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Showing NP-Card for Noradrenochrome (NP0339156)

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Record Information
Version2.0
Created at2024-09-11 19:57:25 UTC
Updated at2024-09-11 19:57:26 UTC
NP-MRD IDNP0339156
Secondary Accession NumbersNone
Natural Product Identification
Common NameNoradrenochrome
Description Noradrenochrome was first documented in 2007 (PMID: 17892264). Based on a literature review a small amount of articles have been published on Noradrenochrome (PMID: 29421433) (PMID: 19570037).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0339156 (Noradrenochrome)


  Mrv2104 05262322292D          

 12 13  0  0  0  0            999 V2000
   14.7922  -21.0357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9639  -20.2288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7176  -19.8932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6313  -19.0732    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8244  -18.9013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4119  -18.1868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5869  -18.1868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1744  -17.4722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1744  -18.9013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3494  -18.9013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5869  -19.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4119  -19.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2 12  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5 12  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
M  END
Download

3D MOL for NP0339156 (Noradrenochrome)

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3D SDF for NP0339156 (Noradrenochrome)

  Mrv2104 05262322292D          

 12 13  0  0  0  0            999 V2000
   14.7922  -21.0357    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.9639  -20.2288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7176  -19.8932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6313  -19.0732    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8244  -18.9013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4119  -18.1868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5869  -18.1868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.1744  -17.4722    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1744  -18.9013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3494  -18.9013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.5869  -19.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4119  -19.6159    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2 12  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5 12  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0339156

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1CN=C2CC(=O)C(=O)C=C12

> <INCHI_IDENTIFIER>
InChI=1/C8H7NO3/c10-6-1-4-5(2-7(6)11)9-3-8(4)12/h1,8,12H,2-3H2

> <INCHI_KEY>
PTQNKGWWIYGAAE-UHFFFAOYNA-N

> <FORMULA>
C8H7NO3

> <MOLECULAR_WEIGHT>
165.148

> <EXACT_MASS>
165.042593089

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
15.370544876801214

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-hydroxy-3,5,6,7-tetrahydro-2H-indole-5,6-dione

> <JCHEM_LOGP>
0.2624895803333334

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.916143625434552

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.753970964847058

> <JCHEM_PKA_STRONGEST_BASIC>
4.621482477915765

> <JCHEM_POLAR_SURFACE_AREA>
66.73

> <JCHEM_REFRACTIVITY>
41.5424

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-hydroxy-3,7-dihydro-2H-indole-5,6-dione

> <JCHEM_VEBER_RULE>
0

$$$$

Download
3D-SDF for NP0339156 (Noradrenochrome)
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PDB for NP0339156 (Noradrenochrome)
HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  O   UNK     0      27.612 -39.267   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      27.933 -37.760   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      29.340 -37.134   0.000  0.00  0.00           C+0
HETATM    4  N   UNK     0      29.178 -35.603   0.000  0.00  0.00           N+0
HETATM    5  C   UNK     0      27.672 -35.282   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      26.902 -33.949   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      25.362 -33.949   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      24.592 -32.615   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      24.592 -35.282   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      23.052 -35.282   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      25.362 -36.616   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      26.902 -36.616   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   12                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12    2    5   11                                                  
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

Download
3D PDB for NP0339156 (Noradrenochrome)
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SMILES for NP0339156 (Noradrenochrome)
OC1CN=C2CC(=O)C(=O)C=C12
Download
INCHI for NP0339156 (Noradrenochrome)
InChI=1/C8H7NO3/c10-6-1-4-5(2-7(6)11)9-3-8(4)12/h1,8,12H,2-3H2
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View in JSmol
SynonymsNot Available
Chemical FormulaC8H7NO3
Average Mass165.1480 Da
Monoisotopic Mass165.04259 Da
IUPAC Name3-hydroxy-3,5,6,7-tetrahydro-2H-indole-5,6-dione
Traditional Name3-hydroxy-3,7-dihydro-2H-indole-5,6-dione
CAS Registry NumberNot Available
SMILES
OC1CN=C2CC(=O)C(=O)C=C12
InChI Identifier
InChI=1/C8H7NO3/c10-6-1-4-5(2-7(6)11)9-3-8(4)12/h1,8,12H,2-3H2
InChI KeyPTQNKGWWIYGAAE-UHFFFAOYNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
ClassificationNot classified
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
logP0.26ChemAxon
pKa (Strongest Acidic)11.75ChemAxon
pKa (Strongest Basic)4.62ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area66.73 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity41.54 m³·mol⁻¹ChemAxon
Polarizability15.37 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Touchette JC, Little JW, Wilken GH, Salvemini D, Macarthur H: The Neurotoxin DSP-4 Induces Hyperalgesia in Rats that is Accompanied by Spinal Oxidative Stress and Cytokine Production. Neuroscience. 2018 Apr 15;376:13-23. doi: 10.1016/j.neuroscience.2018.01.058.  Epub 2018 Feb 5. [PubMed:29421433  ] 
  2. Drinkwater N, Gee CL, Puri M, Criscione KR, McLeish MJ, Grunewald GL, Martin JL: Molecular recognition of physiological substrate noradrenaline by the adrenaline-synthesizing enzyme PNMT and factors influencing its methyltransferase activity. Biochem J. 2009 Aug 27;422(3):463-71. doi: 10.1042/BJ20090702. [PubMed:19570037  ] 
  3. Manini P, Panzella L, Napolitano A, d'Ischia M: Oxidation chemistry of norepinephrine: partitioning of the O-quinone between competing cyclization and chain breakdown pathways and their roles in melanin formation. Chem Res Toxicol. 2007 Oct;20(10):1549-55. doi: 10.1021/tx700254q. Epub 2007 Sep  25. [PubMed:17892264  ]