NP-MRD: Showing NP-Card for 3-(isothiocyanatomethyl)-4-methoxy-1h-indole (NP0306721)

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Record Information

Version

2.0

Created at

2022-09-10 23:23:06 UTC

Updated at

2022-09-10 23:23:06 UTC

NP-MRD ID

NP0306721

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-(isothiocyanatomethyl)-4-methoxy-1h-indole

Description

(4-Methoxyindol-3-ylmethyl)isothiocyanate, also known as 3-(isothiocyanatomethyl)-4-methoxyindole, 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-methoxyindol-3-ylmethyl)isothiocyanate is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. 3-(isothiocyanatomethyl)-4-methoxy-1h-indole is found in Arabidopsis thaliana. Based on a literature review very few articles have been published on (4-methoxyindol-3-ylmethyl)isothiocyanate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112201232D          

 15 16  0  0  0  0            999 V2000
    3.9934    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5249    1.8646    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0769    2.4777    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8220    3.2623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5671    4.0469    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    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  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  2  0  0  0  0
 10 15  1  0  0  0  0
  3 15  2  0  0  0  0
  7 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0306721

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2C(CN=C=S)=CNC2=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H10N2OS/c1-14-10-4-2-3-9-11(10)8(6-13-9)5-12-7-15/h2-4,6,13H,5H2,1H3

> <INCHI_KEY>
IMQUXUBOZWPMFX-UHFFFAOYSA-N

> <FORMULA>
C11H10N2OS

> <MOLECULAR_WEIGHT>
218.27

> <EXACT_MASS>
218.051384124

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
22.73108105294594

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-(isothiocyanatomethyl)-4-methoxy-1H-indole

> <JCHEM_LOGP>
2.7352138986666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.094254930389724

> <JCHEM_PKA_STRONGEST_BASIC>
-4.213006009922794

> <JCHEM_POLAR_SURFACE_AREA>
37.379999999999995

> <JCHEM_REFRACTIVITY>
63.49140000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3-(isothiocyanatomethyl)-4-methoxy-1H-indole

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       7.454   4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.121   3.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       3.322  -0.476   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.322   2.016   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.846   3.481   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       3.877   4.625   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       3.401   6.090   0.000  0.00  0.00           C+0
HETATM   14  S   UNK     0       2.925   7.554   0.000  0.00  0.00           S+0
HETATM   15  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   15                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   15                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   10    3    7                                                  
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Value	Source
3-(Isothiocyanatomethyl)-4-methoxyindole	ChEBI
4-Methoxy-3-indolylmethylisothiocyanate	ChEBI
4-Methoxyindol-3-ylmethyl isothiocyanate	ChEBI
4-Methoxy-3-indolylmethylisothiocyanic acid	Generator
4-Methoxyindol-3-ylmethyl isothiocyanic acid	Generator
(4-Methoxyindol-3-ylmethyl)isothiocyanic acid	Generator

Chemical Formula

C₁₁H₁₀N₂OS

Average Mass

218.2700 Da

Monoisotopic Mass

218.05138 Da

IUPAC Name

3-(isothiocyanatomethyl)-4-methoxy-1H-indole

Traditional Name

3-(isothiocyanatomethyl)-4-methoxy-1H-indole

CAS Registry Number

Not Available

SMILES

COC1=C2C(CN=C=S)=CNC2=CC=C1

InChI Identifier

InChI=1S/C11H10N2OS/c1-14-10-4-2-3-9-11(10)8(6-13-9)5-12-7-15/h2-4,6,13H,5H2,1H3

InChI Key

IMQUXUBOZWPMFX-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
Arabidopsis thaliana	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
Anisole
Phenol ether
Alkyl aryl ether
Substituted pyrrole
Benzenoid
Heteroaromatic compound
Pyrrole
Isothiocyanate
Ether
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Organooxygen compound
Organonitrogen compound
Hydrocarbon derivative
Organosulfur compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

an indole-phytolexin (CPDQT-433 )

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	2.74	ChemAxon
pKa (Strongest Acidic)	16.09	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.38 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	63.49 m³·mol⁻¹	ChemAxon
Polarizability	22.73 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

10709969

KEGG Compound ID

Not Available

BioCyc ID

CPDQT-433

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14206109

PDB ID

Not Available

ChEBI ID

136938

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-(isothiocyanatomethyl)-4-methoxy-1h-indole (NP0306721)

MOL for NP0306721 (3-(isothiocyanatomethyl)-4-methoxy-1h-indole)

3D MOL for NP0306721 (3-(isothiocyanatomethyl)-4-methoxy-1h-indole)

3D SDF for NP0306721 (3-(isothiocyanatomethyl)-4-methoxy-1h-indole)

3D-SDF for NP0306721 (3-(isothiocyanatomethyl)-4-methoxy-1h-indole)

PDB for NP0306721 (3-(isothiocyanatomethyl)-4-methoxy-1h-indole)

3D PDB for NP0306721 (3-(isothiocyanatomethyl)-4-methoxy-1h-indole)

SMILES for NP0306721 (3-(isothiocyanatomethyl)-4-methoxy-1h-indole)

INCHI for NP0306721 (3-(isothiocyanatomethyl)-4-methoxy-1h-indole)

Structure for NP0306721 (3-(isothiocyanatomethyl)-4-methoxy-1h-indole)

3D Structure for NP0306721 (3-(isothiocyanatomethyl)-4-methoxy-1h-indole)