Hmdb loader

Showing metabocard for beta-Carboline (HMDB0012897)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2009-07-25 00:09:26 UTC
Update Date2023-02-21 17:17:51 UTC
HMDB IDHMDB0012897
Secondary Accession Numbers
  • HMDB12897
Metabolite Identification
Common Namebeta-Carboline
Descriptionbeta-Carboline, also known as norharmane, is an organic amine and is the prototype of a class of compounds known as beta-carbolines. beta-Carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety. beta-Carboline is a very strong basic compound (based on its pKa). beta-Carboline alkaloids are widely distributed in plants and animals and many are inverse agonists of the GABA-A receptor complex (PMID: 17334612 ). Other biological activities demonstrated by these compounds include intercalation; inhibition of CDK, topoisomerase, and monoamine oxidase; and interaction with 5-hydroxy serotonin receptors. These compounds have also exhibited sedative, anxiolytic, hypnotic, anticonvulsant, antitumor, antiviral, antiparasitic, and antimicrobial activities (PMID: 17305548 ).
Structure
Data?1676999871
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0012897 (beta-Carboline)


  Mrv1652304272018132D          

 13 15  0  0  0  0            999 V2000
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8783    2.1481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5457    2.6330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3857    1.4769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9646    1.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7182    0.9921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2994    2.2974    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6320    0.1715    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  8  2  0  0  0  0
  4 10  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  2  0  0  0  0
  6 12  2  0  0  0  0
  7 11  2  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 13  1  0  0  0  0
 11 13  1  0  0  0  0
M  END
Download

3D MOL for HMDB0012897 (beta-Carboline)

HMDB0012897
     RDKit          3D
beta-Carboline
 21 23  0  0  0  0  0  0  0  0999 V2000
   -3.1769    0.2059   -0.2872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7290   -1.1032   -0.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3637   -1.3853   -0.2625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4633   -0.3593   -0.0787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9272    0.9352   -0.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2806    1.2357   -0.1034 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1609    1.7003    0.1761 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2804    0.9354    0.2119 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6203    1.2269    0.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5475    0.2508    0.3661 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2293   -1.0447    0.2131 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8999   -1.3616    0.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9064   -0.3933    0.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2385    0.3995   -0.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4535   -1.9075   -0.5135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0422   -2.4155   -0.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6615    2.2425   -0.0451 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1300    2.7343    0.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9112    2.2485    0.4934 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0364   -1.7606    0.2234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6139   -2.3841   -0.0694 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  6  1  1  0
 13  8  1  0
 13  4  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  6 17  1  0
  7 18  1  0
  9 19  1  0
 11 20  1  0
 12 21  1  0
M  END
Download

3D SDF for HMDB0012897 (beta-Carboline)


  Mrv1652304272018132D          

 13 15  0  0  0  0            999 V2000
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8783    2.1481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5457    2.6330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3857    1.4769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9646    1.3276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7182    0.9921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2994    2.2974    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6320    0.1715    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  3  8  2  0  0  0  0
  4 10  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  2  0  0  0  0
  6 12  2  0  0  0  0
  7 11  2  0  0  0  0
  7 12  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 13  1  0  0  0  0
 11 13  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0012897

> <DATABASE_NAME>
hmdb

> <SMILES>
N1C2=CC=CC=C2C2=CC=NC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C11H8N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-7,13H

> <INCHI_KEY>
AIFRHYZBTHREPW-UHFFFAOYSA-N

> <FORMULA>
C11H8N2

> <MOLECULAR_WEIGHT>
168.1946

> <EXACT_MASS>
168.068748266

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
18.066186690991525

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.56

> <JCHEM_LOGP>
1.8732132623333335

> <ALOGPS_LOGS>
-2.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.223870765973725

> <JCHEM_PKA_STRONGEST_BASIC>
5.284479184974655

> <JCHEM_POLAR_SURFACE_AREA>
28.68

> <JCHEM_REFRACTIVITY>
51.31530000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.87e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β-carboline

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0012897 (beta-Carboline)

