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Showing NP-Card for Cyclobrassinin (NP0047621)

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Record Information
Version2.0
Created at2022-03-17 20:43:11 UTC
Updated at2022-03-17 20:43:11 UTC
NP-MRD IDNP0047621
Secondary Accession NumbersNone
Natural Product Identification
Common NameCyclobrassinin
DescriptionCyclobrassinin belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. Cyclobrassinin is a strong basic compound (based on its pKa). Outside of the human body, Cyclobrassinin has been detected, but not quantified in, several different foods, such as brassicas, cauliflowers, chinese cabbages, chinese mustards, and swedes. Cyclobrassinin is found in Brassica campestris ssp.Pekinensis , Brassica carinata , Brassica nigra , Brassica oleracea , Pseudomonas cichorii and Raphanus sativus. This could make cyclobrassinin a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0047621 (Cyclobrassinin)


  Mrv0541 02241218302D          

 15 17  0  0  0  0            999 V2000
   -2.2464    0.8659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5357    0.0681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9950   -0.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1638   -0.3790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4985   -0.8923    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1783   -0.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9213   -0.6431    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5536    0.0154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3146    0.7928    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5087    0.9654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0595    0.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9363    0.3653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4771    0.9882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2967   -0.2120    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.5357   -0.9882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 13  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 12  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 11  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 14  1  0  0  0  0
  9 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
 14 15  1  0  0  0  0
M  END
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3D MOL for NP0047621 (Cyclobrassinin)

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3D SDF for NP0047621 (Cyclobrassinin)

  Mrv0541 02241218302D          

 15 17  0  0  0  0            999 V2000
   -2.2464    0.8659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5357    0.0681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9950   -0.5550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1638   -0.3790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4985   -0.8923    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1783   -0.4144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9213   -0.6431    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.5536    0.0154    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3146    0.7928    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.5087    0.9654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0595    0.3618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9363    0.3653    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4771    0.9882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2967   -0.2120    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.5357   -0.9882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 13  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 12  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6 11  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 14  1  0  0  0  0
  9 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
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047621

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CSC1=NCC2=C(NC3=C2C=CC=C3)S1

> <INCHI_IDENTIFIER>
InChI=1S/C11H10N2S2/c1-14-11-12-6-8-7-4-2-3-5-9(7)13-10(8)15-11/h2-5,13H,6H2,1H3

> <INCHI_KEY>
MVMVWNMQGBYIDM-UHFFFAOYSA-N

> <FORMULA>
C11H10N2S2

> <MOLECULAR_WEIGHT>
234.341

> <EXACT_MASS>
234.02853971

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
25.235437047479714

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-(methylsulfanyl)-4H,9H-[1,3]thiazino[6,5-b]indole

> <ALOGPS_LOGP>
2.90

> <JCHEM_LOGP>
3.6045998263333328

> <ALOGPS_LOGS>
-3.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.102137297251671

> <JCHEM_PKA_STRONGEST_BASIC>
3.019944866484862

> <JCHEM_POLAR_SURFACE_AREA>
28.15

> <JCHEM_REFRACTIVITY>
67.40120000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.87e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(methylsulfanyl)-4H,9H-[1,3]thiazino[6,5-b]indole

> <JCHEM_VEBER_RULE>
1

$$$$

Download
3D-SDF for NP0047621 (Cyclobrassinin)
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PDB for NP0047621 (Cyclobrassinin)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -4.193   1.616   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.733   0.127   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.724  -1.036   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.172  -0.707   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -0.930  -1.666   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       0.333  -0.773   0.000  0.00  0.00           C+0
HETATM    7  S   UNK     0       1.720  -1.200   0.000  0.00  0.00           S+0
HETATM    8  C   UNK     0       2.900   0.029   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       2.454   1.480   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       0.950   1.802   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.111   0.675   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.748   0.682   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.757   1.845   0.000  0.00  0.00           C+0
HETATM   14  S   UNK     0       4.287  -0.396   0.000  0.00  0.00           S+0
HETATM   15  C   UNK     0       4.733  -1.845   0.000  0.00  0.00           C+0
CONECT    1    2   13                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11    6   10   12                                                  
CONECT   12    4   11   13                                                  
CONECT   13    1   12                                                       
CONECT   14    8   15                                                       
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   34    0
END

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3D PDB for NP0047621 (Cyclobrassinin)
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SMILES for NP0047621 (Cyclobrassinin)
CSC1=NCC2=C(NC3=C2C=CC=C3)S1
Download
INCHI for NP0047621 (Cyclobrassinin)
InChI=1S/C11H10N2S2/c1-14-11-12-6-8-7-4-2-3-5-9(7)13-10(8)15-11/h2-5,13H,6H2,1H3
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View in JSmol
Synonyms
ValueSource
4,9-Dihydro-2-(methylthio)-1,3-thiazino[6,5-b]indole, 9ciHMDB
2-(Methylsulphanyl)-4H,9H-[1,3]thiazino[6,5-b]indoleGenerator
CyclobrassininMeSH
Chemical FormulaC11H10N2S2
Average Mass234.3410 Da
Monoisotopic Mass234.02854 Da
IUPAC Name2-(methylsulfanyl)-4H,9H-[1,3]thiazino[6,5-b]indole
Traditional Name2-(methylsulfanyl)-4H,9H-[1,3]thiazino[6,5-b]indole
CAS Registry Number105748-58-1
SMILES
CSC1=NCC2=C(NC3=C2C=CC=C3)S1
InChI Identifier
InChI=1S/C11H10N2S2/c1-14-11-12-6-8-7-4-2-3-5-9(7)13-10(8)15-11/h2-5,13H,6H2,1H3
InChI KeyMVMVWNMQGBYIDM-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Brassica campestris ssp.PekinensisPlant
Brassica carinataPlant
Brassica junceaFooDB
Brassica napusFooDB
Brassica nigraPlant
Brassica oleraceaPlant
Brassica oleracea var. botrytisFooDB
Brassica rapaFooDB
Pseudomonas cichoriiBacteria
Raphanus sativusLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassIndoles and derivatives  
Sub ClassIndoles  
Direct Parent3-alkylindoles  
Alternative Parents
Substituents
  • 3-alkylindole
    • 

  • Aryl thioether
    • 

  • Benzenoid
    • 

  • Heteroaromatic compound
    • 

  • Pyrrole
    • 

  • Azacycle
    • 

  • Organic 1,3-dipolar compound
    • 

  • Propargyl-type 1,3-dipolar organic compound
    • 

  • Sulfenyl compound
    • 

  • Organic nitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organosulfur compound
    • 

  • Organonitrogen compound
    • 

  • 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
logP2.9ALOGPS
logP3.6ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)12.1ChemAxon
pKa (Strongest Basic)3.02ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area28.15 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity67.4 m³·mol⁻¹ChemAxon
Polarizability25.24 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0033352  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011380  
KNApSAcK IDC00033745  
Chemspider ID160492  
KEGG Compound IDNot Available
BioCyc IDCPD-13599  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound184579  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available