(1S,3R,5S,7R,8S,9R,10S,12R,14R,15S,18R,19R,22S,23R)-8,9,10,22-tetrahydroxy-7,18-dimethyl-19-(5-oxo-2H-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.03,12.05,10.015,23.018,22]pentacosane-14-carbaldehyde

Details

• Internal ID: 707210ab-8d72-4454-bca9-3b903e8b2b0e
• Taxonomy: Lipids and lipid-like molecules > Steroids and steroid derivatives > Steroid lactones > Cardenolides and derivatives > Cardenolide glycosides and derivatives
• IUPAC Name: (1S,3R,5S,7R,8S,9R,10S,12R,14R,15S,18R,19R,22S,23R)-8,9,10,22-tetrahydroxy-7,18-dimethyl-19-(5-oxo-2H-furan-3-yl)-4,6,11-trioxahexacyclo[12.11.0.03,12.05,10.015,23.018,22]pentacosane-14-carbaldehyde
• SMILES (Canonical): CC1C(C(C2(C(O1)OC3CC4CCC5C(C4(CC3O2)C=O)CCC6(C5(CCC6C7=CC(=O)OC7)O)C)O)O)O
• SMILES (Isomeric): C[C@@H]1[C@H]([C@H]([C@]2([C@@H](O1)O[C@@H]3C[C@@H]4CC[C@@H]5[C@@H]([C@]4(C[C@H]3O2)C=O)CC[C@]6([C@@]5(CC[C@@H]6C7=CC(=O)OC7)O)C)O)O)O
• InChI: InChI=1S/C29H40O10/c1-14-23(32)24(33)29(35)25(37-14)38-20-10-16-3-4-19-18(27(16,13-30)11-21(20)39-29)5-7-26(2)17(6-8-28(19,26)34)15-9-22(31)36-12-15/h9,13-14,16-21,23-25,32-35H,3-8,10-12H2,1-2H3/t14-,16+,17-,18+,19-,20-,21-,23-,24-,25+,26-,27-,28+,29+/m1/s1
• InChI Key: LYSHVSOMKBORDM-NFYSVIEISA-N
• Popularity: 3 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₄₀O₁₀
• Molecular Weight: 548.60 g/mol
• Exact Mass: 548.26214747 g/mol
• Topological Polar Surface Area (TPSA): 152.00 Ų
• XlogP: 0.00
• Atomic LogP (AlogP): 0.97
• H-Bond Acceptor: 10
• H-Bond Donor: 4
• Rotatable Bonds: 2

Synonyms

• HSDB 3468
• BRN 0072512
• 20304-49-8
• CHEMBL4743046
• 5-alpha-Card-20(22)-enolide, 3-beta-((6-deoxy-beta-D-hexopyranos-2-ulos-1-yl)oxy)2-alpha,14-dihydroxy-19-oxo-
• Card-20(22)-enolide, 3-((6-deoxy-beta-D-hexopyranos-2-ulos-1-yl)oxy)-2,14-dihydroxy-19-oxo-,(2alpha,3beta,5alpha)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9121	91.21%
Caco-2	-	0.8481	84.81%
Blood Brain Barrier	-	0.6750	67.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8527	85.27%
OATP2B1 inhibitior	-	0.7238	72.38%
OATP1B1 inhibitior	+	0.9019	90.19%
OATP1B3 inhibitior	+	0.9724	97.24%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.7078	70.78%
P-glycoprotein inhibitior	-	0.4614	46.14%
P-glycoprotein substrate	+	0.7548	75.48%
CYP3A4 substrate	+	0.7071	70.71%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8937	89.37%
CYP3A4 inhibition	-	0.8981	89.81%
CYP2C9 inhibition	-	0.9304	93.04%
CYP2C19 inhibition	-	0.9492	94.92%
CYP2D6 inhibition	-	0.9408	94.08%
CYP1A2 inhibition	-	0.9402	94.02%
CYP2C8 inhibition	-	0.5694	56.94%
CYP inhibitory promiscuity	-	0.9713	97.13%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	1.0000	100.00%
Carcinogenicity (trinary)	Non-required	0.5209	52.09%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.9464	94.64%
Skin irritation	+	0.5288	52.88%
Skin corrosion	-	0.9207	92.07%
Ames mutagenesis	-	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8049	80.49%
Micronuclear	-	0.7800	78.00%
Hepatotoxicity	-	0.5375	53.75%
skin sensitisation	-	0.9003	90.03%
Respiratory toxicity	+	0.8667	86.67%
Reproductive toxicity	+	0.9111	91.11%
Mitochondrial toxicity	+	0.7625	76.25%
Nephrotoxicity	+	0.4718	47.18%
Acute Oral Toxicity (c)	I	0.8039	80.39%
Estrogen receptor binding	+	0.8150	81.50%
Androgen receptor binding	+	0.8036	80.36%
Thyroid receptor binding	-	0.5477	54.77%
Glucocorticoid receptor binding	+	0.6750	67.50%
Aromatase binding	+	0.6883	68.83%
PPAR gamma	+	0.5477	54.77%
Honey bee toxicity	-	0.6967	69.67%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	+	0.6800	68.00%
Fish aquatic toxicity	+	0.9802	98.02%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.69%	96.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	95.61%	100.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.27%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.87%	95.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	92.97%	96.77%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	91.28%	93.40%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.72%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.55%	85.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	90.07%	95.89%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	88.04%	97.14%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.92%	89.00%
CHEMBL4026	P40763	Signal transducer and activator of transcription 3	87.58%	82.69%
CHEMBL3137262	O60341	LSD1/CoREST complex	86.22%	97.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	85.74%	94.45%
CHEMBL4208	P20618	Proteasome component C5	85.68%	90.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	84.89%	99.23%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	84.88%	81.11%
CHEMBL2955	O95136	Sphingosine 1-phosphate receptor Edg-5	84.88%	92.86%
CHEMBL1871	P10275	Androgen Receptor	84.84%	96.43%
CHEMBL3351	Q13085	Acetyl-CoA carboxylase 1	81.76%	93.04%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.11%	93.00%

Plants that contains it

• Anemone narcissiflora
• Asclepias curassavica
• Asclepias linaria
• Calotropis procera
• Gomphocarpus fruticosus subsp. fruticosus
• Hyperbaena columbica
• Viburnum lantanoides

Cross-Links

• PubChem: 101710282
• NPASS: NPC277374
• LOTUS: LTS0136842
• wikiData: Q104252179