HMDB0012897
     RDKit          3D
beta-Carboline
 21 23  0  0  0  0  0  0  0  0999 V2000
   -3.1769    0.2059   -0.2872 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7290   -1.1032   -0.3676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3637   -1.3853   -0.2625 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4633   -0.3593   -0.0787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9272    0.9352   -0.0012 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2806    1.2357   -0.1034 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1609    1.7003    0.1761 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2804    0.9354    0.2119 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6203    1.2269    0.3688 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5475    0.2508    0.3661 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.2293   -1.0447    0.2131 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8999   -1.3616    0.0548 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9064   -0.3933    0.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2385    0.3995   -0.3714 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4535   -1.9075   -0.5135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0422   -2.4155   -0.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6615    2.2425   -0.0451 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1300    2.7343    0.2708 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9112    2.2485    0.4934 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0364   -1.7606    0.2234 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6139   -2.3841   -0.0694 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  6  1  1  0
 13  8  1  0
 13  4  1  0
  1 14  1  0
  2 15  1  0
  3 16  1  0
  6 17  1  0
  7 18  1  0
  9 19  1  0
 11 20  1  0
 12 21  1  0
M  END
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PDB for HMDB0012897 (beta-Carboline)

HEADER    PROTEIN                                 27-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-APR-20         0                                  
HETATM    1  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.770   1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.640   4.010   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.885   4.915   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.453   2.757   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.800   2.478   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.540   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.207   1.852   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0      -4.292   4.289   0.000  0.00  0.00           N+0
HETATM   13  N   UNK     0      -3.046   0.320   0.000  0.00  0.00           N+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    8                                                       
CONECT    4    2   10                                                       
CONECT    5    6    9                                                       
CONECT    6    5   12                                                       
CONECT    7   11   12                                                       
CONECT    8    3    9   10                                                  
CONECT    9    5    8   11                                                  
CONECT   10    4    8   13                                                  
CONECT   11    7    9   13                                                  
CONECT   12    6    7                                                       
CONECT   13   10   11                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   30    0
END
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3D PDB for HMDB0012897 (beta-Carboline)

COMPND    HMDB0012897
HETATM    1  C1  UNL     1      -3.177   0.206  -0.287  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.729  -1.103  -0.368  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.364  -1.385  -0.262  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.463  -0.359  -0.079  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.927   0.935  -0.001  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.281   1.236  -0.103  1.00  0.00           C  
HETATM    7  N1  UNL     1       0.161   1.700   0.176  1.00  0.00           N  
HETATM    8  C7  UNL     1       1.280   0.935   0.212  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.620   1.227   0.369  1.00  0.00           C  
HETATM   10  N2  UNL     1       3.548   0.251   0.366  1.00  0.00           N  
HETATM   11  C9  UNL     1       3.229  -1.045   0.213  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.900  -1.362   0.055  1.00  0.00           C  
HETATM   13  C11 UNL     1       0.906  -0.393   0.050  1.00  0.00           C  
HETATM   14  H1  UNL     1      -4.238   0.399  -0.371  1.00  0.00           H  
HETATM   15  H2  UNL     1      -3.453  -1.908  -0.514  1.00  0.00           H  
HETATM   16  H3  UNL     1      -1.042  -2.415  -0.329  1.00  0.00           H  
HETATM   17  H4  UNL     1      -2.661   2.243  -0.045  1.00  0.00           H  
HETATM   18  H5  UNL     1       0.130   2.734   0.271  1.00  0.00           H  
HETATM   19  H6  UNL     1       2.911   2.249   0.493  1.00  0.00           H  
HETATM   20  H7  UNL     1       4.036  -1.761   0.223  1.00  0.00           H  
HETATM   21  H8  UNL     1       1.614  -2.384  -0.069  1.00  0.00           H  
CONECT    1    2    2    6   14
CONECT    2    3   15
CONECT    3    4    4   16
CONECT    4    5   13
CONECT    5    6    6    7
CONECT    6   17
CONECT    7    8   18
CONECT    8    9    9   13
CONECT    9   10   19
CONECT   10   11   11
CONECT   11   12   20
CONECT   12   13   13   21
END
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SMILES for HMDB0012897 (beta-Carboline)

N1C2=CC=CC=C2C2=CC=NC=C12
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INCHI for HMDB0012897 (beta-Carboline)

