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Showing NP-Card for Callyspongisine C (NP0331136)

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Record Information
Version1.0
Created at2022-11-17 17:49:52 UTC
Updated at2024-04-19 09:30:38 UTC
NP-MRD IDNP0331136
Secondary Accession NumbersNone
Natural Product Identification
Common NameCallyspongisine C
DescriptionEthyl 2-bromo-4-ethoxy-8-oxo-1H,4H,5H,6H,7H,8H-pyrrolo[2,3-c]azepine-4-carboxylate 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. It was first documented in 2023 (PMID: 37079875). Based on a literature review a significant number of articles have been published on ethyl 2-bromo-4-ethoxy-8-oxo-1H,4H,5H,6H,7H,8H-pyrrolo[2,3-c]azepine-4-carboxylate (PMID: 37079872) (PMID: 37079871) (PMID: 37079861) (PMID: 37079701).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0331136 (Callyspongisine C)


  Mrv1652311172218492D          

 20 21  0  0  0  0            999 V2000
    3.1690    1.5257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526    0.7214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569    0.5378    0.0000 N   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 C   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
    3.7106   -1.8757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5333   -1.9373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8912   -2.6806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076   -1.6467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8306   -2.4625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1855   -2.9769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3085   -3.7927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9396   -1.3453    0.0000 O   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
    2.7076   -0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230   -0.8729    0.0000 C   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 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  1  0  0  0  0
  4  5  1  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
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 10 14  2  0  0  0  0
  2 15  1  0  0  0  0
 15 16  2  0  0  0  0
  6 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 15 20  1  0  0  0  0
M  END
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3D MOL for NP0331136 (Callyspongisine C)

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3D SDF for NP0331136 (Callyspongisine C)

  Mrv1652311172218492D          

 20 21  0  0  0  0            999 V2000
    3.1690    1.5257    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3526    0.7214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1569    0.5378    0.0000 N   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 C   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
    3.7106   -1.8757    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5333   -1.9373    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8912   -2.6806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7076   -1.6467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8306   -2.4625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1855   -2.9769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3085   -3.7927    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9396   -1.3453    0.0000 O   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
    2.7076   -0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9230   -0.8729    0.0000 C   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 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  1  0  0  0  0
  4  5  1  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
  6 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 10 14  2  0  0  0  0
  2 15  1  0  0  0  0
 15 16  2  0  0  0  0
  6 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 15 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331136

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCOC(=O)C1(CCNC(=O)C2=C1C=C(Br)N2)OCC

> <INCHI_IDENTIFIER>
InChI=1S/C13H17BrN2O4/c1-3-19-12(18)13(20-4-2)5-6-15-11(17)10-8(13)7-9(14)16-10/h7,16H,3-6H2,1-2H3,(H,15,17)

> <INCHI_KEY>
XMAXDKHEKBQGSH-UHFFFAOYSA-N

> <FORMULA>
C13H17BrN2O4

> <MOLECULAR_WEIGHT>
345.193

> <EXACT_MASS>
344.03717

$$$$

Download
3D-SDF for NP0331136 (Callyspongisine C)
Download
PDB for NP0331136 (Callyspongisine C)
HEADER    PROTEIN                                 17-NOV-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-NOV-22         0                                  
HETATM    1  O   UNK     0       5.916   2.848   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.258   1.347   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       7.760   1.004   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       8.428  -0.384   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.760  -1.771   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.258  -2.114   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       6.926  -3.501   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.462  -3.616   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.130  -5.004   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.054  -3.074   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.284  -4.597   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       4.080  -5.557   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.309  -7.080   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.621  -2.511   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.054   0.386   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.054  -1.154   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.590  -1.629   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.684  -0.384   0.000  0.00  0.00           C+0
HETATM   19 Br   UNK     0       1.144  -0.384   0.000  0.00  0.00          Br+0
HETATM   20  N   UNK     0       3.590   0.862   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   10   16                                             
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8                                                            
CONECT   10    6   11   14                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12                                                            
CONECT   14   10                                                            
CONECT   15    2   16   20                                                  
CONECT   16   15    6   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   15                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   42    0
END

