3-[(3S,5S,8R,9S,10R,13R,14S,17R)-3,5,14-trihydroxy-13-methyl-10-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one

Details

• Internal ID: 2724e2b6-a354-4801-8748-cd81a2bca5b4
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroidal glycosides
• IUPAC Name: 3-[(3S,5S,8R,9S,10R,13R,14S,17R)-3,5,14-trihydroxy-13-methyl-10-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
• SMILES (Canonical): CC12CCC3C(C1(CCC2C4=CC(=O)OC4)O)CCC5(C3(CCC(C5)O)COC6C(C(C(C(O6)CO)O)O)O)O
• SMILES (Isomeric): C[C@]12CC[C@H]3[C@H]([C@]1(CC[C@@H]2C4=CC(=O)OC4)O)CC[C@]5([C@@]3(CC[C@@H](C5)O)CO[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)O
• InChI: InChI=1S/C29H44O11/c1-26-6-3-18-19(29(26,37)9-5-17(26)15-10-21(32)38-13-15)4-8-28(36)11-16(31)2-7-27(18,28)14-39-25-24(35)23(34)22(33)20(12-30)40-25/h10,16-20,22-25,30-31,33-37H,2-9,11-14H2,1H3/t16-,17+,18-,19+,20+,22+,23-,24+,25+,26+,27-,28-,29-/m0/s1
• InChI Key: KJWPQMICCIJXJF-BETXHDQMSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₄O₁₁
• Molecular Weight: 568.70 g/mol
• Exact Mass: 568.28836222 g/mol
• Topological Polar Surface Area (TPSA): 186.00 Ų
• XlogP: -1.70
• Atomic LogP (AlogP): -0.48
• H-Bond Acceptor: 11
• H-Bond Donor: 7
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8278	82.78%
Caco-2	-	0.8758	87.58%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.8300	83.00%
OATP2B1 inhibitior	-	0.6021	60.21%
OATP1B1 inhibitior	+	0.9037	90.37%
OATP1B3 inhibitior	+	0.9502	95.02%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.6388	63.88%
P-glycoprotein inhibitior	-	0.6118	61.18%
P-glycoprotein substrate	-	0.5213	52.13%
CYP3A4 substrate	+	0.7006	70.06%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9010	90.10%
CYP3A4 inhibition	-	0.9522	95.22%
CYP2C9 inhibition	-	0.9152	91.52%
CYP2C19 inhibition	-	0.9037	90.37%
CYP2D6 inhibition	-	0.9210	92.10%
CYP1A2 inhibition	-	0.8903	89.03%
CYP2C8 inhibition	-	0.5729	57.29%
CYP inhibitory promiscuity	-	0.9186	91.86%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5867	58.67%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.9391	93.91%
Skin irritation	-	0.5909	59.09%
Skin corrosion	-	0.9410	94.10%
Ames mutagenesis	-	0.6670	66.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.8571	85.71%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.7052	70.52%
skin sensitisation	-	0.9137	91.37%
Respiratory toxicity	+	0.8222	82.22%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.7437	74.37%
Acute Oral Toxicity (c)	I	0.7332	73.32%
Estrogen receptor binding	+	0.8422	84.22%
Androgen receptor binding	+	0.8130	81.30%
Thyroid receptor binding	-	0.5783	57.83%
Glucocorticoid receptor binding	+	0.5393	53.93%
Aromatase binding	+	0.7120	71.20%
PPAR gamma	+	0.5861	58.61%
Honey bee toxicity	-	0.7214	72.14%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5850	58.50%
Fish aquatic toxicity	+	0.9409	94.09%

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	98.25%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.80%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.27%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	94.89%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	92.30%	94.45%
CHEMBL253	P34972	Cannabinoid CB2 receptor	91.62%	97.25%
CHEMBL2581	P07339	Cathepsin D	90.68%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.65%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.25%	85.14%
CHEMBL226	P30542	Adenosine A1 receptor	88.43%	95.93%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.75%	95.89%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	86.83%	96.21%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	86.34%	82.69%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.66%	95.56%
CHEMBL5255	O00206	Toll-like receptor 4	84.51%	92.50%
CHEMBL4208	P20618	Proteasome component C5	84.47%	90.00%
CHEMBL1937	Q92769	Histone deacetylase 2	83.12%	94.75%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.81%	97.14%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.74%	93.04%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.06%	94.00%
CHEMBL1871	P10275	Androgen Receptor	80.60%	96.43%

Plants that contains it

• Antiaris toxicaria

Cross-Links

• PubChem: 73347665
• LOTUS: LTS0207110
• wikiData: Q105142009