InChI=1S/C11H8N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-7,13H
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View in JSmolView Stereo Labels
Synonyms
ValueSource
2,9-DiazafluoreneChEBI
2-AzacarbazoleChEBI
9H-beta-CarbolineChEBI
9H-Pyrido(3,4-b)indoleChEBI
9H-Pyrido[3,4-b]indoleChEBI
CarbazolineChEBI
NorharmanChEBI
NorharmaneChEBI
9H-b-CarbolineGenerator
9H-Β-carbolineGenerator
b-CarbolineGenerator
Β-carbolineGenerator
Norharman hydrochlorideMeSH, HMDB
NorhormaneMeSH, HMDB
beta-CarbolineHMDB
Chemical FormulaC11H8N2
Average Molecular Weight168.1946
Monoisotopic Molecular Weight168.068748266
IUPAC Name9H-pyrido[3,4-b]indole
Traditional Nameβ-carboline
CAS Registry Number244-63-3
SMILES
N1C2=CC=CC=C2C2=CC=NC=C12
InChI Identifier
InChI=1S/C11H8N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-7,13H
InChI KeyAIFRHYZBTHREPW-UHFFFAOYSA-N
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
  • Indole
  • Benzenoid
  • Pyridine
  • Heteroaromatic compound
  • Pyrrole
  • Azacycle
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Biological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point199 °CNot Available
Boiling Point391.30 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility9.55 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP3.17BIAGI,GL ET AL. (1989)
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available132.174http://allccs.zhulab.cn/database/detail?ID=AllCCS00001134
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.29 g/LALOGPS
logP2.56ALOGPS
logP1.87ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)13.22ChemAxon
pKa (Strongest Basic)5.28ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area28.68 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity51.32 m³·mol⁻¹ChemAxon
Polarizability18.07 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+136.13331661259
DarkChem[M-H]-136.20631661259
DeepCCS[M-2H]-164.82230932474
DeepCCS[M+Na]+140.24230932474
AllCCS[M+H]+135.232859911
AllCCS[M+H-H2O]+130.532859911
AllCCS[M+NH4]+139.632859911
AllCCS[M+Na]+140.832859911
AllCCS[M-H]-136.932859911
AllCCS[M+Na-2H]-136.932859911
AllCCS[M+HCOO]-136.932859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.3.77 minutes32390414
Predicted by Siyang on May 30, 20229.8867 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20222.94 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid44.7 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1741.2 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid346.6 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid87.7 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid195.1 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid181.8 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid334.4 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid360.9 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)51.8 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid608.4 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid111.5 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1035.7 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid208.4 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid298.5 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate485.5 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA195.6 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water69.5 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
beta-CarbolineN1C2=CC=CC=C2C2=CC=NC=C122689.5Standard polar33892256
beta-CarbolineN1C2=CC=CC=C2C2=CC=NC=C121925.5Standard non polar33892256
beta-CarbolineN1C2=CC=CC=C2C2=CC=NC=C121998.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
beta-Carboline,1TMS,isomer #1C[Si](C)(C)N1C2=CC=CC=C2C2=CC=NC=C212034.8Semi standard non polar33892256
beta-Carboline,1TMS,isomer #1C[Si](C)(C)N1C2=CC=CC=C2C2=CC=NC=C211871.3Standard non polar33892256
beta-Carboline,1TMS,isomer #1C[Si](C)(C)N1C2=CC=CC=C2C2=CC=NC=C212338.4Standard polar33892256
beta-Carboline,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C2=CC=CC=C2C2=CC=NC=C212295.1Semi standard non polar33892256
beta-Carboline,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C2=CC=CC=C2C2=CC=NC=C212071.0Standard non polar33892256
beta-Carboline,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C2=CC=CC=C2C2=CC=NC=C212417.8Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - beta-Carboline EI-B (Non-derivatized)splash10-014i-5900000000-3480c725264b958ffc7f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - beta-Carboline EI-B (Non-derivatized)splash10-014i-5900000000-3480c725264b958ffc7f2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-Carboline GC-MS (Non-derivatized) - 70eV, Positivesplash10-014l-0900000000-fcdb4b3e6837a47248e22017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - beta-Carboline GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Carboline LC-ESI-QQ , positive-QTOFsplash10-014i-0900000000-5f1c82b770634430089f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Carboline , positive-QTOFsplash10-014i-2900000000-ec1e052158bb7ac51fa52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Carboline ESI-QFT 11V, negative-QTOFsplash10-014i-0900000000-8356e3b21f024042498f2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Carboline ESI-QFT 15V, negative-QTOFsplash10-014i-0900000000-309bca0da39eb9bfe16c2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Carboline ESI-QFT 21V, negative-QTOFsplash10-014i-0900000000-5a054045fb18991566ad2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Carboline LC-ESI-QTOF 10V, negative-QTOFsplash10-014i-0900000000-6ae41f21021169fba1582020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Carboline LC-ESI-QTOF 30V, negative-QTOFsplash10-014l-0900000000-18f3f6cb6eddcab3e38c2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Carboline LC-ESI-QTOF 50V, negative-QTOFsplash10-03di-9000000000-eebba0b8b6a195a9bcf62020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Carboline LC-ESI-QTOF 6V, negative-QTOFsplash10-014i-0900000000-bb0bad9db10636d0020a2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Carboline n/a 11V, negative-QTOFsplash10-014i-0900000000-81c9902ae9712620ee7b2020-07-21HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Carboline Orbitrap 10V, negative-QTOFsplash10-014i-0900000000-2ff64ee76e6f4e6e7b472020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Carboline Orbitrap 12V, negative-QTOFsplash10-014i-0900000000-eb22bb403f17b41824ee2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Carboline Orbitrap 13V, negative-QTOFsplash10-014i-0900000000-710549ac9a89ddcb850f2020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Carboline Orbitrap 15V, negative-QTOFsplash10-014l-0900000000-0560d33cc2baa85680682020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Carboline Orbitrap 17V, negative-QTOFsplash10-014i-1900000000-e89060680f0fbbb90fc12020-07-22HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Carboline 6V, Positive-QTOFsplash10-014i-0900000000-7bfe2973a911f7d048822021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Carboline 6V, Positive-QTOFsplash10-014i-0900000000-c64bc52da34801ce4cf52021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Carboline 6V, Positive-QTOFsplash10-014i-0900000000-730c48ee2c09863f6c4d2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - beta-Carboline 10V, Positive-QTOFsplash10-014i-0900000000-c27561fcfb62e1fb8dc02021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Carboline 10V, Positive-QTOFsplash10-014i-0900000000-eb27fd1af093e93739872016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Carboline 20V, Positive-QTOFsplash10-014i-0900000000-675b8bf1bb9442b351a32016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Carboline 40V, Positive-QTOFsplash10-0006-0900000000-6b01d3bcbbc7303b646b2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Carboline 10V, Negative-QTOFsplash10-014i-0900000000-a18ea037f074412ab5bf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Carboline 20V, Negative-QTOFsplash10-014i-0900000000-d9a1aef47a4155b550a72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - beta-Carboline 40V, Negative-QTOFsplash10-014l-0900000000-82fd47fe0f1bc435ec2c2016-08-03Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothEnthesitis-related arthritis details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB007945
KNApSAcK IDC00026537
Chemspider ID58486
KEGG Compound IDC20157
BioCyc IDCPD-15304
BiGG IDNot Available
Wikipedia LinkBeta-Carboline
METLIN IDNot Available
PubChem Compound64961
PDB IDNRH
ChEBI ID109895
Food Biomarker OntologyNot Available
VMH IDCE3087
MarkerDB IDNot Available
Good Scents IDrw1269771
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Hidalgo J, Sanchez-Coronilla A, Balon M, Asuncion Munoz M, Carmona C: Dual emission of temperature-induced betacarboline self-associated hydrogen bond aggregates. Photochem Photobiol Sci. 2009 Mar;8(3):414-20. doi: 10.1039/b816776a. Epub 2009 Jan 20. [PubMed:19255684 ]
  2. Bailey JE, Nutt DJ: GABA-A receptors and the response to CO(2) inhalation - a translational trans-species model of anxiety? Pharmacol Biochem Behav. 2008 Jul;90(1):51-7. doi: 10.1016/j.pbb.2008.04.002. Epub 2008 Apr 9. [PubMed:18485466 ]
  3. Munoz MA, Sama O, Galan M, Guardado P, Carmona C, Balon M: Hydrogen bonding NH/pi interactions between betacarboline and methyl benzene derivatives. Spectrochim Acta A Mol Biomol Spectrosc. 2001 Apr;57A(5):1049-56. [PubMed:11374564 ]
  4. Gynther J, Konschin H, Tylli H, Rouvinen J: Electrostatic requirements for high benzodiazepine receptor affinity among betacarboline-3-carboxylic acid derivatives. Acta Pharm Nord. 1990;2(1):45-52. [PubMed:2160247 ]
  5. Venault P, Chapouthier G: From the behavioral pharmacology of beta-carbolines to seizures, anxiety, and memory. ScientificWorldJournal. 2007 Feb 19;7:204-23. doi: 10.1100/tsw.2007.48. [PubMed:17334612 ]
  6. Cao R, Peng W, Wang Z, Xu A: beta-Carboline alkaloids: biochemical and pharmacological functions. Curr Med Chem. 2007;14(4):479-500. doi: 10.2174/092986707779940998. [PubMed:17305548 ]