NP-MRD: Showing NP-Card for (4s)-2-bromo-4-[(4s)-5-hydroxy-2-imino-3,4-dihydroimidazol-4-yl]-1h,4h,5h,6h,7h-pyrrolo[2,3-c]azepin-8-one (NP0219266)

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Record Information

Version

2.0

Created at

2022-09-05 20:12:19 UTC

Updated at

2022-09-05 20:12:20 UTC

NP-MRD ID

NP0219266

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(4s)-2-bromo-4-[(4s)-5-hydroxy-2-imino-3,4-dihydroimidazol-4-yl]-1h,4h,5h,6h,7h-pyrrolo[2,3-c]azepin-8-one

Description

(4S)-2-Bromo-4-[(5S)-2-amino-4-oxo-2-imidazoline-5-yl]-1,4,5,6,7,8-hexahydropyrrolo[2,3-c]azepine-8-one belongs to the class of organic compounds known as pyrroloazepines. Pyrroloazepines are compounds containing a pyrroloazepine moiety, which is a bicyclic heterocycle which consists of a pyrrole ring fused to an azepine. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Azepine is a 7-membered ring consisting of six carbon and one nitrogen atom. (4s)-2-bromo-4-[(4s)-5-hydroxy-2-imino-3,4-dihydroimidazol-4-yl]-1h,4h,5h,6h,7h-pyrrolo[2,3-c]azepin-8-one is found in Cymbastela cantharella. Based on a literature review very few articles have been published on (4S)-2-Bromo-4-[(5S)-2-amino-4-oxo-2-imidazoline-5-yl]-1,4,5,6,7,8-hexahydropyrrolo[2,3-c]azepine-8-one.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309052222122D          

 19 21  0  0  1  0            999 V2000
    1.8631    3.2144    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4844    2.6716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2887    2.8552    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7118    2.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5335    2.0730    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1690    1.5257    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3526    0.7214    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.1569    0.5378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5149   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569   -0.9488    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526   -1.1324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1690   -1.9367    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076   -0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230   -0.8729    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380   -0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6130   -0.2055    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    1.9230    0.4619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076    0.2070    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4104    1.8499    0.0000 N   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
  4  6  1  0  0  0  0
  6  7  1  6  0  0  0
  7  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
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
 17 18  1  0  0  0  0
 13 18  2  0  0  0  0
  7 18  1  1  0  0  0
  6 19  1  0  0  0  0
  2 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0219266

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=NC(=N)N[C@H]1[C@H]1CCNC(=O)C2=C1C=C(Br)N2

> <INCHI_IDENTIFIER>
InChI=1S/C11H12BrN5O2/c12-6-3-5-4(7-10(19)17-11(13)16-7)1-2-14-9(18)8(5)15-6/h3-4,7,15H,1-2H2,(H,14,18)(H3,13,16,17,19)/t4-,7-/m0/s1

> <INCHI_KEY>
GDKCTONCNCFKMD-FFWSUHOLSA-N

> <FORMULA>
C11H12BrN5O2

> <MOLECULAR_WEIGHT>
326.154

> <EXACT_MASS>
325.017438

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
28.08599722012626

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4S)-2-bromo-4-[(5S)-4-hydroxy-2-imino-2,5-dihydro-1H-imidazol-5-yl]-1H,4H,5H,6H,7H,8H-pyrrolo[2,3-c]azepin-8-one

> <JCHEM_LOGP>
-1.877744786683792

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
11.252560215737406

> <JCHEM_PKA_STRONGEST_ACIDIC>
-4.58032979696348

> <JCHEM_PKA_STRONGEST_BASIC>
16.924730235084116

> <JCHEM_POLAR_SURFACE_AREA>
113.35999999999999

> <JCHEM_REFRACTIVITY>
81.90889999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4S)-2-bromo-4-[(4S)-5-hydroxy-2-imino-3,4-dihydroimidazol-4-yl]-1H,4H,5H,6H,7H-pyrrolo[2,3-c]azepin-8-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  N   UNK     0       3.478   6.000   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       4.637   4.987   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       6.139   5.330   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       6.929   4.008   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       8.463   3.870   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       5.916   2.848   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.258   1.347   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.760   1.004   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.428  -0.384   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       7.760  -1.771   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       6.258  -2.114   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.916  -3.615   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       5.054  -1.154   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       3.590  -1.629   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0       2.684  -0.384   0.000  0.00  0.00           C+0
HETATM   16 Br   UNK     0       1.144  -0.384   0.000  0.00  0.00          Br+0
HETATM   17  C   UNK     0       3.590   0.862   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.054   0.386   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0       4.499   3.453   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   19                                                  
CONECT    7    6    8   18                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   13    7                                                  
CONECT   19    6    2                                                       
MASTER        0    0    0    0    0    0    0    0   19    0   42    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₂BrN₅O₂

