NP-MRD: Showing NP-Card for (+/-)-tetrahydroharmine (NP0164299)

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Record Information

Version

2.0

Created at

2022-09-02 23:09:06 UTC

Updated at

2022-09-02 23:09:06 UTC

NP-MRD ID

NP0164299

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(+/-)-tetrahydroharmine

Description

Leptaflorine, also known as tetrahydroharmine, 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. Harmala alkaloids are considered Schedule 9 prohibited substances under the Poisons Standard (October 2015). Tetrahydroharmine (THH) is a fluorescent indole alkaloid that occurs in the tropical liana species Banisteriopsis caapi. A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities. Leptaflorine is a very strong basic compound (based on its pKa). THH weakly inhibits serotonin reuptake. THH does not inhibit monoamine oxidase B, however two other harmala alkaloids in B. Caapi, harmaline and harmine, are reversible inhibitors of monoamine oxidase A. (+/-)-tetrahydroharmine is found in Banisteriopsis caapi and Peganum harmala. While THH may not play a significant role in the inhibition of MAO it may contribute psychoactivity indirectly by inhibiting the uptake of Serotonin in platelets and presynaptic neurons.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 32 34  0  0  0  0  0  0  0  0999 V2000
    5.1671    1.0420    0.4573 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5793   -0.1911    0.1733 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2249   -0.3846    0.0278 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7263   -1.6351   -0.2524 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3885   -1.8673   -0.4040 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4916   -0.8424   -0.2787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8776   -0.8049   -0.3810 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2331    0.5083   -0.1570 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1301    1.2297    0.0698 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.9482    0.4382    0.0039 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2842    0.6279    0.1472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7090    0.7886   -0.2210 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0167    2.1847    0.1971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3547   -0.1721    0.6122 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0913   -1.5339    0.3158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9559   -1.7710   -0.6530 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1702    0.8391    0.9218 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5807    1.6700    1.1408 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3773    1.6301   -0.4810 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4061   -2.4590   -0.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9809   -2.8625   -0.6279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1227    2.2439    0.2654 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6510    1.6156    0.3664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9803    0.6534   -1.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2695    2.6078    0.8983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0443    2.1992    0.6203 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0317    2.8369   -0.7010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3807    0.0324    0.6560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9827   -2.0637   -0.1327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8395   -2.1297    1.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5864   -2.8120   -0.5029 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3705   -1.6187   -1.6686 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3 11  2  0
 11 10  1  0
 10  6  2  0
  6  5  1  0
  5  4  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
  4  3  1  0
 16  7  1  0
  9 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
 11 23  1  0
  5 21  1  0
  4 20  1  0
  9 22  1  0
 12 24  1  6
 13 25  1  0
 13 26  1  0
 13 27  1  0
 14 28  1  0
 15 29  1  0
 15 30  1  0
 16 31  1  0
 16 32  1  0
M  END


  Mrv1533004241519492D          

 16 18  0  0  0  0            999 V2000
    3.6633   -1.1567    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
    2.6014   -0.2006    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
    2.8985    1.1971    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
    3.9604    0.2410    0.0000 N   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
    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
    0.4595   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.2410    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
    0.9694    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8995    0.0694    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1544   -0.7152    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  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
  3 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  8 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0164299

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC2=C(C=C1)C1=C(N2)C(C)NCC1

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

> <INCHI_KEY>
ZXLDQJLIBNPEFJ-UHFFFAOYSA-N

> <FORMULA>
C13H16N2O

> <MOLECULAR_WEIGHT>
216.284

> <EXACT_MASS>
216.126263143

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
32

> <JCHEM_AVERAGE_POLARIZABILITY>
24.930443888684195

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
7-methoxy-1-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indole

> <ALOGPS_LOGP>
2.09

> <JCHEM_LOGP>
1.8491500276666664

> <ALOGPS_LOGS>
-2.82

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.304032245419247

> <JCHEM_PKA_STRONGEST_BASIC>
8.815955364534469

> <JCHEM_POLAR_SURFACE_AREA>
37.05

> <JCHEM_REFRACTIVITY>
64.4616

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.27e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
7-methoxy-1-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indole

> <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       6.838  -2.159   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.362  -0.695   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.856  -0.374   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.380   1.090   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.410   2.235   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.917   1.914   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       7.393   0.450   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       2.840   1.090   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.364  -0.374   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       3.610  -1.280   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       0.858  -0.695   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.173   0.450   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.303   1.914   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.810   2.235   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.679   0.130   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.155  -1.335   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    2                                                       
CONECT    8    4    9   14                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    3                                                       
CONECT   11    9   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13    8                                                       
CONECT   15   12   16                                                       
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

View in JSmol

Synonyms

Value	Source
Tetrahydroharmine	MeSH
1,2,3,4-Tetrahydroharmine	MeSH

Chemical Formula

C₁₃H₁₆N₂O

Average Mass

216.2840 Da

Monoisotopic Mass

216.12626 Da

IUPAC Name

7-methoxy-1-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indole

Traditional Name

7-methoxy-1-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indole

CAS Registry Number

Not Available

SMILES

COC1=CC2=C(C=C1)C1=C(N2)C(C)NCC1

InChI Identifier

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

InChI Key

ZXLDQJLIBNPEFJ-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
Banisteriopsis caapi	LOTUS Database	35616633
Peganum harmala	LOTUS Database	35616633

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
Harman
Beta-carboline
Pyridoindole
3-alkylindole
Indole
Indole or derivatives
Anisole
Alkyl aryl ether
Aralkylamine
Benzenoid
Pyrrole
Heteroaromatic compound
Secondary amine
Azacycle
Ether
Secondary aliphatic amine
Organoheterocyclic compound
Amine
Organooxygen compound
Organonitrogen compound
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	2.09	ALOGPS
logP	1.85	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	16.3	ChemAxon
pKa (Strongest Basic)	8.82	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	1	ChemAxon
Refractivity	64.46 m³·mol⁻¹	ChemAxon
Polarizability	24.93 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

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

Tetrahydroharmine

METLIN ID

Not Available

PubChem Compound

159809

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (+/-)-tetrahydroharmine (NP0164299)

MOL for NP0164299 ((+/-)-tetrahydroharmine)

3D MOL for NP0164299 ((+/-)-tetrahydroharmine)

3D SDF for NP0164299 ((+/-)-tetrahydroharmine)

3D-SDF for NP0164299 ((+/-)-tetrahydroharmine)

PDB for NP0164299 ((+/-)-tetrahydroharmine)

3D PDB for NP0164299 ((+/-)-tetrahydroharmine)

SMILES for NP0164299 ((+/-)-tetrahydroharmine)

INCHI for NP0164299 ((+/-)-tetrahydroharmine)

Structure for NP0164299 ((+/-)-tetrahydroharmine)

3D Structure for NP0164299 ((+/-)-tetrahydroharmine)