L-Coprine

Basic Info

Common NameL-Coprine(F04685)
2D Structure
Description

L-Coprine is found in mushrooms. L-Coprine is present in the moderately toxic ink cap mushroom Coprinus atramentarius (common ink cap). Produces an oversensitivity to ethanol in some people.

L-Coprine belongs to the family of Alpha Amino Acids and Derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon)[1]. (Reference: [1] Amino Acid: http://en.wikipedia.org/wiki/Amino_acid).

FRCD IDF04685
CAS Number58919-61-2
PubChem CID4479242
FormulaC8H14N2O4
IUPAC Name

2-amino-5-[(1-hydroxycyclopropyl)amino]-5-oxopentanoic acid

InChI Key

OEEZRBUCLFMTLD-UHFFFAOYSA-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)

Canonical SMILES

C1CC1(NC(=O)CCC(C(=O)O)N)O

Isomeric SMILES

C1CC1(NC(=O)CCC(C(=O)O)N)O

WikipediaL-Coprine
Synonyms
        
            2-amino-4-[(1-hydroxycyclopropyl)carbamoyl]butanoic acid
        
            L-coprine
        
            AC1NAMAQ
        
            2-amino-5-[(1-hydroxycyclopropyl)amino]-5-oxopentanoic acid
Classifies
                

                  
                    Fungal Toxin
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
SubclassAmino acids, peptides, and analogues
Intermediate Tree NodesAmino acids and derivatives - Alpha amino acids and derivatives
Direct ParentGlutamine and derivatives
Alternative Parents
Molecular FrameworkAliphatic homomonocyclic compounds
SubstituentsGlutamine or derivatives - Alpha-amino acid - Fatty acyl - Fatty acid - Fatty amide - N-acyl-amine - Carboxamide group - Amino acid - Cyclopropanol - Secondary carboxylic acid amide - Alkanolamine - Carboxylic acid - Monocarboxylic acid or derivatives - Organic nitrogen compound - Organonitrogen compound - Organooxygen compound - Primary aliphatic amine - Primary amine - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Carbonyl group - Amine - Organic oxygen compound - Aliphatic homomonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as glutamine and derivatives. These are compounds containing glutamine or a derivative thereof resulting from reaction of glutamine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.

Properties

Property NameProperty Value
Molecular Weight202.21
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count5
Rotatable Bond Count5
Complexity250
Monoisotopic Mass202.095
Exact Mass202.095
XLogP-3.4
Formal Charge0
Heavy Atom Count14
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.8512
Human Intestinal AbsorptionHIA-0.9389
Caco-2 PermeabilityCaco2-0.8071
P-glycoprotein SubstrateNon-substrate0.6401
P-glycoprotein InhibitorNon-inhibitor0.9775
Non-inhibitor0.9804
Renal Organic Cation TransporterNon-inhibitor0.9474
Distribution
Subcellular localizationMitochondria0.6384
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8066
CYP450 2D6 SubstrateNon-substrate0.8392
CYP450 3A4 SubstrateNon-substrate0.6445
CYP450 1A2 InhibitorNon-inhibitor0.9206
CYP450 2C9 InhibitorNon-inhibitor0.9302
CYP450 2D6 InhibitorNon-inhibitor0.9258
CYP450 2C19 InhibitorNon-inhibitor0.9101
CYP450 3A4 InhibitorNon-inhibitor0.8493
CYP Inhibitory PromiscuityLow CYP Inhibitory Promiscuity0.9922
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.9973
Non-inhibitor0.9808
AMES ToxicityNon AMES toxic0.8164
CarcinogensNon-carcinogens0.9505
Fish ToxicityLow FHMT0.8367
Tetrahymena Pyriformis ToxicityLow TPT0.9305
Honey Bee ToxicityLow HBT0.7528
BiodegradationReady biodegradable0.8367
Acute Oral ToxicityIII0.6271
Carcinogenicity (Three-class)Non-required0.6887
Model Value Unit
Absorption
Aqueous solubility-1.7988LogS
Caco-2 Permeability-0.4991LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.1031LD50, mol/kg
Fish Toxicity2.1747pLC50, mg/L
Tetrahymena Pyriformis Toxicity-0.7602pIGC50, ug/L

Targets

Target Details

Aldehyde dehydrogenase family 16 member A1

General Function:
Aldehyde dehydrogenase (nad) activity
Gene Name:
ALDH16A1
Uniprot ID:
Q8IZ83
Molecular Weight:
85126.605 Da
Mechanism of Action:
It metabolises to 1-aminocyclopropanol, a closely-related chemical to Disulfiram and exhibits the same mechanism of action: inhibition of the enzyme acetaldehyde dehydrogenase, which is required for alchohol metabolism.
References
  1. Wikipedia. Disulfiram. Last Updated 14 June 2009. : http://en.wikipedia.org/wiki/Disulfiram
Target Details

