3-[(1R,3R,5R,8R,9S,10S,13R,14S,17R)-3-(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy-1,14-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: c0803c84-e705-43e4-88d3-fc63e83870de
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: 3-[(1R,3R,5R,8R,9S,10S,13R,14S,17R)-3-(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy-1,14-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)OC2CC3CCC4C(C3(C(C2)O)C)CCC5(C4(CCC5C6=CC(=O)OC6)O)C)O)OC)O
• SMILES (Isomeric): CC1C(C(C(C(O1)O[C@@H]2C[C@H]3CC[C@@H]4[C@@H]([C@]3([C@@H](C2)O)C)CC[C@]5([C@@]4(CC[C@@H]5C6=CC(=O)OC6)O)C)O)OC)O
• InChI: InChI=1S/C30H46O9/c1-15-24(33)26(36-4)25(34)27(38-15)39-18-12-17-5-6-21-20(29(17,3)22(31)13-18)7-9-28(2)19(8-10-30(21,28)35)16-11-23(32)37-14-16/h11,15,17-22,24-27,31,33-35H,5-10,12-14H2,1-4H3/t15?,17-,18-,19-,20+,21-,22-,24?,25?,26?,27?,28-,29+,30+/m1/s1
• InChI Key: DKYDBQQIQAPGMH-FIZVBJIDSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₆O₉
• Molecular Weight: 550.70 g/mol
• Exact Mass: 550.31418304 g/mol
• Topological Polar Surface Area (TPSA): 135.00 Ų
• XlogP: 1.10
• Atomic LogP (AlogP): 2.08
• H-Bond Acceptor: 9
• H-Bond Donor: 4
• Rotatable Bonds: 4

Synonyms

• NSC116787
• 663-95-6
• NSC-116787
• 3-[(1R,3R,5R,8R,9S,10S,13R,14S,17R)-3-(3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl)oxy-1,14-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
• NCI60_000386
• Card-20(22)-enolide,14-dihydroxy-, (1.beta.,3.beta.,5.beta.)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9583	95.83%
Caco-2	-	0.8263	82.63%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7896	78.96%
OATP2B1 inhibitior	-	0.7256	72.56%
OATP1B1 inhibitior	+	0.9375	93.75%
OATP1B3 inhibitior	+	0.9683	96.83%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.5681	56.81%
P-glycoprotein inhibitior	-	0.4654	46.54%
P-glycoprotein substrate	+	0.6856	68.56%
CYP3A4 substrate	+	0.7125	71.25%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9037	90.37%
CYP3A4 inhibition	-	0.8949	89.49%
CYP2C9 inhibition	-	0.9092	90.92%
CYP2C19 inhibition	-	0.9351	93.51%
CYP2D6 inhibition	-	0.9376	93.76%
CYP1A2 inhibition	-	0.9214	92.14%
CYP2C8 inhibition	-	0.6266	62.66%
CYP inhibitory promiscuity	-	0.8900	89.00%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5406	54.06%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.9385	93.85%
Skin irritation	-	0.5363	53.63%
Skin corrosion	-	0.9392	93.92%
Ames mutagenesis	-	0.6888	68.88%
Human Ether-a-go-go-Related Gene inhibition	+	0.7530	75.30%
Micronuclear	-	0.8100	81.00%
Hepatotoxicity	-	0.7195	71.95%
skin sensitisation	-	0.9064	90.64%
Respiratory toxicity	+	0.9111	91.11%
Reproductive toxicity	+	0.9222	92.22%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.7400	74.00%
Acute Oral Toxicity (c)	I	0.7811	78.11%
Estrogen receptor binding	+	0.7168	71.68%
Androgen receptor binding	+	0.8144	81.44%
Thyroid receptor binding	-	0.6021	60.21%
Glucocorticoid receptor binding	+	0.6844	68.44%
Aromatase binding	+	0.6611	66.11%
PPAR gamma	+	0.5640	56.40%
Honey bee toxicity	-	0.6834	68.34%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	+	0.9474	94.74%

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	96.50%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.66%	94.45%
CHEMBL1994	P08235	Mineralocorticoid receptor	95.63%	100.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.16%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.89%	86.33%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	93.89%	81.11%
CHEMBL241	Q14432	Phosphodiesterase 3A	93.74%	92.94%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	92.61%	96.77%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.37%	97.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.54%	95.89%
CHEMBL3714130	P46095	G-protein coupled receptor 6	89.46%	97.36%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.88%	95.56%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.76%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	87.41%	85.14%
CHEMBL1871	P10275	Androgen Receptor	86.45%	96.43%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.78%	89.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	84.76%	82.69%
CHEMBL1951	P21397	Monoamine oxidase A	83.12%	91.49%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	82.95%	93.04%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.93%	99.23%
CHEMBL4530	P00488	Coagulation factor XIII	80.28%	96.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.18%	95.89%

Plants that contains it

• Acokanthera oblongifolia
• Acokanthera oppositifolia
• Acokanthera schimperi

Cross-Links

• PubChem: 272417
• LOTUS: LTS0265666
• wikiData: Q104667327