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(±) -Longamide

CAT: 0804-HY-W834359-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-W834359-01Size:1 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
(±) -Longamide is a polycyclic bioactive metabolite isolated from sponges that has several bromopyrrole fragments, as well as a weak inhibitor of IDO1[1].
CAS Number
219783-00-3
UNSPSC
12352005
Hazard Statement
H302-H315-H319-H335
Target
Endogenous Metabolite; Indoleamine 2,3-Dioxygenase (IDO)
Type
Reference compound
Related Pathways
Metabolic Enzyme/Protease
Field of Research
Others
Assay Protocol
https://www.medchemexpress.com/racemic-longamide.html
Smiles
O=C1NCC(N2C(Br)=C(C=C12)Br)O
Molecular Formula
C7H6Br2N2O2
Molecular Weight
309.94
Precautions
P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P330-P362-P403+P233-P405-P501
References & Citations
[1]S. Marchais, et al. Synthesis of the marine carbinolamine (+/−) longamide control of N-1 and C-3 bromopyrrole nucleophilicity. Tetrahedron Letters. Volume 40, Issue 30, 23 July 1999, Pages 5519-5522.|[2]Shiokawa Z, et al. Discovery of a Novel Scaffold as an Indoleamine 2,3-Dioxygenase 1 (IDO1) Inhibitor Based on the Pyrrolopiperazinone Alkaloid, Longamide B. ChemMedChem. 2016 Dec 16;11 (24) :2682-2689.
Shipping Conditions
Room temperature
Scientific Category
Reference compound1
Clinical Information
No Development Reported

Chemical Information

6,7-dibromo-4-hydroxy-1H,2H,3H,4H-pyrrolo[1,2-a]pyrazin-1-one

6,7-dibromo-4-hydroxy-1H,2H,3H,4H-pyrrolo[1,2-a]pyrazin-1-one has been reported in Homaxinella with data available.

CAS Number219783-00-3
PubChem CID10902963
IUPAC Name6,7-dibromo-4-hydroxy-3,4-dihydro-2H-pyrrolo[1,2-a]pyrazin-1-one
Molecular FormulaC7H6Br2N2O2
Molecular Weight309.94
XLogP1.1
Topological Polar Surface Area54.3
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count0
Heavy Atom Count13
Formal Charge0
Complexity239
SMILES
C1C(N2C(=CC(=C2Br)Br)C(=O)N1)O
InChI
InChI=1S/C7H6Br2N2O2/c8-3-1-4-7(13)10-2-5(12)11(4)6(3)9/h1,5,12H,2H2,(H,10,13)
InChIKey
NUVAABCZBKHWMX-UHFFFAOYSA-N
Chemical Structure
2D Structure
2D structure of 6,7-dibromo-4-hydroxy-1H,2H,3H,4H-pyrrolo[1,2-a]pyrazin-1-one
CAS: 219783-00-3
CID: 10902963
Formula: C7H6Br2N2O2
MW: 309.94
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight309.94
XLogP31.1
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count0
Exact Mass309.87755
Monoisotopic Mass307.87960
Topological Polar Surface Area54.3 Ų
Heavy Atom Count13
Formal Charge0
Complexity239
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
TN7157-01(+/-) -Longamide
MBS5801502(+/-)-Longamide

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