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Showing NP-Card for (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid (NP0048946)

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Record Information
Version2.0
Created at2022-03-17 21:04:41 UTC
Updated at2022-03-17 21:04:41 UTC
NP-MRD IDNP0048946
Secondary Accession NumbersNone
Natural Product Identification
Common Name(1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid
Description(1Xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid, also known as MTCA, 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 (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid is a very strong basic compound (based on its pKa). Outside of the human body, (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid has been detected, but not quantified in, several different foods, such as alcoholic beverages, fruits, herbs and spices, and mushrooms. (1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid is found in Lepidium meyenii, Lethasterias nanimensis and Oxalis pes-caprae. This could make (1XI,3XI)-1,2,3,4-tetrahydro-1-methyl-beta-carboline-3-carboxylic acid a potential biomarker for the consumption of these foods.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0048946 ((1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid)


  Mrv0541 05061310062D          

 17 19  0  0  0  0            999 V2000
    0.2046    1.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6014    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3896   -0.8137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.5840    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339    1.5105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1347   -1.5983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1966   -0.6422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  7  1  1  0  0  0  0
  8  4  2  0  0  0  0
  9  6  1  0  0  0  0
  9  8  1  0  0  0  0
 10  5  2  0  0  0  0
 10  8  1  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
 12  9  2  0  0  0  0
 13 11  1  0  0  0  0
 14  7  1  0  0  0  0
 14 11  1  0  0  0  0
 15 10  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  2  0  0  0  0
 17 13  1  0  0  0  0
M  END
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3D MOL for NP0048946 ((1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid)

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3D SDF for NP0048946 ((1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid)

  Mrv0541 05061310062D          

 17 19  0  0  0  0            999 V2000
    0.2046    1.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6014    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3896   -0.8137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.5840    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339    1.5105    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1347   -1.5983    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1966   -0.6422    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  2  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  7  1  1  0  0  0  0
  8  4  2  0  0  0  0
  9  6  1  0  0  0  0
  9  8  1  0  0  0  0
 10  5  2  0  0  0  0
 10  8  1  0  0  0  0
 11  6  1  0  0  0  0
 12  7  1  0  0  0  0
 12  9  2  0  0  0  0
 13 11  1  0  0  0  0
 14  7  1  0  0  0  0
 14 11  1  0  0  0  0
 15 10  1  0  0  0  0
 15 12  1  0  0  0  0
 16 13  2  0  0  0  0
 17 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048946

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1NC(CC2=C1NC1=CC=CC=C21)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H14N2O2/c1-7-12-9(6-11(14-7)13(16)17)8-4-2-3-5-10(8)15-12/h2-5,7,11,14-15H,6H2,1H3,(H,16,17)

> <INCHI_KEY>
ZUPHXNBLQCSEIA-UHFFFAOYSA-N

> <FORMULA>
C13H14N2O2

> <MOLECULAR_WEIGHT>
230.2625

> <EXACT_MASS>
230.105527702

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
24.795673968979642

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
0.04

> <JCHEM_LOGP>
-0.7722599446673477

> <ALOGPS_LOGS>
-2.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.313952068760873

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.0252906797514934

> <JCHEM_PKA_STRONGEST_BASIC>
9.080034155138645

> <JCHEM_POLAR_SURFACE_AREA>
65.12

> <JCHEM_REFRACTIVITY>
63.82829999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.45e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0048946 ((1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid)
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PDB for NP0048946 ((1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid)
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   3.699   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.917  -0.374   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.393   1.090   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.411  -0.695   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.362   2.235   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.810  -0.695   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.858   2.235   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.380   0.450   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.840   0.450   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.856   1.914   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.303  -0.374   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.364   1.914   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.727  -1.519   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      -0.173   1.090   0.000  0.00  0.00           N+0
HETATM   15  N   UNK     0       3.610   2.820   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0      -0.251  -2.983   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -2.234  -1.199   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    8                                                       
CONECT    5    3   10                                                       
CONECT    6    9   11                                                       
CONECT    7    1   12   14                                                  
CONECT    8    4    9   10                                                  
CONECT    9    6    8   12                                                  
CONECT   10    5    8   15                                                  
CONECT   11    6   13   14                                                  
CONECT   12    7    9   15                                                  
CONECT   13   11   16   17                                                  
CONECT   14    7   11                                                       
CONECT   15   10   12                                                       
CONECT   16   13                                                            
CONECT   17   13                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

