NP-MRD: Showing NP-Card for (2s)-2-amino-4-[(1-hydroxycyclopropyl)-c-hydroxycarbonimidoyl]butanoic acid (NP0173168)

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Record Information

Version

2.0

Created at

2022-09-03 10:15:37 UTC

Updated at

2022-09-03 10:15:38 UTC

NP-MRD ID

NP0173168

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

Coprine belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. Coprine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. (2s)-2-amino-4-[(1-hydroxycyclopropyl)-c-hydroxycarbonimidoyl]butanoic acid is found in Coprinopsis atramentaria. (2s)-2-amino-4-[(1-hydroxycyclopropyl)-c-hydroxycarbonimidoyl]butanoic acid was first documented in 2003 (PMID: 14534493). Based on a literature review a small amount of articles have been published on coprine (PMID: 32685428) (PMID: 21370948).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 28 28  0  0  0  0  0  0  0  0999 V2000
   -2.6534   -0.5578   -1.5191 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3694   -0.0329   -0.1807 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.9020   -1.1285    0.7357 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7035   -1.8800    0.3378 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5697   -1.2287    0.1825 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6147   -2.0443   -0.3233 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9222   -0.0289    0.4267 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2500    0.5083    0.2247 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2537   -0.3028    0.7693 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5777    1.2763   -0.9958 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4656    1.9543    0.3514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5884    1.1973   -0.1764 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1009    1.6471   -1.2316 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3851    1.8791    1.0035 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5111    0.1674   -2.2319 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6257   -0.9312   -1.5914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4161    0.3110    0.1767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7585   -1.8773    0.7467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8853   -0.7753    1.7977 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5433   -2.7301    1.0848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9255   -2.4121   -0.6483 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4383   -2.6177   -1.1546 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6477   -0.9042    0.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6149    1.1668   -1.3873 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8353    1.5729   -1.7428 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6193    2.6741    0.4764 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4148    2.3381    0.7986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8557    2.7592    1.1849 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  5  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
  2 12  1  0
 12 14  1  0
 12 13  2  0
 11  8  1  0
  1 15  1  0
  1 16  1  0
  2 17  1  1
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  6 22  1  0
  9 23  1  0
 10 24  1  0
 10 25  1  0
 11 26  1  0
 11 27  1  0
 14 28  1  0
M  END


  Mrv1652309032212152D          

 14 14  0  0  1  0            999 V2000
    1.9252   -1.1645    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9252   -1.9895    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2107   -2.4020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4963   -1.9895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2182   -2.4020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2182   -3.2270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9327   -1.9895    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6471   -2.4020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1774   -1.7700    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3650   -3.1772    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1774   -3.0340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6397   -2.4020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3542   -1.9895    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6397   -3.2270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  2  0  0  0  0
  7  8  1  4  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  8 11  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0173168

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N[C@@H](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)/t5-/m0/s1

> <INCHI_KEY>
OEEZRBUCLFMTLD-YFKPBYRVSA-N

> <FORMULA>
C8H14N2O4

> <MOLECULAR_WEIGHT>
202.21

> <EXACT_MASS>
202.095356939

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
20.089616031100764

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-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>
5.628406398555496

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.0284316988801385

> <JCHEM_PKA_STRONGEST_BASIC>
9.536041157635005

> <JCHEM_POLAR_SURFACE_AREA>
116.14

> <JCHEM_REFRACTIVITY>
47.4276

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.96e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
coprine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  N   UNK     0       3.594  -2.174   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       3.594  -3.714   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.260  -4.484   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.926  -3.714   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.407  -4.484   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.407  -6.024   0.000  0.00  0.00           O+0
HETATM    7  N   UNK     0      -1.741  -3.714   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -3.075  -4.484   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -4.065  -3.304   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.548  -5.931   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -4.065  -5.663   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.927  -4.484   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.261  -3.714   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       4.927  -6.024   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10    8                                                       
CONECT   12    2   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

View in JSmol

Synonyms

Value	Source
(2S)-2,5-Diamino-5-oxopentanoic acid	ChEBI
L-Coprine	ChEBI
N(5)-(1-Hydroxycyclopropyl)-L-glutamine	ChEBI
(2S)-2,5-Diamino-5-oxopentanoate	Generator

