beta-Peltatin
Basic information
- CAS
518-29-6- Standard SMILES
COc1cc([C@@H]2c3cc4c(c(O)c3C[C@H]3COC(=O)[C@@H]32)OCO4)cc(OC)c1OC- InChIKey
HLBPOYVRLSXWJJ-PDSMFRHLSA-N- Molecular formula
- C22H22O8
- Average molar mass
- 414.4 g/mol
- Monoisotopic mass
- 414.13146766
Overview
Beta-peltatin is an organic heterotetracyclic compound that is alpha-peltatin in which the phenolic hydroxy group of the 4-hydroxy-3,5-dimethoxyphenyl substitutent had been converted into the corresponding methyl ether. It has a role as an antineoplastic agent and a plant metabolite. It is a lignan, a member of phenols, a gamma-lactone, an organic heterotetracyclic compound and a furonaphthodioxole. It is functionally related to an alpha-peltatin.
Names & identifiers
- Preferred name
- beta-Peltatin
- IUPAC
- (5aR,8aR,9R)-4-hydroxy-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one
- English name
- PELTATIN
- Molecular formula
- C22H22O8
- Molecular weight
- 414.41
Names & synonyms
beta-Peltatin518-29-6beta-Peltatin APeltatin methyl etherPELTATIN, BETA.beta.-Peltatinalpha-Peltalin A.beta.-Peltatin ANSC 24819BRN 0099483AI3-50532UNII-3U9W61G72Y
Show more names
b-PeltatinPELTATIN--Peltatinβ-Peltatinβ-Peltatin A(-)-β-Peltatin(-)-beta-Peltatin(5R)-5,8,8aβ,9-Tetrahydro-10-hydroxy-5-(3,4,5-trimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aαH)-oneFuro[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-10-hydroxy-5-(3,4,5-trimethoxyphenyl)-, (5R,5aR,8aR)-
3U9W61G72YNSC-24819NSC-35471.BETA.-PELTATIN [MI]CHEBI:74867DTXSID10199732.BETA.-PELTATIN, (-)-5-19-10-00670 (Beilstein Handbook Reference)
Properties
Computed structural properties
- XLogP
- 2.9
- Topological polar surface area
- 92.7 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 4
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 629
Experimental & physicochemical properties
Endocrine DisruptorsPotential endocrine disrupting compound
Collision Cross Section
189 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
200.12 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 234 °C · 234 °C
- Boiling point
- 586.8 · 586.8±50.0 °C(Predicted)
- alpha
- 20 · D20 -122.9° (c = 0.578 in chloroform)
- Density
- 1.363 · 1.363±0.06 g/cm3(Predicted)
- pka
- 9.49 · 9.49±0.40(Predicted)
- form
- Solid
- color
- White to off-white
- FDA UNII
- 3 U9W61G72Y · 3U9W61G72Y
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Regulatory InformationChemical: Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-10-hydroxy-5-(3,4,5-trimethoxyphenyl)-, [5R-(5.alpha.,5a.beta.,8a.alpha.)]-
Other Safety InformationEvaluation - Chemicals not considered for in depth evaluation - Not commercially active in Australia
Chemistry & industry
Applications
Usesβ-Peltatin is one of the major lignans in Podophyllum peltatum, and is one of the components of Podophyllin, a complex mixture of oils and pigments that was used as a purgative. β-Peltatin also has biological activity against tumours.
Additional notes
DefinitionChEBI: An organic heterotetracyclic compound that is alpha-peltatin in which the phenolic hydroxy group of the 4-hydroxy-3,5-dimethoxyphenyl substitutent had been converted to the corresponding methyl ether.
Related reactions
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Compound notes
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