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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2021-09-11 06:20:30 UTC

Update Date

2021-09-26 23:00:39 UTC

HMDB ID

HMDB0249637

Secondary Accession Numbers

None

Metabolite Identification

Common Name

9H-Pyrido[3,4-b]indole-3-carboxylic acid

Description

9H-Pyrido[3,4-b]indole-3-carboxylic acid, also known as beta-carboline carboxylic acid, belongs to the class of organic compounds known as beta carbolines. Beta carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety. Based on a literature review a small amount of articles have been published on 9H-Pyrido[3,4-b]indole-3-carboxylic acid. This compound has been identified in human blood as reported by (PMID: 31557052 ). 9h-pyrido[3,4-b]indole-3-carboxylic acid is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically 9H-Pyrido[3,4-b]indole-3-carboxylic acid is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

  Mrv1652309112108202D          

 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
    3.4084    1.1971    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
    2.3464    0.2410    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
    1.5214    0.2410    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
    0.1624   -0.2006    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
    0.4595    1.1971    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
    1.9339    1.5105    0.0000 N   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
   -0.1347   -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  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
  7 12  1  0  0  0  0
 12 13  1  0  0  0  0
  4 13  1  0  0  0  0
  9 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0249637

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(=O)C1=NC=C2NC3=CC=CC=C3C2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H8N2O2/c15-12(16)10-5-8-7-3-1-2-4-9(7)14-11(8)6-13-10/h1-6,14H,(H,15,16)

> <INCHI_KEY>
ARLVFKCLBYUINL-UHFFFAOYSA-N

> <FORMULA>
C12H8N2O2

> <MOLECULAR_WEIGHT>
212.208

> <EXACT_MASS>
212.058577506

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
24

> <JCHEM_AVERAGE_POLARIZABILITY>
21.474859164140046

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.28

> <JCHEM_LOGP>
0.680086806141819

> <ALOGPS_LOGS>
-3.01

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.63493622652231

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.3743080167147679

> <JCHEM_PKA_STRONGEST_BASIC>
5.438842668518447

> <JCHEM_POLAR_SURFACE_AREA>
65.98

> <JCHEM_REFRACTIVITY>
58.1995

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.09e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-21         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       6.362   2.235   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.856   1.914   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.380   0.450   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.410  -0.695   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.840   0.450   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.810  -0.695   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.303  -0.374   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      -0.173   1.090   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       0.858   2.235   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  N   UNK     0       3.610   2.820   0.000  0.00  0.00           N+0
HETATM   14  C   UNK     0      -0.727  -1.519   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.251  -2.984   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    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   13                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   12                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7   13                                                  
CONECT   13   12    4                                                       
CONECT   14    9   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
9H-Pyrido[3,4-b]indole-3-carboxylate	Generator
9H-Pyrido(3,4-b)indole-3-carboxylic acid	HMDB
beta-Carboline carboxylic acid	HMDB
Carboline-3-carboxylic acid	HMDB

Chemical Formula

C₁₂H₈N₂O₂

Average Molecular Weight

212.208

Monoisotopic Molecular Weight

212.058577506

IUPAC Name

9H-pyrido[3,4-b]indole-3-carboxylic acid

Traditional Name

9H-pyrido[3,4-b]indole-3-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C1=NC=C2NC3=CC=CC=C3C2=C1

InChI Identifier

InChI=1S/C12H8N2O2/c15-12(16)10-5-8-7-3-1-2-4-9(7)14-11(8)6-13-10/h1-6,14H,(H,15,16)

InChI Key

ARLVFKCLBYUINL-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.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyridoindoles

