3-[(3S,5S,9S,10R,13R,14S,17R)-3-[(2R,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-5,14-dihydroxy-10-(hydroxymethyl)-13-methyl-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: b268ed79-6b9f-4242-b4e3-9ffa13a410f6
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: 3-[(3S,5S,9S,10R,13R,14S,17R)-3-[(2R,4S,5S,6R)-4,5-dihydroxy-6-methyloxan-2-yl]oxy-5,14-dihydroxy-10-(hydroxymethyl)-13-methyl-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): CC1C(C(CC(O1)OC2CCC3(C4CCC5(C(CCC5(C4CCC3(C2)O)O)C6=CC(=O)OC6)C)CO)O)O
• SMILES (Isomeric): C[C@@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2CC[C@@]3([C@H]4CC[C@@]5([C@H](CC[C@@]5(C4CC[C@@]3(C2)O)O)C6=CC(=O)OC6)C)CO)O)O
• InChI: InChI=1S/C29H44O9/c1-16-25(33)22(31)12-24(37-16)38-18-3-8-27(15-30)20-4-7-26(2)19(17-11-23(32)36-14-17)6-10-29(26,35)21(20)5-9-28(27,34)13-18/h11,16,18-22,24-25,30-31,33-35H,3-10,12-15H2,1-2H3/t16-,18+,19-,20+,21?,22+,24+,25-,26-,27+,28+,29+/m1/s1
• InChI Key: KISYRRMFQYIIFQ-YBUIGGMOSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₄O₉
• Molecular Weight: 536.70 g/mol
• Exact Mass: 536.29853298 g/mol
• Topological Polar Surface Area (TPSA): 146.00 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): 1.57
• H-Bond Acceptor: 9
• H-Bond Donor: 5
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8248	82.48%
Caco-2	-	0.8183	81.83%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	+	0.5286	52.86%
Subcellular localzation	Mitochondria	0.8382	83.82%
OATP2B1 inhibitior	-	0.6134	61.34%
OATP1B1 inhibitior	+	0.9271	92.71%
OATP1B3 inhibitior	+	0.9481	94.81%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.6488	64.88%
P-glycoprotein inhibitior	-	0.5170	51.70%
P-glycoprotein substrate	+	0.7271	72.71%
CYP3A4 substrate	+	0.6813	68.13%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.9010	90.10%
CYP3A4 inhibition	-	0.9241	92.41%
CYP2C9 inhibition	-	0.9242	92.42%
CYP2C19 inhibition	-	0.9271	92.71%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.9045	90.45%
CYP2C8 inhibition	-	0.7873	78.73%
CYP inhibitory promiscuity	-	0.9179	91.79%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.6086	60.86%
Eye corrosion	-	0.9907	99.07%
Eye irritation	-	0.9429	94.29%
Skin irritation	-	0.5648	56.48%
Skin corrosion	-	0.9423	94.23%
Ames mutagenesis	-	0.6370	63.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.8393	83.93%
Micronuclear	-	0.8600	86.00%
Hepatotoxicity	-	0.7302	73.02%
skin sensitisation	-	0.9189	91.89%
Respiratory toxicity	+	0.8444	84.44%
Reproductive toxicity	+	0.8889	88.89%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.8206	82.06%
Acute Oral Toxicity (c)	I	0.8357	83.57%
Estrogen receptor binding	+	0.8331	83.31%
Androgen receptor binding	+	0.8171	81.71%
Thyroid receptor binding	-	0.5896	58.96%
Glucocorticoid receptor binding	+	0.6439	64.39%
Aromatase binding	+	0.7265	72.65%
PPAR gamma	-	0.5000	50.00%
Honey bee toxicity	-	0.7521	75.21%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5400	54.00%
Fish aquatic toxicity	+	0.9498	94.98%

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	97.73%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.46%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	97.21%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	95.77%	100.00%
CHEMBL253	P34972	Cannabinoid CB2 receptor	95.62%	97.25%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.73%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.53%	86.33%
CHEMBL226	P30542	Adenosine A1 receptor	93.42%	95.93%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.87%	85.14%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	90.07%	82.69%
CHEMBL2581	P07339	Cathepsin D	89.46%	98.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.37%	95.89%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	86.78%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.48%	95.56%
CHEMBL4208	P20618	Proteasome component C5	83.42%	90.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.92%	89.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.68%	97.14%
CHEMBL1871	P10275	Androgen Receptor	81.48%	96.43%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.18%	94.00%

Plants that contains it

• Strophanthus kombe

Cross-Links

• PubChem: 10369931
• NPASS: NPC139489