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acetylseneciphylline N-oxide

PubChem CID
102144112
Structure
acetylseneciphylline N-oxide_small.png
acetylseneciphylline N-oxide_3D_Structure.png
Molecular Formula
Synonyms
  • acetylseneciphylline N-oxide
  • 123844-00-8
  • acetylseneciphylline oxide
  • CHEBI:136449
  • HY-N6848
Molecular Weight
391.4 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2015-12-24
  • Modify:
    2024-12-06
Description
Acetylseneciphylline N-oxide is a pyrrolizine alkaloid that is seneciphylline in which the hydroxy hydrogen has been replaced by an acetyl group and the tertiary amino function has been oxidised to the corresponding N-oxide. It has a role as a Jacobaea metabolite. It is an acetate ester, a macrocyclic lactone, an olefinic compound, an organic heterotricyclic compound, a pyrrolizine alkaloid and a tertiary amine oxide. It is functionally related to a seneciphylline.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
acetylseneciphylline N-oxide.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(1R,4Z,7R,17R)-4-ethylidene-7-methyl-6-methylidene-14-oxido-3,8-dioxo-2,9-dioxa-14-azoniatricyclo[9.5.1.014,17]heptadec-11-en-7-yl] acetate
Computed by LexiChem 2.6.6 (PubChem release 2019.06.18)

2.1.2 InChI

InChI=1S/C20H25NO7/c1-5-14-10-12(2)20(4,28-13(3)22)19(24)26-11-15-6-8-21(25)9-7-16(17(15)21)27-18(14)23/h5-6,16-17H,2,7-11H2,1,3-4H3/b14-5-/t16-,17-,20-,21?/m1/s1
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

2.1.3 InChIKey

VUEKZTPMPCTKDK-NZQWTBGOSA-N
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

2.1.4 SMILES

C/C=C\1/CC(=C)[C@@](C(=O)OCC2=CC[N+]3([C@H]2[C@@H](CC3)OC1=O)[O-])(C)OC(=O)C
Computed by OEChem 2.1.5 (PubChem release 2019.06.18)

2.2 Molecular Formula

C20H25NO7
Computed by PubChem 2.1 (PubChem release 2019.06.18)

2.3 Other Identifiers

2.3.1 ChEBI ID

2.3.2 Nikkaji Number

2.3.3 Wikidata

2.4 Synonyms

2.4.1 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
391.4 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
0.7
Reference
Computed by XLogP3 3.0 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Acceptor Count
Property Value
7
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Rotatable Bond Count
Property Value
2
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Exact Mass
Property Value
391.16310214 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
391.16310214 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
97Ų
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Heavy Atom Count
Property Value
28
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
798
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
3
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
1
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2015.09.10)

5 Chemical Vendors

6 Classification

6.1 ChEBI Ontology

6.2 MolGenie Organic Chemistry Ontology

7 Information Sources

CONTENTS