NP-MRD: Showing NP-Card for [bis(methylsulfanyl)methylidene][(1-methoxyindol-3-yl)methyl]amine (NP0255745)

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Record Information

Version

1.0

Created at

2022-09-07 20:20:09 UTC

Updated at

2022-09-07 20:20:09 UTC

NP-MRD ID

NP0255745

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[bis(methylsulfanyl)methylidene][(1-methoxyindol-3-yl)methyl]amine

Description

Methoxybrassenin A 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. Methoxybrassenin A is a strong basic compound (based on its pKa). Outside of the human body, Methoxybrassenin A has been detected, but not quantified in, brassicas. [bis(methylsulfanyl)methylidene][(1-methoxyindol-3-yl)methyl]amine is found in Brassica oleracea. This could make methoxybrassenin a a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 35  0  0  0  0  0  0  0  0999 V2000
    4.6966   -2.2938    0.1263 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7509   -1.9268   -0.9165 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6154   -1.2046   -0.6317 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3151   -1.5809   -0.6873 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5291   -0.5563   -0.2139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8820   -0.5031    0.1722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8919   -0.3236   -0.8883 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9983    0.2787   -0.4327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9093    0.6541    1.3426 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4679    0.1132    2.0657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3896    0.7202   -1.2910 S   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9720   -0.3000   -2.5996 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4037    0.5153    0.1485 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1697    1.7933    0.5947 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1893    2.6873    0.7815 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5005    2.2676    0.5189 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7244    0.9693    0.0668 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6675    0.0591   -0.1266 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7215   -2.1155   -0.3223 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5804   -3.3240    0.4298 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4910   -1.6111    0.9686 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9120   -2.5067   -1.0568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0993    0.0835    1.0681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1124   -1.6568    0.4241 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2382   -0.8623    2.6393 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2710   -0.1068    1.3837 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7178    0.7866    2.8921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7342    0.1660   -3.6141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1321   -0.3906   -2.6139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5995   -1.3378   -2.6459 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1319    2.0661    0.7476 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9530    3.6845    1.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3364    2.9421    0.6804 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7270    0.5786   -0.1421 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  7  8  2  3
  8  9  1  0
  9 10  1  0
  8 11  1  0
 11 12  1  0
  5 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18  3  1  0
 18 13  1  0
  1 19  1  0
  1 20  1  0
  1 21  1  0
  4 22  1  0
  6 23  1  0
  6 24  1  0
 10 25  1  0
 10 26  1  0
 10 27  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
 14 31  1  0
 15 32  1  0
 16 33  1  0
 17 34  1  0
M  END


  Mrv0541 05061310332D          

 18 19  0  0  0  0            999 V2000
    1.4358    3.5881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5399   -1.7684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1190   -2.2830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1809   -1.3268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -0.5422    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    2.9750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7329   -1.9399    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    0.3739   -1.4984    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  7  5  1  0  0  0  0
 10  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11  6  2  0  0  0  0
 11 10  1  0  0  0  0
 12  7  2  0  0  0  0
 12 11  1  0  0  0  0
 14  8  1  0  0  0  0
 14 13  2  0  0  0  0
 15  9  1  0  0  0  0
 15 12  1  0  0  0  0
 16  1  1  0  0  0  0
 16 15  1  0  0  0  0
 17  2  1  0  0  0  0
 17 13  1  0  0  0  0
 18  3  1  0  0  0  0
 18 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0255745

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CON1C=C(CN=C(SC)SC)C2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C13H16N2OS2/c1-16-15-9-10(8-14-13(17-2)18-3)11-6-4-5-7-12(11)15/h4-7,9H,8H2,1-3H3

> <INCHI_KEY>
GQIAOJZSWXEICD-UHFFFAOYSA-N

> <FORMULA>
C13H16N2OS2

> <MOLECULAR_WEIGHT>
280.409

> <EXACT_MASS>
280.070404524

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
30.69488595256899

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[bis(methylsulfanyl)methylidene][(1-methoxy-1H-indol-3-yl)methyl]amine

> <ALOGPS_LOGP>
3.28

> <JCHEM_LOGP>
3.8163268589999997

> <ALOGPS_LOGS>
-3.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
3.8105825972403817

