(1S,4aR,4bR,7R,9R,10aR)-7-ethenyl-9-hydroxy-1,4a,7-trimethyl-1-[[(2R,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3,4,4b,5,6,9,10,10a-octahydrophenanthren-2-one

Details

• Internal ID: 29d72540-f339-426d-bfa3-1e523e4a1a8e
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
• IUPAC Name: (1S,4aR,4bR,7R,9R,10aR)-7-ethenyl-9-hydroxy-1,4a,7-trimethyl-1-[[(2R,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3,4,4b,5,6,9,10,10a-octahydrophenanthren-2-one
• SMILES (Canonical): CC1(CCC2C(=C1)C(CC3C2(CCC(=O)C3(C)COC4C(C(C(C(O4)CO)O)O)O)C)O)C=C
• SMILES (Isomeric): C[C@@]1(CC[C@H]2C(=C1)[C@@H](C[C@@H]3[C@@]2(CCC(=O)[C@]3(C)CO[C@H]4[C@H]([C@@H]([C@@H]([C@H](O4)CO)O)O)O)C)O)C=C
• InChI: InChI=1S/C26H40O8/c1-5-24(2)8-6-15-14(11-24)16(28)10-18-25(15,3)9-7-19(29)26(18,4)13-33-23-22(32)21(31)20(30)17(12-27)34-23/h5,11,15-18,20-23,27-28,30-32H,1,6-10,12-13H2,2-4H3/t15-,16+,17+,18+,20+,21+,22-,23+,24-,25+,26+/m0/s1
• InChI Key: YGCDMFKITFIOIB-GHSLUPDCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₄₀O₈
• Molecular Weight: 480.60 g/mol
• Exact Mass: 480.27231823 g/mol
• Topological Polar Surface Area (TPSA): 137.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 1.09
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 5

Synonyms

• (1S,4aR,4bR,7R,9R,10aR)-7-ethenyl-9-hydroxy-1,4a,7-trimethyl-1-[[(2R,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3,4,4b,5,6,9,10,10a-octahydrophenanthren-2-one
• (1S,4aR,4bR,7R,9R,10aR)-7-ethenyl-9-hydroxy-1,4a,7-trimethyl-1-(((2R,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxymethyl)-3,4,4b,5,6,9,10,10a-octahydrophenanthren-2-one
• (1S,4aR,7S,9R,10aR)-7-ethenyl-9-hydroxy-1,4a,7-trimethyl-1-(((2R,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)oxymethyl)-3,4,4b,5,6,8,8a,9,10,10a-decahydrophenanthren-2-one
• (1S,4aR,7S,9R,10aR)-7-ethenyl-9-hydroxy-1,4a,7-trimethyl-1-[[(2R,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-3,4,4b,5,6,8,8a,9,10,10a-decahydrophenanthren-2-one
• RefChem:194402
• 724462-48-0
• CHEBI:216625

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7632	76.32%
Caco-2	-	0.7685	76.85%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.7868	78.68%
OATP2B1 inhibitior	-	0.7185	71.85%
OATP1B1 inhibitior	+	0.8943	89.43%
OATP1B3 inhibitior	-	0.3249	32.49%
MATE1 inhibitior	-	0.9812	98.12%
OCT2 inhibitior	-	0.7026	70.26%
BSEP inhibitior	+	0.6582	65.82%
P-glycoprotein inhibitior	-	0.5331	53.31%
P-glycoprotein substrate	-	0.8078	80.78%
CYP3A4 substrate	+	0.6654	66.54%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8581	85.81%
CYP3A4 inhibition	-	0.8267	82.67%
CYP2C9 inhibition	-	0.8882	88.82%
CYP2C19 inhibition	-	0.8542	85.42%
CYP2D6 inhibition	-	0.9420	94.20%
CYP1A2 inhibition	-	0.8238	82.38%
CYP2C8 inhibition	+	0.4479	44.79%
CYP inhibitory promiscuity	-	0.9605	96.05%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.7097	70.97%
Eye corrosion	-	0.9894	98.94%
Eye irritation	-	0.9648	96.48%
Skin irritation	-	0.5506	55.06%
Skin corrosion	-	0.9451	94.51%
Ames mutagenesis	-	0.7854	78.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.6831	68.31%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.7199	71.99%
skin sensitisation	-	0.8998	89.98%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.4745	47.45%
Acute Oral Toxicity (c)	III	0.7177	71.77%
Estrogen receptor binding	+	0.7053	70.53%
Androgen receptor binding	+	0.6480	64.80%
Thyroid receptor binding	+	0.5424	54.24%
Glucocorticoid receptor binding	+	0.7510	75.10%
Aromatase binding	+	0.7356	73.56%
PPAR gamma	+	0.5561	55.61%
Honey bee toxicity	-	0.7042	70.42%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9653	96.53%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.93%	91.11%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.34%	97.25%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.11%	97.09%
CHEMBL1937	Q92769	Histone deacetylase 2	91.52%	94.75%
CHEMBL1994	P08235	Mineralocorticoid receptor	91.21%	100.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.28%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	88.06%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.50%	86.33%
CHEMBL1977	P11473	Vitamin D receptor	86.53%	99.43%
CHEMBL1907602	P06493	Cyclin-dependent kinase 1/cyclin B1	85.68%	91.24%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.24%	96.09%
CHEMBL2581	P07339	Cathepsin D	83.63%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.00%	95.89%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.47%	89.00%
CHEMBL226	P30542	Adenosine A1 receptor	82.37%	95.93%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	82.04%	95.83%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.57%	92.62%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	80.77%	82.69%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.58%	94.00%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 21580220
• LOTUS: LTS0123271
• wikiData: Q77499628