NP-MRD: Showing NP-Card for (1-Methoxyindol-3-yl)methyl isothiocyanate (NP0086485)

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Record Information

Version

2.0

Created at

2022-04-29 06:46:30 UTC

Updated at

2022-04-29 06:46:30 UTC

NP-MRD ID

NP0086485

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1-Methoxyindol-3-yl)methyl isothiocyanate

Description

3-(Isothiocyanatomethyl)-1-methoxy-1H-indole, also known as (1-methoxyindol-3-yl)methyl isothiocyanate, 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. 3-(Isothiocyanatomethyl)-1-methoxy-1H-indole is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 3-(Isothiocyanatomethyl)-1-methoxy-1H-indole has been detected, but not quantified in, brassicas. (1-Methoxyindol-3-yl)methyl isothiocyanate is found in Arabidopsis thaliana and Brassica napus . This could make 3-(isothiocyanatomethyl)-1-methoxy-1H-indole a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 05061310282D          

 15 16  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
    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
    1.1809   -1.3268    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
    1.4358   -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
    0.9259   -2.1115    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  9  6  1  0  0  0  0
  9  7  2  0  0  0  0
 10  4  2  0  0  0  0
 10  9  1  0  0  0  0
 11  5  2  0  0  0  0
 11 10  1  0  0  0  0
 12  6  1  0  0  0  0
 12  8  2  0  0  0  0
 13  7  1  0  0  0  0
 13 11  1  0  0  0  0
 14  1  1  0  0  0  0
 14 13  1  0  0  0  0
 15  8  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0086485

> <DATABASE_NAME>
NP-MRD

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

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

> <INCHI_KEY>
FLURSKCCKANNKS-UHFFFAOYSA-N

> <FORMULA>
C11H10N2OS

> <MOLECULAR_WEIGHT>
218.275

> <EXACT_MASS>
218.051383642

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
23.133274023521995

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
3.55

> <JCHEM_LOGP>
2.5985408423333336

> <ALOGPS_LOGS>
-3.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.11472261380752

> <JCHEM_POLAR_SURFACE_AREA>
26.52

> <JCHEM_REFRACTIVITY>
64.6858

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.95e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(isothiocyanatomethyl)-1-methoxyindole

> <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       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.650   0.132   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.204  -2.477   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       2.680  -1.012   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0       2.126   4.089   0.000  0.00  0.00           N+0
HETATM   14  O   UNK     0       1.650   5.553   0.000  0.00  0.00           O+0
HETATM   15  S   UNK     0       1.728  -3.941   0.000  0.00  0.00           S+0
CONECT    1   14                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2   10                                                       
CONECT    5    3   11                                                       
CONECT    6    9   12                                                       
CONECT    7    9   13                                                       
CONECT    8   12   15                                                       
CONECT    9    6    7   10                                                  
CONECT   10    4    9   11                                                  
CONECT   11    5   10   13                                                  
CONECT   12    6    8                                                       
CONECT   13    7   11   14                                                  
CONECT   14    1   13                                                       
CONECT   15    8                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Value	Source
(1-Methoxyindol-3-yl)methyl isothiocyanate	ChEBI
1-Methoxyindol-3-ylmethyl isothiocyanate	ChEBI
(1-Methoxyindol-3-yl)methyl isothiocyanic acid	Generator
1-Methoxyindol-3-ylmethyl isothiocyanic acid	Generator

Chemical Formula

C₁₁H₁₀N₂OS

Average Mass

218.2750 Da

Monoisotopic Mass

218.05138 Da

IUPAC Name

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

Traditional Name

3-(isothiocyanatomethyl)-1-methoxyindole

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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

InChI Key

FLURSKCCKANNKS-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
Arabidopsis thaliana	LOTUS Database	35616633
Brassica napus	Plant	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
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Isothiocyanate
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic 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	3.55	ALOGPS
logP	2.6	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Basic)	-4.1	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	3	ChemAxon
Refractivity	64.69 m³·mol⁻¹	ChemAxon
Polarizability	23.13 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

HMDB0038463

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB017822

KNApSAcK ID

Not Available

Chemspider ID

10709973

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14206111

PDB ID

Not Available

ChEBI ID

136932

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (1-Methoxyindol-3-yl)methyl isothiocyanate (NP0086485)

MOL for NP0086485 ((1-Methoxyindol-3-yl)methyl isothiocyanate)

3D MOL for NP0086485 ((1-Methoxyindol-3-yl)methyl isothiocyanate)

3D SDF for NP0086485 ((1-Methoxyindol-3-yl)methyl isothiocyanate)

3D-SDF for NP0086485 ((1-Methoxyindol-3-yl)methyl isothiocyanate)

PDB for NP0086485 ((1-Methoxyindol-3-yl)methyl isothiocyanate)

3D PDB for NP0086485 ((1-Methoxyindol-3-yl)methyl isothiocyanate)

SMILES for NP0086485 ((1-Methoxyindol-3-yl)methyl isothiocyanate)

INCHI for NP0086485 ((1-Methoxyindol-3-yl)methyl isothiocyanate)

Structure for NP0086485 ((1-Methoxyindol-3-yl)methyl isothiocyanate)

3D Structure for NP0086485 ((1-Methoxyindol-3-yl)methyl isothiocyanate)