NP-MRD: Showing NP-Card for (5r)-5-[(4s)-8-hydroxy-1h,4h,5h,6h-pyrrolo[2,3-c]azepin-4-yl]-2-imino-1,5-dihydroimidazol-4-ol (NP0149197)

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Record Information

Version

2.0

Created at

2022-09-02 05:02:54 UTC

Updated at

2022-09-02 05:02:54 UTC

NP-MRD ID

NP0149197

Secondary Accession Numbers

None

Natural Product Identification

Common Name

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

Description

(4S)-4-[(5R)-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. (5r)-5-[(4s)-8-hydroxy-1h,4h,5h,6h-pyrrolo[2,3-c]azepin-4-yl]-2-imino-1,5-dihydroimidazol-4-ol is found in Cymbastela cantharella. Based on a literature review very few articles have been published on (4S)-4-[(5R)-2-Amino-4-oxo-2-imidazoline-5-yl]-1,4,5,6,7,8-hexahydropyrrolo[2,3-c]azepine-8-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 33  0  0  0  0  0  0  0  0999 V2000
    5.0561   -1.1347   -0.6800 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8237   -0.1377   -0.4928 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6259    0.1445   -0.0529 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0951    1.4220    0.2667 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8647    1.3178    0.6721 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1492    2.4663    1.0461 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3794   -0.0440    0.6791 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3268   -0.3856   -0.3837 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0559   -1.7970   -0.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3440   -2.3152   -0.6374 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4475   -1.9409    0.3056 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7554   -0.7201    0.5632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7683   -0.4824    1.4294 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0772    0.4483   -0.0256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6965    1.6223   -0.2857 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8244    2.4531   -0.8617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6027    1.8429   -0.9946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7773    0.5531   -0.4499 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5772   -0.7779    0.2058 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2741    2.9203    1.9246 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0311   -0.4125    1.6427 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8742   -0.3075   -1.3702 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7944   -2.5086   -0.2747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1778   -1.8875    1.0490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3109   -3.4197   -0.5829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5794   -1.9627   -1.6498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6758   -0.7091    2.4000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7077    1.8025   -0.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0288    3.4864   -1.1932 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2865    2.2684   -1.4407 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6713   -1.8050    0.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  3  2  2  0
  3 19  1  0
 19  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 18  2  0
 18 17  1  0
 17 16  2  0
 16 15  1  0
  7  5  1  0
 18  8  1  0
 15 14  1  0
  6 20  1  0
  2  1  1  0
 19 31  1  0
  7 21  1  1
  8 22  1  6
  9 23  1  0
  9 24  1  0
 10 25  1  0
 10 26  1  0
 13 27  1  0
 17 30  1  0
 16 29  1  0
 15 28  1  0
M  END


  Mrv1652309022207022D          

 18 20  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  1  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
    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  1  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  2  0  0  0  0
 11 12  1  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  2  0  0  0  0
 16 17  1  0  0  0  0
 13 17  2  0  0  0  0
  7 17  1  1  0  0  0
  6 18  1  0  0  0  0
  2 18  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0149197

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=NC(=N)N[C@@H]1[C@H]1CCN=C(O)C2=C1C=CN2

> <INCHI_IDENTIFIER>
InChI=1S/C11H13N5O2/c12-11-15-8(10(18)16-11)6-2-4-14-9(17)7-5(6)1-3-13-7/h1,3,6,8,13H,2,4H2,(H,14,17)(H3,12,15,16,18)/t6-,8+/m0/s1

