Strophanthin

Details

• Internal ID: 4eba71ee-2fd3-458e-8660-4ef6a59d9d6d
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: 5,14-dihydroxy-3-[4-methoxy-6-methyl-5-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-13-methyl-17-(5-oxo-2H-furan-3-yl)-2,3,4,6,7,8,9,11,12,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthrene-10-carbaldehyde
• SMILES (Canonical): CC1C(C(CC(O1)OC2CCC3(C4CCC5(C(CCC5(C4CCC3(C2)O)O)C6=CC(=O)OC6)C)C=O)OC)OC7C(C(C(C(O7)CO)O)O)O
• SMILES (Isomeric): CC1C(C(CC(O1)OC2CCC3(C4CCC5(C(CCC5(C4CCC3(C2)O)O)C6=CC(=O)OC6)C)C=O)OC)OC7C(C(C(C(O7)CO)O)O)O
• InChI: InChI=1S/C36H54O14/c1-18-31(50-32-30(42)29(41)28(40)25(15-37)49-32)24(45-3)13-27(47-18)48-20-4-9-34(17-38)22-5-8-33(2)21(19-12-26(39)46-16-19)7-11-36(33,44)23(22)6-10-35(34,43)14-20/h12,17-18,20-25,27-32,37,40-44H,4-11,13-16H2,1-3H3
• InChI Key: FHIREUBIEIPPMC-UHFFFAOYSA-N
• Popularity: 2,253 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₅₄O₁₄
• Molecular Weight: 710.80 g/mol
• Exact Mass: 710.35135639 g/mol
• Topological Polar Surface Area (TPSA): 211.00 Ų
• XlogP: -0.80
• Atomic LogP (AlogP): 0.26
• H-Bond Acceptor: 14
• H-Bond Donor: 6
• Rotatable Bonds: 8

Synonyms

• STROPHANTHIN
• .beta.-k-Strophanthin
• K-Strophanthin-.beta.
• Strophanthin K (crystalline)
• NSC4320
• .beta.-Strophanthobioside, strophanthidin-3
• 560-53-2
• Strophanthidin-glucocymarosid
• NSC 4320
• NSC-7670
• 5.beta.-Card-20(22)-enolide,6-dideoxy-4-o-.beta.-D-glucopyranosyl-3-o-methyl-.beta.-D-ribo-hexopyranosyl)oxy]-5,14-dihydroxy-19-oxo-
• Card-20(22)-enolide,6-dideoxy-4-O-.beta.-D-glucopyranosyl-3-O-methyl-.beta.-D-ribo-hexopyranosyl)oxy]-5,14-dihydroxy-19-oxo-, (3.beta.,5.beta.)-
• STROPHANTHIN-K, BETA
• NSC7670
• FHIREUBIEIPPMC-UHFFFAOYSA-N
• Card-20(22)-enolide, 3-[(2,6-dideoxy-4-O-.beta.-D-glucopyranosyl-3-O-methyl-.beta.-D-ribo-hexopyranosyl)oxy]-5,14-dihydroxy-19-oxo-, (3.beta.,5.beta.)-
• NCI60_004001
• 3-[(2,6-Dideoxy-4-O-hexopyranosyl-3-O-methylhexopyranosyl)oxy]-5,14-dihydroxy-19-oxocard-20(22)-enolide #
• 5.beta.-Card-20(22)-enolide, 3.beta.-((2,6-dideoxy-4-O-.beta.-D-glucopyranosyl-3-o-methyl-.beta.-D-ribo-hexopyranosyl)oxy)-5,14-dihydroxy-19-oxo-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7964	79.64%
Caco-2	-	0.8803	88.03%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7571	75.71%
Subcellular localzation	Mitochondria	0.8047	80.47%
OATP2B1 inhibitior	-	0.7414	74.14%
OATP1B1 inhibitior	+	0.9093	90.93%
OATP1B3 inhibitior	+	0.9615	96.15%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8989	89.89%
P-glycoprotein inhibitior	+	0.7195	71.95%
P-glycoprotein substrate	+	0.7137	71.37%
CYP3A4 substrate	+	0.7267	72.67%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8956	89.56%
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	+	0.5239	52.39%
CYP inhibitory promiscuity	-	0.9513	95.13%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5527	55.27%
Eye corrosion	-	0.9892	98.92%
Eye irritation	-	0.9257	92.57%
Skin irritation	-	0.5611	56.11%
Skin corrosion	-	0.9387	93.87%
Ames mutagenesis	-	0.5670	56.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.7339	73.39%
Micronuclear	-	0.7700	77.00%
Hepatotoxicity	-	0.7677	76.77%
skin sensitisation	-	0.9209	92.09%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.9000	90.00%
Mitochondrial toxicity	+	0.6375	63.75%
Nephrotoxicity	-	0.8347	83.47%
Acute Oral Toxicity (c)	I	0.8305	83.05%
Estrogen receptor binding	+	0.7982	79.82%
Androgen receptor binding	+	0.8095	80.95%
Thyroid receptor binding	-	0.6491	64.91%
Glucocorticoid receptor binding	+	0.6459	64.59%
Aromatase binding	+	0.6713	67.13%
PPAR gamma	+	0.6618	66.18%
Honey bee toxicity	-	0.6364	63.64%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
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	98.64%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.01%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	96.77%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.74%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	94.91%	97.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.59%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.00%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.85%	85.14%
CHEMBL226	P30542	Adenosine A1 receptor	91.23%	95.93%
CHEMBL253	P34972	Cannabinoid CB2 receptor	88.56%	97.25%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.65%	96.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.34%	95.89%
CHEMBL2581	P07339	Cathepsin D	85.68%	98.95%
CHEMBL4208	P20618	Proteasome component C5	85.15%	90.00%
CHEMBL1871	P10275	Androgen Receptor	83.79%	96.43%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.63%	97.14%
CHEMBL241	Q14432	Phosphodiesterase 3A	82.10%	92.94%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	81.70%	96.77%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	81.31%	91.71%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	80.87%	94.00%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	80.74%	94.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	80.24%	89.00%
CHEMBL5255	O00206	Toll-like receptor 4	80.03%	92.50%

Plants that contains it

• Maquira coriacea
• Strophanthus kombe

Cross-Links

• PubChem: 220861
• LOTUS: LTS0195277
• wikiData: Q104995284