> <JCHEM_POLAR_SURFACE_AREA>
26.52

> <JCHEM_REFRACTIVITY>
81.9383

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.15e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[bis(methylsulfanyl)methylidene][(1-methoxyindol-3-yl)methyl]amine

> <JCHEM_VEBER_RULE>
1

$$$$

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       2.680   6.698   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.741  -3.301   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.222  -4.262   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.650   0.132   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.204  -2.477   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       2.680  -1.012   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0       2.126   4.089   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0       1.650   5.553   0.000  0.00  0.00           O+0
HETATM   17  S   UNK     0       3.235  -3.621   0.000  0.00  0.00           S+0
HETATM   18  S   UNK     0       0.698  -2.797   0.000  0.00  0.00           S+0
CONECT    1   16                                                            
CONECT    2   17                                                            
CONECT    3   18                                                            
CONECT    4    5    6                                                       
CONECT    5    4    7                                                       
CONECT    6    4   11                                                       
CONECT    7    5   12                                                       
CONECT    8   10   14                                                       
CONECT    9   10   15                                                       
CONECT   10    8    9   11                                                  
CONECT   11    6   10   12                                                  
CONECT   12    7   11   15                                                  
CONECT   13   14   17   18                                                  
CONECT   14    8   13                                                       
CONECT   15    9   12   16                                                  
CONECT   16    1   15                                                       
CONECT   17    2   13                                                       
CONECT   18    3   13                                                       
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

View in JSmol

Synonyms

Value	Source
[Bis(methylsulphanyl)methylidene][(1-methoxy-1H-indol-3-yl)methyl]amine	Generator

Chemical Formula

C₁₃H₁₆N₂OS₂

Average Mass

280.4090 Da

Monoisotopic Mass

280.07040 Da

IUPAC Name

[bis(methylsulfanyl)methylidene][(1-methoxy-1H-indol-3-yl)methyl]amine

Traditional Name

[bis(methylsulfanyl)methylidene][(1-methoxyindol-3-yl)methyl]amine

CAS Registry Number

Not Available

SMILES

CON1C=C(CN=C(SC)SC)C2=CC=CC=C12

InChI Identifier

InChI=1S/C13H16N2OS2/c1-16-15-9-10(8-14-13(17-2)18-3)11-6-4-5-7-12(11)15/h4-7,9H,8H2,1-3H3

InChI Key

GQIAOJZSWXEICD-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Brassica oleracea	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
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Sulfenyl compound
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
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	3.28	ALOGPS
logP	3.82	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Basic)	3.81	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.52 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	81.94 m³·mol⁻¹	ChemAxon
Polarizability	30.69 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0038635

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018030

KNApSAcK ID

Not Available

Chemspider ID

30777274

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101618767

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [bis(methylsulfanyl)methylidene][(1-methoxyindol-3-yl)methyl]amine (NP0255745)

MOL for NP0255745 ([bis(methylsulfanyl)methylidene][(1-methoxyindol-3-yl)methyl]amine)

3D MOL for NP0255745 ([bis(methylsulfanyl)methylidene][(1-methoxyindol-3-yl)methyl]amine)

3D SDF for NP0255745 ([bis(methylsulfanyl)methylidene][(1-methoxyindol-3-yl)methyl]amine)

3D-SDF for NP0255745 ([bis(methylsulfanyl)methylidene][(1-methoxyindol-3-yl)methyl]amine)

PDB for NP0255745 ([bis(methylsulfanyl)methylidene][(1-methoxyindol-3-yl)methyl]amine)

3D PDB for NP0255745 ([bis(methylsulfanyl)methylidene][(1-methoxyindol-3-yl)methyl]amine)

SMILES for NP0255745 ([bis(methylsulfanyl)methylidene][(1-methoxyindol-3-yl)methyl]amine)

INCHI for NP0255745 ([bis(methylsulfanyl)methylidene][(1-methoxyindol-3-yl)methyl]amine)

Structure for NP0255745 ([bis(methylsulfanyl)methylidene][(1-methoxyindol-3-yl)methyl]amine)

3D Structure for NP0255745 ([bis(methylsulfanyl)methylidene][(1-methoxyindol-3-yl)methyl]amine)