Podophyllotoxin

C₂₂H₂₂O₈CAS 518-28-5414.41 g/mol

Open in Covalent MOL file

Acetal Alcohol Ester Ether Lactone

Properties

Molecular formula: C₂₂H₂₂O₈
Molar mass: 414.41 g/mol
Exact mass: 414.1315 Da
Melting point: 183 °C
Water solubility: 150 mg/L (25 °C)
logP: 2.41Crippen estimate
Polar surface area: 92.7 Å²
H-bond donors / acceptors: 1 / 8
Rotatable bonds: 4
Stereocentres: R, R, R, Rin SMILES atom order

Hazards

Danger

H301 Toxic if swallowed93.5% of notifiers
H310 Fatal in contact with skin95.7% of notifiers
H315 Causes skin irritation97.8% of notifiers
H319 Causes serious eye irritation97.8% of notifiers
H335 May cause respiratory irritation95.7% of notifiers

Aggregated from 46 ECHA notifications, via PubChem; a share says how many notifiers assign that statement.

Precautionary statements

P261, P262, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P316, P319, P321, P330, P332+P317, P337+P317, P361+P364, P362+P364, P403+P233, P405, P501

Identifiers

CAS number

518-28-5

SMILES

COc1cc([C@@H]2c3cc4c(cc3[C@H](O)[C@H]3COC(=O)[C@H]23)OCO4)cc(OC)c1OC

InChIKey

YJGVMLPVUAXIQN-XVVDYKMHSA-N

InChI

InChI=1S/C22H22O8/c1-25-16-4-10(5-17(26-2)21(16)27-3)18-11-6-14-15(30-9-29-14)7-12(11)20(23)13-8-28-22(24)19(13)18/h4-7,13,18-20,23H,8-9H2,1-3H3/t13-,18+,19-,20-/m0/s1

Weigh it out

Type any one amount. The others follow from the molar mass.

Names and synonyms

8 names

Furo[3′,4′:6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-, (5R,5aR,8aR,9R)-
Furo[3′,4′:6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one, 5,8,8a,9-tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)-, [5R-(5α,5aβ,8aα,9α)]-
(5R,5aR,8aR,9R)-5,8,8a,9-Tetrahydro-9-hydroxy-5-(3,4,5-trimethoxyphenyl)furo[3′,4′:6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one
Condylox
Podofilox
(-)-Podophyllotoxin
NSC 24818
Condyline

Work with Podophyllotoxin

Predict the NMR spectrum1H and 13C shifts with multiplicities Make a solutionWhat to weigh for any molarity and volume Check drug-likenessLipinski, Veber and lead-likeness Isotope patternExact mass and the mass spectrum pattern

Stereoisomers, salts and isotopologues

The same compound in another form: other stereochemistry, a salt or hydrate, the free acid or base, or an isotope-labelled version.

Picropodophyllin477-47-4Diastereomer

Similar compounds

4'-Demethylpodophyllotoxin40505-27-983 % similar (-)-4′-Demethylepipodophyllotoxin6559-91-783 % similar Podophyllum (resin)9000-55-981 % similar Podophyllotoxin glucoside16481-54-263 % similar Etoposide33419-42-051 % similar Etoposide phosphate117091-64-249 % similar Teniposide29767-20-247 % similar (+)-Yangambin13060-14-536 % similar

Tanimoto similarity of circular fingerprints over the whole catalogue.

All similar compounds

Elsewhere

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