Chemical Formula

C₈H₁₄N₂O₄

Average Mass

202.2100 Da

Monoisotopic Mass

202.09536 Da

IUPAC Name

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

Traditional Name

coprine

CAS Registry Number

Not Available

SMILES

N[C@@H](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)/t5-/m0/s1

InChI Key

OEEZRBUCLFMTLD-YFKPBYRVSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Coprinopsis atramentaria	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as l-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

L-alpha-amino acids

Alternative Parents

Substituents

L-alpha-amino acid
Fatty acid
Cyclopropanol
Amino acid
Alkanolamine
Carboximidic acid
Carboximidic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Propargyl-type 1,3-dipolar organic compound
Organic 1,3-dipolar compound
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic nitrogen compound
Primary amine
Amine
Carbonyl group
Organic oxygen compound
Organopnictogen compound
Hydrocarbon derivative
Organic oxide
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:3875 )
dicarboxylic acid monoamide (CHEBI:3875 )
cyclopropanes (CHEBI:3875 )
L-glutamine derivative (CHEBI:3875 )
Mushroom toxins (C08271 )

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	20.09 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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00001349

Chemspider ID

97180

KEGG Compound ID

C08271

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Coprine

METLIN ID

Not Available

PubChem Compound

108079

PDB ID

Not Available

ChEBI ID

3875

Good Scents ID

Not Available

References

General References

Parnmen S, Nooron N, Leudang S, Sikaphan S, Polputpisatkul D, Rangsiruji A: Phylogenetic evidence revealed Cantharocybe virosa (Agaricales, Hygrophoraceae) as a new clinical record for gastrointestinal mushroom poisoning in Thailand. Toxicol Res. 2019 Nov 26;36(3):239-248. doi: 10.1007/s43188-019-00024-2. eCollection 2020 Jul. [PubMed:32685428 ]
Haberl B, Pfab R, Berndt S, Greifenhagen C, Zilker T: Case series: Alcohol intolerance with Coprine-like syndrome after consumption of the mushroom Lepiota aspera (Pers.:Fr.) Quel., 1886 (Freckled Dapperling). Clin Toxicol (Phila). 2011 Feb;49(2):113-4. doi: 10.3109/15563650.2011.554840. [PubMed:21370948 ]
Saviuc P, Flesch F: [Acute higher funghi mushroom poisoning and its treatment]. Presse Med. 2003 Sep 20;32(30):1427-35. [PubMed:14534493 ]
LOTUS database [Link]

Showing NP-Card for (2s)-2-amino-4-[(1-hydroxycyclopropyl)-c-hydroxycarbonimidoyl]butanoic acid (NP0173168)

MOL for NP0173168 ((2s)-2-amino-4-[(1-hydroxycyclopropyl)-c-hydroxycarbonimidoyl]butanoic acid)

3D MOL for NP0173168 ((2s)-2-amino-4-[(1-hydroxycyclopropyl)-c-hydroxycarbonimidoyl]butanoic acid)

3D SDF for NP0173168 ((2s)-2-amino-4-[(1-hydroxycyclopropyl)-c-hydroxycarbonimidoyl]butanoic acid)

3D-SDF for NP0173168 ((2s)-2-amino-4-[(1-hydroxycyclopropyl)-c-hydroxycarbonimidoyl]butanoic acid)

PDB for NP0173168 ((2s)-2-amino-4-[(1-hydroxycyclopropyl)-c-hydroxycarbonimidoyl]butanoic acid)

3D PDB for NP0173168 ((2s)-2-amino-4-[(1-hydroxycyclopropyl)-c-hydroxycarbonimidoyl]butanoic acid)

SMILES for NP0173168 ((2s)-2-amino-4-[(1-hydroxycyclopropyl)-c-hydroxycarbonimidoyl]butanoic acid)

INCHI for NP0173168 ((2s)-2-amino-4-[(1-hydroxycyclopropyl)-c-hydroxycarbonimidoyl]butanoic acid)

Structure for NP0173168 ((2s)-2-amino-4-[(1-hydroxycyclopropyl)-c-hydroxycarbonimidoyl]butanoic acid)

3D Structure for NP0173168 ((2s)-2-amino-4-[(1-hydroxycyclopropyl)-c-hydroxycarbonimidoyl]butanoic acid)