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Showing NP-Card for 2-Amino-a-carboline (NP0337021)

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Record Information
Version2.0
Created at2024-09-11 08:55:32 UTC
Updated at2024-09-11 08:55:32 UTC
NP-MRD IDNP0337021
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-Amino-a-carboline
Description2-Amino-a-carboline, also known as a-alpha-C or a-a-C, belongs to the class of organic compounds known as alpha carbolines. These are organic compounds containing a pyrido[2,3-b]indole core (which is a pyridine fused to an indole). 2-Amino-a-carboline is a strong basic compound (based on its pKa). 2-Amino-a-carboline was first documented in 2009 (PMID: 19588936). 2-Amino-a-carboline is a potentially toxic compound (PMID: 19086795).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0337021 (2-Amino-a-carboline)


  Mrv0541 02241216012D          

 14 16  0  0  0  0            999 V2000
    2.3525   -0.5774    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5270   -0.4950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0316   -1.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2060   -1.0729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1242   -0.3299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9490   -0.0822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6094   -0.4950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3525   -0.0822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3525    0.7426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6094    1.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9490    0.7426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1242    0.9903    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3712    0.3299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1967    0.2473    0.0000 N   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
  2 14  2  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
  5 13  2  0  0  0  0
  6  7  2  0  0  0  0
  6 11  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
M  END
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3D MOL for NP0337021 (2-Amino-a-carboline)

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3D SDF for NP0337021 (2-Amino-a-carboline)

  Mrv0541 02241216012D          

 14 16  0  0  0  0            999 V2000
    2.3525   -0.5774    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.5270   -0.4950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0316   -1.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2060   -1.0729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1242   -0.3299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9490   -0.0822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6094   -0.4950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3525   -0.0822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3525    0.7426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6094    1.1554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9490    0.7426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1242    0.9903    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.3712    0.3299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1967    0.2473    0.0000 N   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
  2 14  2  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
  5 13  2  0  0  0  0
  6  7  2  0  0  0  0
  6 11  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0337021

> <DATABASE_NAME>
NP-MRD

> <SMILES>
NC1=NC2=C(C=C1)C1=CC=CC=C1N2

> <INCHI_IDENTIFIER>
InChI=1S/C11H9N3/c12-10-6-5-8-7-3-1-2-4-9(7)13-11(8)14-10/h1-6H,(H3,12,13,14)

> <INCHI_KEY>
FJTNLJLPLJDTRM-UHFFFAOYSA-N

> <FORMULA>
C11H9N3

> <MOLECULAR_WEIGHT>
183.2093

> <EXACT_MASS>
183.079647303

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
19.80849764251107

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
9H-pyrido[2,3-b]indol-2-amine

> <ALOGPS_LOGP>
2.08

> <JCHEM_LOGP>
2.0062068933333332

> <ALOGPS_LOGS>
-2.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.117878293458016

> <JCHEM_PKA_STRONGEST_BASIC>
4.824941677956441

> <JCHEM_POLAR_SURFACE_AREA>
54.7

> <JCHEM_REFRACTIVITY>
56.281800000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.51e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-amino-9H-pyrido[2,3-b]indole

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0337021 (2-Amino-a-carboline)
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PDB for NP0337021 (2-Amino-a-carboline)
HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  N   UNK     0       4.391  -1.078   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       2.850  -0.924   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.926  -2.157   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.384  -2.003   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.232  -0.616   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.771  -0.153   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -3.004  -0.924   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.391  -0.153   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.391   1.386   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.004   2.157   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.771   1.386   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      -0.232   1.849   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       0.693   0.616   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0       2.234   0.462   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3   14                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   13                                                  
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11    6   10   12                                                  
CONECT   12   11   13                                                       
CONECT   13    5   12   14                                                  
CONECT   14    2   13                                                       
MASTER        0    0    0    0    0    0    0    0   14    0   32    0
END

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3D PDB for NP0337021 (2-Amino-a-carboline)
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SMILES for NP0337021 (2-Amino-a-carboline)
NC1=NC2=C(C=C1)C1=CC=CC=C1N2
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INCHI for NP0337021 (2-Amino-a-carboline)
InChI=1S/C11H9N3/c12-10-6-5-8-7-3-1-2-4-9(7)13-11(8)14-10/h1-6H,(H3,12,13,14)
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View in JSmol
Synonyms
ValueSource
2-Amino-alpha-carbolineKegg
a-alpha-CKegg
2-Amino-α-carbolineGenerator
a-a-CGenerator
a-Α-CGenerator
1H-Pyrido(2,3-b)indol-2-amineHMDB
2-Amino-9H-pyrido(2,3-b)indoleHMDB
2-Amino-9H-pyrido[2,3-b]indoleHMDB
3-Amino-3-carboline (obsol.)HMDB
9H-Pyrido[2,3-b]indol-2-amineHMDB
Amino-alpha-carbolineHMDB
Glob-p-2HMDB
2-Amino-9H-pyrido(2,3-b)indole, D-labeledHMDB
2-Amino-a-carbolineGenerator
Chemical FormulaC11H9N3
Average Mass183.2093 Da
Monoisotopic Mass183.07965 Da
IUPAC Name9H-pyrido[2,3-b]indol-2-amine
Traditional Name2-amino-9H-pyrido[2,3-b]indole
CAS Registry NumberNot Available
SMILES
NC1=NC2=C(C=C1)C1=CC=CC=C1N2
InChI Identifier
InChI=1S/C11H9N3/c12-10-6-5-8-7-3-1-2-4-9(7)13-11(8)14-10/h1-6H,(H3,12,13,14)
InChI KeyFJTNLJLPLJDTRM-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha carbolines. These are organic compounds containing a pyrido[2,3-b]indole core (which is a pyridine fused to an indole).
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassIndoles and derivatives  
Sub ClassPyridoindoles  
Direct ParentAlpha carbolines  
Alternative Parents
Substituents
  • Alpha-carboline
    • 

  • Pyrrolopyridine
    • 

  • Indole
    • 

  • Imidolactam
    • 

  • Benzenoid
    • 

  • Pyridine
    • 

  • Heteroaromatic compound
    • 

  • Pyrrole
    • 

  • Azacycle
    • 

  • Organic nitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organonitrogen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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
logP2.08ALOGPS
logP2.01ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)14.12ChemAxon
pKa (Strongest Basic)4.82ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area54.7 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity56.28 m³·mol⁻¹ChemAxon
Polarizability19.81 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0033141  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011142  
KNApSAcK IDNot Available
Chemspider ID56541  
KEGG Compound IDC19186  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound62805  
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Bessette EE, Yasa I, Dunbar D, Wilkens LR, Le Marchand L, Turesky RJ: Biomonitoring of carcinogenic heterocyclic aromatic amines in hair: a validation study. Chem Res Toxicol. 2009 Aug;22(8):1454-63. doi: 10.1021/tx900155f. [PubMed:19588936  ] 
  2. Bessette EE, Goodenough AK, Langouet S, Yasa I, Kozekov ID, Spivack SD, Turesky RJ: Screening for DNA adducts by data-dependent constant neutral loss-triple stage mass spectrometry with a linear quadrupole ion trap mass spectrometer. Anal Chem. 2009 Jan 15;81(2):809-19. doi: 10.1021/ac802096p. [PubMed:19086795  ]