5-((3S,8R,9S,10R,13R,14S,17R)-14-hydroxy-10,13-dimethyl-3-((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2H-pyran-2-one

Details

• Internal ID: 2d41d072-f364-4484-984a-a676a184c3c2
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Bufanolides and derivatives
• IUPAC Name: 5-[(3S,8R,9R,10R,13R,14S,17R)-14-hydroxy-10,13-dimethyl-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-1,2,3,6,7,8,9,11,12,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]pyran-2-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2CCC3(C4CCC5(C(CCC5(C4CCC3=C2)O)C6=COC(=O)C=C6)C)C)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2CC[C@@]3([C@@H]4CC[C@@]5([C@H](CC[C@@]5([C@@H]4CCC3=C2)O)C6=COC(=O)C=C6)C)C)O)O)O
• InChI: InChI=1S/C30H42O8/c1-16-24(32)25(33)26(34)27(37-16)38-19-8-11-28(2)18(14-19)5-6-22-21(28)9-12-29(3)20(10-13-30(22,29)35)17-4-7-23(31)36-15-17/h4,7,14-16,19-22,24-27,32-35H,5-6,8-13H2,1-3H3/t16-,19-,20+,21+,22+,24-,25+,26+,27-,28-,29+,30-/m0/s1
• InChI Key: MYEJFUXQJGHEQK-XSSFRCMRSA-N
• Popularity: 109 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₂O₈
• Molecular Weight: 530.60 g/mol
• Exact Mass: 530.28796829 g/mol
• Topological Polar Surface Area (TPSA): 126.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 3.01
• H-Bond Acceptor: 8
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

• 5-((3S,8R,9S,10R,13R,14S,17R)-14-hydroxy-10,13-dimethyl-3-((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2H-pyran-2-one

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9598	95.98%
Caco-2	-	0.9373	93.73%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.7620	76.20%
OATP2B1 inhibitior	-	0.7236	72.36%
OATP1B1 inhibitior	+	0.8672	86.72%
OATP1B3 inhibitior	+	0.8356	83.56%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9321	93.21%
BSEP inhibitior	+	0.7061	70.61%
P-glycoprotein inhibitior	-	0.4297	42.97%
P-glycoprotein substrate	-	0.7351	73.51%
CYP3A4 substrate	+	0.7079	70.79%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8666	86.66%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9070	90.70%
CYP2C19 inhibition	-	0.9025	90.25%
CYP2D6 inhibition	-	0.9230	92.30%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	+	0.6369	63.69%
CYP inhibitory promiscuity	-	0.8738	87.38%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.5173	51.73%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.9541	95.41%
Skin irritation	-	0.5499	54.99%
Skin corrosion	-	0.9294	92.94%
Ames mutagenesis	-	0.6600	66.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7579	75.79%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	-	0.5872	58.72%
skin sensitisation	-	0.8631	86.31%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.8000	80.00%
Nephrotoxicity	-	0.8058	80.58%
Acute Oral Toxicity (c)	II	0.7732	77.32%
Estrogen receptor binding	+	0.8906	89.06%
Androgen receptor binding	+	0.7412	74.12%
Thyroid receptor binding	-	0.5202	52.02%
Glucocorticoid receptor binding	+	0.7548	75.48%
Aromatase binding	+	0.7003	70.03%
PPAR gamma	+	0.5727	57.27%
Honey bee toxicity	-	0.7481	74.81%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9934	99.34%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4096	P04637	Cellular tumor antigen p53	7.9 nM	Potency	via Super-PRED
CHEMBL1293277	O15118	Niemann-Pick C1 protein	79.4 nM; 125.9 nM	Potency; Potency	via Super-PRED; via Super-PRED
CHEMBL1293235	P02545	Prelamin-A/C	35.5 nM	Potency	via Super-PRED
CHEMBL1293294	P51151	Ras-related protein Rab-9A	28.2 nM	Potency	via Super-PRED
CHEMBL1293232	Q16637	Survival motor neuron protein	251.2 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.04%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.08%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.27%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.18%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.51%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.51%	89.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	90.90%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.45%	95.89%
CHEMBL2581	P07339	Cathepsin D	89.83%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.81%	94.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.66%	99.23%
CHEMBL253	P34972	Cannabinoid CB2 receptor	84.27%	97.25%
CHEMBL3714130	P46095	G-protein coupled receptor 6	83.92%	97.36%
CHEMBL4208	P20618	Proteasome component C5	83.07%	90.00%

Plants that contains it

• Drimia indica
• Drimia maritima

Cross-Links

• PubChem: 124328164
• LOTUS: LTS0225403
• wikiData: Q104388022