NP-MRD: Showing NP-Card for (1xi,3S)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-1,3-dicarboxylic acid (NP0335380)

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Record Information

Version

2.0

Created at

2024-09-11 01:20:22 UTC

Updated at

2024-09-11 01:20:23 UTC

NP-MRD ID

NP0335380

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1xi,3S)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-1,3-dicarboxylic acid

Description

(1Xi,3S)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-1,3-dicarboxylic acid 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. Based on a literature review very few articles have been published on (1xi,3S)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-1,3-dicarboxylic acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05262303522D          

 20 22  0  0  0  0            999 V2000
   -0.2401    1.6343    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
    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
    0.7686    1.9620    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
    1.9339    1.5105    0.0000 N   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
   -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
    1.5856    2.0769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2607    2.6122    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  4  2  0  0  0  0
  8  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  5  2  0  0  0  0
  9  7  1  0  0  0  0
 10  6  1  0  0  0  0
 11  8  2  0  0  0  0
 12 10  1  0  0  0  0
 14  1  1  0  0  0  0
 14 11  1  0  0  0  0
 14 13  1  0  0  0  0
 15  9  1  0  0  0  0
 15 11  1  0  0  0  0
 16 10  1  0  0  0  0
 16 14  1  0  0  0  0
 17 12  2  0  0  0  0
 18 12  1  0  0  0  0
 19 13  2  0  0  0  0
 20 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0335380

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1(NC(CC2=C1NC1=CC=CC=C21)C(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1/C14H14N2O4/c1-14(13(19)20)11-8(6-10(16-14)12(17)18)7-4-2-3-5-9(7)15-11/h2-5,10,15-16H,6H2,1H3,(H,17,18)(H,19,20)

> <INCHI_KEY>
ZKGAKYZRRFOFGK-UHFFFAOYNA-N

> <FORMULA>
C14H14N2O4

> <MOLECULAR_WEIGHT>
274.276

> <EXACT_MASS>
274.095356939

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
27.748010532175616

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
-1.3100410619151266

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
3.376213969841815

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.66714582245177

> <JCHEM_PKA_STRONGEST_BASIC>
9.855186368134657

> <JCHEM_POLAR_SURFACE_AREA>
102.42

> <JCHEM_REFRACTIVITY>
69.9527

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0      -0.448   3.051   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       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  C   UNK     0       1.435   3.662   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.858   2.235   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       3.610   2.820   0.000  0.00  0.00           N+0
HETATM   16  N   UNK     0      -0.173   1.090   0.000  0.00  0.00           N+0
HETATM   17  O   UNK     0      -0.251  -2.983   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -2.234  -1.199   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       2.960   3.877   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.487   4.876   0.000  0.00  0.00           O+0
CONECT    1   14                                                            
CONECT    2    3    4                                                       
CONECT    3    2    5                                                       
CONECT    4    2    7                                                       
CONECT    5    3    9                                                       
CONECT    6    8   10                                                       
CONECT    7    4    8    9                                                  
CONECT    8    6    7   11                                                  
CONECT    9    5    7   15                                                  
CONECT   10    6   12   16                                                  
CONECT   11    8   14   15                                                  
CONECT   12   10   17   18                                                  
CONECT   13   14   19   20                                                  
CONECT   14    1   11   13   16                                             
CONECT   15    9   11                                                       
CONECT   16   10   14                                                       
CONECT   17   12                                                            
CONECT   18   12                                                            
CONECT   19   13                                                            
CONECT   20   13                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   44    0
END

View in JSmol

Synonyms

Value	Source
(1XI,3S)-1,2,3,4-tetrahydro-1-methyl-b-carboline-1,3-dicarboxylate	Generator
(1XI,3S)-1,2,3,4-tetrahydro-1-methyl-b-carboline-1,3-dicarboxylic acid	Generator
(1XI,3S)-1,2,3,4-tetrahydro-1-methyl-beta-carboline-1,3-dicarboxylate	Generator
(1XI,3S)-1,2,3,4-tetrahydro-1-methyl-β-carboline-1,3-dicarboxylate	Generator
(1XI,3S)-1,2,3,4-tetrahydro-1-methyl-β-carboline-1,3-dicarboxylic acid	Generator

Chemical Formula

C₁₄H₁₄N₂O₄

Average Mass

274.2760 Da

Monoisotopic Mass

274.09536 Da

IUPAC Name

1-methyl-1H,2H,3H,4H,9H-pyrido[3,4-b]indole-1,3-dicarboxylic acid

Traditional Name

1-methyl-2H,3H,4H,9H-pyrido[3,4-b]indole-1,3-dicarboxylic acid

CAS Registry Number

Not Available

SMILES

CC1(NC(CC2=C1NC1=CC=CC=C21)C(O)=O)C(O)=O

InChI Identifier

InChI=1/C14H14N2O4/c1-14(13(19)20)11-8(6-10(16-14)12(17)18)7-4-2-3-5-9(7)15-11/h2-5,10,15-16H,6H2,1H3,(H,17,18)(H,19,20)

InChI Key

ZKGAKYZRRFOFGK-UHFFFAOYNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as harmala alkaloids. These 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

Harman
Beta-carboline
Pyridoindole
Alpha-amino acid
Alpha-amino acid or derivatives
3-alkylindole
Indole
Indole or derivatives
Aralkylamine
Dicarboxylic acid or derivatives
Benzenoid
Heteroaromatic compound
Pyrrole
Amino acid or derivatives
Amino acid
Carboxylic acid derivative
Carboxylic acid
Secondary aliphatic amine
Azacycle
Organoheterocyclic compound
Secondary amine
Amine
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organopnictogen compound
Organic oxide
Organonitrogen compound
Organooxygen 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	-1.3	ChemAxon
pKa (Strongest Acidic)	2.67	ChemAxon
pKa (Strongest Basic)	9.86	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	102.42 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	69.95 m³·mol⁻¹	ChemAxon
Polarizability	27.75 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	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

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (1xi,3S)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-1,3-dicarboxylic acid (NP0335380)

MOL for NP0335380 ((1xi,3S)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-1,3-dicarboxylic acid)

3D MOL for NP0335380 ((1xi,3S)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-1,3-dicarboxylic acid)

3D SDF for NP0335380 ((1xi,3S)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-1,3-dicarboxylic acid)

3D-SDF for NP0335380 ((1xi,3S)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-1,3-dicarboxylic acid)

PDB for NP0335380 ((1xi,3S)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-1,3-dicarboxylic acid)

3D PDB for NP0335380 ((1xi,3S)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-1,3-dicarboxylic acid)

SMILES for NP0335380 ((1xi,3S)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-1,3-dicarboxylic acid)

INCHI for NP0335380 ((1xi,3S)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-1,3-dicarboxylic acid)

Structure for NP0335380 ((1xi,3S)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-1,3-dicarboxylic acid)

3D Structure for NP0335380 ((1xi,3S)-1,2,3,4-Tetrahydro-1-methyl-beta-carboline-1,3-dicarboxylic acid)