.9254	92.54%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.5583	55.83%
Acute Oral Toxicity (c)	III	0.4565	45.65%
Estrogen receptor binding	+	0.7753	77.53%
Androgen receptor binding	+	0.7648	76.48%
Thyroid receptor binding	-	0.6111	61.11%
Glucocorticoid receptor binding	+	0.6164	61.64%
Aromatase binding	+	0.5995	59.95%
PPAR gamma	+	0.6915	69.15%
Honey bee toxicity	-	0.6697	66.97%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5600	56.00%
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
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.17%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.81%	97.09%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	93.73%	95.89%
CHEMBL5103	Q969S8	Histone deacetylase 10	92.91%	90.08%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.73%	91.11%
CHEMBL1937	Q92769	Histone deacetylase 2	92.55%	94.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.02%	95.56%
CHEMBL2581	P07339	Cathepsin D	91.32%	98.95%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.48%	100.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.29%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.15%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.84%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.46%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.98%	99.23%
CHEMBL226	P30542	Adenosine A1 receptor	85.87%	95.93%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	84.86%	96.95%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	84.80%	97.33%
CHEMBL1871	P10275	Androgen Receptor	84.13%	96.43%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.11%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	83.15%	94.73%
CHEMBL3359	P21462	Formyl peptide receptor 1	82.77%	93.56%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.66%	93.04%
CHEMBL253	P34972	Cannabinoid CB2 receptor	82.62%	97.25%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.52%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.26%	97.14%
CHEMBL5028	O14672	ADAM10	81.47%	97.50%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	80.04%	96.38%

Plants that contains it

• Withania somnifera

Cross-Links

• PubChem: 101168807
• LOTUS: LTS0237182
• wikiData: Q105152368