(3beta,4alpha,15alpha,16beta)-4,9-Epoxycevane-3,4,14,15,16,20-hexol
Basic information
- CAS
545-45-9- Standard SMILES
C[C@H]1CC[C@@H]2N(C1)C[C@@H]1[C@H]([C@@H](O)[C@H](O)[C@]3(O)[C@H]1C[C@@]14O[C@@]5(O)[C@@H](CC[C@@H]31)[C@]4(C)CC[C@@H]5O)[C@]2(C)O- InChIKey
NPNDUIMQBJIGQS-IDFKWMMPSA-N- Molecular formula
- C27H43NO7
- Average molar mass
- 493.6 g/mol
- Monoisotopic mass
- 493.30395271
Overview
Zygadenine is an alkaloid.
Names & identifiers
- Preferred name
- (3beta,4alpha,15alpha,16beta)-4,9-Epoxycevane-3,4,14,15,16,20-hexol
- IUPAC
- (1S,2S,6S,9S,10S,11R,12R,13S,14S,15S,18S,19S,22S,23S,25R)-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.02,11.04,9.015,25.018,23.019,25]hexacosane-10,12,13,14,22,23-hexol
- English name
- Zygadenine
- Molecular formula
- C27H43NO7
- Molecular weight
- 493.63
Names & synonyms
ZygadenineZygadenin545-45-90N72U4OAF7(1S,2S,6S,9S,10S,11R,12R,13S,14S,15S,18S,19S,22S,23S,25R)-6,10,19-trimethyl-24-oxa-4-azaheptacyclo[12.12.0.02,11.04,9.015,25.018,23.019,25]hexacosane-10,12,13,14,22,23-hexolCevane-3,4,14,15,16,20-hexol, 4,9-epoxy-, (3beta,4alpha,15alpha,16beta)-(1S,2S,6S,9S,10S,11R,12R,13S,14S,15S,18S,19S,22S,23S,25R)-6,10,19-trimethyl-24-oxa-4-azaheptacyclo(12.12.0.02,11.04,9.015,25.018,23.019,25)hexacosane-10,12,13,14,22,23-hexol(2R,3S,5R)-2-((1S)-1-((3S,5S,8R,9S,10S,13S,14S,16R,17R)-3-amino-16-hydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta(a)phenanthren-17-yl)ethyl)-5-methyl-piperidin-3-olRefChem:1050179(3beta,4alpha,15alpha,16beta)-4,9-Epoxycevane-3,4,14,15,16,20-hexolUNII-0N72U4OAF7C10831
Show more names
4α,9-Epoxycevane-3β,4,14,15α,16β,20-hexolCevane-3,4,14,15,16,20-hexol, 4,9-epoxy-, (3β,4α,15α,16β)-
ZYGADENINE [MI]SCHEMBL28282128CHEBI:10130DTXSID40969682NS000942934,9-Epoxycevane-3,4,14,15,16,20-hexolQ271085974,9-Epoxycevane-3beta,4alpha,14,15alpha,16beta,20-hexol
Properties
Computed structural properties
- XLogP
- -0.1
- Topological polar surface area
- 134 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 0
- Heavy atoms
- 35
- Formal charge
- 0
- Complexity
- 935
Physicochemical properties
- Melting point
- 214 · 214-216°
- alpha
- 20 · D20 -48.4° (c = 1.26 in chloroform)
- FDA UNII
- 0 N72U4OAF7 · 0N72U4OAF7
Chemistry & industry
Applications
DescriptionA steroidal alkaloid isolated from the leaves of Zygadenus intermedius, this base forms clusters of colourless needles from C6H6 or Et20 or prisms of the diethanolate from EtOH. It is laevorotatory with [α]20/sup>D - 48.2° (c 1.26, CHCl3). The salts and derivative crystallize well: hydrochloride, m.p. 23l-4°C; sulphate, m.p. 237-242°C; aurichloride monohydrate, decomposing at l40-l65°C; hexaacetate, m.p. 265-270°C and the vanilloyl derivative, m.p. 258-9°C; [α]23/sup>D - 27.5° (CHCl3). The monoacetate is identical with Zygacine (q.v.) and the veratroyl derivative also occurs naturally in the rhizomes of Veratrum album. The structure of the alkaloid as 7-deoxygermine, has been established by chemical and spectroscopic investigation. The alkaloid is highly toxic and resembles cevadine in its action.
Additional notes
DefinitionChEBI: Zygadenine is an alkaloid.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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