Cerberin

Cerberin
Names
	IUPAC name 14-Hydroxy-5β-card-20(22)-enolid-3β-yl α-D-quinovopyranoside 2-acetate
	Systematic IUPAC name (2R,3S,4R,5S,6S)-5-Hydroxy-2-[(1R,3aS,3bR,5aR,7S,9aS,9bS,11aR)-3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2,5-dihydrofuran-3-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-7-yl]-4-methoxy-6-methyloxan-3-yl acetate
	Other names 2′-Acetylneriifolin; (3β,5β)-3-[(2-O-Acetyl-6-deoxy-3-O-methyl-α-L-glucopyranosyl)oxy]-14-hydroxycard-20(22)-enolide
Identifiers
CAS Number	25633-33-4 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:75049;
ChemSpider	8206634;
PubChem CID	10031063;
UNII	KW5A155S64 ;
CompTox Dashboard (EPA)	DTXSID30893922 ;
	InChI InChI=1S/C32H48O9/c1-17-26(35)27(37-5)28(40-18(2)33)29(39-17)41-21-8-11-30(3)20(15-21)6-7-24-23(30)9-12-31(4)22(10-13-32(24,31)36)19-14-25(34)38-16-19/h14,17,20-24,26-29,35-36H,6-13,15-16H2,1-5H3/t17-,20+,21-,22+,23-,24+,26-,27+,28-,29-,30-,31+,32-/m0/s1 Key: UYQMTWMXBKEHJQ-IVHDSYOHSA-N;
	SMILES CC1C(C(C(C(O1)OC2CCC3(C(C2)CCC4C3CCC5(C4(CCC5C6=CC(=O)OC6)O)C)C)OC(=O)C)OC)O;
Properties
Chemical formula	C32H48O9
Molar mass	576.727 g·mol−1
Melting point	212 °C (414 °F)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Cerberin is a type of cardiac glycoside, found in the seeds of the dicotyledonous angiosperm genus Cerbera; including the suicide tree (Cerbera odollam) and the sea mango (Cerbera manghas). As a cardiac glycoside, cerberin disrupts the function of the heart by blocking its sodium and potassium ATPase.^[2] Cerberin can be used as a treatment for heart failure and arrhythmia.^[3]

Overconsumption of cerberin results in poisoning. Symptoms include nausea, vomiting, and bradycardia, often leading to death.^[4] Cerberin containing plants such as Cerbera odollam have historically been used for suicide and homicide in their growth regions due to their high toxicity.

^ "cerberin | 25633-33-4". ChemicalBook. Retrieved 5 May 2024.
^ Botelho, Ana Flávia M.; Pierezan, Felipe; Soto-Blanco, Benito; Melo, Marília Martins (February 2019). "A review of cardiac glycosides: Structure, toxicokinetics, clinical signs, diagnosis and antineoplastic potential". Toxicon. 158: 63–68. doi:10.1016/j.toxicon.2018.11.429. PMID 30529380.
^ "Cardiac glycoside overdose: MedlinePlus Medical Encyclopedia". medlineplus.gov. Retrieved 5 May 2024.
^ Gaillard, Yvan; Krishnamoorthy, Ananthasankaran; Bevalot, Fabien (December 2004). "Cerbera odollam: a 'suicide tree' and cause of death in the state of Kerala, India". Journal of Ethnopharmacology. 95 (2–3): 123–126. doi:10.1016/j.jep.2004.08.004. PMID 15507323.

[1] "cerberin | 25633-33-4". ChemicalBook. Retrieved 5 May 2024.

[2] Botelho, Ana Flávia M.; Pierezan, Felipe; Soto-Blanco, Benito; Melo, Marília Martins (February 2019). "A review of cardiac glycosides: Structure, toxicokinetics, clinical signs, diagnosis and antineoplastic potential". Toxicon. 158: 63–68. doi:10.1016/j.toxicon.2018.11.429. PMID 30529380.

[3] "Cardiac glycoside overdose: MedlinePlus Medical Encyclopedia". medlineplus.gov. Retrieved 5 May 2024.

[4] Gaillard, Yvan; Krishnamoorthy, Ananthasankaran; Bevalot, Fabien (December 2004). "Cerbera odollam: a 'suicide tree' and cause of death in the state of Kerala, India". Journal of Ethnopharmacology. 95 (2–3): 123–126. doi:10.1016/j.jep.2004.08.004. PMID 15507323.

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Names

IUPAC name 14-Hydroxy-5β-card-20(22)-enolid-3β-yl α-D-quinovopyranoside 2-acetate
Systematic IUPAC name (2R,3S,4R,5S,6S)-5-Hydroxy-2-[(1R,3aS,3bR,5aR,7S,9aS,9bS,11aR)-3a-hydroxy-9a,11a-dimethyl-1-(5-oxo-2,5-dihydrofuran-3-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-7-yl]-4-methoxy-6-methyloxan-3-yl acetate
Other names 2′-Acetylneriifolin (3β,5β)-3-[(2-O-Acetyl-6-deoxy-3-O-methyl-α-L-glucopyranosyl)oxy]-14-hydroxycard-20(22)-enolide
Identifiers
CAS Number	25633-33-4^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:75049
ChemSpider	8206634
PubChem CID	10031063
UNII	KW5A155S64^Y
CompTox Dashboard (EPA)	DTXSID30893922
InChI InChI=1S/C32H48O9/c1-17-26(35)27(37-5)28(40-18(2)33)29(39-17)41-21-8-11-30(3)20(15-21)6-7-24-23(30)9-12-31(4)22(10-13-32(24,31)36)19-14-25(34)38-16-19/h14,17,20-24,26-29,35-36H,6-13,15-16H2,1-5H3/t17-,20+,21-,22+,23-,24+,26-,27+,28-,29-,30-,31+,32-/m0/s1 Key: UYQMTWMXBKEHJQ-IVHDSYOHSA-N
SMILES CC1C(C(C(C(O1)OC2CCC3(C(C2)CCC4C3CCC5(C4(CCC5C6=CC(=O)OC6)O)C)C)OC(=O)C)OC)O
Properties
Chemical formula	C₃₂H₄₈O₉
Molar mass	576.727 g·mol⁻¹
Melting point	212 °C (414 °F)^[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

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Cerberin

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