NP-MRD: Showing NP-Card for Ugibohlin (NP0070554)

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Record Information

Version

2.0

Created at

2022-04-28 15:57:12 UTC

Updated at

2022-04-28 15:57:12 UTC

NP-MRD ID

NP0070554

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ugibohlin

Description

N-{2,3-dibromo-9-oxo-1H,5H,6H,7H,9H-pyrrolo[2,3-f]indolizin-4-yl}guanidine belongs to the class of organic compounds known as pyridinones. Pyridinones are compounds containing a pyridine ring, which bears a ketone. Ugibohlin is found in Axinella carteri. N-{2,3-dibromo-9-oxo-1H,5H,6H,7H,9H-pyrrolo[2,3-f]indolizin-4-yl}guanidine is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 30 32  0  0  0  0  0  0  0  0999 V2000
    3.3901   -1.9644   -0.9353 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1362   -1.6026   -0.3160 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6489   -2.5478    0.6302 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6477   -0.5110   -0.6545 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5068    0.2032   -0.3296 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7938   -0.2313   -0.4345 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8603    0.4981   -0.0669 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6837    1.7305    0.4368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6823    2.4043    0.7776 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4122    2.2328    0.5704 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0574    3.4231    1.0380 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3928    3.4802    0.9823 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5185    4.9357    1.5216 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.7999    2.2702    0.4542 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6057    1.7707    0.1384 Br  0  0  0  0  0  0  0  0  0  0  0  0
    0.6872    1.4952    0.1977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0906   -0.2698   -0.3224 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5862   -1.6872   -0.1991 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2750   -1.5460   -0.9939 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3459   -2.3944   -1.8698 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2878   -1.8010   -0.4665 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2267   -3.4621    0.3314 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6875   -2.3781    1.6634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5631    4.1793    1.3895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8543   -0.0022    0.4134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4271   -0.1075   -1.3808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3352   -1.8480    0.8702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2468   -2.4382   -0.6252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6234   -2.3662   -0.7530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5050   -1.4656   -2.0674 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  2  0
  6 19  1  0
 19 18  1  0
 18 17  1  0
 17  7  1  0
  7  8  1  0
  8  9  2  0
  8 10  1  0
 10 16  2  0
 16 14  1  0
 14 15  1  0
 14 12  2  0
 12 13  1  0
 12 11  1  0
 16  5  1  0
  7  6  1  0
 11 10  1  0
  1 20  1  0
  1 21  1  0
  3 22  1  0
  3 23  1  0
 19 29  1  0
 19 30  1  0
 18 27  1  0
 18 28  1  0
 17 25  1  0
 17 26  1  0
 11 24  1  0
M  END


  Mrv1533004261513322D          

 19 21  0  0  0  0            999 V2000
    4.7079    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7780    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2629    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7780   -0.2549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4699    0.4125    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    3.3000    0.0000 N   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  2  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  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
  4 18  1  0  0  0  0
 12 18  2  0  0  0  0
  2 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0070554

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC(N)=NC1=C2CCCN2C(=O)C2=C1C(Br)=C(Br)N2

> <INCHI_IDENTIFIER>
InChI=1S/C11H11Br2N5O/c12-6-5-7(17-11(14)15)4-2-1-3-18(4)10(19)8(5)16-9(6)13/h16H,1-3H2,(H4,14,15,17)

> <INCHI_KEY>
WNFGJYRDKBZYOI-UHFFFAOYSA-N

> <FORMULA>
C11H11Br2N5O

> <MOLECULAR_WEIGHT>
389.051

> <EXACT_MASS>
386.933036

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
30

> <JCHEM_AVERAGE_POLARIZABILITY>
30.762714148468365

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N''-{2,3-dibromo-9-oxo-1H,5H,6H,7H,9H-pyrrolo[2,3-f]indolizin-4-yl}guanidine

> <ALOGPS_LOGP>
1.25

> <JCHEM_LOGP>
-1.425876254024344

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.998704222359453

> <JCHEM_PKA_STRONGEST_BASIC>
10.10838262210482

> <JCHEM_POLAR_SURFACE_AREA>
100.49999999999999

> <JCHEM_REFRACTIVITY>
80.5795

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.90e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N''-{2,3-dibromo-9-oxo-1H,5H,6H,7H-pyrrolo[2,3-f]indolizin-4-yl}guanidine

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  N   UNK     0       8.788   3.850   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       7.454   4.620   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       6.121   3.850   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.919   2.016   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.824   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.919  -0.476   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       7.454   0.000   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.121  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       3.322  -0.476   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   15 Br   UNK     0       0.877   0.770   0.000  0.00  0.00          Br+0
HETATM   16  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   17 Br   UNK     0       2.846   3.481   0.000  0.00  0.00          Br+0
HETATM   18  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       7.454   6.160   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   18                                                  
CONECT    5    4    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   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    4   12                                                  
CONECT   19    2                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₁Br₂N₅O

Average Mass

389.0510 Da

Monoisotopic Mass

386.93304 Da

IUPAC Name

N''-{2,3-dibromo-9-oxo-1H,5H,6H,7H,9H-pyrrolo[2,3-f]indolizin-4-yl}guanidine

Traditional Name

N''-{2,3-dibromo-9-oxo-1H,5H,6H,7H-pyrrolo[2,3-f]indolizin-4-yl}guanidine

CAS Registry Number

Not Available

SMILES

NC(N)=NC1=C2CCCN2C(=O)C2=C1C(Br)=C(Br)N2

InChI Identifier

InChI=1S/C11H11Br2N5O/c12-6-5-7(17-11(14)15)4-2-1-3-18(4)10(19)8(5)16-9(6)13/h16H,1-3H2,(H4,14,15,17)

InChI Key

WNFGJYRDKBZYOI-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Axinella carteri	Animalia	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyridinones. Pyridinones are compounds containing a pyridine ring, which bears a ketone.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyridines and derivatives

Sub Class

Hydropyridines

Direct Parent

Pyridinones

Alternative Parents

Substituents

Pyridinone
Aryl bromide
Aryl halide
Substituted pyrrole
Pyrrole
Heteroaromatic compound
Lactam
Guanidine
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Azacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organobromide
Organohalogen compound
Organic oxygen compound
Organic nitrogen 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	1.25	ALOGPS
logP	-1.4	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	8	ChemAxon
pKa (Strongest Basic)	10.11	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	100.5 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	80.58 m³·mol⁻¹	ChemAxon
Polarizability	30.76 Å³	ChemAxon
Number of Rings	3	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

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

11079644

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Ugibohlin (NP0070554)

MOL for NP0070554 (Ugibohlin)

3D MOL for NP0070554 (Ugibohlin)

3D SDF for NP0070554 (Ugibohlin)

3D-SDF for NP0070554 (Ugibohlin)

PDB for NP0070554 (Ugibohlin)

3D PDB for NP0070554 (Ugibohlin)

SMILES for NP0070554 (Ugibohlin)

INCHI for NP0070554 (Ugibohlin)

Structure for NP0070554 (Ugibohlin)

3D Structure for NP0070554 (Ugibohlin)