(2S)-2-[(1S)-1-[(1S,3R,6S,7R,8R,11S,12S,14R,15R,16R)-6-[(2S,3R,4S,5S)-4,5-dihydroxy-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]oxyoxan-2-yl]oxy-14-hydroxy-7-(hydroxymethyl)-7,12,16-trimethyl-15-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]ethyl]-5-methyl-2,3-dihydropyran-6-one

Details

• Internal ID: c17738fb-997f-426b-96c2-9d24d9373736
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives > Withanolide glycosides and derivatives
• IUPAC Name: (2S)-2-[(1S)-1-[(1S,3R,6S,7R,8R,11S,12S,14R,15R,16R)-6-[(2S,3R,4S,5S)-4,5-dihydroxy-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]oxyoxan-2-yl]oxy-14-hydroxy-7-(hydroxymethyl)-7,12,16-trimethyl-15-pentacyclo[9.7.0.01,3.03,8.012,16]octadecanyl]ethyl]-5-methyl-2,3-dihydropyran-6-one
• SMILES (Canonical): CC1=CCC(OC1=O)C(C)C2C(CC3(C2(CCC45C3CCC6C4(C5)CCC(C6(C)CO)OC7C(C(C(CO7)O)O)OC8C(C(C(C(O8)COC9C(C(C(C(O9)CO)O)O)O)O)O)O)C)C)O
• SMILES (Isomeric): CC1=CC[C@H](OC1=O)[C@@H](C)[C@H]2[C@@H](C[C@@]3([C@@]2(CC[C@]45[C@H]3CC[C@@H]6[C@]4(C5)CC[C@@H]([C@@]6(C)CO)O[C@H]7[C@@H]([C@H]([C@H](CO7)O)O)O[C@@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO[C@H]9[C@@H]([C@H]([C@@H]([C@H](O9)CO)O)O)O)O)O)O)C)C)O
• InChI: InChI=1S/C47H74O19/c1-20-6-7-24(62-39(20)59)21(2)30-22(50)14-45(5)28-9-8-27-43(3,19-49)29(10-11-46(27)18-47(28,46)13-12-44(30,45)4)65-42-38(31(52)23(51)16-60-42)66-41-37(58)35(56)33(54)26(64-41)17-61-40-36(57)34(55)32(53)25(15-48)63-40/h6,21-38,40-42,48-58H,7-19H2,1-5H3/t21-,22-,23+,24+,25-,26-,27+,28+,29+,30+,31+,32-,33-,34+,35+,36-,37-,38-,40-,41-,42+,43+,44-,45+,46-,47+/m1/s1
• InChI Key: YUCORSXPQUBWMI-PRNIWAPBSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₇H₇₄O₁₉
• Molecular Weight: 943.10 g/mol
• Exact Mass: 942.48243013 g/mol
• Topological Polar Surface Area (TPSA): 304.00 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): -1.26
• H-Bond Acceptor: 19
• H-Bond Donor: 11
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7392	73.92%
Caco-2	-	0.8898	88.98%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.7140	71.40%
OATP2B1 inhibitior	-	0.8789	87.89%
OATP1B1 inhibitior	+	0.8427	84.27%
OATP1B3 inhibitior	+	0.8905	89.05%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.6776	67.76%
BSEP inhibitior	+	0.9256	92.56%
P-glycoprotein inhibitior	+	0.7497	74.97%
P-glycoprotein substrate	+	0.6118	61.18%
CYP3A4 substrate	+	0.7312	73.12%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8799	87.99%
CYP3A4 inhibition	-	0.9461	94.61%
CYP2C9 inhibition	-	0.8232	82.32%
CYP2C19 inhibition	-	0.8854	88.54%
CYP2D6 inhibition	-	0.9415	94.15%
CYP1A2 inhibition	-	0.8829	88.29%
CYP2C8 inhibition	+	0.6852	68.52%
CYP inhibitory promiscuity	-	0.9485	94.85%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6790	67.90%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9078	90.78%
Skin irritation	-	0.5548	55.48%
Skin corrosion	-	0.9426	94.26%
Ames mutagenesis	-	0.5800	58.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8629	86.29%
Micronuclear	-	0.8000	80.00%
Hepatotoxicity	-	0.7209	72.09%
skin sensitisation	-	0.9021	90.21%
Respiratory toxicity	+	0.5222	52.22%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.7037	70.37%
Acute Oral Toxicity (c)	I	0.6647	66.47%
Estrogen receptor binding	+	0.8284	82.84%
Androgen receptor binding	+	0.7474	74.74%
Thyroid receptor binding	-	0.5851	58.51%
Glucocorticoid receptor binding	+	0.7514	75.14%
Aromatase binding	+	0.6839	68.39%
PPAR gamma	+	0.8057	80.57%
Honey bee toxicity	-	0.6577	65.77%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	+	0.9303	93.03%

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	99.32%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.28%	91.11%
CHEMBL1937	Q92769	Histone deacetylase 2	98.23%	94.75%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.22%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.06%	97.09%
CHEMBL2581	P07339	Cathepsin D	94.18%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.23%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.63%	89.00%
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	90.79%	83.57%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.55%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.26%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.25%	86.33%
CHEMBL226	P30542	Adenosine A1 receptor	85.24%	95.93%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.18%	94.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.17%	97.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.09%	100.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	84.86%	96.77%
CHEMBL3401	O75469	Pregnane X receptor	84.63%	94.73%
CHEMBL218	P21554	Cannabinoid CB1 receptor	84.14%	96.61%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	81.95%	92.88%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.80%	97.36%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.79%	86.92%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	81.19%	95.71%
CHEMBL5103	Q969S8	Histone deacetylase 10	80.60%	90.08%

Plants that contains it

• Aquilegia flabellata

Cross-Links

• PubChem: 162973317
• LOTUS: LTS0169670
• wikiData: Q105362594