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Showing NP-Card for Tetrahydronorharman (NP0083620)

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Record Information
Version2.0
Created at2022-04-29 04:36:12 UTC
Updated at2022-04-29 04:36:12 UTC
NP-MRD IDNP0083620
Secondary Accession NumbersNone
Natural Product Identification
Common NameTetrahydronorharman
Description1,2,3,4-Tetrahydro-beta-carboline, also known as 1,2,3,4-tetrahydronorharmane or THBC, belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety. 1,2,3,4-Tetrahydro-beta-carboline is a very strong basic compound (based on its pKa). It is concluded that the formation of these THBCs is an artifact produced by the enzymatic liberation of formaldehyde from the methyl donors and the subsequent non-enzymatic condensation of this formaldehyde with the indole substrates. Tetrahydronorharman is found in Homo sapiens Linn. and Phalaris coerulescens. Tetrahydronorharman was first documented in 1981 (PMID: 7213417). 1,2,3,4-Tetrahydro-beta-carboline is a biomarker for the consumption of beer.
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0083620 (Tetrahydronorharman)


  Mrv0541 02251208052D          

 13 15  0  0  0  0            999 V2000
   10.6880  -14.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4026  -14.8562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1171  -14.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1171  -13.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4026  -13.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6880  -13.6187    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9018  -13.3638    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3862  -14.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2068  -14.1174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5424  -14.8710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0574  -15.5385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2373  -15.4523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9018  -14.6986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3 13  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 13  2  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
M  END
Download

3D MOL for NP0083620 (Tetrahydronorharman)

     RDKit          3D

 25 27  0  0  0  0  0  0  0  0999 V2000
    3.6662    0.1578   -0.3516 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2779   -1.1107    0.0102 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9329   -1.3439    0.2296 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9806   -0.3471    0.0963 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3829   -0.2943    0.2468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8192    0.9853   -0.0187 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2636    1.7037   -0.3272 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3704    0.9279   -0.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7152    1.1587   -0.4861 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2459    1.3458    0.0631 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1496    0.2566   -0.0130 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6027   -1.0216   -0.2987 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4125   -1.2971    0.6190 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7222    0.3263   -0.5202 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0199   -1.8930    0.1154 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5740   -2.3136    0.5136 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2597    2.7197   -0.5791 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0769    2.1357   -0.7722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4794    1.9137    1.0114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4820    2.0880   -0.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7637    0.1691    0.8362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2918   -1.0439   -1.3705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4007   -1.7836   -0.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7694   -1.1024    1.6468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0597   -2.3371    0.4859 H   0  0  0  0  0  0  0  0  0  0  0  0
 12 13  1  0
 13  5  1  0
  5  6  2  0
  6 10  1  0
 10 11  1  0
  6  7  1  0
  7  8  1  0
  8  4  2  0
  4  3  1  0
  3  2  2  0
  2  1  1  0
  1  9  2  0
 11 12  1  0
  9  8  1  0
  4  5  1  0
 12 22  1  0
 12 23  1  0
 13 24  1  0
 13 25  1  0
 10 19  1  0
 10 20  1  0
 11 21  1  0
  7 17  1  0
  3 16  1  0
  2 15  1  0
  1 14  1  0
  9 18  1  0
M  END
Download

3D SDF for NP0083620 (Tetrahydronorharman)


  Mrv0541 02251208052D          

 13 15  0  0  0  0            999 V2000
   10.6880  -14.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4026  -14.8562    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1171  -14.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1171  -13.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4026  -13.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6880  -13.6187    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.9018  -13.3638    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.3862  -14.0312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2068  -14.1174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5424  -14.8710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0574  -15.5385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2373  -15.4523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9018  -14.6986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  3 13  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 13  2  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
M  END
> <DATABASE_ID>
NP0083620

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C1CC2=C(CN1)NC1=C2C=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C11H12N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-4,12-13H,5-7H2

> <INCHI_KEY>
CFTOTSJVQRFXOF-UHFFFAOYSA-N

> <FORMULA>
C11H12N2

> <MOLECULAR_WEIGHT>
172.2264

> <EXACT_MASS>
172.100048394

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
19.624546528648118

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.31

> <JCHEM_LOGP>
1.5902462686666667

> <ALOGPS_LOGS>
-2.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.45623394456253

