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Coprine

CAT: 0931-T31009-01Size: 1 mL - 10 mM (in DMSO)Dry Ice: NoHazardous: No
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CAT#:0931-T31009-01Size:1 mL - 10 mM (in DMSO)
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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CAS Number
58919-61-2
Target
Dehydrogenase, Others
Related Pathways
Metabolism, Others
Bioactivity
Coprine is a poisonous toxin that exists in mushrooms resulting in coprinus syndrome.
Smiles
N[C@@H](CCC(=O)NC1(O)CC1)C(O)=O
Molecular Formula
C8H14N2O4
Molecular Weight
202.21
Shipping Conditions
Ice Packs
Storage Temperature
-20°C

Chemical Information

Coprine

Coprine is a non-proteinogenic L-alpha-amino acid that is L-glutamine in which one of the hydrogens attached to the amide nitrogen is replaced by a 1-hydroxycyclopropyl group. Found in the ink-cap mushroom, Coprinus atramentarius, it causes an unpleasant hypersensitivity to alcohol (the 'disulfiram effect'). It has a role as a metabolite, a mycotoxin and an EC 1.2.1.3 [aldehyde dehydrogenase (NAD(+))] inhibitor. It is a L-glutamine derivative, a dicarboxylic acid monoamide, a member of cyclopropanes and a non-proteinogenic L-alpha-amino acid.

CAS Number58919-61-2
PubChem CID108079
IUPAC Name(2S)-2-amino-5-[(1-hydroxycyclopropyl)amino]-5-oxopentanoic acid
Molecular FormulaC8H14N2O4
Molecular Weight202.21
XLogP-3.4
Topological Polar Surface Area113
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count5
Rotatable Bond Count5
Heavy Atom Count14
Formal Charge0
Complexity250
SMILES
C1CC1(NC(=O)CC[C@@H](C(=O)O)N)O
InChI
InChI=1S/C8H14N2O4/c9-5(7(12)13)1-2-6(11)10-8(14)3-4-8/h5,14H,1-4,9H2,(H,10,11)(H,12,13)/t5-/m0/s1
InChIKey
OEEZRBUCLFMTLD-YFKPBYRVSA-N
Chemical Structure
2D Structure
2D structure of Coprine
CAS: 58919-61-2
CID: 108079
Formula: C8H14N2O4
MW: 202.21
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight202.21
XLogP3-3.4
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count5
Rotatable Bond Count5
Exact Mass202.09535693
Monoisotopic Mass202.09535693
Topological Polar Surface Area113 Ų
Heavy Atom Count14
Formal Charge0
Complexity250
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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