Aldehyde dehydrogenase family 8 member A1

General Function:
Retinal dehydrogenase activity
Specific Function:
Converts 9-cis-retinal to 9-cis-retinoic acid. Has lower activity towards 13-cis-retinal. Has much lower activity towards all-trans-retinal. Has highest activity with benzaldehyde and decanal (in vitro). Has a preference for NAD, but shows considerable activity with NADP (in vitro).
Gene Name:
ALDH8A1
Uniprot ID:
Q9H2A2
Molecular Weight:
53400.88 Da
Mechanism of Action:
It metabolises to 1-aminocyclopropanol, a closely-related chemical to Disulfiram and exhibits the same mechanism of action: inhibition of the enzyme acetaldehyde dehydrogenase, which is required for alchohol metabolism.
References
  1. Wikipedia. Disulfiram. Last Updated 14 June 2009. : http://en.wikipedia.org/wiki/Disulfiram
Target Details

Aldehyde dehydrogenase X, mitochondrial

General Function:
Aldehyde dehydrogenase (nad) activity
Specific Function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation.
Gene Name:
ALDH1B1
Uniprot ID:
P30837
Molecular Weight:
57205.93 Da
Mechanism of Action:
It metabolises to 1-aminocyclopropanol, a closely-related chemical to Disulfiram and exhibits the same mechanism of action: inhibition of the enzyme acetaldehyde dehydrogenase, which is required for alchohol metabolism.
References
  1. Wikipedia. Disulfiram. Last Updated 14 June 2009. : http://en.wikipedia.org/wiki/Disulfiram
Target Details

Aldehyde dehydrogenase family 1 member A3

General Function:
Thyroid hormone binding
Specific Function:
Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Seems to be the key enzyme in the formation of an RA gradient along the dorso-ventral axis during the early eye development and also in the development of the olfactory system (By similarity).
Gene Name:
ALDH1A3
Uniprot ID:
P47895
Molecular Weight:
56107.995 Da
Mechanism of Action:
It metabolises to 1-aminocyclopropanol, a closely-related chemical to Disulfiram and exhibits the same mechanism of action: inhibition of the enzyme acetaldehyde dehydrogenase, which is required for alchohol metabolism.
References
  1. Wikipedia. Disulfiram. Last Updated 14 June 2009. : http://en.wikipedia.org/wiki/Disulfiram
Target Details

Aldehyde dehydrogenase, mitochondrial

General Function:
Electron carrier activity
Gene Name:
ALDH2
Uniprot ID:
P05091
Molecular Weight:
56380.93 Da
Mechanism of Action:
It metabolises to 1-aminocyclopropanol, a closely-related chemical to Disulfiram and exhibits the same mechanism of action: inhibition of the enzyme acetaldehyde dehydrogenase, which is required for alchohol metabolism.
References
  1. Wikipedia. Disulfiram. Last Updated 14 June 2009. : http://en.wikipedia.org/wiki/Disulfiram
Target Details

Aldehyde dehydrogenase family 3 member B2

General Function:
Aldehyde dehydrogenase [nad(p)+] activity
Gene Name:
ALDH3B2
Uniprot ID:
P48448
Molecular Weight:
42634.6 Da
Mechanism of Action:
It metabolises to 1-aminocyclopropanol, a closely-related chemical to Disulfiram and exhibits the same mechanism of action: inhibition of the enzyme acetaldehyde dehydrogenase, which is required for alchohol metabolism.
References
  1. Wikipedia. Disulfiram. Last Updated 14 June 2009. : http://en.wikipedia.org/wiki/Disulfiram
Target Details

Aldehyde dehydrogenase family 3 member B1

General Function:
Aldehyde dehydrogenase [nad(p)+] activity
Specific Function:
Oxidizes medium and long chain saturated and unsaturated aldehydes. Metabolizes also benzaldehyde. Low activity towards acetaldehyde and 3,4-dihydroxyphenylacetaldehyde. May not metabolize short chain aldehydes. May use both NADP(+) and NAD(+) as cofactors. May have a protective role against the cytotoxicity induced by lipid peroxidation.
Gene Name:
ALDH3B1
Uniprot ID:
P43353
Molecular Weight:
51839.245 Da
Mechanism of Action:
It metabolises to 1-aminocyclopropanol, a closely-related chemical to Disulfiram and exhibits the same mechanism of action: inhibition of the enzyme acetaldehyde dehydrogenase, which is required for alchohol metabolism.
References
  1. Wikipedia. Disulfiram. Last Updated 14 June 2009. : http://en.wikipedia.org/wiki/Disulfiram
Target Details

Aldehyde dehydrogenase, dimeric NADP-preferring

General Function:
Benzaldehyde dehydrogenase (nad+) activity
Specific Function:
ALDHs play a major role in the detoxification of alcohol-derived acetaldehyde. They are involved in the metabolism of corticosteroids, biogenic amines, neurotransmitters, and lipid peroxidation. This protein preferentially oxidizes aromatic aldehyde substrates. It may play a role in the oxidation of toxic aldehydes.
Gene Name:
ALDH3A1
Uniprot ID:
P30838
Molecular Weight:
50394.57 Da
Mechanism of Action:
It metabolises to 1-aminocyclopropanol, a closely-related chemical to Disulfiram and exhibits the same mechanism of action: inhibition of the enzyme acetaldehyde dehydrogenase, which is required for alchohol metabolism.
References
  1. Wikipedia. Disulfiram. Last Updated 14 June 2009. : http://en.wikipedia.org/wiki/Disulfiram