NP-MRD: Showing NP-Card for 5-(3-methylbut-2-en-1-yl)-1h-pyrrolo[3,4-d]imidazole-4,6-dione (NP0222214)

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Record Information

Version

2.0

Created at

2022-09-05 23:59:56 UTC

Updated at

2022-09-05 23:59:56 UTC

NP-MRD ID

NP0222214

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-(3-methylbut-2-en-1-yl)-1h-pyrrolo[3,4-d]imidazole-4,6-dione

Description

5-(3-Methylbut-2-en-1-yl)-1H,4H,5H,6H-pyrrolo[3,4-d]imidazole-4,6-dione belongs to the class of organic compounds known as n-substituted carboxylic acid imides. N-substituted carboxylic acid imides are compounds comprising an N-substituted carboxylic acid imide group, with the general structure R1N(C(R2)=O)C(R3)=O (R2,R3=H, alkyl, aryl; R1=Anything but H). 5-(3-methylbut-2-en-1-yl)-1h-pyrrolo[3,4-d]imidazole-4,6-dione is found in Bridelia balansae. 5-(3-Methylbut-2-en-1-yl)-1H,4H,5H,6H-pyrrolo[3,4-d]imidazole-4,6-dione is a moderately basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191515402D          

 15 16  0  0  0  0            999 V2000
   -1.6904   -1.6839    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2779   -0.9694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4529   -0.9694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0404   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7846   -0.2549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0146    1.1971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542    0.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8388    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3237   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8388   -0.9224    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -0.6674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2695   -0.9224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0146   -1.7070    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6904   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  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
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  8 12  2  0  0  0  0
 12 13  1  0  0  0  0
  5 13  1  0  0  0  0
 13 14  2  0  0  0  0
  2 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0222214

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCN1C(=O)C2=C(N=CN2)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C10H11N3O2/c1-6(2)3-4-13-9(14)7-8(10(13)15)12-5-11-7/h3,5H,4H2,1-2H3,(H,11,12)

> <INCHI_KEY>
WAOGVUUKMCZPQO-UHFFFAOYSA-N

> <FORMULA>
C10H11N3O2

> <MOLECULAR_WEIGHT>
205.217

> <EXACT_MASS>
205.085126606

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
21.090395087838548

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-(3-methylbut-2-en-1-yl)-1H,4H,5H,6H-pyrrolo[3,4-d]imidazole-4,6-dione

> <ALOGPS_LOGP>
0.57

> <JCHEM_LOGP>
0.46572662000000054

> <ALOGPS_LOGS>
-1.35

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.675641255038071

> <JCHEM_PKA_STRONGEST_BASIC>
2.0830493950294473

> <JCHEM_POLAR_SURFACE_AREA>
66.06

> <JCHEM_REFRACTIVITY>
55.79

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.27e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-(3-methylbut-2-en-1-yl)-1H-pyrrolo[3,4-d]imidazole-4,6-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0      -3.155  -3.143   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.385  -1.810   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.845  -1.810   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.075  -0.476   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       1.465  -0.476   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       2.370   0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.894   2.235   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       3.834   0.294   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       5.299   0.770   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       6.204  -0.476   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       5.299  -1.722   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       3.834  -1.246   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.370  -1.722   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.894  -3.186   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -3.155  -0.476   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   12                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    8   13                                                  
CONECT   13   12    5   14                                                  
CONECT   14   13                                                            
CONECT   15    2                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₀H₁₁N₃O₂

Average Mass

205.2170 Da

Monoisotopic Mass

205.08513 Da

IUPAC Name

5-(3-methylbut-2-en-1-yl)-1H,4H,5H,6H-pyrrolo[3,4-d]imidazole-4,6-dione

Traditional Name

5-(3-methylbut-2-en-1-yl)-1H-pyrrolo[3,4-d]imidazole-4,6-dione

CAS Registry Number

Not Available

SMILES

CC(C)=CCN1C(=O)C2=C(N=CN2)C1=O

InChI Identifier

InChI=1S/C10H11N3O2/c1-6(2)3-4-13-9(14)7-8(10(13)15)12-5-11-7/h3,5H,4H2,1-2H3,(H,11,12)

InChI Key

WAOGVUUKMCZPQO-UHFFFAOYSA-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
Bridelia balansae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-substituted carboxylic acid imides. N-substituted carboxylic acid imides are compounds comprising an N-substituted carboxylic acid imide group, with the general structure R1N(C(R2)=O)C(R3)=O (R2,R3=H, alkyl, aryl; R1=Anything but H).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

N-substituted carboxylic acid imides

Alternative Parents

Substituents

Carboxylic acid imide, n-substituted
Heteroaromatic compound
Vinylogous amide
Imidazole
Azole
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen 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	0.57	ALOGPS
logP	0.47	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	9.68	ChemAxon
pKa (Strongest Basic)	2.08	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	66.06 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	55.79 m³·mol⁻¹	ChemAxon
Polarizability	21.09 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

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

85913694

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-(3-methylbut-2-en-1-yl)-1h-pyrrolo[3,4-d]imidazole-4,6-dione (NP0222214)

MOL for NP0222214 (5-(3-methylbut-2-en-1-yl)-1h-pyrrolo[3,4-d]imidazole-4,6-dione)

3D MOL for NP0222214 (5-(3-methylbut-2-en-1-yl)-1h-pyrrolo[3,4-d]imidazole-4,6-dione)

3D SDF for NP0222214 (5-(3-methylbut-2-en-1-yl)-1h-pyrrolo[3,4-d]imidazole-4,6-dione)

3D-SDF for NP0222214 (5-(3-methylbut-2-en-1-yl)-1h-pyrrolo[3,4-d]imidazole-4,6-dione)

PDB for NP0222214 (5-(3-methylbut-2-en-1-yl)-1h-pyrrolo[3,4-d]imidazole-4,6-dione)

3D PDB for NP0222214 (5-(3-methylbut-2-en-1-yl)-1h-pyrrolo[3,4-d]imidazole-4,6-dione)

SMILES for NP0222214 (5-(3-methylbut-2-en-1-yl)-1h-pyrrolo[3,4-d]imidazole-4,6-dione)

INCHI for NP0222214 (5-(3-methylbut-2-en-1-yl)-1h-pyrrolo[3,4-d]imidazole-4,6-dione)

Structure for NP0222214 (5-(3-methylbut-2-en-1-yl)-1h-pyrrolo[3,4-d]imidazole-4,6-dione)

3D Structure for NP0222214 (5-(3-methylbut-2-en-1-yl)-1h-pyrrolo[3,4-d]imidazole-4,6-dione)