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Showing NP-Card for L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid (NP0048288)

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Record Information
Version2.0
Created at2022-03-17 20:54:04 UTC
Updated at2022-03-17 20:54:05 UTC
NP-MRD IDNP0048288
Secondary Accession NumbersNone
Natural Product Identification
Common NameL-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid
DescriptionL-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid, also known as 3-carboxy-1,2,3,4-tetrahydro-2-carboline or ccris 6486, belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety. L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid is a very strong basic compound (based on its pKa). Outside of the human body, L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid has been detected, but not quantified in, garden tomato (var.). L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid is found in Allium tuberosum , Arabidopsis thaliana, Solanum lycopersicum and Taraxacum formosanum. L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid was first documented in 1987 (PMID: 2447902). This could make L-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid a potential biomarker for the consumption of these foods (PMID: 10606547) (PMID: 10735282) (PMID: 1929872) (PMID: 2019874).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0048288 (L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid)


  Mrv0541 05061308372D          

 16 18  0  0  0  0            999 V2000
    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
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  7  3  2  0  0  0  0
  8  5  1  0  0  0  0
  8  7  1  0  0  0  0
  9  4  2  0  0  0  0
  9  7  1  0  0  0  0
 10  5  1  0  0  0  0
 11  6  1  0  0  0  0
 11  8  2  0  0  0  0
 12 10  1  0  0  0  0
 13  6  1  0  0  0  0
 13 10  1  0  0  0  0
 14  9  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  2  0  0  0  0
 16 12  1  0  0  0  0
M  END
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3D MOL for NP0048288 (L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid)

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3D SDF for NP0048288 (L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid)

  Mrv0541 05061308372D          

 16 18  0  0  0  0            999 V2000
    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
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  7  3  2  0  0  0  0
  8  5  1  0  0  0  0
  8  7  1  0  0  0  0
  9  4  2  0  0  0  0
  9  7  1  0  0  0  0
 10  5  1  0  0  0  0
 11  6  1  0  0  0  0
 11  8  2  0  0  0  0
 12 10  1  0  0  0  0
 13  6  1  0  0  0  0
 13 10  1  0  0  0  0
 14  9  1  0  0  0  0
 14 11  1  0  0  0  0
 15 12  2  0  0  0  0
 16 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048288

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1CC2=C(CN1)NC1=CC=CC=C21

> <INCHI_IDENTIFIER>
InChI=1S/C12H12N2O2/c15-12(16)10-5-8-7-3-1-2-4-9(7)14-11(8)6-13-10/h1-4,10,13-14H,5-6H2,(H,15,16)

> <INCHI_KEY>
FSNCEEGOMTYXKY-UHFFFAOYSA-N

> <FORMULA>
C12H12N2O2

> <MOLECULAR_WEIGHT>
216.2359

> <EXACT_MASS>
216.089877638

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
22.851196643315806

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.47

> <JCHEM_LOGP>
-1.1886015525830436

> <ALOGPS_LOGS>
-2.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.386404689795448

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.9711947636796197

> <JCHEM_PKA_STRONGEST_BASIC>
8.990963781121424

> <JCHEM_POLAR_SURFACE_AREA>
65.12

> <JCHEM_REFRACTIVITY>
59.409499999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.24e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0048288 (L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid)
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PDB for NP0048288 (L-1,2,3,4-Tetrahydro-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       6.917  -0.374   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.393   1.090   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.411  -0.695   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.362   2.235   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.810  -0.695   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.858   2.235   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.380   0.450   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.840   0.450   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.856   1.914   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.303  -0.374   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.364   1.914   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.727  -1.519   0.000  0.00  0.00           C+0
HETATM   13  N   UNK     0      -0.173   1.090   0.000  0.00  0.00           N+0
HETATM   14  N   UNK     0       3.610   2.820   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0      -0.251  -2.983   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -2.234  -1.199   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    7                                                       
CONECT    4    2    9                                                       
CONECT    5    8   10                                                       
CONECT    6   11   13                                                       
CONECT    7    3    8    9                                                  
CONECT    8    5    7   11                                                  
CONECT    9    4    7   14                                                  
CONECT   10    5   12   13                                                  
CONECT   11    6    8   14                                                  
CONECT   12   10   15   16                                                  
CONECT   13    6   10                                                       
CONECT   14    9   11                                                       
CONECT   15   12                                                            
CONECT   16   12                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

