(3S,5R,8R,9S,10R,13R,14S,17R)-14-hydroxy-3-[(2R,3S,4S,5S,6S)-3-hydroxy-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyoxan-2-yl]oxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-10-carboxylic acid

Details

• Internal ID: 84326f1f-2556-48d8-be29-aa4cbe44092a
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: (3S,5R,8R,9S,10R,13R,14S,17R)-14-hydroxy-3-[(2R,3S,4S,5S,6S)-3-hydroxy-4-methoxy-6-methyl-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyoxan-2-yl]oxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-1,2,3,4,5,6,7,8,9,11,12,15,16,17-tetradecahydrocyclopenta[a]phenanthrene-10-carboxylic acid
• SMILES (Canonical): CC1C(C(C(C(O1)OC2CCC3(C(C2)CCC4C3CCC5(C4(CCC5C6=CC(=O)OC6)O)C)C(=O)O)O)OC)OC7C(C(C(C(O7)COC8C(C(C(C(O8)CO)O)O)O)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](C2)CC[C@@H]4[C@@H]3CC[C@]5([C@@]4(CC[C@@H]5C6=CC(=O)OC6)O)C)C(=O)O)O)OC)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O)O)O
• InChI: InChI=1S/C42H64O20/c1-17-34(62-37-32(50)30(48)28(46)25(61-37)16-57-36-31(49)29(47)27(45)24(14-43)60-36)35(55-3)33(51)38(58-17)59-20-6-10-41(39(52)53)19(13-20)4-5-23-22(41)7-9-40(2)21(8-11-42(23,40)54)18-12-26(44)56-15-18/h12,17,19-25,27-38,43,45-51,54H,4-11,13-16H2,1-3H3,(H,52,53)/t17-,19+,20-,21+,22-,23+,24+,25+,27+,28+,29-,30-,31+,32+,33-,34-,35-,36+,37-,38-,40+,41+,42-/m0/s1
• InChI Key: AYRCTGHTWRPKRK-JAOABGLJSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₄₂H₆₄O₂₀
• Molecular Weight: 888.90 g/mol
• Exact Mass: 888.39909443 g/mol
• Topological Polar Surface Area (TPSA): 310.00 Ų
• XlogP: -2.90
• Atomic LogP (AlogP): -2.18
• H-Bond Acceptor: 19
• H-Bond Donor: 10
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7964	79.64%
Caco-2	-	0.8919	89.19%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.8047	80.47%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8887	88.87%
OATP1B3 inhibitior	+	0.9615	96.15%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8578	85.78%
P-glycoprotein inhibitior	+	0.7377	73.77%
P-glycoprotein substrate	+	0.7200	72.00%
CYP3A4 substrate	+	0.7288	72.88%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8995	89.95%
CYP3A4 inhibition	-	0.8841	88.41%
CYP2C9 inhibition	-	0.9054	90.54%
CYP2C19 inhibition	-	0.9238	92.38%
CYP2D6 inhibition	-	0.9467	94.67%
CYP1A2 inhibition	-	0.9221	92.21%
CYP2C8 inhibition	+	0.5887	58.87%
CYP inhibitory promiscuity	-	0.9513	95.13%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5527	55.27%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9183	91.83%
Skin irritation	-	0.5611	56.11%
Skin corrosion	-	0.9387	93.87%
Ames mutagenesis	-	0.6553	65.53%
Human Ether-a-go-go-Related Gene inhibition	+	0.8292	82.92%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.7051	70.51%
skin sensitisation	-	0.9209	92.09%
Respiratory toxicity	+	0.8556	85.56%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.8175	81.75%
Acute Oral Toxicity (c)	I	0.8305	83.05%
Estrogen receptor binding	+	0.8490	84.90%
Androgen receptor binding	+	0.7959	79.59%
Thyroid receptor binding	-	0.6347	63.47%
Glucocorticoid receptor binding	+	0.6981	69.81%
Aromatase binding	+	0.6972	69.72%
PPAR gamma	+	0.7870	78.70%
Honey bee toxicity	-	0.6531	65.31%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9314	93.14%

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	98.50%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.91%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.50%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.45%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.73%	85.14%
CHEMBL1994	P08235	Mineralocorticoid receptor	94.11%	100.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.85%	97.09%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	93.05%	81.11%
CHEMBL3714130	P46095	G-protein coupled receptor 6	91.93%	97.36%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	88.53%	93.04%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.32%	94.00%
CHEMBL5255	O00206	Toll-like receptor 4	86.68%	92.50%
CHEMBL241	Q14432	Phosphodiesterase 3A	86.65%	92.94%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.62%	95.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.11%	96.77%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.64%	95.89%
CHEMBL226	P30542	Adenosine A1 receptor	83.98%	95.93%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.65%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	83.53%	96.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.58%	99.23%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.36%	95.89%
CHEMBL2581	P07339	Cathepsin D	81.87%	98.95%
CHEMBL1937	Q92769	Histone deacetylase 2	81.06%	94.75%
CHEMBL5028	O14672	ADAM10	80.95%	97.50%
CHEMBL1871	P10275	Androgen Receptor	80.32%	96.43%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.18%	94.33%

Plants that contains it

• Cascabela thevetia

Cross-Links

• PubChem: 101677499
• LOTUS: LTS0267015
• wikiData: Q104921332