Peruvoside

Details

• Internal ID: a010b661-0228-418d-9af1-fc7a16e9232b
• 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)-3-[(2R,3S,4R,5S,6S)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-14-hydroxy-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-carbaldehyde
• InChI: InChI=1S/C30H44O9/c1-16-24(33)26(36-3)25(34)27(38-16)39-19-6-10-29(15-31)18(13-19)4-5-22-21(29)7-9-28(2)20(8-11-30(22,28)35)17-12-23(32)37-14-17/h12,15-16,18-22,24-27,33-35H,4-11,13-14H2,1-3H3/t16-,18+,19-,20+,21-,22+,24-,25-,26+,27-,28+,29+,30-/m0/s1
• InChI Key: PMTSPAGBAFCORP-HBUONDEYSA-N
• Popularity: 32 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₄₄O₉
• Molecular Weight: 548.70 g/mol
• Exact Mass: 548.29853298 g/mol
• Topological Polar Surface Area (TPSA): 132.00 Ų
• XlogP: 0.70
• Atomic LogP (AlogP): 2.29
• H-Bond Acceptor: 9
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

• Peruvosid
• Encordin
• Cannogenin thevetoside
• 1182-87-2
• CT36KGC6A6
• Cannogenin .alpha.-l-thevetoside
• (3S,5R,8R,9S,10R,13R,14S,17R)-3-[(2R,3S,4R,5S,6S)-3,5-dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-14-hydroxy-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-carbaldehyde
• (3S,5R,8R,9S,10R,13R,14S,17R)-3-[(2S,3R,4S,5R,6R)-3,5-Dihydroxy-4-methoxy-6-methyloxan-2-yl]oxy-14-hydroxy-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-carbaldehyde
• UNII-CT36KGC6A6
• Cannogenin alpha-L-thevetoside
• EINECS 214-659-9
• PERUVOSIDE [MI]
• PERUVOSIDE [WHO-DD]
• SCHEMBL700735
• CHEMBL1075790
• DTXSID70881388
• CHEBI:135825
• DB13756
• 3-((6-Deoxy-3-O-methyl-alpha-L-glucopyranosyl)oxy)-14-hydroxy-19-oxo-card-20(22)-enolide
• HY-108016
• CS-0027154
• E88664
• J-003726
• Q7171218
• (3beta,5beta)-3-((6-Deoxy-3-O-methyl-alpha-L -glucopyranosyl)oxy)-14-hydroxy-19-oxocard-20(22)-enolide
• CARD-20(22)-ENOLIDE, 3-((6-DEOXY-3-O-METHYL-.ALPHA.-L-GLUCOPYRANOSYL)OXY)-14-HYDROXY-19-OXO-, (3.BETA.,5.BETA.)-
• Card-20(22)-enolide, 3-((6-deoxy-3-O-methyl-alpha-L-glucopyranosyl)oxy)-14-hydroxy-19-oxo-, (3-beta,5-beta)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9507	95.07%
Caco-2	-	0.8357	83.57%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7993	79.93%
OATP2B1 inhibitior	-	0.5878	58.78%
OATP1B1 inhibitior	+	0.9414	94.14%
OATP1B3 inhibitior	+	0.9765	97.65%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8614	86.14%
BSEP inhibitior	+	0.7694	76.94%
P-glycoprotein inhibitior	+	0.5956	59.56%
P-glycoprotein substrate	+	0.7356	73.56%
CYP3A4 substrate	+	0.7085	70.85%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8989	89.89%
CYP3A4 inhibition	-	0.8667	86.67%
CYP2C9 inhibition	-	0.9068	90.68%
CYP2C19 inhibition	-	0.9471	94.71%
CYP2D6 inhibition	-	0.9473	94.73%
CYP1A2 inhibition	-	0.9330	93.30%
CYP2C8 inhibition	-	0.5676	56.76%
CYP inhibitory promiscuity	-	0.9265	92.65%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5140	51.40%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.9483	94.83%
Skin irritation	-	0.5328	53.28%
Skin corrosion	-	0.9349	93.49%
Ames mutagenesis	-	0.5724	57.24%
Human Ether-a-go-go-Related Gene inhibition	+	0.8031	80.31%
Micronuclear	-	0.7400	74.00%
Hepatotoxicity	-	0.7371	73.71%
skin sensitisation	-	0.9124	91.24%
Respiratory toxicity	+	0.8889	88.89%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.7875	78.75%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	I	0.8350	83.50%
Estrogen receptor binding	+	0.7806	78.06%
Androgen receptor binding	+	0.8133	81.33%
Thyroid receptor binding	-	0.5722	57.22%
Glucocorticoid receptor binding	+	0.7105	71.05%
Aromatase binding	+	0.6152	61.52%
PPAR gamma	+	0.5434	54.34%
Honey bee toxicity	-	0.6818	68.18%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.9625	96.25%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293232	Q16637	Survival motor neuron protein	177.8 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.31%	91.11%
CHEMBL1994	P08235	Mineralocorticoid receptor	95.60%	100.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.29%	94.45%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.24%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	94.56%	91.49%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	94.10%	96.77%
CHEMBL241	Q14432	Phosphodiesterase 3A	93.57%	92.94%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.22%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.89%	95.56%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.73%	97.09%
CHEMBL3714130	P46095	G-protein coupled receptor 6	91.35%	97.36%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.63%	85.14%
CHEMBL5608	Q16288	NT-3 growth factor receptor	89.88%	95.89%
CHEMBL3492	P49721	Proteasome Macropain subunit	87.11%	90.24%
CHEMBL1806	P11388	DNA topoisomerase II alpha	85.96%	89.00%
CHEMBL3038469	P24941	CDK2/Cyclin A	85.66%	91.38%
CHEMBL1293277	O15118	Niemann-Pick C1 protein	85.65%	81.11%
CHEMBL4208	P20618	Proteasome component C5	85.10%	90.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.14%	94.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	81.84%	97.14%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.75%	99.23%
CHEMBL1871	P10275	Androgen Receptor	80.89%	96.43%

Plants that contains it

• Cascabela thevetia

Cross-Links

• PubChem: 12314120
• LOTUS: LTS0201855
• wikiData: Q7171218