NP-MRD: Showing NP-Card for 5-meo-nmt (NP0153784)

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Record Information

Version

2.0

Created at

2022-09-02 10:30:23 UTC

Updated at

2022-09-02 10:30:23 UTC

NP-MRD ID

NP0153784

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-meo-nmt

Description

N,O-dimethylserotonin 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. N,O-dimethylserotonin is a very strong basic compound (based on its pKa). 5-meo-nmt is found in Anadenanthera peregrina, Arundo donax, Phalaris arundinacea and Phyllodium pulchellum. A tryptamine derivative hahing a methoxy group at position 5 of the indole portion and a methyl substituent on the side-chain nitrogen.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 31 32  0  0  0  0  0  0  0  0999 V2000
   -3.9393    1.7107    0.8973 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1835    1.3819   -0.3211 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2147    0.3707   -0.0506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4452    0.0274   -1.2932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4347   -1.0157   -1.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5611   -2.3661   -1.3747 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5408   -3.0298   -0.9999 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.4023   -2.1433   -0.4328 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6686   -2.2879    0.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3137   -1.1678    0.6210 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7242    0.0811    0.5939 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4157    1.1624    1.1124 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9576    2.4765    1.1471 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4586    0.2210    0.0481 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8044   -0.8874   -0.4613 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3754    1.4091    1.8113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8687    1.0850    0.8756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1608    2.7956    0.9228 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8715    1.1759   -1.0487 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6055    0.6690    0.7950 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7832   -0.5654    0.2296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9956    0.9473   -1.7628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1620   -0.3548   -2.0478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4192   -2.8115   -1.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7741   -4.0429   -1.0919 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1293   -3.2681    0.1341 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2976   -1.2642    1.0490 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5232    2.8136    0.1793 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8453    3.1304    1.3116 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2178    2.5775    1.9523 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9471    1.1695   -0.0021 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  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8 15  2  0
 15 14  1  0
 14 11  2  0
 11 12  1  0
 12 13  1  0
 11 10  1  0
 10  9  2  0
 15  5  1  0
  9  8  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  6 24  1  0
  7 25  1  0
 14 31  1  0
 13 28  1  0
 13 29  1  0
 13 30  1  0
 10 27  1  0
  9 26  1  0
M  END


  Mrv1533004241519552D          

 15 16  0  0  0  0            999 V2000
   -2.2673    1.8818    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4604    1.7103    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2054    0.9256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3984    0.7541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -0.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6284   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.3654    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6411   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0701   -1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3556   -1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7845    0.9521    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  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  5  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
  8 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0153784

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CNCCC1=CNC2=C1C=C(OC)C=C2

> <INCHI_IDENTIFIER>
InChI=1S/C12H16N2O/c1-13-6-5-9-8-14-12-4-3-10(15-2)7-11(9)12/h3-4,7-8,13-14H,5-6H2,1-2H3

> <INCHI_KEY>
NFDDCRIHMZGWBP-UHFFFAOYSA-N

> <FORMULA>
C12H16N2O

> <MOLECULAR_WEIGHT>
204.273

> <EXACT_MASS>
204.126263143

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
31

> <JCHEM_AVERAGE_POLARIZABILITY>
23.47320252406564

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[2-(5-methoxy-1H-indol-3-yl)ethyl](methyl)amine

> <ALOGPS_LOGP>
1.83

> <JCHEM_LOGP>
1.7613465780000002

> <ALOGPS_LOGS>
-2.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.44413212215917

> <JCHEM_PKA_STRONGEST_BASIC>
10.334279893272234

> <JCHEM_POLAR_SURFACE_AREA>
37.05

> <JCHEM_REFRACTIVITY>
61.6107

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.27e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-MeO-NMT

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -4.232   3.513   0.000  0.00  0.00           C+0
HETATM    2  N   UNK     0      -2.726   3.192   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0      -2.250   1.728   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.744   1.408   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.268  -0.057   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.173  -1.303   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0      -0.268  -2.549   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       1.197  -2.073   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.197  -0.533   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.530   0.237   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.864  -0.533   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.864  -2.073   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.530  -2.843   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       5.198   0.237   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.198   1.777   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8    5   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   14                                                  
CONECT   12   11   13                                                       
CONECT   13   12    8                                                       
CONECT   14   11   15                                                       
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

View in JSmol

Synonyms

Value	Source
5-Methoxy-3-(2-methylamino)ethylindole	ChEBI
5-Methoxy-N-methyl-1H-indole-3-ethanamine	ChEBI
5-Methoxy-N-methyltryptamine	ChEBI
alpha,O-Dimethylserotonin	MeSH
5-Methoxy-alpha-methyltryptamine hydrochloride	MeSH
5-Methoxy-alpha-methyltryptamine, (-)-isomer	MeSH
5-Methoxy-alpha-methyltryptamine monohydrochloride, (+-)-isomer	MeSH
5-Methoxy-alpha-methyltryptamine, (+)-isomer	MeSH
5-Methoxy-alpha-methyltryptamine	MeSH
5-Methoxy-alpha-methyltryptamine dipicrate	MeSH
5-Methoxy-alpha-methyltryptamine, (+-)-isomer	MeSH

Chemical Formula

C₁₂H₁₆N₂O

Average Mass

204.2730 Da

Monoisotopic Mass

204.12626 Da

IUPAC Name

[2-(5-methoxy-1H-indol-3-yl)ethyl](methyl)amine

Traditional Name

5-MeO-NMT

CAS Registry Number

Not Available

SMILES

CNCCC1=CNC2=C1C=C(OC)C=C2

InChI Identifier

InChI=1S/C12H16N2O/c1-13-6-5-9-8-14-12-4-3-10(15-2)7-11(9)12/h3-4,7-8,13-14H,5-6H2,1-2H3

InChI Key

NFDDCRIHMZGWBP-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
Anadenanthera peregrina	LOTUS Database	35616633
Arundo donax	LOTUS Database	35616633
Phalaris arundinacea	LOTUS Database	35616633
Phyllodium pulchellum	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
3-alkylindole
Indole
Anisole
Alkyl aryl ether
Aralkylamine
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Secondary aliphatic amine
Ether
Secondary amine
Azacycle
Organonitrogen compound
Organopnictogen compound
Amine
Organic nitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tryptamines (CHEBI:189635 )

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	1.83	ALOGPS
logP	1.76	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	17.44	ChemAxon
pKa (Strongest Basic)	10.33	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	37.05 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	61.61 m³·mol⁻¹	ChemAxon
Polarizability	23.47 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

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

16184

PDB ID

Not Available

ChEBI ID

189635

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-meo-nmt (NP0153784)

MOL for NP0153784 (5-meo-nmt)

3D MOL for NP0153784 (5-meo-nmt)

3D SDF for NP0153784 (5-meo-nmt)

3D-SDF for NP0153784 (5-meo-nmt)

PDB for NP0153784 (5-meo-nmt)

3D PDB for NP0153784 (5-meo-nmt)

SMILES for NP0153784 (5-meo-nmt)

INCHI for NP0153784 (5-meo-nmt)

Structure for NP0153784 (5-meo-nmt)

3D Structure for NP0153784 (5-meo-nmt)