(3S,5S,9R,10R,13R,14S,17R)-17-[(2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl]-5,14-dihydroxy-10,13-dimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,4,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-6-one

Details

• Internal ID: a81526a9-79d1-402f-8a3d-6584118b3828
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
• IUPAC Name: (3S,5S,9R,10R,13R,14S,17R)-17-[(2S,3R)-3,6-dihydroxy-6-methylheptan-2-yl]-5,14-dihydroxy-10,13-dimethyl-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,2,3,4,9,11,12,15,16,17-decahydrocyclopenta[a]phenanthren-6-one
• SMILES (Canonical): CC(C1CCC2(C1(CCC3C2=CC(=O)C4(C3(CCC(C4)OC5C(C(C(C(O5)CO)O)O)O)C)O)C)O)C(CCC(C)(C)O)O
• SMILES (Isomeric): C[C@@H]([C@H]1CC[C@@]2([C@@]1(CC[C@H]3C2=CC(=O)[C@]4([C@@]3(CC[C@@H](C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C)O)C)O)[C@@H](CCC(C)(C)O)O
• InChI: InChI=1S/C33H54O11/c1-17(22(35)9-10-29(2,3)40)19-8-13-32(41)21-14-24(36)33(42)15-18(6-11-31(33,5)20(21)7-12-30(19,32)4)43-28-27(39)26(38)25(37)23(16-34)44-28/h14,17-20,22-23,25-28,34-35,37-42H,6-13,15-16H2,1-5H3/t17-,18-,19+,20-,22+,23+,25+,26-,27+,28+,30+,31+,32+,33+/m0/s1
• InChI Key: FKNRTOPVRYXTRX-GPAKJSBGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₅₄O₁₁
• Molecular Weight: 626.80 g/mol
• Exact Mass: 626.36661253 g/mol
• Topological Polar Surface Area (TPSA): 197.00 Ų
• XlogP: 0.30
• Atomic LogP (AlogP): 0.71
• H-Bond Acceptor: 11
• H-Bond Donor: 8
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9026	90.26%
Caco-2	-	0.8244	82.44%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.8474	84.74%
OATP2B1 inhibitior	-	0.5814	58.14%
OATP1B1 inhibitior	+	0.8711	87.11%
OATP1B3 inhibitior	-	0.2724	27.24%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.6568	65.68%
BSEP inhibitior	+	0.5650	56.50%
P-glycoprotein inhibitior	+	0.6641	66.41%
P-glycoprotein substrate	-	0.5097	50.97%
CYP3A4 substrate	+	0.6934	69.34%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8901	89.01%
CYP3A4 inhibition	-	0.8752	87.52%
CYP2C9 inhibition	-	0.8084	80.84%
CYP2C19 inhibition	-	0.9022	90.22%
CYP2D6 inhibition	-	0.9331	93.31%
CYP1A2 inhibition	-	0.8266	82.66%
CYP2C8 inhibition	+	0.4885	48.85%
CYP inhibitory promiscuity	-	0.9107	91.07%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.6947	69.47%
Eye corrosion	-	0.9912	99.12%
Eye irritation	-	0.9287	92.87%
Skin irritation	+	0.5185	51.85%
Skin corrosion	-	0.9448	94.48%
Ames mutagenesis	-	0.7000	70.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7286	72.86%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.5802	58.02%
skin sensitisation	-	0.9059	90.59%
Respiratory toxicity	+	0.7000	70.00%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.6750	67.50%
Nephrotoxicity	-	0.8054	80.54%
Acute Oral Toxicity (c)	III	0.6684	66.84%
Estrogen receptor binding	+	0.7402	74.02%
Androgen receptor binding	+	0.7921	79.21%
Thyroid receptor binding	-	0.5474	54.74%
Glucocorticoid receptor binding	+	0.6236	62.36%
Aromatase binding	+	0.6646	66.46%
PPAR gamma	+	0.5555	55.55%
Honey bee toxicity	-	0.7974	79.74%
Biodegradation	-	0.7500	75.00%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.9645	96.45%

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	99.86%	97.25%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.55%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.15%	96.09%
CHEMBL2581	P07339	Cathepsin D	96.77%	98.95%
CHEMBL218	P21554	Cannabinoid CB1 receptor	96.04%	96.61%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.30%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	92.39%	95.89%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.12%	85.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.41%	89.00%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	90.75%	85.94%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.48%	94.45%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	89.53%	97.14%
CHEMBL2094135	Q96BI3	Gamma-secretase	89.39%	98.05%
CHEMBL1994	P08235	Mineralocorticoid receptor	87.97%	100.00%
CHEMBL3746	P80365	11-beta-hydroxysteroid dehydrogenase 2	87.52%	94.78%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	87.22%	100.00%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	86.89%	89.34%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	86.68%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.41%	86.33%
CHEMBL4227	P25090	Lipoxin A4 receptor	86.16%	100.00%
CHEMBL2996	Q05655	Protein kinase C delta	85.10%	97.79%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	84.91%	94.23%
CHEMBL4581	P52732	Kinesin-like protein 1	84.32%	93.18%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	84.22%	91.03%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.32%	92.62%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	83.22%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	82.79%	95.56%
CHEMBL5255	O00206	Toll-like receptor 4	82.37%	92.50%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	82.30%	91.24%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	82.28%	97.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.42%	94.00%
CHEMBL226	P30542	Adenosine A1 receptor	80.87%	95.93%

Plants that contains it

• Silene brahuica

Cross-Links

• PubChem: 21626689
• LOTUS: LTS0000946
• wikiData: Q104996702