Basic information
- CAS
475-75-2- Standard SMILES
O=C1c2ccccc2-c2c3c(cc4ccnc1c24)OCO3- InChIKey
MUMCCPUVOAUBAN-UHFFFAOYSA-N- Molecular formula
- C17H9NO3
- Average molar mass
- 275.26 g/mol
- Monoisotopic mass
- 275.05824315
Overview
Liriodenine is an oxoaporphine alkaloid that is 4,5,6,6a-tetradehydronoraporphin-7-one substituted by a methylenedioxy group across positions 1 and 2. It is isolated from Annona glabra and has been shown to exhibit antimicrobial and cytotoxic activities. It has a role as a metabolite, an antimicrobial agent, an antineoplastic agent, an antifungal agent, an EC 3.1.1.7 (acetylcholinesterase) inhibitor and an EC 3.2.1.20 (alpha-glucosidase) inhibitor. It is an oxoaporphine alkaloid, an oxacycle, an organic heteropentacyclic compound, a cyclic ketone and an alkaloid antibiotic. It is functionally related to an aporphine.
Names & identifiers
- Preferred name
- Liriodenine
- IUPAC
- 3,5-dioxa-11-azapentacyclo[10.7.1.02,6.08,20.014,19]icosa-1(20),2(6),7,9,11,14,16,18-octaen-13-one
- English name
- liriodenine
- Molecular formula
- C17H9NO3
- Molecular weight
- 275.26
Names & synonyms
Liriodenine475-75-2Micheline BOxoushinsunineSpermatheridineSpermatheridinOxoushinsuninUshinsunine, oxo-8H-Benzo[g]-1,3-benzodioxolo[6,5,4-de]quinolin-8-one8H-Benzo(g)-1,3-benzodioxolo(6,5,4-de)quinolin-8-oneNoraporphin-7-one, 4,5,6,6a-tetradehydro-1,2-(methylenedioxy)-E134R7X4O9
Show more names
Nsc93681IiriodenineLiriodenine (6CI)
NSC-93681NSC-215254CHEBI:70649DTXSID401971658H-[1,3]Benzodioxolo[6,5,4-de]benzo[g]quinolin-8-one8H-(1,3)benzodioxolo(6,5,4-de)benzo(g)quinolin-8-oneRefChem:153652DTXCID50119656
Database identifiers
- CAS
475-75-2- PubChem CID
- 10144
- DTXSID
DTXSID40197165- ChEMBL
CHEMBL37736- ChEBI
CHEBI:70649- UNII
- E134R7X4O9
- EC Number
Properties
Computed structural properties
- XLogP
- 3.4
- Topological polar surface area
- 48.4 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 0
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 453
Physicochemical properties
- Melting point
- 282 °C · 282°C
- Boiling point
- 531 · 531.0±19.0 °C(Predicted)
- Density
- 1.501 · 1.501±0.06 g/cm3(Predicted)
- solubility
- Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
- form
- powder
- pka
- 2.67 · 2.67±0.20(Predicted)
- color
- Yellow
- InChI
- InChI=1S/C17H9NO3/c19-16-11-4-2-1-3-10(11)14-13-9(5-6-18-15(13)16)7-12-17(14)21-8-20-12/h1-7H,8H2
- InChIKey
- MUMCCPUVOAUBAN-UHFFFAOYSA-N
- SMILES
- N1C2=C3C(=C4C(=CC3=CC=1)OCO4)C1=CC=CC=C1C2=O
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 134 R7X4O9 · E134R7X4O9
- Symbol(GHS)
- 6 · GHS06
- Signal word
- Danger
- Hazard statements
- 311 · H311-H331-H301
- Precautionary statements
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, P262, P264, P270, P271, P280, P301+P316, P302+P352, P304+P340, P316, P321, P330, P361+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
- H311-H331-H301
- Precautionary statements
- P261-P271-P304+P340-P311-P321-P403+P233-P405-P501-P280-P302+P352-P312-P322-P361-P363-P405-P501-P264-P270-P301+P310-P321-P330-P405-P501
Chemistry & industry
Applications
DescriptionIsolated from the heartwood extract of Liriodendron tulip/era, this base may be purified by crystallization from CHCI3. It contains one methylenedioxy group and a keto group, forming a crystalline oxime, m.p. 271°C. The structure has been confirmed by synthesis, the synthetic alkaloid having a higher melting point of 287°C.
UsesLiriodenine is an isoquinoline alkaloid found in extracts of medicinal Asian vegetation such as Michelia alba and Liriodendron chinense.
Suppliers45 total
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
成都埃法生物科技有限公司028-028-85142057 19983342022 · [email protected]
成都彼样生物科技有限公司18108052721 · [email protected]
武汉众志诚生物技术有限公司13628624121 13628604890 · [email protected]
南宁赛菲尔生物科技有限公司18877121284;15078879878 · [email protected]
United Life Science020-82099279 18988968278 · [email protected]
佛山宝诺生物科技有限公司0757-85921206 18520245316 · [email protected]
云南西力生物技术股份有限公司0871-65217109 · [email protected]
TargetMol 中国（陶术生物）400-821-0310 15002144251 · [email protected]
重庆福腾医药有限公司18696571988 · [email protected]
Related reactions
1 records
Compound notes
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