Withalongolide J

Details

• Internal ID: 539edf8f-03d8-4c21-baec-906494066ee2
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Withanolides and derivatives
• IUPAC Name: (2R)-2-[(1S)-1-[(1S,3R,8S,9S,10R,13S,14S,17R)-1,3-dihydroxy-10-(hydroxymethyl)-13-methyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethyl]-5-methyl-4-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,3-dihydropyran-6-one
• SMILES (Canonical): CC1=C(CC(OC1=O)C(C)C2CCC3C2(CCC4C3CC=C5C4(C(CC(C5)O)O)CO)C)COC6C(C(C(C(O6)CO)O)O)O
• SMILES (Isomeric): CC1=C(C[C@@H](OC1=O)[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)O)CO)C)CO[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O
• InChI: InChI=1S/C34H52O11/c1-16-18(14-43-32-30(41)29(40)28(39)26(13-35)45-32)10-25(44-31(16)42)17(2)22-6-7-23-21-5-4-19-11-20(37)12-27(38)34(19,15-36)24(21)8-9-33(22,23)3/h4,17,20-30,32,35-41H,5-15H2,1-3H3/t17-,20+,21-,22+,23-,24-,25+,26+,27-,28+,29-,30+,32+,33+,34-/m0/s1
• InChI Key: JDYYLQIQTRWVFW-ILJUDCBVSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₅₂O₁₁
• Molecular Weight: 636.80 g/mol
• Exact Mass: 636.35096247 g/mol
• Topological Polar Surface Area (TPSA): 186.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 0.95
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 7

Synonyms

• CHEBI:69114
• CHEMBL1934462
• DTXSID201110191
• Q27137455
• 28-O-beta-D-glucopyranosyl-1alpha,3beta,19-trihydroxywitha-5,24-dienolide
• (22R)-1alpha,3beta,19-trihydroxy-26-oxo-22,26-epoxyergosta-5,24-dien-28-yl beta-D-glucopyranoside
• 1350448-51-9
• Ergosta-5,24-dien-26-oic acid, 28-(beta-D-glucopyranosyloxy)-1,3,19,22-tetrahydroxy-, delta-lactone, (1alpha,3beta,22R)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7838	78.38%
Caco-2	-	0.8783	87.83%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.8076	80.76%
OATP2B1 inhibitior	-	0.7185	71.85%
OATP1B1 inhibitior	+	0.8594	85.94%
OATP1B3 inhibitior	-	0.2313	23.13%
MATE1 inhibitior	-	0.9412	94.12%
OCT2 inhibitior	-	0.6776	67.76%
BSEP inhibitior	+	0.8441	84.41%
P-glycoprotein inhibitior	+	0.6565	65.65%
P-glycoprotein substrate	+	0.5929	59.29%
CYP3A4 substrate	+	0.7539	75.39%
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	+	0.7095	70.95%
CYP inhibitory promiscuity	-	0.9590	95.90%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.6109	61.09%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.9375	93.75%
Skin irritation	+	0.5259	52.59%
Skin corrosion	-	0.9457	94.57%
Ames mutagenesis	-	0.6644	66.44%
Human Ether-a-go-go-Related Gene inhibition	+	0.8413	84.13%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.6353	63.53%
skin sensitisation	-	0.9254	92.54%
Respiratory toxicity	+	0.8000	80.00%
Reproductive toxicity	+	0.9556	95.56%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	-	0.5823	58.23%
Acute Oral Toxicity (c)	III	0.4565	45.65%
Estrogen receptor binding	+	0.7921	79.21%
Androgen receptor binding	+	0.7746	77.46%
Thyroid receptor binding	-	0.6204	62.04%
Glucocorticoid receptor binding	+	0.5819	58.19%
Aromatase binding	+	0.6216	62.16%
PPAR gamma	+	0.6521	65.21%
Honey bee toxicity	-	0.6708	67.08%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
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
CHEMBL3137262	O60341	LSD1/CoREST complex	95.02%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.77%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	93.76%	95.93%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	93.63%	95.89%
CHEMBL2581	P07339	Cathepsin D	92.81%	98.95%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	92.81%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	91.34%	95.56%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.64%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.12%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.82%	89.00%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	86.62%	96.47%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.03%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.95%	97.14%
CHEMBL220	P22303	Acetylcholinesterase	85.46%	94.45%
CHEMBL3359	P21462	Formyl peptide receptor 1	85.30%	93.56%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.53%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	84.28%	90.17%
CHEMBL2996	Q05655	Protein kinase C delta	83.91%	97.79%
CHEMBL1871	P10275	Androgen Receptor	83.75%	96.43%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	83.75%	97.33%
CHEMBL5255	O00206	Toll-like receptor 4	83.04%	92.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.46%	99.23%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	82.35%	96.38%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.69%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.90%	94.45%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	80.88%	93.04%
CHEMBL204	P00734	Thrombin	80.25%	96.01%

Plants that contains it

• Physalis longifolia

Cross-Links

• PubChem: 56926206
• LOTUS: LTS0196789
• wikiData: Q27137455