NP-MRD: Showing NP-Card for {3-[2-(dimethylamino)ethyl]-1h-indol-5-yl}oxidanesulfonic acid (NP0174001)

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Record Information

Version

1.0

Created at

2022-09-03 11:12:30 UTC

Updated at

2022-09-03 11:12:30 UTC

NP-MRD ID

NP0174001

Secondary Accession Numbers

None

Natural Product Identification

Common Name

{3-[2-(dimethylamino)ethyl]-1h-indol-5-yl}oxidanesulfonic acid

Description

{3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl}oxidanesulfonic acid belongs to the class of organic compounds known as tryptamines and derivatives. Tryptamines and derivatives are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine. {3-[2-(dimethylamino)ethyl]-1h-indol-5-yl}oxidanesulfonic acid is found in Bufotes viridis. {3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl}oxidanesulfonic acid is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 36  0  0  0  0  0  0  0  0999 V2000
   -4.2106    0.4384    1.1575 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4831    0.6733   -0.0932 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0002    2.0598   -0.0739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3643   -0.2509   -0.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6322   -0.2998   -1.4158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5089   -1.2817   -1.2032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4175   -2.5945   -1.5338 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7650   -3.0825   -1.1125 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4389   -2.0835   -0.5069 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6930   -2.0940    0.0856 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1859   -0.9310    0.6489 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4102    0.2160    0.6062 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9405    1.3636    1.1832 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9127    2.4178    0.2570 S   0  0  0  0  0  6  0  0  0  0  0  0
    3.7970    3.8102    0.7873 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4900    2.3178   -1.1946 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5244    1.8834    0.3199 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1550    0.2131    0.0108 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6715   -0.9457   -0.5462 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8138    1.3543    1.3482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9351   -0.3797    0.9425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5688    0.2427    2.0082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0521    2.4309   -1.1114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7086    2.7068    0.5134 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0167    2.1542    0.4126 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6451   -0.0345    0.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7692   -1.2566    0.1001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1543    0.6512   -1.6995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2649   -0.6704   -2.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1693   -3.1856   -2.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1246   -4.0545   -1.2197 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2763   -2.9941    0.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1539   -0.9179    1.1144 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6040    1.0271    0.8253 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5716    1.0963   -0.0143 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 17  1  0
 14 15  2  0
 14 16  2  0
 12 18  1  0
 18 19  2  0
 19  6  1  0
 19  9  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
  3 23  1  0
  3 24  1  0
  3 25  1  0
  4 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  7 30  1  0
  8 31  1  0
 10 32  1  0
 11 33  1  0
 17 34  1  0
 18 35  1  0
M  END


  Mrv1533004161514412D          

 19 20  0  0  0  0            999 V2000
   -0.9851   -3.2777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1781   -3.1062    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3739   -3.7192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0768   -2.3215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    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
    4.0668   -1.5229    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812   -1.1104    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.4957   -0.6979    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1937   -1.8249    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3687   -0.3960    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -1.5229    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  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  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  2  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  2  0  0  0  0
 14 17  1  0  0  0  0
 12 18  1  0  0  0  0
 18 19  2  0  0  0  0
  6 19  1  0  0  0  0
  9 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0174001

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CN(C)CCC1=CNC2=CC=C(OS(O)(=O)=O)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C12H16N2O4S/c1-14(2)6-5-9-8-13-12-4-3-10(7-11(9)12)18-19(15,16)17/h3-4,7-8,13H,5-6H2,1-2H3,(H,15,16,17)

> <INCHI_KEY>
OYOOWLVMRZQOMJ-UHFFFAOYSA-N

> <FORMULA>
C12H16N2O4S

> <MOLECULAR_WEIGHT>
284.33

> <EXACT_MASS>
284.083078177

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
28.449982005783017

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}oxidanesulfonic acid

> <ALOGPS_LOGP>
0.34

> <JCHEM_LOGP>
0.04539323513546917

> <ALOGPS_LOGS>
-2.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
17.205324625804565

