3-[(3S,5R,8R,9S,10S,11R,13R,14S,17R)-3-[(2R,3R,4S,5R,6S)-3,4-dihydroxy-6-methyl-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-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: bc007ee0-e4e1-47a0-aa4c-c31597161a23
• 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)-3,4-dihydroxy-6-methyl-5-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-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)OC2C(OC(C(C2O)O)OC3CCC4(C(C3)CCC5C4C(CC6(C5(CCC6C7=CC(=O)OC7)O)C)O)C)C)O)O)O
• SMILES (Isomeric): C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@H]2[C@@H](O[C@H]([C@@H]([C@@H]2O)O)O[C@H]3CC[C@]4([C@@H](C3)CC[C@@H]5[C@@H]4[C@@H](C[C@]6([C@@]5(CC[C@@H]6C7=CC(=O)OC7)O)C)O)C)C)O)O)O
• InChI: InChI=1S/C35H54O13/c1-15-25(38)26(39)28(41)32(45-15)48-30-16(2)46-31(29(42)27(30)40)47-19-7-9-33(3)18(12-19)5-6-21-24(33)22(36)13-34(4)20(8-10-35(21,34)43)17-11-23(37)44-14-17/h11,15-16,18-22,24-32,36,38-43H,5-10,12-14H2,1-4H3/t15-,16-,18+,19-,20+,21+,22+,24+,25-,26+,27-,28+,29+,30-,31-,32-,33-,34+,35-/m0/s1
• InChI Key: JKJVDVVASXIAMQ-SWIBRNOXSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₅H₅₄O₁₃
• Molecular Weight: 682.80 g/mol
• Exact Mass: 682.35644177 g/mol
• Topological Polar Surface Area (TPSA): 205.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): 0.28
• H-Bond Acceptor: 13
• 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	+	0.9219	92.19%
Caco-2	-	0.8840	88.40%
Blood Brain Barrier	-	0.9000	90.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.8297	82.97%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9436	94.36%
OATP1B3 inhibitior	+	0.9518	95.18%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.5055	50.55%
P-glycoprotein inhibitior	+	0.6818	68.18%
P-glycoprotein substrate	+	0.6705	67.05%
CYP3A4 substrate	+	0.7174	71.74%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9026	90.26%
CYP3A4 inhibition	-	0.9279	92.79%
CYP2C9 inhibition	-	0.9196	91.96%
CYP2C19 inhibition	-	0.9385	93.85%
CYP2D6 inhibition	-	0.9359	93.59%
CYP1A2 inhibition	-	0.9261	92.61%
CYP2C8 inhibition	-	0.6951	69.51%
CYP inhibitory promiscuity	-	0.9279	92.79%
UGT catelyzed	+	1.0000	100.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5632	56.32%
Eye corrosion	-	0.9902	99.02%
Eye irritation	-	0.9271	92.71%
Skin irritation	+	0.5359	53.59%
Skin corrosion	-	0.9388	93.88%
Ames mutagenesis	-	0.6770	67.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7658	76.58%
Micronuclear	-	0.8300	83.00%
Hepatotoxicity	-	0.8018	80.18%
skin sensitisation	-	0.9042	90.42%
Respiratory toxicity	+	0.8333	83.33%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.7149	71.49%
Acute Oral Toxicity (c)	I	0.7867	78.67%
Estrogen receptor binding	+	0.7769	77.69%
Androgen receptor binding	+	0.8146	81.46%
Thyroid receptor binding	-	0.7013	70.13%
Glucocorticoid receptor binding	+	0.6071	60.71%
Aromatase binding	+	0.7163	71.63%
PPAR gamma	+	0.6893	68.93%
Honey bee toxicity	-	0.6464	64.64%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.6000	60.00%
Fish aquatic toxicity	+	0.9750	97.50%

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	98.72%	91.11%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	96.93%	96.77%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	96.34%	85.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	96.23%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.73%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.58%	86.33%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.00%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.72%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	90.98%	92.94%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	90.97%	81.11%
CHEMBL3714130	P46095	G-protein coupled receptor 6	90.75%	97.36%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.28%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.28%	95.56%
CHEMBL3038469	P24941	CDK2/Cyclin A	88.88%	91.38%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.83%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.65%	94.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	86.25%	82.69%
CHEMBL2581	P07339	Cathepsin D	82.13%	98.95%
CHEMBL226	P30542	Adenosine A1 receptor	81.48%	95.93%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.17%	99.23%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.60%	95.89%

Plants that contains it

• Ornithogalum nutans

Cross-Links

• PubChem: 163036130
• LOTUS: LTS0108976
• wikiData: Q105130282