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3D PDB for NP0048288 (L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid)
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SMILES for NP0048288 (L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid)
OC(=O)C1CC2=C(CN1)NC1=CC=CC=C21
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INCHI for NP0048288 (L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid)
InChI=1S/C12H12N2O2/c15-12(16)10-5-8-7-3-1-2-4-9(7)14-11(8)6-13-10/h1-4,10,13-14H,5-6H2,(H,15,16)
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View in JSmol
Synonyms
ValueSource
3-Carboxy-1,2,3,4-tetrahydro-2-carbolineChEBI
CCRIS 6486ChEBI
NSC 96912ChEBI
L-1,2,3,4-Tetrahydro-b-carboline-3-carboxylateGenerator
L-1,2,3,4-Tetrahydro-b-carboline-3-carboxylic acidGenerator
L-1,2,3,4-Tetrahydro-beta-carboline-3-carboxylateGenerator
L-1,2,3,4-Tetrahydro-β-carboline-3-carboxylateGenerator
L-1,2,3,4-Tetrahydro-β-carboline-3-carboxylic acidGenerator
(-)-3-Carboxy-1,2,3,4-tetrahydro-beta-carbolineHMDB
3-Carboxy-1,2,3,4-tetrahydro-beta-carbolineHMDB
CyclomethyltryptophanHMDB
L-1,2,3,4-Tetrahydronorharman-3-carboxylic acidHMDB
1,2,3,4-Tetrahydro-b-carboline-3-carboxylateGenerator
1,2,3,4-Tetrahydro-b-carboline-3-carboxylic acidGenerator
1,2,3,4-Tetrahydro-beta-carboline-3-carboxylateGenerator
1,2,3,4-Tetrahydro-β-carboline-3-carboxylateGenerator
1,2,3,4-Tetrahydro-β-carboline-3-carboxylic acidGenerator
3S-Tetrahydro-beta-carboline-3-carboxylic acidMeSH
1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid, (S)-isomerMeSH
1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acid,(+-)-isomerMeSH
THBC-CAMeSH
1,2,3,4-Tetrahydro-beta-carboline-3-carboxylic acidMeSH
Chemical FormulaC12H12N2O2
Average Mass216.2359 Da
Monoisotopic Mass216.08988 Da
IUPAC Name1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylic acid
Traditional Name1H,2H,3H,4H,9H-pyrido[3,4-b]indole-3-carboxylic acid
CAS Registry Number42438-90-4
SMILES
OC(=O)C1CC2=C(CN1)NC1=CC=CC=C21
InChI Identifier
InChI=1S/C12H12N2O2/c15-12(16)10-5-8-7-3-1-2-4-9(7)14-11(8)6-13-10/h1-4,10,13-14H,5-6H2,(H,15,16)
InChI KeyFSNCEEGOMTYXKY-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Allium tuberosumPlant
Arabidopsis thalianaLOTUS Database
Solanum lycopersicumPlant
Solanum lycopersicum var. lycopersicumFooDB
Taraxacum formosanumPlant
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
    • 

  • Alpha-amino acid
    • 

  • Alpha-amino acid or derivatives
    • 

  • 3-alkylindole
    • 

  • Indole
    • 

  • Aralkylamine
    • 

  • Benzenoid
    • 

  • Pyrrole
    • 

  • Heteroaromatic compound
    • 

  • Amino acid
    • 

  • Amino acid or derivatives
    • 

  • Carboxylic acid derivative
    • 

  • Secondary amine
    • 

  • Carboxylic acid
    • 

  • Secondary aliphatic amine
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Azacycle
    • 

  • Organic nitrogen compound
    • 

  • Organonitrogen compound
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Amine
    • 

  • Organic oxygen compound
    • 

  • 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
logP-0.47ALOGPS
logP-1.2ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)1.97ChemAxon
pKa (Strongest Basic)8.99ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area65.12 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity59.41 m³·mol⁻¹ChemAxon
Polarizability22.85 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0035665  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB014381  
KNApSAcK IDC00026660  
Chemspider ID88749  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound98285  
PDB IDNot Available
ChEBI ID91151  
Good Scents IDNot Available
References
General References
  1. Herraiz T: 1-methyl-1,2,3,4-tetrahydro-beta-carboline-3-carboxylic acid and 1,2, 3,4-tetrahydro-beta-carboline-3-carboxylic acid in fruits. J Agric Food Chem. 1999 Dec;47(12):4883-7. doi: 10.1021/jf990233d. [PubMed:10606547  ] 
  2. Herraiz T: Analysis of tetrahydro-beta-carboline-3-carboxylic acids in foods by solid-phase extraction and reversed-phase high-performance liquid chromatography combined with fluorescence detection. J Chromatogr A. 2000 Feb 25;871(1-2):23-30. doi: 10.1016/s0021-9673(99)00993-0. [PubMed:10735282  ] 
  3. Adachi J, Yamamoto K, Ogawa Y, Ueno Y, Mizoi Y, Tatsuno Y: Endogenous formation of 1-methyl-1,2,3,4-tetrahydro-beta-carboline-3- carboxylic acid in man as the possible causative substance of eosinophilia-myalgia syndrome associated with ingestion of L-tryptophan. Arch Toxicol. 1991;65(6):505-9. doi: 10.1007/BF01977365. [PubMed:1929872  ] 
  4. Adachi J, Mizoi Y, Naito T, Ogawa Y, Uetani Y, Ninomiya I: Identification of tetrahydro-beta-carboline-3-carboxylic acid in foodstuffs, human urine and human milk. J Nutr. 1991 May;121(5):646-52. doi: 10.1093/jn/121.5.646. [PubMed:2019874  ] 
  5. Bosin TR, Krogh SE, Zabik JE: Tetrahydro-beta-carbolines in alcoholic beverages: quantitation, neurochemical and ethanol drinking effects. Alcohol Alcohol Suppl. 1987;1:323-7. [PubMed:2447902  ]