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Showing NP-Card for Brassilexin (NP0049465)

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Record Information
Version2.0
Created at2022-03-17 21:12:58 UTC
Updated at2022-03-17 21:12:58 UTC
NP-MRD IDNP0049465
Secondary Accession NumbersNone
Natural Product Identification
Common NameBrassilexin
DescriptionBrassilexin belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole. Brassilexin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Brassilexin has been detected, but not quantified in, several different foods, such as brassicas, cauliflowers, chinese cabbages, chinese mustards, and herbs and spices. Brassilexin is found in Brassica carinata , Brassica napus L.ssp.rapifera , Brassica nigra , Brassica oleracea and Sinapis arvensis . Brassilexin was first documented in 2005 (PMID: 15730307). This could make brassilexin a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0049465 (Brassilexin)


  Mrv0541 05061311172D          

 12 14  0  0  0  0            999 V2000
    4.1008    2.0501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3402    2.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2973    1.8627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7762    3.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2507    1.9506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7333    2.4648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9085    2.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9727    3.2543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6381    3.2280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5739    2.4223    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2959    3.7260    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8133    3.2118    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  3  2  0  0  0  0
  7  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  4  2  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 10  5  2  0  0  0  0
 11  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12  9  1  0  0  0  0
 12 10  1  0  0  0  0
M  END
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3D MOL for NP0049465 (Brassilexin)

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3D SDF for NP0049465 (Brassilexin)

  Mrv0541 05061311172D          

 12 14  0  0  0  0            999 V2000
    4.1008    2.0501    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3402    2.8396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2973    1.8627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7762    3.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2507    1.9506    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7333    2.4648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9085    2.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9727    3.2543    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6381    3.2280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5739    2.4223    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.2959    3.7260    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8133    3.2118    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  3  2  0  0  0  0
  7  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  4  2  0  0  0  0
  8  6  1  0  0  0  0
  9  7  2  0  0  0  0
 10  5  2  0  0  0  0
 11  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12  9  1  0  0  0  0
 12 10  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049465

> <DATABASE_NAME>
NP-MRD

> <SMILES>
N1C2=C(C=NS2)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C9H6N2S/c1-2-4-8-6(3-1)7-5-10-12-9(7)11-8/h1-5,11H

> <INCHI_KEY>
NHMBEDDKDVIBQD-UHFFFAOYSA-N

> <FORMULA>
C9H6N2S

> <MOLECULAR_WEIGHT>
174.222

> <EXACT_MASS>
174.025168892

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
17.82509992339495

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8H-[1,2]thiazolo[5,4-b]indole

> <ALOGPS_LOGP>
2.43

> <JCHEM_LOGP>
2.415802667

> <ALOGPS_LOGS>
-3.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.778529667097857

> <JCHEM_PKA_STRONGEST_BASIC>
0.7861223957167757

> <JCHEM_POLAR_SURFACE_AREA>
28.68

> <JCHEM_REFRACTIVITY>
48.3377

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.07e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8H-[1,2]thiazolo[5,4-b]indole

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0049465 (Brassilexin)
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PDB for NP0049465 (Brassilexin)
HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       7.655   3.827   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.102   5.301   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.155   3.477   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.049   6.425   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.335   3.641   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.102   4.601   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.563   4.571   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.549   6.075   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.058   6.026   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       1.071   4.522   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0       4.286   6.955   0.000  0.00  0.00           N+0
HETATM   12  S   UNK     0       1.518   5.995   0.000  0.00  0.00           S+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    6                                                       
CONECT    4    2    8                                                       
CONECT    5    7   10                                                       
CONECT    6    3    7    8                                                  
CONECT    7    5    6    9                                                  
CONECT    8    4    6   11                                                  
CONECT    9    7   11   12                                                  
CONECT   10    5   12                                                       
CONECT   11    8    9                                                       
CONECT   12    9   10                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   28    0
END

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3D PDB for NP0049465 (Brassilexin)
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SMILES for NP0049465 (Brassilexin)
N1C2=C(C=NS2)C2=CC=CC=C12
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INCHI for NP0049465 (Brassilexin)
InChI=1S/C9H6N2S/c1-2-4-8-6(3-1)7-5-10-12-9(7)11-8/h1-5,11H
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Synonyms
ValueSource
8H-Isothiazolo(5,4-b)indoleHMDB
BrassilexineHMDB
Chemical FormulaC9H6N2S
Average Mass174.2220 Da
Monoisotopic Mass174.02517 Da
IUPAC Name8H-[1,2]thiazolo[5,4-b]indole
Traditional Name8H-[1,2]thiazolo[5,4-b]indole
CAS Registry Number119752-76-0
SMILES
N1C2=C(C=NS2)C2=CC=CC=C12
InChI Identifier
InChI=1S/C9H6N2S/c1-2-4-8-6(3-1)7-5-10-12-9(7)11-8/h1-5,11H
InChI KeyNHMBEDDKDVIBQD-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Brassica carinataPlant
Brassica junceaFooDB
Brassica napus L.ssp.rapiferaPlant
Brassica nigraPlant
Brassica oleraceaPlant
Brassica oleracea var. botrytisFooDB
Brassica rapaFooDB
Sinapis arvensisPlant
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene  to form 2,3-benzopyrrole.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassIndoles and derivatives  
Sub ClassIndoles  
Direct ParentIndoles  
Alternative Parents
Substituents
  • Indole
    • 

  • Benzenoid
    • 

  • Heteroaromatic compound
    • 

  • Thiazole
    • 

  • Pyrrole
    • 

  • Azole
    • 

  • Azacycle
    • 

  • Organic nitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organonitrogen 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
logP2.43ALOGPS
logP2.42ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)10.78ChemAxon
pKa (Strongest Basic)0.79ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area28.68 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity48.34 m³·mol⁻¹ChemAxon
Polarizability17.83 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0039638  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB019266  
KNApSAcK IDC00027108  
Chemspider ID19992709  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound135413564  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Pedras MS, Jha M: Concise syntheses of the cruciferous phytoalexins brassilexin, sinalexin, wasalexins, and analogues: expanding the scope of the vilsmeier formylation. J Org Chem. 2005 Mar 4;70(5):1828-34. doi: 10.1021/jo0479866. [PubMed:15730307  ]