(7aR)-6,7,7a,8-Tetrahydro-10-methoxy-5H-benzo(g)-1,3-benzodioxolo(6,5,4-de)quinoline
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Basic information
- CAS
517-71-5- Standard SMILES
COc1ccc2c(c1)C[C@H]1NCCc3cc4c(c-2c31)OCO4- InChIKey
RFWCCZDSXIZJMF-CQSZACIVSA-N- Molecular formula
- C18H17NO3
- Average molar mass
- 295.3 g/mol
- Monoisotopic mass
- 295.1208434
Overview
Xylopine is an aporphine alkaloid.
Names & identifiers
- Preferred name
- (7aR)-6,7,7a,8-Tetrahydro-10-methoxy-5H-benzo(g)-1,3-benzodioxolo(6,5,4-de)quinoline
- IUPAC
- (12R)-16-methoxy-3,5-dioxa-11-azapentacyclo[10.7.1.02,6.08,20.014,19]icosa-1(20),2(6),7,14(19),15,17-hexaene
- English name
- Xylopine
- Molecular formula
- C18H17NO3
- Molecular weight
- 295.33
Names & synonyms
Xylopine517-71-5NNZ7TH999HXylopine, (-)-6abeta-Noraporphine, 9-methoxy-1,2-(methylenedioxy)-(12R)-16-methoxy-3,5-dioxa-11-azapentacyclo[10.7.1.02,6.08,20.014,19]icosa-1(20),2(6),7,14(19),15,17-hexaene(7AR)-6,7,7A,8-TETRAHYDRO-10-METHOXY-5H-BENZO(G)-1,3-BENZODIOXOLO(6,5,4-DE)QUINOLINE(12R)-16-methoxy-3,5-dioxa-11-azapentacyclo(10.7.1.02,6.08,20.014,19)icosa-1(20),2(6),7,14(19),15,17-hexaeneRefChem:906276(-)-xylopineCHEMBL452201CHEBI:10083
Show more names
(7aR)-6,7,7a,8-Tetrahydro-10-methoxy-5H-benzo[g]-1,3-benzodioxolo[6,5,4-de]quinoline5H-Benzo[g]-1,3-benzodioxolo[6,5,4-de]quinoline, 6,7,7a,8-tetrahydro-10-methoxy-, (7aR)-
AC1L4NQMAC1Q6ZQZAnolobine, O-methyl-UNII-NNZ7TH999Horb1981751SCHEMBL6686161DTXSID70965975HY-N9534
Properties
Computed structural propertiesFilling in
- XLogP
- 2.8
- Topological polar surface area
- 39.7 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 1
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 431
Physicochemical properties
- Melting point
- 78 · 78-102°C
- storage temp.
- 4 °C, · 4°C, away from moisture and light
- form
- Solid
- color
- Light yellow to yellow
- FDA UNII
- 7 TH999H · NNZ7TH999H
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 301 · H301-H311-H331
- Precautionary statements
- 261 · P261-P264-P270-P271-P280-P302+P352-P304+P340-P310-P330-P361-P403+P233-P405-P501
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- Hazard statements
- H301-H311-H331
- Precautionary statements
- P261-P264-P270-P271-P280-P302+P352-P304+P340-P310-P330-P361-P403+P233-P405-P501
Chemistry & industry
Applications
DescriptionAn alkaloid obtained from Xylopia discreta, this base belongs to the noraporphine class of bases. It crystallizes from Me2CO as colourless needles and has [α]25/sup>D - 23.4°C (MeOH). The crystalline hydrochloride has m.p. 250°C and the N-acetyl derivative, m.p. 213-4°C. One methoxyl group and one methylenedioxy group are present, the structure being that of O-methylanolobine.
UsesXylopine is an aporphine alkaloid with cytotoxic activity on cancer cells. Xylopine induces oxidative stress, causes G2/M cell cycle arrest and apoptosis in cancer cells[1].
Additional notes
DefinitionChEBI: Xylopine is an aporphine alkaloid.
Related reactions
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Compound notes
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