3-[(3S,5R,8R,9S,10S,11R,13R,14S,17R)-3-[(2R,3R,4S,5R,6S)-5-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-3,4-dihydroxy-6-methyloxan-2-yl]oxy-11,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one

Details

• Internal ID: 72ac7692-e2ce-43ed-adea-d8dc1cc09758
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: 3-[(3S,5R,8R,9S,10S,11R,13R,14S,17R)-3-[(2R,3R,4S,5R,6S)-5-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-3,4-dihydroxy-6-methyloxan-2-yl]oxy-11,14-dihydroxy-10,13-dimethyl-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2H-furan-5-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2CCC3(C(C2)CCC4C3C(CC5(C4(CCC5C6=CC(=O)OC6)O)C)O)C)O)O)OC7C(C(CO7)(CO)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](C2)CC[C@@H]4[C@@H]3[C@@H](C[C@]5([C@@]4(CC[C@@H]5C6=CC(=O)OC6)O)C)O)C)O)O)O[C@H]7[C@@H]([C@](CO7)(CO)O)O
• InChI: InChI=1S/C34H52O13/c1-16-27(47-30-28(40)33(41,14-35)15-44-30)25(38)26(39)29(45-16)46-19-6-8-31(2)18(11-19)4-5-21-24(31)22(36)12-32(3)20(7-9-34(21,32)42)17-10-23(37)43-13-17/h10,16,18-22,24-30,35-36,38-42H,4-9,11-15H2,1-3H3/t16-,18+,19-,20+,21+,22+,24+,25-,26+,27-,28-,29-,30-,31-,32+,33+,34-/m0/s1
• InChI Key: KIQMPXRVKKVROQ-AXMZTVKISA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₅₂O₁₃
• Molecular Weight: 668.80 g/mol
• Exact Mass: 668.34079171 g/mol
• Topological Polar Surface Area (TPSA): 205.00 Ų
• XlogP: -0.30
• Atomic LogP (AlogP): -0.11
• H-Bond Acceptor: 13
• H-Bond Donor: 7
• Rotatable Bonds: 6

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8285	82.85%
Caco-2	-	0.8815	88.15%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.8184	81.84%
OATP2B1 inhibitior	-	0.6097	60.97%
OATP1B1 inhibitior	+	0.9188	91.88%
OATP1B3 inhibitior	+	0.9329	93.29%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.5789	57.89%
P-glycoprotein inhibitior	+	0.6676	66.76%
P-glycoprotein substrate	+	0.7126	71.26%
CYP3A4 substrate	+	0.7352	73.52%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9010	90.10%
CYP3A4 inhibition	-	0.9194	91.94%
CYP2C9 inhibition	-	0.9182	91.82%
CYP2C19 inhibition	-	0.9284	92.84%
CYP2D6 inhibition	-	0.9380	93.80%
CYP1A2 inhibition	-	0.9197	91.97%
CYP2C8 inhibition	+	0.4750	47.50%
CYP inhibitory promiscuity	-	0.9237	92.37%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5893	58.93%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.9261	92.61%
Skin irritation	-	0.5142	51.42%
Skin corrosion	-	0.9440	94.40%
Ames mutagenesis	-	0.6470	64.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.8161	81.61%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.6092	60.92%
skin sensitisation	-	0.9231	92.31%
Respiratory toxicity	+	0.7778	77.78%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.5579	55.79%
Acute Oral Toxicity (c)	I	0.8499	84.99%
Estrogen receptor binding	+	0.7896	78.96%
Androgen receptor binding	+	0.8059	80.59%
Thyroid receptor binding	-	0.6489	64.89%
Glucocorticoid receptor binding	+	0.5715	57.15%
Aromatase binding	+	0.6685	66.85%
PPAR gamma	+	0.6560	65.60%
Honey bee toxicity	-	0.6487	64.87%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.5100	51.00%
Fish aquatic toxicity	+	0.9475	94.75%

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	98.62%	91.11%
CHEMBL226	P30542	Adenosine A1 receptor	97.64%	95.93%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	97.45%	96.77%
CHEMBL1994	P08235	Mineralocorticoid receptor	97.12%	100.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.88%	86.33%
CHEMBL3137262	O60341	LSD1/CoREST complex	95.70%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.43%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.04%	96.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.89%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	92.92%	92.94%
CHEMBL3714130	P46095	G-protein coupled receptor 6	91.88%	97.36%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	90.97%	82.69%
CHEMBL1806	P11388	DNA topoisomerase II alpha	89.93%	89.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.41%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.71%	94.00%
CHEMBL3038469	P24941	CDK2/Cyclin A	87.24%	91.38%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.74%	95.89%
CHEMBL2581	P07339	Cathepsin D	86.31%	98.95%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	86.15%	81.11%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	84.78%	96.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.57%	99.23%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.55%	85.14%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	84.53%	94.33%
CHEMBL4685	P14902	Indoleamine 2,3-dioxygenase	83.83%	96.38%
CHEMBL4530	P00488	Coagulation factor XIII	83.03%	96.00%

Plants that contains it

• Ornithogalum nutans

Cross-Links

• PubChem: 162932075
• LOTUS: LTS0137249
• wikiData: Q105141641