> <INCHI_KEY>
IZDCPWUUGIDGOX-POYBYMJQSA-N

> <FORMULA>
C11H13N5O2

> <MOLECULAR_WEIGHT>
247.258

> <EXACT_MASS>
247.106924679

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
24.10511739523736

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.25

> <JCHEM_LOGP>
-1.5317496019781278

> <ALOGPS_LOGS>
-3.25

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
2

> <JCHEM_PKA>
9.270874538732093

> <JCHEM_PKA_STRONGEST_ACIDIC>
-4.108545097040872

> <JCHEM_PKA_STRONGEST_BASIC>
18.126776039771297

> <JCHEM_POLAR_SURFACE_AREA>
116.85

> <JCHEM_REFRACTIVITY>
75.02579999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.39e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-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  C   UNK     0       3.590   0.862   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.054   0.386   0.000  0.00  0.00           C+0
HETATM   18  N   UNK     0       4.499   3.453   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   18                                                  
CONECT    7    6    8   17                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   17                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   13    7                                                  
CONECT   18    6    2                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   40    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₁H₁₃N₅O₂

Average Mass

247.2580 Da

Monoisotopic Mass

247.10692 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

OC1=NC(=N)N[C@@H]1[C@H]1CCN=C(O)C2=C1C=CN2

InChI Identifier

InChI=1S/C11H13N5O2/c12-11-15-8(10(18)16-11)6-2-4-14-9(17)7-5(6)1-3-13-7/h1,3,6,8,13H,2,4H2,(H,14,17)(H3,12,15,16,18)/t6-,8+/m0/s1

InChI Key

IZDCPWUUGIDGOX-POYBYMJQSA-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
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
Imidazolinone
2-imidazoline
Heteroaromatic compound
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
Amine
Hydrocarbon derivative
Organic oxide
Organic nitrogen compound
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organic oxygen compound
Carbonyl group
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

27025844

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53309337

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (5r)-5-[(4s)-8-hydroxy-1h,4h,5h,6h-pyrrolo[2,3-c]azepin-4-yl]-2-imino-1,5-dihydroimidazol-4-ol (NP0149197)

MOL for NP0149197 ((5r)-5-[(4s)-8-hydroxy-1h,4h,5h,6h-pyrrolo[2,3-c]azepin-4-yl]-2-imino-1,5-dihydroimidazol-4-ol)

3D MOL for NP0149197 ((5r)-5-[(4s)-8-hydroxy-1h,4h,5h,6h-pyrrolo[2,3-c]azepin-4-yl]-2-imino-1,5-dihydroimidazol-4-ol)

3D SDF for NP0149197 ((5r)-5-[(4s)-8-hydroxy-1h,4h,5h,6h-pyrrolo[2,3-c]azepin-4-yl]-2-imino-1,5-dihydroimidazol-4-ol)

3D-SDF for NP0149197 ((5r)-5-[(4s)-8-hydroxy-1h,4h,5h,6h-pyrrolo[2,3-c]azepin-4-yl]-2-imino-1,5-dihydroimidazol-4-ol)

PDB for NP0149197 ((5r)-5-[(4s)-8-hydroxy-1h,4h,5h,6h-pyrrolo[2,3-c]azepin-4-yl]-2-imino-1,5-dihydroimidazol-4-ol)

3D PDB for NP0149197 ((5r)-5-[(4s)-8-hydroxy-1h,4h,5h,6h-pyrrolo[2,3-c]azepin-4-yl]-2-imino-1,5-dihydroimidazol-4-ol)

SMILES for NP0149197 ((5r)-5-[(4s)-8-hydroxy-1h,4h,5h,6h-pyrrolo[2,3-c]azepin-4-yl]-2-imino-1,5-dihydroimidazol-4-ol)

INCHI for NP0149197 ((5r)-5-[(4s)-8-hydroxy-1h,4h,5h,6h-pyrrolo[2,3-c]azepin-4-yl]-2-imino-1,5-dihydroimidazol-4-ol)

Structure for NP0149197 ((5r)-5-[(4s)-8-hydroxy-1h,4h,5h,6h-pyrrolo[2,3-c]azepin-4-yl]-2-imino-1,5-dihydroimidazol-4-ol)

3D Structure for NP0149197 ((5r)-5-[(4s)-8-hydroxy-1h,4h,5h,6h-pyrrolo[2,3-c]azepin-4-yl]-2-imino-1,5-dihydroimidazol-4-ol)