2-[1-[5,9-Dihydroxy-10,14-dimethyl-7-[3,4,5-trihydroxy-6-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]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

Details

• Internal ID: 6b69fa31-1ee9-44fe-a94f-7aa721b200ef
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives > Withanolide glycosides and derivatives
• IUPAC Name: 2-[1-[5,9-dihydroxy-10,14-dimethyl-7-[3,4,5-trihydroxy-6-[[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]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)COC8C(C(C(C(O8)CO)O)O)O)O)O)O)O)C)O)C)CO
• SMILES (Isomeric): CC1=C(C(=O)OC(C1)C(C)C2CCC3C2(CCC4C3C5C(O5)C6(C4(C(CC(C6)OC7C(C(C(C(O7)COC8C(C(C(C(O8)CO)O)O)O)O)O)O)O)C)O)C)CO
• InChI: InChI=1S/C40H62O17/c1-15-9-22(54-35(50)18(15)12-41)16(2)19-5-6-20-26-21(7-8-38(19,20)3)39(4)25(43)10-17(11-40(39,51)34-33(26)57-34)53-37-32(49)30(47)28(45)24(56-37)14-52-36-31(48)29(46)27(44)23(13-42)55-36/h16-17,19-34,36-37,41-49,51H,5-14H2,1-4H3
• InChI Key: UVFCEKPEVQCPCQ-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₀H₆₂O₁₇
• Molecular Weight: 814.90 g/mol
• Exact Mass: 814.39870051 g/mol
• Topological Polar Surface Area (TPSA): 278.00 Ų
• XlogP: -0.60
• Atomic LogP (AlogP): -2.01
• H-Bond Acceptor: 17
• H-Bond Donor: 10
• Rotatable Bonds: 9

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7320	73.20%
Caco-2	-	0.8864	88.64%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.7021	70.21%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8339	83.39%
OATP1B3 inhibitior	+	0.9040	90.40%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.6526	65.26%
BSEP inhibitior	+	0.6990	69.90%
P-glycoprotein inhibitior	+	0.7254	72.54%
P-glycoprotein substrate	+	0.6484	64.84%
CYP3A4 substrate	+	0.7500	75.00%
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	+	0.6261	62.61%
CYP inhibitory promiscuity	-	0.9564	95.64%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6854	68.54%
Eye corrosion	-	0.9891	98.91%
Eye irritation	-	0.9150	91.50%
Skin irritation	-	0.5734	57.34%
Skin corrosion	-	0.9381	93.81%
Ames mutagenesis	-	0.6127	61.27%
Human Ether-a-go-go-Related Gene inhibition	+	0.8090	80.90%
Micronuclear	-	0.7300	73.00%
Hepatotoxicity	-	0.6440	64.40%
skin sensitisation	-	0.8903	89.03%
Respiratory toxicity	+	0.7667	76.67%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.5625	56.25%
Nephrotoxicity	+	0.6211	62.11%
Acute Oral Toxicity (c)	I	0.7023	70.23%
Estrogen receptor binding	+	0.8020	80.20%
Androgen receptor binding	+	0.7316	73.16%
Thyroid receptor binding	-	0.6248	62.48%
Glucocorticoid receptor binding	+	0.6074	60.74%
Aromatase binding	+	0.6800	68.00%
PPAR gamma	+	0.7141	71.41%
Honey bee toxicity	-	0.6849	68.49%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5000	50.00%
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	98.03%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.80%	97.09%
CHEMBL220	P22303	Acetylcholinesterase	95.21%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.61%	91.11%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	92.75%	93.04%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.73%	95.56%
CHEMBL226	P30542	Adenosine A1 receptor	92.27%	95.93%
CHEMBL5103	Q969S8	Histone deacetylase 10	92.14%	90.08%
CHEMBL1937	Q92769	Histone deacetylase 2	92.10%	94.75%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.43%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.30%	96.09%
CHEMBL2996	Q05655	Protein kinase C delta	89.31%	97.79%
CHEMBL4072	P07858	Cathepsin B	88.18%	93.67%
CHEMBL1871	P10275	Androgen Receptor	87.53%	96.43%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.03%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.83%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.42%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	86.20%	99.23%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.26%	89.00%
CHEMBL299	P17252	Protein kinase C alpha	84.18%	98.03%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.61%	97.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.59%	94.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.06%	97.36%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	82.45%	96.47%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	81.72%	95.89%
CHEMBL218	P21554	Cannabinoid CB1 receptor	81.15%	96.61%
CHEMBL5028	O14672	ADAM10	80.94%	97.50%
CHEMBL3310	Q96DB2	Histone deacetylase 11	80.64%	88.56%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	80.04%	92.86%

Plants that contains it

• Withania somnifera

Cross-Links

• PubChem: 163005928
• LOTUS: LTS0238952
• wikiData: Q105279793