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Pyrrolizine-2,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-5,6-dimethyl(1,6)dioxacyclododecino(2,3,4-gh)-

PubChem CID
5321232
Structure
Pyrrolizine-2,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-5,6-dimethyl(1,6)dioxacyclododecino(2,3,4-gh)-_small.png
Pyrrolizine-2,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-5,6-dimethyl(1,6)dioxacyclododecino(2,3,4-gh)-_3D_Structure.png
Molecular Formula
Synonyms
  • Inegerrimine
  • Intergerrimine
  • 12-Hydroxysenecionan-11,16-dione #
  • HKODIGSRFALUTA-QCDXTXTGSA-N
  • NSC79540
Molecular Weight
335.4 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-27
  • Modify:
    2025-01-25
See also: Integerrimine (annotation moved to).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Pyrrolizine-2,7-dione, 3-ethylidene-3,4,5,6,9,11,13,14,14a,14b-decahydro-6-hydroxy-5,6-dimethyl(1,6)dioxacyclododecino(2,3,4-gh)-.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(4Z)-4-ethylidene-7-hydroxy-6,7-dimethyl-2,9-dioxa-14-azatricyclo[9.5.1.014,17]heptadec-11-ene-3,8-dione
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C18H25NO5/c1-4-12-9-11(2)18(3,22)17(21)23-10-13-5-7-19-8-6-14(15(13)19)24-16(12)20/h4-5,11,14-15,22H,6-10H2,1-3H3/b12-4-
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

HKODIGSRFALUTA-QCDXTXTGSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

C/C=C\1/CC(C(C(=O)OCC2=CCN3C2C(CC3)OC1=O)(C)O)C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C18H25NO5
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

480-79-5

2.3.2 NSC Number

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • integerrimine
  • intergerrimine
  • senecionine
  • senecionine citrate (1:1)
  • senecionine citratre
  • senecionine, (15E)-isomer
  • squalidine

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
335.4 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
1.1
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
335.17327290 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
335.17327290 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
76.1 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
24
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
611
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
4
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 2021.10.14)

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 13C NMR Spectra

1 of 2
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 GC-MS

NIST Number
103696
Library
Main library
Total Peaks
44
m/z Top Peak
119
m/z 2nd Highest
93
m/z 3rd Highest
120
Thumbnail
Thumbnail

6 Pharmacology and Biochemistry

6.1 MeSH Pharmacological Classification

Antineoplastic Agents, Phytogenic
Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity. (See all compounds classified as Antineoplastic Agents, Phytogenic.)

7 Literature

7.1 Consolidated References

7.2 NLM Curated PubMed Citations

7.3 Chemical Co-Occurrences in Literature

8 Taxonomy

9 Classification

9.1 MeSH Tree

10 Information Sources

  1. DTP/NCI
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  2. Natural Product Activity and Species Source (NPASS)
  3. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
  4. SpectraBase
  5. PubChem
  6. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
    Antineoplastic Agents, Phytogenic
    https://www.ncbi.nlm.nih.gov/mesh/68000972
CONTENTS