16beta-(alpha-L-Arabinopyranosyloxy)-3beta-(beta-D-glucopyranosyloxy)-17-hydroxycholesta-5-ene-22-one

Details

• Internal ID: 159b6bcc-cd5a-4a14-875a-415bb8c9511c
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
• IUPAC Name: (2S)-2-[(3S,8R,9S,10R,13S,14S,16S,17S)-17-hydroxy-10,13-dimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-16-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl]-6-methylheptan-3-one
• SMILES (Canonical): CC(C)CCC(=O)C(C)C1(C(CC2C1(CCC3C2CC=C4C3(CCC(C4)OC5C(C(C(C(O5)CO)O)O)O)C)C)OC6C(C(C(CO6)O)O)O)O
• SMILES (Isomeric): C[C@H](C(=O)CCC(C)C)[C@]1([C@H](C[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C)C)O[C@H]6[C@@H]([C@H]([C@H](CO6)O)O)O)O
• InChI: InChI=1S/C38H62O13/c1-18(2)6-9-25(40)19(3)38(47)28(51-34-32(45)29(42)26(41)17-48-34)15-24-22-8-7-20-14-21(10-12-36(20,4)23(22)11-13-37(24,38)5)49-35-33(46)31(44)30(43)27(16-39)50-35/h7,18-19,21-24,26-35,39,41-47H,6,8-17H2,1-5H3/t19-,21+,22-,23+,24+,26+,27-,28+,29+,30-,31+,32-,33-,34+,35-,36+,37+,38-/m1/s1
• InChI Key: NQDDCCOUDFVXKO-AMDOWXPWSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₈H₆₂O₁₃
• Molecular Weight: 726.90 g/mol
• Exact Mass: 726.41904203 g/mol
• Topological Polar Surface Area (TPSA): 216.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 0.94
• H-Bond Acceptor: 13
• H-Bond Donor: 8
• Rotatable Bonds: 10

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8258	82.58%
Caco-2	-	0.8773	87.73%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.8432	84.32%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8481	84.81%
OATP1B3 inhibitior	-	0.3515	35.15%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6526	65.26%
BSEP inhibitior	-	0.4734	47.34%
P-glycoprotein inhibitior	+	0.7322	73.22%
P-glycoprotein substrate	+	0.6296	62.96%
CYP3A4 substrate	+	0.7428	74.28%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8687	86.87%
CYP3A4 inhibition	-	0.9446	94.46%
CYP2C9 inhibition	-	0.8769	87.69%
CYP2C19 inhibition	-	0.9253	92.53%
CYP2D6 inhibition	-	0.9396	93.96%
CYP1A2 inhibition	-	0.9147	91.47%
CYP2C8 inhibition	+	0.6705	67.05%
CYP inhibitory promiscuity	-	0.9524	95.24%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6051	60.51%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9225	92.25%
Skin irritation	-	0.5396	53.96%
Skin corrosion	-	0.9439	94.39%
Ames mutagenesis	-	0.6878	68.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.7146	71.46%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.7944	79.44%
skin sensitisation	-	0.9029	90.29%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.9444	94.44%
Mitochondrial toxicity	-	0.5750	57.50%
Nephrotoxicity	-	0.8996	89.96%
Acute Oral Toxicity (c)	III	0.6642	66.42%
Estrogen receptor binding	+	0.7764	77.64%
Androgen receptor binding	+	0.7469	74.69%
Thyroid receptor binding	-	0.6068	60.68%
Glucocorticoid receptor binding	+	0.5649	56.49%
Aromatase binding	+	0.6219	62.19%
PPAR gamma	+	0.6641	66.41%
Honey bee toxicity	-	0.6768	67.68%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6155	61.55%
Fish aquatic toxicity	+	0.9477	94.77%

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	99.32%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	99.18%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.09%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.37%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.79%	97.09%
CHEMBL2581	P07339	Cathepsin D	94.23%	98.95%
CHEMBL226	P30542	Adenosine A1 receptor	93.64%	95.93%
CHEMBL1994	P08235	Mineralocorticoid receptor	91.39%	100.00%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	90.82%	91.24%
CHEMBL220	P22303	Acetylcholinesterase	90.60%	94.45%
CHEMBL3359	P21462	Formyl peptide receptor 1	88.75%	93.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.84%	89.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.89%	85.14%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	86.83%	89.05%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.55%	95.89%
CHEMBL218	P21554	Cannabinoid CB1 receptor	86.22%	96.61%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.94%	95.56%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	85.73%	91.07%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	83.44%	92.88%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.88%	99.17%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.62%	97.14%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.37%	96.00%
CHEMBL5255	O00206	Toll-like receptor 4	82.18%	92.50%
CHEMBL4227	P25090	Lipoxin A4 receptor	81.64%	100.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.40%	90.71%
CHEMBL5028	O14672	ADAM10	81.25%	97.50%
CHEMBL1293316	Q9HBX9	Relaxin receptor 1	80.39%	82.50%

Plants that contains it

• Ornithogalum candicans

Cross-Links

• PubChem: 11061584
• LOTUS: LTS0130438
• wikiData: Q105183712