Kurchessine
Basic information
- CAS
6869-45-0- Standard SMILES
C[C@@H]([C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](N(C)C)CC[C@]4(C)[C@H]3CC[C@]12C)N(C)C- InChIKey
YTNIUPZRMQLHNV-XSIUSZODSA-N- Molecular formula
- C25H44N2
- Average molar mass
- 372.6 g/mol
- Monoisotopic mass
- 372.35044941
Overview
Kurchessine is an aza-steroid.
Names & identifiers
- Preferred name
- Kurchessine
- IUPAC
- (3S,8S,9S,10R,13S,14S,17S)-17-[(1S)-1-(dimethylamino)ethyl]-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine
- English name
- (20S)-3β,20-Bis(dimethylamino)pregna-5-ene
- Molecular formula
- C25H44N2
- Molecular weight
- 372.63026
Names & synonyms
KurchessineIrehdiamine ISarcodinineKurchessine [MI]KurchessinUNII-618227L15H618227L15H(3beta,20S)-N,N,N,N-Tetramethylpregn-5-ene-3,20-diamineDTXSID30332028Pregn-5-ene-3,20-diamine, N3,N3,N20,N20-tetramethyl-, (3beta,20S)-(3S,8S,9S,10R,13S,14S,17S)-17-[(1S)-1-(dimethylamino)ethyl]-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-aminePregn-5-ene-3.beta.,20.alpha.-diamine, N,N,N',N'-tetramethyl-
Show more names
(20S)-3β,20-Bis(dimethylamino)pregna-5-ene(20S)-N,N,N',N'-Tetramethylpregn-5-ene-3β,20-diamine
Pregn-5-ene-3,20-diamine, N,N,N',N'-tetramethyl-, (3.beta.,20S)-3.beta.,20.alpha.-Bis(dimethylamino)pregn-5-ene(3.BETA.,20S)-N,N,N,N-TETRAMETHYLPREGN-5-ENE-3,20-DIAMINEPREGN-5-ENE-3,20-DIAMINE, N3,N3,N20,N20-TETRAMETHYL-, (3.BETA.,20S)-(3S,8S,9S,10R,13S,14S,17S)-17-((1S)-1-(Dimethylamino)Ethyl)-N,N,10,13-Tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-Dodecahydro-1H-Cyclopenta(A)Phenanthren-3-AmineRefChem:151538DTXCID302831223beta,20alpha-Bis(dimethylamino)pregn-5-ene
Properties
Computed structural properties
- XLogP
- 5.8
- Topological polar surface area
- 6.5 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 2
- Rotatable bonds
- 3
- Heavy atoms
- 27
- Formal charge
- 0
- Complexity
- 593
Physicochemical properties
- Melting point
- 140 · 140-141° (from acetone)
- alpha
- 20 · D20 -37° (c = 1.9); D22 -36° (c = 1.112 in CHCl3); D22 -17° (c = 1.050 in methanol)
- FDA UNII
- 618227 L15H · 618227L15H
Chemistry & industry
Applications
DescriptionA pregnene alkaloid found in the bark of Holarrhena antidysenterica Wall. and also present in the leaves of Sarcococca pruni!ormis Lindl., the base forms colour_x0002_less crystals from Me2CO and has [α]20D - 37° (c 1.90, CHCl3), - 17° (c 1.OS, MeOH). It contains three methyl groups and two dimethylamino groups in the molecule. The alkaloid is characterized as the crystalline perchlorate, m.p. 277- 9°C (dec.) or the picrate, m.p. 228-230°C. The structure has been established as 3 ,20 -bis (dimethylamino)pregn-S-ene. It is identical with saracodinine.
UsesKurchessine (Sarcodinine) is an alkaloid that can be isolated from the stem bark of Holarrhena antidysenterica[1].
Additional notes
DefinitionChEBI: Kurchessine is an aza-steroid.
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