NP-MRD: Showing NP-Card for Dispacamide C (NP0069840)

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Record Information

Version

2.0

Created at

2022-04-28 15:09:54 UTC

Updated at

2022-04-28 15:09:55 UTC

NP-MRD ID

NP0069840

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Dispacamide C

Description

4,5-Dibromo-N-[(2S)-2-hydroxy-3-[(5Z)-4-hydroxy-2-imino-2,5-dihydro-1H-imidazol-5-ylidene]propyl]-1H-pyrrole-2-carboxamide belongs to the class of organic compounds known as 2-heteroaryl carboxamides. 2-Heteroaryl carboxamides are compounds containing a heteroaromatic ring that carries a carboxamide group. Dispacamide C is found in Agelas clathrodes, Agelas conifera, Agelas dispar and Agelas longissima. Based on a literature review very few articles have been published on 4,5-dibromo-N-[(2S)-2-hydroxy-3-[(5Z)-4-hydroxy-2-imino-2,5-dihydro-1H-imidazol-5-ylidene]propyl]-1H-pyrrole-2-carboxamide.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 33  0  0  0  0  0  0  0  0999 V2000
   -4.8346    2.3100   -0.9143 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4573    1.0153   -0.4738 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2558    0.0169   -0.3450 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5605   -1.1284    0.1147 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9974   -2.2725    0.3548 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1457   -0.7268    0.2745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1704   -1.5112    0.6860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8008   -0.9549    0.7932 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8657    0.2606    1.4259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2310   -0.8436   -0.6141 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0866   -0.3002   -0.5251 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1690   -0.8733    0.1605 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0666   -1.9624    0.7806 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4794   -0.2199    0.1833 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7685    0.9934   -0.4521 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0844    1.2439   -0.1861 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0085    2.7954   -0.8233 Br  0  0  0  0  0  0  0  0  0  0  0  0
    5.6067    0.2291    0.5869 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4066    0.1270    1.2172 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.5998   -0.6366    0.7872 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1299    0.6421   -0.1109 N   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0385    2.4157   -1.9446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9232    3.1399   -0.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4111   -2.5362    0.9303 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1400   -1.6248    1.3789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0111    0.6276    1.7232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8781   -0.2868   -1.2906 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1424   -1.8780   -1.0648 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2493    0.6240   -1.0289 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0494    1.5698   -1.0247 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6979   -1.5122    1.3427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2791    1.2570   -0.1208 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6 21  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  2  0
 18 19  1  0
 18 20  1  0
 21  2  1  0
 20 14  1  0
  1 22  1  0
  1 23  1  0
 21 32  1  0
  7 24  1  0
  8 25  1  1
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 15 30  1  0
 20 31  1  0
M  END


  Mrv1652304282217092D          

 21 22  0  0  1  0            999 V2000
   -3.1936   -3.0862    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6061   -2.3718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0541   -1.7587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3004   -2.0942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3867   -2.9147    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5859   -1.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5859   -0.8567    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8715   -2.0942    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1570   -1.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5575   -2.0942    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2719   -1.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2719   -0.8567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6045   -0.3718    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8594    0.4128    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6844    0.4128    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9394   -0.3718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7240   -0.6267    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3745    1.0803    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5575   -2.9192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4266   -2.2855    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -3.5292   -3.8399    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  1  5  1  0  0  0  0
  4  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  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  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
 12 16  1  0  0  0  0
 16 17  2  0  0  0  0
 14 18  1  0  0  0  0
 10 19  1  6  0  0  0
  2 20  1  0  0  0  0
  1 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0069840

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=NC(=O)\C(N1)=C\[C@H](O)CNC(=O)C1=CC(Br)=C(Br)N1

> <INCHI_IDENTIFIER>
InChI=1S/C11H11Br2N5O3/c12-5-2-7(16-8(5)13)9(20)15-3-4(19)1-6-10(21)18-11(14)17-6/h1-2,4,16,19H,3H2,(H,15,20)(H3,14,17,18,21)/b6-1-/t4-/m0/s1

> <INCHI_KEY>
AOPZOWUSQQHDPT-RDTQVNCESA-N

> <FORMULA>
C11H11Br2N5O3

> <MOLECULAR_WEIGHT>
421.049

> <EXACT_MASS>
418.922865

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
32.99906233415829

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
N-[(2S)-3-[(5Z)-2-amino-4-oxo-4,5-dihydro-1H-imidazol-5-ylidene]-2-hydroxypropyl]-4,5-dibromo-1H-pyrrole-2-carboxamide

> <ALOGPS_LOGP>
1.13

> <JCHEM_LOGP>
-0.9173972323333333

> <ALOGPS_LOGS>
-3.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.923797863841695

