NP-MRD: Showing NP-Card for L-Coprine (NP0047918)

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Record Information

Version

2.0

Created at

2022-03-17 20:48:04 UTC

Updated at

2022-03-17 20:48:04 UTC

NP-MRD ID

NP0047918

Secondary Accession Numbers

None

Natural Product Identification

Common Name

L-Coprine

Description

L-Coprine belongs to the class of organic compounds known as glutamine and derivatives. Glutamine and derivatives 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. This causes the build of of acetaldehyde in the body. 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. L-Coprine is a very strong basic compound (based on its pKa). Outside of the human body, L-Coprine has been detected, but not quantified in, mushrooms. This could make L-coprine a potential biomarker for the consumption of these foods. L-Coprine is a potentially toxic compound. Coprine may cause symptoms such as flushing, headache, nausea, palpitations, dyspnea, dizziness. L-Coprine is found in Coprinus atramentarius . Coprine interferes with the bodys ability to metabolize alcohol.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 09051417012D          

 14 14  0  0  0  0            999 V2000
   -1.6392    3.1660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3537    3.5785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1729    3.6392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2448    2.8174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9247    3.5785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0682    3.1660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2103    3.1660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4971    3.1660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9247    4.4035    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7826    3.5785    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0682    2.3410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5042    3.5785    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2103    2.3410    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8651    2.6357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  4  3  1  0  0  0  0
  5  1  1  0  0  0  0
  6  2  1  0  0  0  0
  7  5  1  0  0  0  0
  8  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 10  8  1  4  0  0  0
 11  6  1  0  0  0  0
 12  7  2  0  0  0  0
 13  7  1  0  0  0  0
 14  8  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047918

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(CCC(O)=NC1(O)CC1)C(O)=O

> <INCHI_IDENTIFIER>
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)

> <INCHI_KEY>
OEEZRBUCLFMTLD-UHFFFAOYSA-N

> <FORMULA>
C8H14N2O4

> <MOLECULAR_WEIGHT>
202.2078

> <EXACT_MASS>
202.095356946

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
20.0716518512251

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-amino-4-[(1-hydroxycyclopropyl)-C-hydroxycarbonimidoyl]butanoic acid

> <ALOGPS_LOGP>
-3.03

> <JCHEM_LOGP>
-3.1532299012916543

> <ALOGPS_LOGS>
-1.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
5.628406398555498

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.0284316988801385

> <JCHEM_PKA_STRONGEST_BASIC>
9.536041157635005

> <JCHEM_POLAR_SURFACE_AREA>
116.14000000000001

> <JCHEM_REFRACTIVITY>
47.4276

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.96e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-4-[(1-hydroxycyclopropyl)-C-hydroxycarbonimidoyl]butanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-14         0                                  
HETATM    1  C   UNK     0      -3.060   5.910   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.394   6.680   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.656   6.793   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -9.790   5.259   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.726   6.680   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.727   5.910   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.393   5.910   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -8.395   5.910   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -1.726   8.220   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      -7.061   6.680   0.000  0.00  0.00           N+0
HETATM   11  O   UNK     0      -5.727   4.370   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       0.941   6.680   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      -0.393   4.370   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -7.215   4.920   0.000  0.00  0.00           O+0
CONECT    1    2    5                                                       
CONECT    2    1    6                                                       
CONECT    3    4    8                                                       
CONECT    4    3    8                                                       
CONECT    5    1    7    9                                                  
CONECT    6    2   10   11                                                  
CONECT    7    5   12   13                                                  
CONECT    8    3    4   10   14                                             
CONECT    9    5                                                            
CONECT   10    6    8                                                       
CONECT   11    6                                                            
CONECT   12    7                                                            
CONECT   13    7                                                            
CONECT   14    8                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol

Synonyms

Value	Source
Coprine	HMDB
N(5)-(1-Hydroxycyclopropyl)-L-glutamine	HMDB
N-(1-Hydroxycyclopropyl)-L-glutamine	HMDB
2-Amino-4-[(1-hydroxycyclopropyl)-C-hydroxycarbonimidoyl]butanoate	Generator

Chemical Formula

C₈H₁₄N₂O₄

Average Mass

202.2078 Da

Monoisotopic Mass

202.09536 Da

IUPAC Name

2-amino-4-[(1-hydroxycyclopropyl)-C-hydroxycarbonimidoyl]butanoic acid

Traditional Name

2-amino-4-[(1-hydroxycyclopropyl)-C-hydroxycarbonimidoyl]butanoic acid

CAS Registry Number

58919-61-2

SMILES

NC(CCC(O)=NC1(O)CC1)C(O)=O

InChI Identifier

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)

InChI Key

OEEZRBUCLFMTLD-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Agaricus bisporus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Coprinus atramentarius	Fungi	KNApSAcK
Pleurotus ostreatus	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as glutamine and derivatives. Glutamine and derivatives 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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Glutamine and derivatives

Alternative Parents

Substituents

Glutamine 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

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-3	ALOGPS
logP	-3.2	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	2.03	ChemAxon
pKa (Strongest Basic)	9.54	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	116.14 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	47.43 m³·mol⁻¹	ChemAxon
Polarizability	20.07 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon