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(4aS,10bR)-Noroxomaritidine

PubChem CID
11184826
Structure
(4aS,10bR)-Noroxomaritidine_small.png
(4aS,10bR)-Noroxomaritidine_3D_Structure.png
Molecular Formula
Synonyms
  • (4aS,10bR)-Noroxomaritidine
  • CHEBI:136557
  • (4aS,10bR)-8-hydroxy-9-methoxy-4,4a-dihydro-3H,6H-5,10b-ethanophenanthridin-3-one
  • (1R,10S)-5-hydroxy-4-methoxy-9-azatetracyclo[7.5.2.01,10.02,7]hexadeca-2,4,6,13-tetraen-12-one
  • (1R,10S)-5-hydroxy-4-methoxy-9-azatetracyclo(7.5.2.01,10.02,7)hexadeca-2,4,6,13-tetraen-12-one
Molecular Weight
271.31 g/mol
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Dates
  • Create:
    2006-10-26
  • Modify:
    2025-01-10
Description
(4aS,10bR)-noroxomaritidine is an isoquinoline alkaloid that is 4,4a-dihydro-3H,6H-5,10b-ethanophenanthridin-3-one carrying additional hydroxy and methoxy substituents at positions 8 and 9 respectively (the 4aS,10bR-diastereomer). It has a role as a plant metabolite. It is an aromatic ether, an isoquinoline alkaloid, an organic heterotetracyclic compound, a member of phenols, an enone, a cyclic ketone, a bridged compound and a tertiary amino compound. It is a conjugate base of a (4aS,10bR)-noroxomaritidine(1+). It is an enantiomer of a (4aR,10bS)-noroxomaritidine.
(4aS,10bR)-Noroxomaritidine has been reported in Crinum asiaticum with data available.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
(4aS,10bR)-Noroxomaritidine.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1R,10S)-5-hydroxy-4-methoxy-9-azatetracyclo[7.5.2.01,10.02,7]hexadeca-2,4,6,13-tetraen-12-one
Computed by LexiChem 2.6.6 (PubChem release 2019.06.18)

2.1.2 InChI

InChI=1S/C16H17NO3/c1-20-14-8-12-10(6-13(14)19)9-17-5-4-16(12)3-2-11(18)7-15(16)17/h2-3,6,8,15,19H,4-5,7,9H2,1H3/t15-,16-/m0/s1
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

2.1.3 InChIKey

VEXDOCFQMVMPHJ-HOTGVXAUSA-N
Computed by InChI 1.0.5 (PubChem release 2019.06.18)

2.1.4 SMILES

COC1=C(C=C2CN3CC[C@]4([C@@H]3CC(=O)C=C4)C2=C1)O
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C16H17NO3
Computed by PubChem 2.1 (PubChem release 2019.06.18)

2.3 Other Identifiers

2.3.1 ChEBI ID

2.3.2 ChEMBL ID

2.3.3 KEGG ID

2.3.4 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
271.31 g/mol
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
XLogP3-AA
Property Value
1.4
Reference
Computed by XLogP3 3.0 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Hydrogen Bond Acceptor Count
Property Value
4
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Rotatable Bond Count
Property Value
1
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Exact Mass
Property Value
271.12084340 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Monoisotopic Mass
Property Value
271.12084340 Da
Reference
Computed by PubChem 2.1 (PubChem release 2021.05.07)
Property Name
Topological Polar Surface Area
Property Value
49.8 Ų
Reference
Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Property Name
Heavy Atom Count
Property Value
20
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
463
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
2
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
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 2010.01.29)

5 Chemical Vendors

6 Pharmacology and Biochemistry

6.1 Biochemical Reactions

7 Literature

7.1 Consolidated References

8 Interactions and Pathways

8.1 Pathways

9 Biological Test Results

9.1 BioAssay Results

10 Taxonomy

The LOTUS Initiative for Open Natural Products Research: frozen dataset union wikidata (with metadata) | DOI:10.5281/zenodo.5794106

11 Classification

11.1 ChEBI Ontology

11.2 LOTUS Tree

11.3 MolGenie Organic Chemistry Ontology

12 Information Sources

CONTENTS