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3D PDB for NP0048946 ((1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid)
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SMILES for NP0048946 ((1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid)
CC1NC(CC2=C1NC1=CC=CC=C21)C(O)=O
Download
INCHI for NP0048946 ((1xi,3xi)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-3-carboxylic acid)
InChI=1S/C13H14N2O2/c1-7-12-9(6-11(14-7)13(16)17)8-4-2-3-5-10(8)15-12/h2-5,7,11,14-15H,6H2,1H3,(H,16,17)
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View in JSmol
Synonyms
ValueSource
(1XI,3xi)-1,2,3,4-tetrahydro-1-methyl-b-carboline-3-carboxylateGenerator
(1XI,3xi)-1,2,3,4-tetrahydro-1-methyl-b-carboline-3-carboxylic acidGenerator
(1XI,3xi)-1,2,3,4-tetrahydro-1-methyl-beta-carboline-3-carboxylateGenerator
(1XI,3xi)-1,2,3,4-tetrahydro-1-methyl-β-carboline-3-carboxylateGenerator
(1XI,3xi)-1,2,3,4-tetrahydro-1-methyl-β-carboline-3-carboxylic acidGenerator
MTCAHMDB
1-Methyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acidHMDB
1-Methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylateGenerator
Chemical FormulaC13H14N2O2
Average Mass230.2625 Da
Monoisotopic Mass230.10553 Da
IUPAC Name1-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylic acid
Traditional Name1-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylic acid
CAS Registry NumberNot Available
SMILES
CC1NC(CC2=C1NC1=CC=CC=C21)C(O)=O
InChI Identifier
InChI=1S/C13H14N2O2/c1-7-12-9(6-11(14-7)13(16)17)8-4-2-3-5-10(8)15-12/h2-5,7,11,14-15H,6H2,1H3,(H,16,17)
InChI KeyZUPHXNBLQCSEIA-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Agaricus bisporusFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
Lepidium meyeniiLOTUS Database
Lethasterias nanimensisLOTUS Database
Oxalis pes-capraeLOTUS Database
Pleurotus ostreatusFooDB
    • Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...
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.
KingdomOrganic compounds  
Super ClassAlkaloids and derivatives  
ClassHarmala alkaloids  
Sub ClassNot Available
Direct ParentHarmala alkaloids  
Alternative Parents
Substituents
  • Harman
    • 

  • Beta-carboline
    • 

  • Pyridoindole
    • 

  • Alpha-amino acid
    • 

  • Alpha-amino acid or derivatives
    • 

  • 3-alkylindole
    • 

  • Indole
    • 

  • Indole or derivatives
    • 

  • Aralkylamine
    • 

  • Benzenoid
    • 

  • Heteroaromatic compound
    • 

  • Pyrrole
    • 

  • Amino acid or derivatives
    • 

  • Amino acid
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Secondary aliphatic amine
    • 

  • Azacycle
    • 

  • Organoheterocyclic compound
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Secondary amine
    • 

  • Amine
    • 

  • Organic oxygen compound
    • 

  • Organic nitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Organonitrogen compound
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • 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
logP0.04ALOGPS
logP-0.77ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)2.03ChemAxon
pKa (Strongest Basic)9.08ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area65.12 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity63.83 m³·mol⁻¹ChemAxon
Polarizability24.8 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0037942  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB017111  
KNApSAcK IDNot Available
Chemspider ID66213  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound73530  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General ReferencesNot Available