NP-MRD: Showing NP-Card for Nigellimine N-oxide (NP0335890)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2024-09-11 03:43:58 UTC

Updated at

2024-09-11 03:43:58 UTC

NP-MRD ID

NP0335890

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Nigellimine N-oxide

Description

(2S,3'S)-alpha-Amino-2-carboxy-5-oxo-1-pyrrolidinebutanoic acid belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom (2S,3'S)-alpha-Amino-2-carboxy-5-oxo-1-pyrrolidinebutanoic acid is a very strong basic compound (based on its pKa). Outside of the human body, (2S,3'S)-alpha-Amino-2-carboxy-5-oxo-1-pyrrolidinebutanoic acid has been detected, but not quantified in, mushrooms. This could make (2S,3's)-alpha-amino-2-carboxy-5-oxo-1-pyrrolidinebutanoic acid a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061307072D          

 16 17  0  0  0  0            999 V2000
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  8  1  1  0  0  0  0
  9  4  1  0  0  0  0
  9  6  2  0  0  0  0
 10  7  2  0  0  0  0
 10  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
 12 11  2  0  0  0  0
 13  5  1  0  0  0  0
 13  8  2  0  0  0  0
 14 13  2  0  0  0  0
 15  2  1  0  0  0  0
 15 11  1  0  0  0  0
 16  3  1  0  0  0  0
 16 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0335890

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C=C2C(C)=N(=O)C=CC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H13NO3/c1-8-10-7-12(16-3)11(15-2)6-9(10)4-5-13(8)14/h4-7H,1-3H3

> <INCHI_KEY>
GVQWAJKTFATJEW-UHFFFAOYSA-N

> <FORMULA>
C12H13NO3

> <MOLECULAR_WEIGHT>
219.2365

> <EXACT_MASS>
219.089543287

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
22.9164626687919

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,7-dimethoxy-1-methyl-2λ⁵-isoquinolin-2-one

> <ALOGPS_LOGP>
0.90

> <JCHEM_LOGP>
0.8866989736666664

> <ALOGPS_LOGS>
-3.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
2.0021005864257884

> <JCHEM_POLAR_SURFACE_AREA>
43.92

> <JCHEM_REFRACTIVITY>
62.08540000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.34e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,7-dimethoxy-1-methyl-2λ⁵-isoquinolin-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       1.334  -2.310   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       8.002   0.000   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2   15                                                            
CONECT    3   16                                                            
CONECT    4    5    9                                                       
CONECT    5    4   13                                                       
CONECT    6    9   11                                                       
CONECT    7   10   12                                                       
CONECT    8    1   10   13                                                  
CONECT    9    4    6   10                                                  
CONECT   10    7    8    9                                                  
CONECT   11    6   12   15                                                  
CONECT   12    7   11   16                                                  
CONECT   13    5    8   14                                                  
CONECT   14   13                                                            
CONECT   15    2   11                                                       
CONECT   16    3   12                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
(2S,3's)-a-Amino-2-carboxy-5-oxo-1-pyrrolidinebutanoate	Generator
(2S,3's)-a-Amino-2-carboxy-5-oxo-1-pyrrolidinebutanoic acid	Generator
(2S,3's)-alpha-Amino-2-carboxy-5-oxo-1-pyrrolidinebutanoate	Generator
(2S,3's)-Α-amino-2-carboxy-5-oxo-1-pyrrolidinebutanoate	Generator
(2S,3's)-Α-amino-2-carboxy-5-oxo-1-pyrrolidinebutanoic acid	Generator

Chemical Formula

C₁₂H₁₃NO₃

Average Mass

219.2365 Da

Monoisotopic Mass

219.08954 Da

IUPAC Name

6,7-dimethoxy-1-methyl-2λ⁵-isoquinolin-2-one

Traditional Name

6,7-dimethoxy-1-methyl-2λ⁵-isoquinolin-2-one

CAS Registry Number

Not Available

SMILES

COC1=C(OC)C=C2C(C)=N(=O)C=CC2=C1

InChI Identifier

InChI=1S/C12H13NO3/c1-8-10-7-12(16-3)11(15-2)6-9(10)4-5-13(8)14/h4-7H,1-3H3

InChI Key

GVQWAJKTFATJEW-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline 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

Proline and derivatives

Alternative Parents

Substituents

Proline or derivatives
Alpha-amino acid
Oxoproline
Pyrrolidine carboxylic acid
Pyrrolidine carboxylic acid or derivatives
Heterocyclic fatty acid
Dicarboxylic acid or derivatives
Fatty acyl
Fatty acid
Pyrrolidone
N-alkylpyrrolidine
2-pyrrolidone
Pyrrolidine
Tertiary carboxylic acid amide
Carboxamide group
Lactam
Amino acid
Carboxylic acid
Azacycle
Organoheterocyclic compound
Amine
Primary amine
Organic oxide
Organooxygen compound
Organonitrogen compound
Primary aliphatic amine
Organic nitrogen compound
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	0.9	ALOGPS
logP	0.89	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Basic)	2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.92 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	62.09 m³·mol⁻¹	ChemAxon
Polarizability	22.92 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0039110

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018619

KNApSAcK ID

Not Available

Chemspider ID

26773844

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14101166

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Nigellimine N-oxide (NP0335890)

MOL for NP0335890 (Nigellimine N-oxide)

3D MOL for NP0335890 (Nigellimine N-oxide)

3D SDF for NP0335890 (Nigellimine N-oxide)

3D-SDF for NP0335890 (Nigellimine N-oxide)

PDB for NP0335890 (Nigellimine N-oxide)

3D PDB for NP0335890 (Nigellimine N-oxide)

SMILES for NP0335890 (Nigellimine N-oxide)

INCHI for NP0335890 (Nigellimine N-oxide)

Structure for NP0335890 (Nigellimine N-oxide)

3D Structure for NP0335890 (Nigellimine N-oxide)