Withanoside III

Details

• Internal ID: e115ca99-afb0-4844-9b4a-ff72a87f3fee
• 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,2S,4S,5R,7S,9S,10S,11S,14R,15R,18S)-5,9-dihydroxy-10,14-dimethyl-7-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-oxapentacyclo[9.7.0.02,4.05,10.014,18]octadecan-15-yl]ethyl]-5-(hydroxymethyl)-4-methyl-2,3-dihydropyran-6-one
• SMILES (Canonical): CC1=C(C(=O)OC(C1)C(C)C2CCC3C2(CCC4C3C5C(O5)C6(C4(C(CC(C6)OC7C(C(C(C(O7)CO)O)O)O)O)C)O)C)CO
• 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]3[C@H]5[C@H](O5)[C@@]6([C@@]4([C@H](C[C@@H](C6)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O)O)O)C)O)C)CO
• InChI: InChI=1S/C34H52O12/c1-14-9-21(44-30(41)17(14)12-35)15(2)18-5-6-19-24-20(7-8-32(18,19)3)33(4)23(37)10-16(11-34(33,42)29-28(24)46-29)43-31-27(40)26(39)25(38)22(13-36)45-31/h15-16,18-29,31,35-40,42H,5-13H2,1-4H3/t15-,16-,18+,19-,20-,21+,22+,23-,24-,25+,26-,27+,28-,29-,31+,32+,33-,34-/m0/s1
• InChI Key: RRWWSMHWDKRGQC-NKRUIYOCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₅₂O₁₂
• Molecular Weight: 652.80 g/mol
• Exact Mass: 652.34587709 g/mol
• Topological Polar Surface Area (TPSA): 199.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 0.16
• H-Bond Acceptor: 12
• H-Bond Donor: 7
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7320	73.20%
Caco-2	-	0.8763	87.63%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7021	70.21%
OATP2B1 inhibitior	-	0.5847	58.47%
OATP1B1 inhibitior	+	0.8350	83.50%
OATP1B3 inhibitior	+	0.9040	90.40%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6526	65.26%
BSEP inhibitior	-	0.6333	63.33%
P-glycoprotein inhibitior	+	0.6883	68.83%
P-glycoprotein substrate	+	0.6013	60.13%
CYP3A4 substrate	+	0.7468	74.68%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8855	88.55%
CYP3A4 inhibition	-	0.9371	93.71%
CYP2C9 inhibition	-	0.8045	80.45%
CYP2C19 inhibition	-	0.8673	86.73%
CYP2D6 inhibition	-	0.9354	93.54%
CYP1A2 inhibition	-	0.8724	87.24%
CYP2C8 inhibition	+	0.5564	55.64%
CYP inhibitory promiscuity	-	0.9564	95.64%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6854	68.54%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.9265	92.65%
Skin irritation	-	0.5734	57.34%
Skin corrosion	-	0.9381	93.81%
Ames mutagenesis	-	0.6027	60.27%
Human Ether-a-go-go-Related Gene inhibition	-	0.3790	37.90%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	-	0.6315	63.15%
skin sensitisation	-	0.8903	89.03%
Respiratory toxicity	+	0.7889	78.89%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.5763	57.63%
Acute Oral Toxicity (c)	I	0.7023	70.23%
Estrogen receptor binding	+	0.6862	68.62%
Androgen receptor binding	+	0.7301	73.01%
Thyroid receptor binding	-	0.6504	65.04%
Glucocorticoid receptor binding	+	0.5602	56.02%
Aromatase binding	+	0.6887	68.87%
PPAR gamma	+	0.6309	63.09%
Honey bee toxicity	-	0.6953	69.53%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9309	93.09%

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	96.86%	97.25%
CHEMBL220	P22303	Acetylcholinesterase	95.14%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.01%	97.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	93.35%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.25%	95.56%
CHEMBL5103	Q969S8	Histone deacetylase 10	92.05%	90.08%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.95%	94.45%
CHEMBL1937	Q92769	Histone deacetylase 2	90.37%	94.75%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.79%	96.09%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	88.77%	93.04%
CHEMBL226	P30542	Adenosine A1 receptor	87.51%	95.93%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.48%	95.89%
CHEMBL2996	Q05655	Protein kinase C delta	86.89%	97.79%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.83%	100.00%
CHEMBL4072	P07858	Cathepsin B	85.24%	93.67%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.19%	99.23%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.50%	86.33%
CHEMBL299	P17252	Protein kinase C alpha	84.41%	98.03%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.40%	89.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.89%	97.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	82.69%	94.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	82.58%	97.36%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.72%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	81.23%	85.14%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	80.82%	92.86%

Plants that contains it

• Withania somnifera

Cross-Links

• PubChem: 101168810
• LOTUS: LTS0136668
• wikiData: Q105244406