NP-MRD: Showing NP-Card for 4-Methoxybrassinin (NP0075006)

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Record Information

Version

2.0

Created at

2022-04-28 20:19:36 UTC

Updated at

2022-04-28 20:19:36 UTC

NP-MRD ID

NP0075006

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-Methoxybrassinin

Description

4-Methoxybrassinin, also known as MA5I, 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. 4-Methoxybrassinin is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 4-Methoxybrassinin has been detected, but not quantified in, brassicas. 4-Methoxybrassinin is found in Brassica oleracea , Brassica rapa and Pseudomonas cichorii. This could make 4-methoxybrassinin a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 32  0  0  0  0  0  0  0  0999 V2000
   -2.6357   -2.9768   -0.1919 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6603   -1.9278   -0.0894 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1430   -0.6233   -0.0711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4881   -0.3234   -0.1464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9592    0.9730   -0.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0825    2.0342   -0.0310 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7362    1.7398    0.0446 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6984    2.5820    0.1433 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.4369    1.8359    0.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1112    0.5018    0.1167 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0138   -0.6525    0.1311 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4033   -0.2982    0.2340 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3769   -1.3174    0.2581 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9972   -2.9112    0.1732 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.1374   -0.9385    0.3859 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.3544    0.8404    0.4675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2619    0.4407    0.0259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1365   -3.9663   -0.1339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3654   -2.8749    0.6238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1606   -2.9136   -1.1660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1881   -1.1556   -0.2229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0255    1.2088   -0.1873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4495    3.0547   -0.0160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7442    3.6370    0.1803 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4025    2.2683    0.2667 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7858   -1.2839    1.0392 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8458   -1.3429   -0.7457 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6943    0.6912    0.2902 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3741    1.1694    0.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2236    1.1966    1.5287 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5780    1.3326   -0.1591 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7 17  2  0
 17 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 10  9  2  0
  9  8  1  0
 17  3  1  0
  8  7  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  5 22  1  0
  6 23  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 16 29  1  0
 16 30  1  0
 16 31  1  0
  9 25  1  0
  8 24  1  0
M  END


  Mrv0541 02241218232D          

 17 18  0  0  0  0            999 V2000
   -0.6596   -2.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4021   -1.6909    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4846   -0.8658    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2271   -0.5359    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8246   -0.3709    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9071    0.4534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2471    0.9484    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2471    1.7733    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5771    2.0208    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.0721    1.3608    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5771    0.7008    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9071   -0.0409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7321   -0.1234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2271    0.5359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8971    1.2783    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4946   -0.7833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9071   -1.4433    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
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7 11  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
 10 15  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 16  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0075006

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=CC2=C1C(CNC(=S)SC)=CN2

> <INCHI_IDENTIFIER>
InChI=1S/C12H14N2OS2/c1-15-10-5-3-4-9-11(10)8(6-13-9)7-14-12(16)17-2/h3-6,13H,7H2,1-2H3,(H,14,16)

> <INCHI_KEY>
JVKOHVNWMQYCIN-UHFFFAOYSA-N

> <FORMULA>
C12H14N2OS2

> <MOLECULAR_WEIGHT>
266.382

> <EXACT_MASS>
266.05475446

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
28.026190560942695

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-[(4-methoxy-1H-indol-3-yl)methyl](methylsulfanyl)carbothioamide

> <ALOGPS_LOGP>
2.43

> <JCHEM_LOGP>
3.1227418096666666

> <ALOGPS_LOGS>
-4.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.243797278858878

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.487158851251522

> <JCHEM_PKA_STRONGEST_BASIC>
-4.857500229977964

> <JCHEM_POLAR_SURFACE_AREA>
37.05

> <JCHEM_REFRACTIVITY>
77.4351

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.57e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
N-[(4-methoxy-1H-indol-3-yl)methyl]methylsulfanylcarbothioamide

> <JCHEM_VEBER_RULE>
1

$$$$

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      -1.231  -3.772   0.000  0.00  0.00           C+0
HETATM    2  S   UNK     0      -2.617  -3.156   0.000  0.00  0.00           S+0
HETATM    3  C   UNK     0      -2.771  -1.616   0.000  0.00  0.00           C+0
HETATM    4  S   UNK     0      -4.157  -1.000   0.000  0.00  0.00           S+0
HETATM    5  N   UNK     0      -1.539  -0.692   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -1.693   0.846   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.461   1.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.461   3.310   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       1.077   3.772   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       2.001   2.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.077   1.308   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.693  -0.076   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.233  -0.230   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.157   1.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.541   2.386   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.923  -1.462   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       1.693  -2.694   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11    7   10   12                                                  
CONECT   12   11   13   16                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   10   14                                                       
CONECT   16   12   17                                                       
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Value	Source
4-(1H-Indazol-5-ylazo)-N-methyl-benzenamine	HMDB
5-(4-Methylaminophenylazo)indazole	HMDB
Ma5i	HMDB
N-[(4-Methoxy-1H-indol-3-yl)methyl](methylsulfanyl)carboimidothioate	Generator
N-[(4-Methoxy-1H-indol-3-yl)methyl](methylsulphanyl)carboimidothioate	Generator
N-[(4-Methoxy-1H-indol-3-yl)methyl](methylsulphanyl)carboimidothioic acid	Generator

Chemical Formula

C₁₂H₁₄N₂OS₂

Average Mass

266.3820 Da

Monoisotopic Mass

266.05475 Da

IUPAC Name

N-[(4-methoxy-1H-indol-3-yl)methyl](methylsulfanyl)carbothioamide

Traditional Name

N-[(4-methoxy-1H-indol-3-yl)methyl]methylsulfanylcarbothioamide

CAS Registry Number

Not Available

SMILES

COC1=CC=CC2=C1C(CNC(=S)SC)=CN2

InChI Identifier

InChI=1S/C12H14N2OS2/c1-15-10-5-3-4-9-11(10)8(6-13-9)7-14-12(16)17-2/h3-6,13H,7H2,1-2H3,(H,14,16)

InChI Key

JVKOHVNWMQYCIN-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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	Plant	KNApSAcK
Brassica rapa	Plant	KNApSAcK
Pseudomonas cichorii	Bacteria	KNApSAcK

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
Anisole
Alkyl aryl ether
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Dithiocarbamic acid ester
Ether
Sulfenyl compound
Azacycle
Organopnictogen compound
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxygen compound
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	2.43	ALOGPS
logP	3.12	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	7.49	ChemAxon
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	37.05 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	77.44 m³·mol⁻¹	ChemAxon
Polarizability	28.03 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

HMDB0040790

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB020606

KNApSAcK ID

Not Available

Chemspider ID

9186134

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11010948

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 4-Methoxybrassinin (NP0075006)

MOL for NP0075006 (4-Methoxybrassinin)

3D MOL for NP0075006 (4-Methoxybrassinin)

3D SDF for NP0075006 (4-Methoxybrassinin)

3D-SDF for NP0075006 (4-Methoxybrassinin)

PDB for NP0075006 (4-Methoxybrassinin)

3D PDB for NP0075006 (4-Methoxybrassinin)

SMILES for NP0075006 (4-Methoxybrassinin)

INCHI for NP0075006 (4-Methoxybrassinin)

Structure for NP0075006 (4-Methoxybrassinin)

3D Structure for NP0075006 (4-Methoxybrassinin)