> <JCHEM_PKA_STRONGEST_BASIC>
9.01113449757174

> <JCHEM_POLAR_SURFACE_AREA>
27.82

> <JCHEM_REFRACTIVITY>
53.579600000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.27e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tryptoline

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0083620 (Tetrahydronorharman)

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PDB for NP0083620 (Tetrahydronorharman)
HEADER    PROTEIN                                 25-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-FEB-12         0                                  
HETATM    1  C   UNK     0      19.951 -26.962   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      21.285 -27.732   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      22.619 -26.962   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      22.619 -25.422   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      21.285 -24.652   0.000  0.00  0.00           C+0
HETATM    6  N   UNK     0      19.951 -25.422   0.000  0.00  0.00           N+0
HETATM    7  N   UNK     0      24.083 -24.946   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0      24.988 -26.192   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      26.519 -26.352   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      27.146 -27.759   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      26.240 -29.005   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.710 -28.844   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      24.083 -27.437   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    1    5                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13    3    8   12                                                  
MASTER        0    0    0    0    0    0    0    0   13    0   30    0
END

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3D PDB for NP0083620 (Tetrahydronorharman)
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SMILES for NP0083620 (Tetrahydronorharman)
C1CC2=C(CN1)NC1=C2C=CC=C1
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INCHI for NP0083620 (Tetrahydronorharman)
InChI=1S/C11H12N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-4,12-13H,5-7H2
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View in JSmol
Synonyms
ValueSource
1,2,3,4-Tetrahydro-b-carbolineGenerator
1,2,3,4-Tetrahydro-β-carbolineGenerator
1,2,3,4-TetrahydronorharmaneHMDB
THBCHMDB
Tryptoline hydrochlorideHMDB
THbetaCHMDB
TetrahydronorharmaneHMDB
9H-1,2,3,4-Tetrahydropyrido(3,4-b)indoleHMDB
NoreleagnineHMDB
Tetrahydro-beta-carbolineHMDB
Tryptoline monohydrochlorideHMDB
TriptolineHMDB
1,2,3,4-Tetrahydro-beta-carbolineMeSH
TryptolineMeSH
Chemical FormulaC11H12N2
Average Mass172.2264 Da
Monoisotopic Mass172.10005 Da
IUPAC Name1H,2H,3H,4H,9H-pyrido[3,4-b]indole
Traditional Nametryptoline
CAS Registry NumberNot Available
SMILES
C1CC2=C(CN1)NC1=C2C=CC=C1
InChI Identifier
InChI=1S/C11H12N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-4,12-13H,5-7H2
InChI KeyCFTOTSJVQRFXOF-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Homo sapiens Linn.Animalia
Phalaris coerulescensLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassIndoles and derivatives  
Sub ClassPyridoindoles  
Direct ParentBeta carbolines  
Alternative Parents
Substituents
  • Beta-carboline
    • 

  • 3-alkylindole
    • 

  • Indole
    • 

  • Aralkylamine
    • 

  • Benzenoid
    • 

  • Heteroaromatic compound
    • 

  • Pyrrole
    • 

  • Azacycle
    • 

  • Secondary amine
    • 

  • Secondary aliphatic amine
    • 

  • Organopnictogen compound
    • 

  • Organonitrogen compound
    • 

  • Amine
    • 

  • Organic nitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.31ALOGPS
logP1.59ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)16.46ChemAxon
pKa (Strongest Basic)9.01ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area27.82 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity53.58 m³·mol⁻¹ChemAxon
Polarizability19.62 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0012488  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB029095  
KNApSAcK IDNot Available
Chemspider ID96979  
KEGG Compound IDNot Available
BioCyc IDDIHYDRO-DIOH-BENZOATE  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound107838  
PDB IDNot Available
ChEBI ID100417  
Good Scents IDNot Available
References
General References
  1. Barker SA, Harrison RE, Monti JA, Brown GB, Christian ST: Identification and quantification of 1,2,3,4-tetrahydro-beta-carboline, 2-methyl-1,2,3,4-tetrahydro-beta-carboline, and 6-methoxy-1,2,3,4-tetrahydro-beta-carboline as in vivo constituents of rat brain and adrenal gland. Biochem Pharmacol. 1981 Jan 1;30(1):9-17. doi: 10.1016/0006-2952(81)90278-1. [PubMed:7213417  ]