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3D PDB for NP0331136 (Callyspongisine C)
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SMILES for NP0331136 (Callyspongisine C)
CCOC(=O)C1(CCNC(=O)C2=C1C=C(Br)N2)OCC
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INCHI for NP0331136 (Callyspongisine C)
InChI=1S/C13H17BrN2O4/c1-3-19-12(18)13(20-4-2)5-6-15-11(17)10-8(13)7-9(14)16-10/h7,16H,3-6H2,1-2H3,(H,15,17)
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Synonyms
ValueSource
Ethyl 2-bromo-4-ethoxy-8-oxo-1H,4H,5H,6H,7H,8H-pyrrolo[2,3-c]azepine-4-carboxylic acidGenerator
Chemical FormulaC13H17BrN2O4
Average Mass345.1930 Da
Monoisotopic Mass344.03717 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
CCOC(=O)C1(CCNC(=O)C2=C1C=C(Br)N2)OCC
InChI Identifier
InChI=1S/C13H17BrN2O4/c1-3-19-12(18)13(20-4-2)5-6-15-11(17)10-8(13)7-9(14)16-10/h7,16H,3-6H2,1-2H3,(H,15,17)
InChI KeyXMAXDKHEKBQGSH-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
COSY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)a.salim@uq.edu.auNot AvailableNot Available2022-11-17View Spectrum
ROESY NMR[1H, 1H] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)a.salim@uq.edu.auNot AvailableNot Available2022-11-17View Spectrum
HMBC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)a.salim@uq.edu.auNot AvailableNot Available2022-11-17View Spectrum
1D NMR[1H, ] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)a.salim@uq.edu.auNot AvailableNot Available2022-11-17View Spectrum
HSQC NMR[1H, 13C] NMR Spectrum (2D, 600 MHz, C2D6OS, experimental)a.salim@uq.edu.auNot AvailableNot Available2022-11-17View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
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.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassPyrroloazepines  
Sub ClassNot Available
Direct ParentPyrroloazepines  
Alternative Parents
Substituents
  • Pyrroloazepine
    • 

  • 2-heteroaryl carboxamide
    • 

  • Azepine
    • 

  • Aryl bromide
    • 

  • Aryl halide
    • 

  • Substituted pyrrole
    • 

  • Pyrrole
    • 

  • Heteroaromatic compound
    • 

  • Carboxamide group
    • 

  • Carboxylic acid ester
    • 

  • Lactam
    • 

  • Secondary carboxylic acid amide
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Ether
    • 

  • Dialkyl ether
    • 

  • Carboxylic acid derivative
    • 

  • Azacycle
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organobromide
    • 

  • Organohalogen compound
    • 

  • Organic oxygen compound
    • 

  • Organic nitrogen compound
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organopnictogen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID32674803  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound163085190  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Liao KF, Lai SW: Aspirin Use and the Risk of Hepatocellular Carcinoma: A Meta-analysis. J Clin Gastroenterol. 2023 Jul 1;57(6):640-641. doi:  10.1097/MCG.0000000000001856. [PubMed:37079875  ] 
  2. Ashton JJ, Gurung A, Davis C, Seaby EG, Coelho T, Batra A, Afzal NA, Ennis S, Beattie RM: The Pediatric Crohn Disease Morbidity Index (PCD-MI): Development of a Tool to Assess Long-Term Disease Burden Using a Data-Driven Approach. J Pediatr Gastroenterol Nutr. 2023 Jul 1;77(1):70-78. doi:  10.1097/MPG.0000000000003793. Epub 2023 Apr 20. [PubMed:37079872  ] 
  3. Mougey EB, Judy WC, Venkatesh RD, Berg E, Lee JA, Rosen JM, Li BUK, Koster A, Maiden K, Gao Z, Franciosi JP: Equity and Inclusion in Pediatric Gastroenterology Telehealth: A Study of Demographic, Socioeconomic and Digital Disparities. J Pediatr Gastroenterol Nutr. 2023 Apr 21. doi: 10.1097/MPG.0000000000003797. [PubMed:37079871  ] 
  4. Weeks I, Abber SR, Thomas JJ, Calabrese S, Kuo B, Staller K, Murray HB: The Intersection of Disorders of Gut-Brain Interaction With Avoidant/Restrictive Food Intake Disorder. J Clin Gastroenterol. 2023 Apr 21. doi: 10.1097/MCG.0000000000001853. [PubMed:37079861  ] 
  5. Imperiale TF, Myers LJ, Barker BC, Larson J, Stump TE, Daggy JK: Risk Factors for Early Onset Sporadic Colorectal Cancer in Male Veterans. Cancer Prev Res (Phila). 2023 Apr 21:CAPR-22-0506. doi:  10.1158/1940-6207.CAPR-22-0506. [PubMed:37079701  ]