NP-MRD: Showing NP-Card for Nb-Methyltetrahydroharmol (NP0084608)

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Record Information

Version

2.0

Created at

2022-04-29 05:18:04 UTC

Updated at

2022-04-29 05:18:05 UTC

NP-MRD ID

NP0084608

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Nb-Methyltetrahydroharmol

Description

Nb-Methyltetrahydroharmol belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole. Nb-Methyltetrahydroharmol is a very strong basic compound (based on its pKa). Outside of the human body, Nb-Methyltetrahydroharmol has been detected, but not quantified in, fruits. Nb-Methyltetrahydroharmol is found in Elaeagnus angustifolia . This could make NB-methyltetrahydroharmol a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 34  0  0  0  0  0  0  0  0999 V2000
   -2.3732   -2.0009    0.1674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7953   -0.6797   -0.3020 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.3245   -0.6312   -0.1125 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6444   -1.5369    0.1566 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8459   -0.9059    0.2175 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1319   -1.3544    0.4574 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1892   -0.4702    0.4599 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5056   -0.8904    0.6994 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9125    0.8584    0.2167 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6397    1.3410   -0.0268 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5957    0.4308   -0.0234 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2529    0.6368   -0.2331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6613    1.7717   -0.5282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8068    1.6170    0.4471 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5140    0.3823    0.3144 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8305    0.5717   -0.2745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5897   -2.7786    0.3051 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1117   -2.3737   -0.5673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9420   -1.8481    1.1229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9901   -0.6076   -1.4130 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4891   -2.5688    0.2965 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3543   -2.3916    0.6481 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8332   -0.8933    1.6775 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7105    1.5953    0.2077 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4259    2.3745   -0.2157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0017    1.7589   -1.5815 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1951    2.7498   -0.3425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3316    1.6102    1.4707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5273    2.4542    0.3847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9749   -0.2006   -1.0470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9680    1.6098   -0.6631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5934    0.3697    0.5301 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2 15  1  0
 15 16  1  0
 15 14  1  0
 14 13  1  0
 13 12  1  0
 12  3  2  0
  3  4  1  0
  4  5  1  0
  5 11  2  0
 11 10  1  0
 10  9  2  0
  9  7  1  0
  7  8  1  0
  7  6  2  0
  3  2  1  0
  6  5  1  0
 11 12  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  6
 16 30  1  0
 16 31  1  0
 16 32  1  0
 14 28  1  0
 14 29  1  0
 13 26  1  0
 13 27  1  0
  4 21  1  0
 10 25  1  0
  9 24  1  0
  8 23  1  0
  6 22  1  0
M  END


  Mrv0541 05061307422D          

 16 18  0  0  0  0            999 V2000
    0.2046   -1.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8995    0.0694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6014   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339   -0.6855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.2410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.7674    0.0694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  2  0  0  0  0
  6  5  1  0  0  0  0
  8  1  1  0  0  0  0
  9  3  1  0  0  0  0
  9  7  2  0  0  0  0
 10  4  1  0  0  0  0
 11  5  1  0  0  0  0
 11 10  1  0  0  0  0
 12  7  1  0  0  0  0
 12 10  2  0  0  0  0
 13  8  1  0  0  0  0
 13 11  2  0  0  0  0
 14 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15  2  1  0  0  0  0
 15  6  1  0  0  0  0
 15  8  1  0  0  0  0
 16  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0084608

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1N(C)CCC2=C1NC1=C2C=CC(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C13H16N2O/c1-8-13-11(5-6-15(8)2)10-4-3-9(16)7-12(10)14-13/h3-4,7-8,14,16H,5-6H2,1-2H3

> <INCHI_KEY>
AGILGFCOHSGLIT-UHFFFAOYSA-N

> <FORMULA>
C13H16N2O

> <MOLECULAR_WEIGHT>
216.2789

> <EXACT_MASS>
216.126263144

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
24.583323945215184

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,2-dimethyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-7-ol

> <ALOGPS_LOGP>
2.37

> <JCHEM_LOGP>
2.0863039089999997

> <ALOGPS_LOGS>
-1.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
17.3024470862984

