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Amino acids and derivatives

Coprine

Also known as n-(1-hydroxycyclopropyl)-l-glutamine, N(5)-(1-Hydroxycyclopropyl)-L-glutamine, (2S)-2-amino-5-[(1-hydroxycyclopropyl)amino]-5-oxopentanoic acid

CAS 58919-61-2Formula C8H14N2O4Molar mass 202.21 g/mol
1 supplier listed
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Coprine chemical structure, C8H14N2O4, CAS 58919-61-2
2D chemical structure

Key facts

What buyers check first

All properties
CAS number
58919-61-2
Formula
C8H14N2O4
Molar mass
202.21 g/mol
HS code
292429
Category
Amino acids and derivatives

What is Coprine?

Plain description, key identifiers and synonyms

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.

Identifiers

Registry numbers, names and line notations, tap to copy

IUPAC name
(2S)-2-amino-5-[(1-hydroxycyclopropyl)amino]-5-oxopentanoic acid
CAS number
58919-61-2 CAS number cross-checked
Molecular formula
C8H14N2O4
UNII
28L2R8DM94
InChIKey
OEEZRBUCLFMTLD-YFKPBYRVSA-N
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
Canonical SMILES
NC(CCC(=O)NC1(O)CC1)C(=O)O
Isomeric SMILES
C1CC1(NC(=O)CC[C@@H](C(=O)O)N)O

Synonyms

  • n-(1-hydroxycyclopropyl)-l-glutamine
  • N(5)-(1-Hydroxycyclopropyl)-L-glutamine
  • (2S)-2-amino-5-[(1-hydroxycyclopropyl)amino]-5-oxopentanoic acid
  • L-Glutamine, N-(1-hydroxycyclopropyl)-
  • (2S)-2-amino-5-((1-hydroxycyclopropyl)amino)-5-oxopentanoic acid
  • L-coprine
  • n5-(1-hydroxycyclopropyl)glutamine
  • (2S)-5-amino-2-[(1-hydroxycyclopropyl)amino]-5-oxopentanoic acid
  • N5-1-hydroxycyclopropyl-l-glutamine

Physical and chemical properties

Measured values and descriptors computed from the structure

Physical and chemical properties

Measured values, check the supplier specification for your grade

No measured properties are recorded for this substance yet. Ask suppliers for a technical data sheet.

Values vary by grade. Ask suppliers for the COA or TDS of the batch you buy.

Computed descriptors

Calculated from the structure, useful for screening and formulation

Molecular weight
202.21 g/molcalc.
Exact mass
202.0954 Dacalc.
LogP (octanol/water)
-1.22calc.
Topological polar surface area
112.7 Ųcalc.
Hydrogen bond donors
4calc.
Hydrogen bond acceptors
4calc.
Rotatable bonds
5calc.
Heavy atoms
14calc.
Rings
1calc.
Aromatic rings
0calc.
Fraction sp3 carbons
0.75calc.
Formal charge
0calc.
Stereocentres
1calc.
Lipinski rule of five
Passes (0 violations)calc.

Calculated for screening. Confirm critical figures with the supplier.

Murcko scaffold

The ring system that remains when every side chain is removed

Murcko scaffold of this chemical, C1CC1

C1CC1

1 ring, 3 atoms, the Cyclopropane ring system.

17,446 other chemicals share this scaffold

Safety and hazards

GHS classification summary, not a safety data sheet

No GHS hazard classification is recorded for this substance yet. That does not mean it is harmless.

GHS classification summary, not a safety data sheet (SDS). Classifications can differ by supplier, grade and concentration. Always check the supplier's SDS.

Coprine suppliers

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Where suppliers are based

1 supplier in 1 country

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Coprine price

Indicative price range per kg from live supplier offers

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Uses and applications

What the substance is used for, by industry and function

Roles

  • enzyme inhibitor
  • eukaryotic metabolite
  • fungal metabolite
  • metabolite
  • mycotoxin
  • poison
  • toxin

Regulatory status

Inventories, regulations and trade controls that list this substance

No regulatory list memberships are recorded for this substance yet. Always check the rules of the importing and exporting country before trade.

HS code and trade data

Customs classification and reported world trade statistics

Global trade

World import and export statistics for the HS code Coprine is traded under.

HS 2924.29Indicative HS code

Cyclic amides (including cyclic carbamates) and their derivatives, salts thereof, other

World exports in 2024
$5.69B
−5.1% vs 2023, imports $5.8B
2019 to 2024
Top exporters
  1. China32.3%
  2. Switzerland * partner reported13.6%
  3. Norway * partner reported12.8%
Top importers
  1. United States15.9%
  2. Ireland15.8%
  3. Germany11.9%

* Partner reported figures, a lower bound.

Reported customs values in USD, not prices.Full trade data

The HS code shown for Coprine is indicative (it was assigned by structure rules). Confirm the classification with your customs broker before shipping.

Frequently asked questions

Quick answers about Coprine, based on the data on this page

What is 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').

What is the CAS number of Coprine?

The CAS registry number of Coprine is 58919-61-2.

What is the molecular formula and weight of Coprine?

The molecular formula of Coprine is C8H14N2O4 and its molar mass is 202.21 g/mol.

What is Coprine used for?

Known uses and roles of Coprine include enzyme inhibitor, eukaryotic metabolite, fungal metabolite, metabolite, mycotoxin and 2 more.

Is Coprine hazardous?

No GHS hazard classification for Coprine is recorded on CompoundList yet. That does not prove it is safe. Always read the supplier safety data sheet.

What is the HS code of Coprine?

Coprine is usually classified under HS code 292429 (Cyclic amides (including cyclic carbamates) and their derivatives, salts thereof, other). This is indicative, confirm it with your customs broker before shipping.

Where can I buy Coprine?

CompoundList lists 1 supplier of Coprine in China. Send one free request to get and compare quotes. Your contact details stay private until you accept a quote.

What is the price of Coprine?

Suppliers quote Coprine on request because prices depend on grade, purity, quantity and destination. A free request on CompoundList gets you several quotes to compare.

Guides for buyers

Practical guides that help when you source, ship or handle Coprine

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Data last updated 7 Oct 2026. Details may have changed, please confirm them with the supplier. Report an error on this page
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