Average Mass

326.1540 Da

Monoisotopic Mass

325.01744 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

OC1=NC(=N)N[C@H]1[C@H]1CCNC(=O)C2=C1C=C(Br)N2

InChI Identifier

InChI=1S/C11H12BrN5O2/c12-6-3-5-4(7-10(19)17-11(13)16-7)1-2-14-9(18)8(5)15-6/h3-4,7,15H,1-2H2,(H,14,18)(H3,13,16,17,19)/t4-,7-/m0/s1

InChI Key

GDKCTONCNCFKMD-FFWSUHOLSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Cymbastela cantharella	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrroloazepines. Pyrroloazepines are compounds containing a pyrroloazepine moiety, which is a bicyclic heterocycle which consists of a pyrrole ring fused to an azepine. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Azepine is a 7-membered ring consisting of six carbon and one nitrogen atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Pyrroloazepines

Sub Class

Not Available

Direct Parent

Pyrroloazepines

Alternative Parents

Substituents

Alpha-amino acid or derivatives
Pyrroloazepine
2-heteroaryl carboxamide
Azepine
Aryl bromide
Aryl halide
Imidazolinone
Substituted pyrrole
Heteroaromatic compound
2-imidazoline
Pyrrole
Carboxamide group
Guanidine
Lactam
Secondary carboxylic acid amide
Carboxylic acid derivative
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Carboximidamide
Organic oxygen compound
Amine
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organopnictogen compound
Organohalogen compound
Organobromide
Organonitrogen compound
Organooxygen 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

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

27025494

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53309336

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (4s)-2-bromo-4-[(4s)-5-hydroxy-2-imino-3,4-dihydroimidazol-4-yl]-1h,4h,5h,6h,7h-pyrrolo[2,3-c]azepin-8-one (NP0219266)

MOL for NP0219266 ((4s)-2-bromo-4-[(4s)-5-hydroxy-2-imino-3,4-dihydroimidazol-4-yl]-1h,4h,5h,6h,7h-pyrrolo[2,3-c]azepin-8-one)

3D MOL for NP0219266 ((4s)-2-bromo-4-[(4s)-5-hydroxy-2-imino-3,4-dihydroimidazol-4-yl]-1h,4h,5h,6h,7h-pyrrolo[2,3-c]azepin-8-one)

3D SDF for NP0219266 ((4s)-2-bromo-4-[(4s)-5-hydroxy-2-imino-3,4-dihydroimidazol-4-yl]-1h,4h,5h,6h,7h-pyrrolo[2,3-c]azepin-8-one)

3D-SDF for NP0219266 ((4s)-2-bromo-4-[(4s)-5-hydroxy-2-imino-3,4-dihydroimidazol-4-yl]-1h,4h,5h,6h,7h-pyrrolo[2,3-c]azepin-8-one)

PDB for NP0219266 ((4s)-2-bromo-4-[(4s)-5-hydroxy-2-imino-3,4-dihydroimidazol-4-yl]-1h,4h,5h,6h,7h-pyrrolo[2,3-c]azepin-8-one)

3D PDB for NP0219266 ((4s)-2-bromo-4-[(4s)-5-hydroxy-2-imino-3,4-dihydroimidazol-4-yl]-1h,4h,5h,6h,7h-pyrrolo[2,3-c]azepin-8-one)

SMILES for NP0219266 ((4s)-2-bromo-4-[(4s)-5-hydroxy-2-imino-3,4-dihydroimidazol-4-yl]-1h,4h,5h,6h,7h-pyrrolo[2,3-c]azepin-8-one)

INCHI for NP0219266 ((4s)-2-bromo-4-[(4s)-5-hydroxy-2-imino-3,4-dihydroimidazol-4-yl]-1h,4h,5h,6h,7h-pyrrolo[2,3-c]azepin-8-one)

Structure for NP0219266 ((4s)-2-bromo-4-[(4s)-5-hydroxy-2-imino-3,4-dihydroimidazol-4-yl]-1h,4h,5h,6h,7h-pyrrolo[2,3-c]azepin-8-one)

3D Structure for NP0219266 ((4s)-2-bromo-4-[(4s)-5-hydroxy-2-imino-3,4-dihydroimidazol-4-yl]-1h,4h,5h,6h,7h-pyrrolo[2,3-c]azepin-8-one)