Basic information
- CAS
4356-43-8- Standard SMILES
O=C1CCC[C@@H]2[C@H]3C[C@@H](CN12)[C@@H]1CCCCN1C3- InChIKey
JYIJIIVLEOETIQ-XDQVBPFNSA-N- Molecular formula
- C15H24N2O
- Average molar mass
- 248.36 g/mol
- Monoisotopic mass
- 248.18886339
Overview
Lupanine is the delta-lactam obtained by formal oxidation at the 2-position of sparteine. The major alkaloid from the seeds of Lupinus exaltatus, L. mexicanus and L. rotundiflorus, it is among the most important of the tetracyclic quinolizidine alkaloids. It is a quinolizidine alkaloid, a tertiary amine and a delta-lactam. It is a conjugate base of a lupanine(1+). It derives from a hydride of a sparteine.
Names & identifiers
- Preferred name
- (+)-Lupanine
- IUPAC
- (1S,2R,9S,10S)-7,15-diazatetracyclo[7.7.1.02,7.010,15]heptadecan-6-one
- English name
- lupanine
- Molecular formula
- C15H24N2O
- Molecular weight
- 248.36
Names & synonyms
Lupanine550-90-3Lupanin(+)-Lupanined-Lupanine2-Oxosparteine(+)-2-OxosparteineSpartein-2-one(1S,2R,9S,10S)-7,15-diazatetracyclo[7.7.1.02,7.010,15]heptadecan-6-one183KU7535ACHEBI:28193DTXSID001023908
Show more names
LUPANINE(SH)(7aβ,14aα)-Dodecahydro-7α,14α-methano-4H,6H-dipyrido[1,2-a:1',2'-e][1,5]diazocin-4-one7,14-Methano-2H,11H-dipyrido[1,2-a:1',2'-e][1,5]diazocin-11-one,dodecahydro-, (7S,7aR,14S,14aS)-
(1S,2R,9S,10S)-7,15-diazatetracyclo(7.7.1.02,7.010,15)heptadecan-6-oneRefChem:41753DTXCID401508215Lupanine d-formLupanine, (+/-)-9K48888N9P4356-43-8(7alpha,7aalpha,14alpha,14abeta)-dodecahydro-7,14-methano-2H,11H-dipyridol[1,2-a:1',2'-e][1,5]diazocin-11-one
Database identifiers
- CAS
4356-43-8、550-90-3- PubChem CID
- 91471
- DTXSID
DTXSID001023908- ChEMBL
CHEMBL459396- ChEBI
CHEBI:28193
Properties
Computed structural properties
- XLogP
- 1.6
- Topological polar surface area
- 23.6 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 0
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 356
Physicochemical properties
- Melting point
- 40 · 40-44°
- alpha
- 25 · D25 +84° (c = 4.8 in alc)
- Boiling point
- 3 · bp3 190-193°
- Density
- 0.9789 · 0.9789 (rough estimate)
- refractive index
- 24 · nD24 1.5444
- form
- Liquid
- pka
- 9.47 · 9.47±0.20(Predicted)
- color
- Colorless to light yellow
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 183 KU7535A · 183KU7535A
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319
- Precautionary statements
- 501 · P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330
Safety & regulation
Hazard information
Regulatory InformationRegulation (EC) No 178/2002 (amended)
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H315-H319
- Precautionary statements
- P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330
Chemistry & industry
Applications
Uses(+)-Lupanine is used in biological studies with quinolizidine alkaloids in seeds of lupin genotypes of different origins.
Suppliers46 total
陕西缔都医药有限责任公司029-81124775 17791530730 · [email protected]
南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
艾吉析科技（上海）有限公司17717235263 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
武汉众志诚生物技术有限公司13628624121 13628604890 · [email protected]
Aladdin Scientific[email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
安耐吉化学&3A（安徽泽升科技有限公司）021-58432009 400-005-6266 · [email protected]
上海维亦特生物科技有限公司15317051735 · [email protected]
佛山宝诺生物科技有限公司0757-85921206 18520245316 · [email protected]
湖北成海化工有限公司027-59220433 18327245847 · [email protected]
Related reactions
1 records
Compound notes
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