(S)-2-((3S,8R,9S,10R,13S,14S,16S,17S)-16-(((2S,3R,4S,5S)-3,5-Dihydroxy-4-(((2S,3R,4S,5R)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl)oxy)tetrahydro-2H-pyran-2-yl)oxy)-3,17-dihydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-6-methylheptan-3-one

Details

• Internal ID: 39419faa-d619-4699-907c-9bf69ab2a3b9
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
• IUPAC Name: (2S)-2-[(3S,8R,9S,10R,13S,14S,16S,17S)-16-[(2S,3R,4S,5S)-3,5-dihydroxy-4-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxy-3,17-dihydroxy-10,13-dimethyl-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)O)C)C)OC5C(C(C(CO5)O)OC6C(C(C(CO6)O)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)C)O[C@H]5[C@@H]([C@H]([C@H](CO5)O)O[C@H]6[C@@H]([C@H]([C@@H](CO6)O)O)O)O)O
• InChI: InChI=1S/C37H60O12/c1-18(2)6-9-25(39)19(3)37(45)28(48-34-31(44)32(27(41)17-47-34)49-33-30(43)29(42)26(40)16-46-33)15-24-22-8-7-20-14-21(38)10-12-35(20,4)23(22)11-13-36(24,37)5/h7,18-19,21-24,26-34,38,40-45H,6,8-17H2,1-5H3/t19-,21+,22-,23+,24+,26-,27+,28+,29+,30-,31-,32+,33+,34+,35+,36+,37-/m1/s1
• InChI Key: NBDNCFSGTFOYKR-GDHSCZBXSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₇H₆₀O₁₂
• Molecular Weight: 696.90 g/mol
• Exact Mass: 696.40847734 g/mol
• Topological Polar Surface Area (TPSA): 196.00 Ų
• XlogP: 1.60
• Atomic LogP (AlogP): 1.58
• H-Bond Acceptor: 12
• H-Bond Donor: 7
• Rotatable Bonds: 9

Synonyms

• CHEMBL509794
• DTXSID601117432
• (3beta,16beta)-3,17-Dihydroxy-16-[(3-O-beta-D-xylopyranosyl-alpha-L-arabinopyranosyl)oxy]cholest-5-en-22-one
• 145075-83-8

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8605	86.05%
Caco-2	-	0.8764	87.64%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.8527	85.27%
OATP2B1 inhibitior	-	0.8632	86.32%
OATP1B1 inhibitior	+	0.8665	86.65%
OATP1B3 inhibitior	-	0.2502	25.02%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7276	72.76%
BSEP inhibitior	+	0.6326	63.26%
P-glycoprotein inhibitior	+	0.7093	70.93%
P-glycoprotein substrate	+	0.7402	74.02%
CYP3A4 substrate	+	0.7472	74.72%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8661	86.61%
CYP3A4 inhibition	-	0.9575	95.75%
CYP2C9 inhibition	-	0.8728	87.28%
CYP2C19 inhibition	-	0.9158	91.58%
CYP2D6 inhibition	-	0.9382	93.82%
CYP1A2 inhibition	-	0.9176	91.76%
CYP2C8 inhibition	+	0.6903	69.03%
CYP inhibitory promiscuity	-	0.9500	95.00%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6023	60.23%
Eye corrosion	-	0.9905	99.05%
Eye irritation	-	0.9254	92.54%
Skin irritation	-	0.5215	52.15%
Skin corrosion	-	0.9429	94.29%
Ames mutagenesis	-	0.6178	61.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.6985	69.85%
Micronuclear	-	0.8500	85.00%
Hepatotoxicity	-	0.5426	54.26%
skin sensitisation	-	0.8899	88.99%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.9150	91.50%
Acute Oral Toxicity (c)	III	0.5791	57.91%
Estrogen receptor binding	+	0.7474	74.74%
Androgen receptor binding	+	0.7530	75.30%
Thyroid receptor binding	-	0.6256	62.56%
Glucocorticoid receptor binding	+	0.5663	56.63%
Aromatase binding	+	0.6402	64.02%
PPAR gamma	+	0.6467	64.67%
Honey bee toxicity	-	0.6581	65.81%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	+	0.5545	55.45%
Fish aquatic toxicity	+	0.9707	97.07%

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	99.30%	96.09%
CHEMBL253	P34972	Cannabinoid CB2 receptor	98.54%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.56%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.67%	98.95%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.73%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	91.59%	94.45%
CHEMBL226	P30542	Adenosine A1 receptor	91.02%	95.93%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	90.09%	90.71%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.20%	100.00%
CHEMBL3359	P21462	Formyl peptide receptor 1	88.87%	93.56%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	88.49%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.58%	89.00%
CHEMBL4051	P13569	Cystic fibrosis transmembrane conductance regulator	86.32%	95.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.54%	95.56%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.58%	82.69%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.45%	97.14%
CHEMBL4681	P42330	Aldo-keto-reductase family 1 member C3	83.48%	89.05%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.70%	99.17%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	82.53%	92.88%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	82.21%	91.24%
CHEMBL1914	P06276	Butyrylcholinesterase	81.23%	95.00%
CHEMBL5255	O00206	Toll-like receptor 4	81.07%	92.50%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	80.79%	91.07%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.69%	92.62%
CHEMBL5028	O14672	ADAM10	80.44%	97.50%

Plants that contains it

• Ornithogalum saundersiae

Cross-Links

• PubChem: 44584790
• LOTUS: LTS0186859
• wikiData: Q105176709