NP-MRD: Showing NP-Card for (3e,8ar)-2-methyl-3-(phenylmethylidene)-tetrahydropyrrolo[1,2-a]pyrazine-1,4-dione (NP0225979)

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Record Information

Version

2.0

Created at

2022-09-06 04:52:01 UTC

Updated at

2022-09-06 04:52:01 UTC

NP-MRD ID

NP0225979

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3e,8ar)-2-methyl-3-(phenylmethylidene)-tetrahydropyrrolo[1,2-a]pyrazine-1,4-dione

Description

(3E,8aR)-2-methyl-3-(phenylmethylidene)-octahydropyrrolo[1,2-a]pyrazine-1,4-dione belongs to the class of organic compounds known as 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), or a derivative thereof. (3e,8ar)-2-methyl-3-(phenylmethylidene)-tetrahydropyrrolo[1,2-a]pyrazine-1,4-dione is found in Garcinia atroviridis. Based on a literature review very few articles have been published on (3E,8aR)-2-methyl-3-(phenylmethylidene)-octahydropyrrolo[1,2-a]pyrazine-1,4-dione.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062206522D          

 19 21  0  0  1  0            999 V2000
    2.7845    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.1104    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.1104    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1435    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411    1.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    4.8229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    4.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4990    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  5  9  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
  2 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 14 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0225979

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN1C(=O)[C@H]2CCCN2C(=O)\C1=C/C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H16N2O2/c1-16-13(10-11-6-3-2-4-7-11)15(19)17-9-5-8-12(17)14(16)18/h2-4,6-7,10,12H,5,8-9H2,1H3/b13-10+/t12-/m1/s1

> <INCHI_KEY>
SNYXWODAEROITA-GMCKNXKJSA-N

> <FORMULA>
C15H16N2O2

> <MOLECULAR_WEIGHT>
256.305

> <EXACT_MASS>
256.121177763

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
27.442249829936657

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3E,8aR)-2-methyl-3-(phenylmethylidene)-octahydropyrrolo[1,2-a]pyrazine-1,4-dione

> <JCHEM_LOGP>
0.9822626309999996

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.96353357561611

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6971752760947391

> <JCHEM_POLAR_SURFACE_AREA>
40.620000000000005

> <JCHEM_REFRACTIVITY>
73.36810000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(3E,8aR)-2-methyl-3-(phenylmethylidene)-tetrahydropyrrolo[1,2-a]pyrazine-1,4-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       5.198   1.303   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0       3.864   2.073   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       2.530   1.303   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.530  -0.237   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.197   2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.268   1.597   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.173   2.843   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.268   4.089   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       1.197   3.613   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       2.530   4.383   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.530   5.923   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.864   3.613   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.198   4.383   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.198   5.923   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.864   6.693   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.864   8.233   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.198   9.003   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.531   8.233   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.531   6.693   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    5   10                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    2   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   14                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₆N₂O₂

Average Mass

256.3050 Da

Monoisotopic Mass

256.12118 Da

IUPAC Name

(3E,8aR)-2-methyl-3-(phenylmethylidene)-octahydropyrrolo[1,2-a]pyrazine-1,4-dione

Traditional Name

(3E,8aR)-2-methyl-3-(phenylmethylidene)-tetrahydropyrrolo[1,2-a]pyrazine-1,4-dione

CAS Registry Number

Not Available

SMILES

CN1C(=O)[C@H]2CCCN2C(=O)\C1=C/C1=CC=CC=C1

InChI Identifier

InChI=1S/C15H16N2O2/c1-16-13(10-11-6-3-2-4-7-11)15(19)17-9-5-8-12(17)14(16)18/h2-4,6-7,10,12H,5,8-9H2,1H3/b13-10+/t12-/m1/s1

InChI Key

SNYXWODAEROITA-GMCKNXKJSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Garcinia atroviridis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 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), or a derivative thereof.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acids and derivatives

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Dioxopiperazine
2,5-dioxopiperazine
N-methylpiperazine
N-alkylpiperazine
Monocyclic benzene moiety
1,4-diazinane
Piperazine
Benzenoid
Pyrrolidine
Tertiary carboxylic acid amide
Lactam
Carboxamide group
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	0.98	ChemAxon
pKa (Strongest Acidic)	17.96	ChemAxon
pKa (Strongest Basic)	-0.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	40.62 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	73.37 m³·mol⁻¹	ChemAxon
Polarizability	27.44 Å³	ChemAxon
Number of Rings	3	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163191172

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3e,8ar)-2-methyl-3-(phenylmethylidene)-tetrahydropyrrolo[1,2-a]pyrazine-1,4-dione (NP0225979)

MOL for NP0225979 ((3e,8ar)-2-methyl-3-(phenylmethylidene)-tetrahydropyrrolo[1,2-a]pyrazine-1,4-dione)

3D MOL for NP0225979 ((3e,8ar)-2-methyl-3-(phenylmethylidene)-tetrahydropyrrolo[1,2-a]pyrazine-1,4-dione)

3D SDF for NP0225979 ((3e,8ar)-2-methyl-3-(phenylmethylidene)-tetrahydropyrrolo[1,2-a]pyrazine-1,4-dione)

3D-SDF for NP0225979 ((3e,8ar)-2-methyl-3-(phenylmethylidene)-tetrahydropyrrolo[1,2-a]pyrazine-1,4-dione)

PDB for NP0225979 ((3e,8ar)-2-methyl-3-(phenylmethylidene)-tetrahydropyrrolo[1,2-a]pyrazine-1,4-dione)

3D PDB for NP0225979 ((3e,8ar)-2-methyl-3-(phenylmethylidene)-tetrahydropyrrolo[1,2-a]pyrazine-1,4-dione)

SMILES for NP0225979 ((3e,8ar)-2-methyl-3-(phenylmethylidene)-tetrahydropyrrolo[1,2-a]pyrazine-1,4-dione)

INCHI for NP0225979 ((3e,8ar)-2-methyl-3-(phenylmethylidene)-tetrahydropyrrolo[1,2-a]pyrazine-1,4-dione)

Structure for NP0225979 ((3e,8ar)-2-methyl-3-(phenylmethylidene)-tetrahydropyrrolo[1,2-a]pyrazine-1,4-dione)

3D Structure for NP0225979 ((3e,8ar)-2-methyl-3-(phenylmethylidene)-tetrahydropyrrolo[1,2-a]pyrazine-1,4-dione)