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.733657342372875

> <JCHEM_PKA_STRONGEST_BASIC>
9.839001943968787

> <JCHEM_POLAR_SURFACE_AREA>
39.260000000000005

> <JCHEM_REFRACTIVITY>
65.274

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.24e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,2-dimethyl-1H,3H,4H,9H-pyrido[3,4-b]indol-7-ol

> <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       0.382  -2.159   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.679   0.130   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.917   1.914   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.411   2.235   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.810   2.235   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.303   1.914   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.362  -0.695   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.858  -0.695   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.393   0.450   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.380   1.090   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.840   1.090   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.856  -0.374   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.364  -0.374   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       3.610  -1.280   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0      -0.173   0.450   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0       8.899   0.130   0.000  0.00  0.00           O+0
CONECT    1    8                                                            
CONECT    2   15                                                            
CONECT    3    4    9                                                       
CONECT    4    3   10                                                       
CONECT    5    6   11                                                       
CONECT    6    5   15                                                       
CONECT    7    9   12                                                       
CONECT    8    1   13   15                                                  
CONECT    9    3    7   16                                                  
CONECT   10    4   11   12                                                  
CONECT   11    5   10   13                                                  
CONECT   12    7   10   14                                                  
CONECT   13    8   11   14                                                  
CONECT   14   12   13                                                       
CONECT   15    2    6    8                                                  
CONECT   16    9                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₁₆N₂O

Average Mass

216.2789 Da

Monoisotopic Mass

216.12626 Da

IUPAC Name

1,2-dimethyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indol-7-ol

Traditional Name

1,2-dimethyl-1H,3H,4H,9H-pyrido[3,4-b]indol-7-ol

CAS Registry Number

Not Available

SMILES

CC1N(C)CCC2=C1NC1=C2C=CC(O)=C1

InChI Identifier

InChI=1S/C13H16N2O/c1-8-13-11(5-6-15(8)2)10-4-3-9(16)7-12(10)14-13/h3-4,7-8,14,16H,5-6H2,1-2H3

InChI Key

AGILGFCOHSGLIT-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
Elaeagnus angustifolia	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as harmala alkaloids. Harmala alkaloids are compounds with a structure based on harmaline, harmine, harmalol, harman or a derivative of those parents. These parents are beta-carbolines, consisting of a pyrimidine fused to the pyrrole moiety of an indole to form a pyrido[3,4-b]indole.

Kingdom

Organic compounds

Super Class

Alkaloids and derivatives

Class

Harmala alkaloids

Sub Class

Not Available

Direct Parent

Harmala alkaloids

Alternative Parents

Substituents

Harmaline
Harmalol
Harman
Beta-carboline
Pyridoindole
Hydroxyindole
3-alkylindole
Indole
Indole or derivatives
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Benzenoid
Heteroaromatic compound
Pyrrole
Tertiary amine
Tertiary aliphatic amine
Organoheterocyclic compound
Azacycle
Organooxygen compound
Organonitrogen compound
Amine
Hydrocarbon derivative
Organopnictogen compound
Organic oxygen compound
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	2.37	ALOGPS
logP	2.09	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	6.73	ChemAxon
pKa (Strongest Basic)	9.84	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	39.26 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	65.27 m³·mol⁻¹	ChemAxon
Polarizability	24.58 Å³	ChemAxon
Number of Rings	3	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

HMDB0034292

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB012631

KNApSAcK ID

Not Available

Chemspider ID

26770427

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14219281

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Nb-Methyltetrahydroharmol (NP0084608)

MOL for NP0084608 (Nb-Methyltetrahydroharmol)

3D MOL for NP0084608 (Nb-Methyltetrahydroharmol)

3D SDF for NP0084608 (Nb-Methyltetrahydroharmol)

3D-SDF for NP0084608 (Nb-Methyltetrahydroharmol)

PDB for NP0084608 (Nb-Methyltetrahydroharmol)

3D PDB for NP0084608 (Nb-Methyltetrahydroharmol)

SMILES for NP0084608 (Nb-Methyltetrahydroharmol)

INCHI for NP0084608 (Nb-Methyltetrahydroharmol)

Structure for NP0084608 (Nb-Methyltetrahydroharmol)

3D Structure for NP0084608 (Nb-Methyltetrahydroharmol)