> <JCHEM_PKA_STRONGEST_ACIDIC>
-1.8141396444646105

> <JCHEM_PKA_STRONGEST_BASIC>
9.559546257930837

> <JCHEM_POLAR_SURFACE_AREA>
82.63

> <JCHEM_REFRACTIVITY>
72.4149

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.55e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}oxidanesulfonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      -1.839  -6.118   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -0.333  -5.798   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       0.698  -6.943   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.143  -4.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       7.591  -2.843   0.000  0.00  0.00           O+0
HETATM   14  S   UNK     0       8.925  -2.073   0.000  0.00  0.00           S+0
HETATM   15  O   UNK     0      10.259  -1.303   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       9.695  -3.407   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       8.155  -0.739   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   19                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   19                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   18                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   16   17                                             
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   14                                                            
CONECT   18   12   19                                                       
CONECT   19   18    6    9                                                  
MASTER        0    0    0    0    0    0    0    0   19    0   40    0
END

View in JSmol

Synonyms

Value	Source
{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}oxidanesulfonate	Generator
{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}oxidanesulphonate	Generator
{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}oxidanesulphonic acid	Generator

Chemical Formula

C₁₂H₁₆N₂O₄S

Average Mass

284.3300 Da

Monoisotopic Mass

284.08308 Da

IUPAC Name

{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}oxidanesulfonic acid

Traditional Name

{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}oxidanesulfonic acid

CAS Registry Number

Not Available

SMILES

CN(C)CCC1=CNC2=CC=C(OS(O)(=O)=O)C=C12

InChI Identifier

InChI=1S/C12H16N2O4S/c1-14(2)6-5-9-8-13-12-4-3-10(7-11(9)12)18-19(15,16)17/h3-4,7-8,13H,5-6H2,1-2H3,(H,15,16,17)

InChI Key

OYOOWLVMRZQOMJ-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
Bufotes viridis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tryptamines and derivatives. Tryptamines and derivatives are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Tryptamines and derivatives

Direct Parent

Tryptamines and derivatives

Alternative Parents

Substituents

Tryptamine
Arylsulfate
3-alkylindole
Indole
Alkaloid or derivatives
Aralkylamine
Substituted pyrrole
Sulfuric acid monoester
Sulfate-ester
Sulfuric acid ester
Benzenoid
Organic sulfuric acid or derivatives
Pyrrole
Heteroaromatic compound
Tertiary aliphatic amine
Tertiary amine
Azacycle
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organooxygen compound
Organonitrogen compound
Amine
Hydrocarbon derivative
Organic nitrogen 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	0.34	ALOGPS
logP	0.045	ChemAxon
logS	-2.9	ALOGPS
pKa (Strongest Acidic)	-1.8	ChemAxon
pKa (Strongest Basic)	9.56	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	82.63 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	72.41 m³·mol⁻¹	ChemAxon
Polarizability	28.45 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for {3-[2-(dimethylamino)ethyl]-1h-indol-5-yl}oxidanesulfonic acid (NP0174001)

MOL for NP0174001 ({3-[2-(dimethylamino)ethyl]-1h-indol-5-yl}oxidanesulfonic acid)

3D MOL for NP0174001 ({3-[2-(dimethylamino)ethyl]-1h-indol-5-yl}oxidanesulfonic acid)

3D SDF for NP0174001 ({3-[2-(dimethylamino)ethyl]-1h-indol-5-yl}oxidanesulfonic acid)

3D-SDF for NP0174001 ({3-[2-(dimethylamino)ethyl]-1h-indol-5-yl}oxidanesulfonic acid)

PDB for NP0174001 ({3-[2-(dimethylamino)ethyl]-1h-indol-5-yl}oxidanesulfonic acid)

3D PDB for NP0174001 ({3-[2-(dimethylamino)ethyl]-1h-indol-5-yl}oxidanesulfonic acid)

SMILES for NP0174001 ({3-[2-(dimethylamino)ethyl]-1h-indol-5-yl}oxidanesulfonic acid)

INCHI for NP0174001 ({3-[2-(dimethylamino)ethyl]-1h-indol-5-yl}oxidanesulfonic acid)

Structure for NP0174001 ({3-[2-(dimethylamino)ethyl]-1h-indol-5-yl}oxidanesulfonic acid)

3D Structure for NP0174001 ({3-[2-(dimethylamino)ethyl]-1h-indol-5-yl}oxidanesulfonic acid)