NP-MRD: Showing NP-Card for Methoxybrassitin (NP0049182)

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Record Information

Version

2.0

Created at

2022-03-17 21:08:24 UTC

Updated at

2022-03-17 21:08:24 UTC

NP-MRD ID

NP0049182

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Methoxybrassitin

Description

Methoxybrassitin 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. Methoxybrassitin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Methoxybrassitin has been detected, but not quantified in, a few different foods, such as brassicas, cauliflowers, and chinese cabbages. Methoxybrassitin is found in Brassica campestris ssp.pekinensis , Brassica oleracea, Brassica oleracea var.botrytis , Brassica sativus, Pseudomonas cichorii and Raphanus sativus. This could make methoxybrassitin a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241217572D          

 17 18  0  0  0  0            999 V2000
   -2.2798   -1.5957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6446   -0.9574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2798   -0.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3674   -0.2287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0026   -0.9574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4585   -1.6869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2732    1.6869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9114    1.1398    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8202    0.3192    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0916   -0.0463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1828   -0.8662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4556   -1.4133    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1857   -1.2310    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4592   -0.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0945    0.3192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2798   -0.3199    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.6446    0.5015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  2  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  9  1  0  0  0  0
  5  6  1  0  0  0  0
  5 11  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0049182

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CON1C=C(CNC(=O)SC)C2=C1C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C12H14N2O2S/c1-16-14-8-9(7-13-12(15)17-2)10-5-3-4-6-11(10)14/h3-6,8H,7H2,1-2H3,(H,13,15)

> <INCHI_KEY>
BHXCFNZULGNWRA-UHFFFAOYSA-N

> <FORMULA>
C12H14N2O2S

> <MOLECULAR_WEIGHT>
250.317

> <EXACT_MASS>
250.077598392

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
26.607879287071274

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[(1-methoxy-1H-indol-3-yl)methyl](methylsulfanyl)formamide

> <ALOGPS_LOGP>
1.60

> <JCHEM_LOGP>
2.0961991689999993

> <ALOGPS_LOGS>
-2.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.753801349894488

> <JCHEM_PKA_STRONGEST_BASIC>
-4.5876671699718425

> <JCHEM_POLAR_SURFACE_AREA>
43.26

> <JCHEM_REFRACTIVITY>
70.6386

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.37e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[(1-methoxyindol-3-yl)methyl]methylsulfanylformamide

> <JCHEM_VEBER_RULE>
0

$$$$

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      -4.256  -2.979   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.937  -1.787   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.256  -0.427   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.552  -0.427   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.872  -1.787   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.723  -3.149   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.510   3.149   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -1.701   2.128   0.000  0.00  0.00           O+0
HETATM    9  N   UNK     0      -1.531   0.596   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -0.171  -0.086   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.341  -1.617   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.850  -2.638   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0       2.213  -2.298   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0       2.724  -0.766   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.043   0.596   0.000  0.00  0.00           O+0
HETATM   16  S   UNK     0       4.256  -0.597   0.000  0.00  0.00           S+0
HETATM   17  C   UNK     0       4.937   0.936   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6   11                                                  
CONECT    6    1    5                                                       
CONECT    7    8                                                            
CONECT    8    7    9                                                       
CONECT    9    4    8   10                                                  
CONECT   10    9   11                                                       
CONECT   11    5   10   12                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Value	Source
1-Methoxybrassitin	HMDB
N-[(1-Methoxy-1H-indol-3-yl)methyl](methylsulfanyl)carboximidate	Generator
N-[(1-Methoxy-1H-indol-3-yl)methyl](methylsulphanyl)carboximidate	Generator
N-[(1-Methoxy-1H-indol-3-yl)methyl](methylsulphanyl)carboximidic acid	Generator

Chemical Formula

C₁₂H₁₄N₂O₂S

Average Mass

250.3170 Da

Monoisotopic Mass

250.07760 Da

IUPAC Name

N-[(1-methoxy-1H-indol-3-yl)methyl](methylsulfanyl)formamide

Traditional Name

N-[(1-methoxyindol-3-yl)methyl]methylsulfanylformamide

CAS Registry Number

113900-63-3

SMILES

CON1C=C(CNC(=O)SC)C2=C1C=CC=C2

InChI Identifier

InChI=1S/C12H14N2O2S/c1-16-14-8-9(7-13-12(15)17-2)10-5-3-4-6-11(10)14/h3-6,8H,7H2,1-2H3,(H,13,15)

InChI Key

BHXCFNZULGNWRA-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Brassica campestris ssp.Pekinensis	Plant	KNApSAcK
Brassica oleracea	LOTUS Database	35616633
Brassica oleracea var. botrytis	FooDB	KNAPSACK
Brassica oleracea var.botrytis	Plant	KNApSAcK
Brassica rapa	FooDB	KNAPSACK
Brassica sativus	Plant	KNApSAcK
Pseudomonas cichorii	Bacteria	KNApSAcK
Raphanus sativus	LOTUS Database	35616633

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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indoles

Direct Parent

3-alkylindoles

Alternative Parents

Substituents

3-alkylindole
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Carbonic acid derivative
Thiocarbamic acid derivative
Sulfenyl compound
Azacycle
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.6	ALOGPS
logP	2.1	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	15.75	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	43.26 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	70.64 m³·mol⁻¹	ChemAxon
Polarizability	26.61 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0038637

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018032

KNApSAcK ID

C00034922

Chemspider ID

28674925

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

13993677

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Methoxybrassitin (NP0049182)

MOL for NP0049182 (Methoxybrassitin)

3D MOL for NP0049182 (Methoxybrassitin)

3D SDF for NP0049182 (Methoxybrassitin)

3D-SDF for NP0049182 (Methoxybrassitin)

PDB for NP0049182 (Methoxybrassitin)

3D PDB for NP0049182 (Methoxybrassitin)

SMILES for NP0049182 (Methoxybrassitin)

INCHI for NP0049182 (Methoxybrassitin)

Structure for NP0049182 (Methoxybrassitin)

3D Structure for NP0049182 (Methoxybrassitin)