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.994811256951225

> <JCHEM_PKA_STRONGEST_BASIC>
2.20024005228178

> <JCHEM_POLAR_SURFACE_AREA>
132.6

> <JCHEM_REFRACTIVITY>
82.78460000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.24e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[(2S)-3-[(4Z)-2-amino-5-oxo-3H-imidazol-4-ylidene]-2-hydroxypropyl]-4,5-dibromo-1H-pyrrole-2-carboxamide

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -5.961  -5.761   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.731  -4.427   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.701  -3.283   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.294  -3.909   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -4.455  -5.441   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -2.960  -3.139   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.960  -1.599   0.000  0.00  0.00           O+0
HETATM    8  N   UNK     0      -1.627  -3.909   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0      -0.293  -3.139   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.041  -3.909   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.374  -3.139   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.374  -1.599   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       1.128  -0.694   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       1.604   0.771   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       3.144   0.771   0.000  0.00  0.00           N+0
HETATM   16  C   UNK     0       3.620  -0.694   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       5.085  -1.170   0.000  0.00  0.00           O+0
HETATM   18  N   UNK     0       0.699   2.016   0.000  0.00  0.00           N+0
HETATM   19  O   UNK     0       1.041  -5.449   0.000  0.00  0.00           O+0
HETATM   20 Br   UNK     0      -8.263  -4.266   0.000  0.00  0.00          Br+0
HETATM   21 Br   UNK     0      -6.588  -7.168   0.000  0.00  0.00          Br+0
CONECT    1    2    5   21                                                  
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4    1                                                       
CONECT    6    4    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   19                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   18                                                  
CONECT   15   14   16                                                       
CONECT   16   15   12   17                                                  
CONECT   17   16                                                            
CONECT   18   14                                                            
CONECT   19   10                                                            
CONECT   20    2                                                            
CONECT   21    1                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₁Br₂N₅O₃

Average Mass

421.0490 Da

Monoisotopic Mass

418.92286 Da

IUPAC Name

N-[(2S)-3-[(5Z)-2-amino-4-oxo-4,5-dihydro-1H-imidazol-5-ylidene]-2-hydroxypropyl]-4,5-dibromo-1H-pyrrole-2-carboxamide

Traditional Name

N-[(2S)-3-[(4Z)-2-amino-5-oxo-3H-imidazol-4-ylidene]-2-hydroxypropyl]-4,5-dibromo-1H-pyrrole-2-carboxamide

CAS Registry Number

Not Available

SMILES

NC1=NC(=O)\C(N1)=C\[C@H](O)CNC(=O)C1=CC(Br)=C(Br)N1

InChI Identifier

InChI=1S/C11H11Br2N5O3/c12-5-2-7(16-8(5)13)9(20)15-3-4(19)1-6-10(21)18-11(14)17-6/h1-2,4,16,19H,3H2,(H,15,20)(H3,14,17,18,21)/b6-1-/t4-/m0/s1

InChI Key

AOPZOWUSQQHDPT-RDTQVNCESA-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
Agelas clathrodes	Animalia	KNApSAcK
Agelas conifera	Animalia	KNApSAcK
Agelas dispar	Animalia	KNApSAcK
Agelas longissima	Animalia	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-heteroaryl carboxamides. 2-Heteroaryl carboxamides are compounds containing a heteroaromatic ring that carries a carboxamide group.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Carboxylic acid derivatives

Direct Parent

2-heteroaryl carboxamides

Alternative Parents

Substituents

2-heteroaryl carboxamide
Pyrrole-2-carboxamide
Pyrrole-2-carboxylic acid or derivatives
Aryl bromide
Aryl halide
Substituted pyrrole
3-imidazoline
Heteroaromatic compound
Pyrrole
Secondary alcohol
Secondary carboxylic acid amide
Carboximidamide
Organoheterocyclic compound
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Azacycle
Alcohol
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organobromide
Organohalogen compound
Imine
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic 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	1.13	ALOGPS
logP	-0.92	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	11.99	ChemAxon
pKa (Strongest Basic)	2.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	132.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	82.78 m³·mol⁻¹	ChemAxon
Polarizability	33 Å³	ChemAxon
Number of Rings	2	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

163037498

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Dispacamide C (NP0069840)

MOL for NP0069840 (Dispacamide C)

3D MOL for NP0069840 (Dispacamide C)

3D SDF for NP0069840 (Dispacamide C)

3D-SDF for NP0069840 (Dispacamide C)

PDB for NP0069840 (Dispacamide C)

3D PDB for NP0069840 (Dispacamide C)

SMILES for NP0069840 (Dispacamide C)

INCHI for NP0069840 (Dispacamide C)

Structure for NP0069840 (Dispacamide C)

3D Structure for NP0069840 (Dispacamide C)