Podophyllotoxone
Basic information
- CAS
477-49-6- Standard SMILES
COc1cc([C@@H]2c3cc4c(cc3C(=O)[C@H]3COC(=O)[C@H]23)OCO4)cc(OC)c1OC- InChIKey
ISCQYPPCSYRZOT-BKTGTZMESA-N- Molecular formula
- C22H20O8
- Average molar mass
- 412.4 g/mol
- Monoisotopic mass
- 412.11581759
Overview
Podophyllotoxone is a lactone and a lignan.
Names & identifiers
- Preferred name
- Podophyllotoxone
- IUPAC
- (5aR,8aR,9R)-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-[2]benzofuro[5,6-f][1,3]benzodioxole-5,8-dione
- English name
- Podophyllotoxone
- Molecular formula
- C22H20O8
- Molecular weight
- 412.39
Names & synonyms
Podophyllotoxone477-49-6(5aR,8aR,9R)-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-[2]benzofuro[5,6-f][1,3]benzodioxole-5,8-dione(5aR,8aR,9R)-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-(2)benzofuro(5,6-f)(1,3)benzodioxole-5,8-dione(5aR,8aR,9R)-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydroisobenzofuro(5,6-f)(1,3)benzodioxole-5,8-dione(5aR,8aR,9R)-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydroisobenzofuro[5,6-f][1,3]benzodioxole-5,8-dioneRefChem:175003Podophyllotoxinone(5aR,8aR,9R)-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5,8-dioneC10875(5aR,8aR,9R)-5a,6,8a,9-Tetrahydro-9-(3,4,5-trimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxole-5,8-dione(5aR,8aR,9R)-9-(3,4,5-Trimethoxyphenyl)-5a,6,8a,9-tetrahydro-2H-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5,8-dione
Show more names
(-)-podophyllotoxon(-)-podophyllotoxonPodophyllotoxone, 10 mM in DMSOInhibitor,DU145,inhibit,Podophyllotoxone,cancer,Microtubule/Tubulin,PC3,cells,prostate(5R)-5aα,8aβ-Dihydro-5β-(3,4,5-trimethoxyphenyl)furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxole-6,9(5H,8H)-dione
Properties
Computed structural properties
- XLogP
- 2.5
- Topological polar surface area
- 89.5 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 4
- Heavy atoms
- 30
- Formal charge
- 0
- Complexity
- 668
Experimental & physicochemical properties
Endocrine DisruptorsPotential endocrine disrupting compound
Physicochemical properties
- Melting point
- 191.73 ℃ · 191.73℃
- Boiling point
- 602.3 · 602.3±55.0 °C(Predicted)
- Density
- 1.365 · 1.365±0.06 g/cm3 (20 ºC 760 Torr)
- storage temp.
- 4 °C, · 4°C, away from moisture and light
- solubility
- 100 mg/mL · DMSO : 100 mg/mL (242.49 mM; Need ultrasonic)
- form
- Solid
- color
- White to off-white
- InChI
- InChI=1S/C22H20O8/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/h4-7,13,18-19H,8-9H2,1-3H3/t13-,18+,19-/m0/s1
- InChIKey
- ISCQYPPCSYRZOT-BKTGTZMESA-N
- SMILES
- O1C2=CC3=C(C=C2OC1)C(=O)[C@@]1([H])COC(=O)[C@]1([H])[C@@H]3C1=CC(OC)=C(OC)C(OC)=C1
- Symbol(GHS)
- 6 · GHS06
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 3 (100%)
Safety data
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- Hazard statements
- H332-H301-H335-H312-H315-H319
- Precautionary statements
- P261-P271-P304+P340-P312-P280-P302+P352-P312-P322-P363-P501-P264-P280-P305+P351+P338-P337+P313P-P264-P280-P302+P352-P321-P332+P313-P362-P264-P270-P301+P310-P321-P330-P405-P501
Chemistry & industry
Applications
UsesPodophyllotoxone is a naturally occurring flavonoid that shown significant cell apoptosis and antiproliferative affect against human PC-3 and Bcap-37 cancer cell lines
Additional notes
DefinitionChEBI: Podophyllotoxone is a lactone and a lignan.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…