Direct Parent

Beta carbolines

Alternative Parents

Substituents

Beta-carboline
Indole
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
Pyridine
Benzenoid
Heteroaromatic compound
Pyrrole
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Azacycle
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	2.28	ALOGPS
logP	0.68	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	1.37	ChemAxon
pKa (Strongest Basic)	5.44	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	65.98 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	58.2 m³·mol⁻¹	ChemAxon
Polarizability	21.47 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	148.302	30932474
DeepCCS	[M-H]-	145.926	30932474
DeepCCS	[M-2H]-	179.302	30932474
DeepCCS	[M+Na]+	154.377	30932474
AllCCS	[M+H]+	148.9	32859911
AllCCS	[M+H-H2O]+	145.1	32859911
AllCCS	[M+NH4]+	152.5	32859911
AllCCS	[M+Na]+	153.6	32859911
AllCCS	[M-H]-	146.9	32859911
AllCCS	[M+Na-2H]-	146.5	32859911
AllCCS	[M+HCOO]-	146.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
9H-Pyrido[3,4-b]indole-3-carboxylic acid	OC(=O)C1=NC=C2NC3=CC=CC=C3C2=C1	3167.0	Standard polar	33892256
9H-Pyrido[3,4-b]indole-3-carboxylic acid	OC(=O)C1=NC=C2NC3=CC=CC=C3C2=C1	2224.0	Standard non polar	33892256
9H-Pyrido[3,4-b]indole-3-carboxylic acid	OC(=O)C1=NC=C2NC3=CC=CC=C3C2=C1	2415.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
9H-Pyrido[3,4-b]indole-3-carboxylic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC2=C(C=N1)N([Si](C)(C)C)C1=CC=CC=C21	2623.8	Semi standard non polar	33892256
9H-Pyrido[3,4-b]indole-3-carboxylic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC2=C(C=N1)N([Si](C)(C)C)C1=CC=CC=C21	2355.1	Standard non polar	33892256
9H-Pyrido[3,4-b]indole-3-carboxylic acid,2TMS,isomer #1	C[Si](C)(C)OC(=O)C1=CC2=C(C=N1)N([Si](C)(C)C)C1=CC=CC=C21	2629.7	Standard polar	33892256
9H-Pyrido[3,4-b]indole-3-carboxylic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC2=C(C=N1)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C21	2928.9	Semi standard non polar	33892256
9H-Pyrido[3,4-b]indole-3-carboxylic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC2=C(C=N1)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C21	2759.9	Standard non polar	33892256
9H-Pyrido[3,4-b]indole-3-carboxylic acid,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)C1=CC2=C(C=N1)N([Si](C)(C)C(C)(C)C)C1=CC=CC=C21	2833.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 9H-Pyrido[3,4-b]indole-3-carboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0297-1920000000-a0eb9f5debe97fcedcff	2021-09-23	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9H-Pyrido[3,4-b]indole-3-carboxylic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9H-Pyrido[3,4-b]indole-3-carboxylic acid GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9H-Pyrido[3,4-b]indole-3-carboxylic acid GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9H-Pyrido[3,4-b]indole-3-carboxylic acid GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 9H-Pyrido[3,4-b]indole-3-carboxylic acid GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-11-03	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9H-Pyrido[3,4-b]indole-3-carboxylic acid 10V, Positive-QTOF	splash10-03dj-0590000000-bc7591e3ebd52695f2f0	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9H-Pyrido[3,4-b]indole-3-carboxylic acid 20V, Positive-QTOF	splash10-03dj-0490000000-8f57580a3a45c52141cf	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9H-Pyrido[3,4-b]indole-3-carboxylic acid 40V, Positive-QTOF	splash10-014l-0900000000-9c1f2bbc37aa6bf3124a	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9H-Pyrido[3,4-b]indole-3-carboxylic acid 10V, Negative-QTOF	splash10-014i-0900000000-1ba6c7cf3004ee08cdb7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9H-Pyrido[3,4-b]indole-3-carboxylic acid 20V, Negative-QTOF	splash10-014i-0900000000-1ba6c7cf3004ee08cdb7	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9H-Pyrido[3,4-b]indole-3-carboxylic acid 40V, Negative-QTOF	splash10-014i-0900000000-a8d430623432f3e436ef	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	31557052	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00050461

Chemspider ID

151273

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

173262

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]

Showing metabocard for 9H-Pyrido[3,4-b]indole-3-carboxylic acid (HMDB0249637)

MOL for HMDB0249637 (9H-Pyrido[3,4-b]indole-3-carboxylic acid)

3D MOL for HMDB0249637 (9H-Pyrido[3,4-b]indole-3-carboxylic acid)

3D SDF for HMDB0249637 (9H-Pyrido[3,4-b]indole-3-carboxylic acid)

3D-SDF for HMDB0249637 (9H-Pyrido[3,4-b]indole-3-carboxylic acid)

PDB for HMDB0249637 (9H-Pyrido[3,4-b]indole-3-carboxylic acid)

3D PDB for HMDB0249637 (9H-Pyrido[3,4-b]indole-3-carboxylic acid)

SMILES for HMDB0249637 (9H-Pyrido[3,4-b]indole-3-carboxylic acid)

INCHI for HMDB0249637 (9H-Pyrido[3,4-b]indole-3-carboxylic acid)

Structure for HMDB0249637 (9H-Pyrido[3,4-b]indole-3-carboxylic acid)

3D Structure for HMDB0249637 (9H-Pyrido[3,4-b]indole-3-carboxylic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra