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Showing NP-Card for Zarzissine (NP0140244)

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Record Information
Version2.0
Created at2022-06-29 21:16:02 UTC
Updated at2022-06-29 21:16:02 UTC
NP-MRD IDNP0140244
Secondary Accession NumbersNone
Natural Product Identification
Common NameZarzissine
DescriptionZarzissine belongs to the class of organic compounds known as pyridazines and derivatives. Pyridazines and derivatives are compounds containing a pyridazine ring, which is a six-member aromatic ring containing two nitrogen atoms at positions 1 and 2, and four carbon atoms. Zarzissine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Zarzissine is found in Hymedesmia paupertas and Oroxylum indicum. Zarzissine was first documented in 1994 (PMID: 7807130). Based on a literature review a small amount of articles have been published on zarzissine (PMID: 23672042) (PMID: 14970879).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0140244 (Zarzissine)


  Mrv1652306292223162D          

 10 11  0  0  0  0            999 V2000
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846    1.0799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2695    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846   -0.2549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0945    0.4125    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
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  2  9  1  0  0  0  0
  8 10  1  0  0  0  0
M  END
Download

3D MOL for NP0140244 (Zarzissine)

     RDKit          3D

 15 16  0  0  0  0  0  0  0  0999 V2000
    2.9812    0.1986   -0.0384 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5495    0.1904   -0.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7098    1.2209   -0.2373 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5589    0.8298   -0.1599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8030    1.4047   -0.2718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9450    0.7140   -0.1357 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9000   -0.5905    0.1199 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7272   -1.2095    0.2405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5481   -0.5414    0.1088 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7701   -0.8835    0.1751 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5463    0.9944    0.3319 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4473   -0.6453   -0.4357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8818    2.4584   -0.4783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7099   -2.2612    0.4466 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0699   -1.8797    0.3702 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
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10  2  1  0
  9  4  1  0
  1 11  1  0
  1 12  1  0
  5 13  1  0
  8 14  1  0
 10 15  1  0
M  END
Download

3D SDF for NP0140244 (Zarzissine)


  Mrv1652306292223162D          

 10 11  0  0  0  0            999 V2000
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846    1.0799    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2695    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7846   -0.2549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0945    0.4125    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
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  3  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  2  9  1  0  0  0  0
  8 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0140244

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=NC2=CN=NC=C2N1

> <INCHI_IDENTIFIER>
InChI=1S/C5H5N5/c6-5-9-3-1-7-8-2-4(3)10-5/h1-2H,(H3,6,9,10)

> <INCHI_KEY>
BUYBPEINWQQOFV-UHFFFAOYSA-N

> <FORMULA>
C5H5N5

> <MOLECULAR_WEIGHT>
135.13

> <EXACT_MASS>
135.054495181

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
12.453977790092424

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1H-imidazo[4,5-d]pyridazin-2-amine

> <ALOGPS_LOGP>
-0.46

> <JCHEM_LOGP>
-1.0826143286666667

> <ALOGPS_LOGS>
-1.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.290981705318302

> <JCHEM_PKA_STRONGEST_BASIC>
4.584542179064237

> <JCHEM_POLAR_SURFACE_AREA>
80.48

> <JCHEM_REFRACTIVITY>
36.8486

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.65e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1H-imidazo[4,5-d]pyridazin-2-amine

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0140244 (Zarzissine)

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PDB for NP0140244 (Zarzissine)
HEADER    PROTEIN                                 29-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-JUN-22         0                                  
HETATM    1  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.000   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       2.667   1.540   0.000  0.00  0.00           N+0
HETATM    6  N   UNK     0       2.667   0.000   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      -1.465   2.016   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      -2.370   0.770   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      -1.465  -0.476   0.000  0.00  0.00           N+0
HETATM   10  N   UNK     0      -3.910   0.770   0.000  0.00  0.00           N+0
CONECT    1    2    6                                                       
CONECT    2    1    3    9                                                  
CONECT    3    2    4    7                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    3    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8    2                                                       
CONECT   10    8                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   22    0
END

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3D PDB for NP0140244 (Zarzissine)
Download
SMILES for NP0140244 (Zarzissine)
NC1=NC2=CN=NC=C2N1
Download
INCHI for NP0140244 (Zarzissine)
InChI=1S/C5H5N5/c6-5-9-3-1-7-8-2-4(3)10-5/h1-2H,(H3,6,9,10)
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View in JSmol
SynonymsNot Available
Chemical FormulaC5H5N5
Average Mass135.1300 Da
Monoisotopic Mass135.05450 Da
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry NumberNot Available
SMILES
NC1=NC2=CN=NC=C2N1
InChI Identifier
InChI=1S/C5H5N5/c6-5-9-3-1-7-8-2-4(3)10-5/h1-2H,(H3,6,9,10)
InChI KeyBUYBPEINWQQOFV-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Hymedesmia paupertasLOTUS Database
Oroxylum indicumLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as pyridazines and derivatives. Pyridazines and derivatives are compounds containing a pyridazine ring, which is a six-member aromatic ring containing two nitrogen atoms at positions 1 and 2, and four carbon atoms.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassDiazines  
Sub ClassPyridazines and derivatives  
Direct ParentPyridazines and derivatives  
Alternative Parents
Substituents
  • Pyridazine
    • 

  • Aminoimidazole
    • 

  • Heteroaromatic compound
    • 

  • Imidazole
    • 

  • Azole
    • 

  • Azacycle
    • 

  • Organic nitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Primary amine
    • 

  • Organonitrogen compound
    • 

  • Amine
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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 ID4912106  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound6400641  
PDB IDNot Available
ChEBI ID66501  
Good Scents IDNot Available
References
General References
  1. Wei XN, Lin BB, Xie GY, Li JW, Qin MJ: [Chemical constitunents of seeds of Oroxylum indicum]. Zhongguo Zhong Yao Za Zhi. 2013 Jan;38(2):204-7. [PubMed:23672042  ] 
  2. Li LY, Deng ZW, Li J, Fu HZ, Lin WH: [Chemical constituents from Chinese marine sponge Cinachyrella australiensis]. Beijing Da Xue Xue Bao Yi Xue Ban. 2004 Feb;36(1):12-7. [PubMed:14970879  ] 
  3. Bouaicha N, Amade P, Puel D, Roussakis C: Zarzissine, a new cytotoxic guanidine alkaloid from the Mediterranean sponge Anchinoe paupertas. J Nat Prod. 1994 Oct;57(10):1455-7. doi: 10.1021/np50112a019. [PubMed:7807130  ]