NP-MRD: Showing NP-Card for 6-hydroxy-9h-pyrido[3,4-b]indole-1-carboxylic acid (NP0187460)

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Record Information

Version

2.0

Created at

2022-09-04 03:38:08 UTC

Updated at

2022-09-04 03:38:08 UTC

NP-MRD ID

NP0187460

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-hydroxy-9h-pyrido[3,4-b]indole-1-carboxylic acid

Description

6-Hydroxy-beta-carboline-1-carboxylic 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. 6-hydroxy-9h-pyrido[3,4-b]indole-1-carboxylic acid is found in Picrasma quassioides. 6-hydroxy-9h-pyrido[3,4-b]indole-1-carboxylic acid was first documented in 2012 (PMID: 22888096). Based on a literature review very few articles have been published on 6-Hydroxy-beta-carboline-1-carboxylic acid (PMID: 29642544).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309042205382D          

 17 19  0  0  0  0            999 V2000
    4.4703   -1.3283    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6633   -1.1567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1113   -1.7698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4084   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9604    0.2410    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7054    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8985    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3464    0.5840    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6014   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9339   -0.6855    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.2665   -0.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4595   -0.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0925    0.2410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1624    1.0256    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3896    1.6387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9694    1.1971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5214    0.5840    0.0000 C   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
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  4  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 11 17  2  0  0  0  0
  8 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0187460

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1=NC=CC2=C1NC1=C2C=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H8N2O3/c15-6-1-2-9-8(5-6)7-3-4-13-11(12(16)17)10(7)14-9/h1-5,14-15H,(H,16,17)

> <INCHI_KEY>
JFYIBBYEVIXFDE-UHFFFAOYSA-N

> <FORMULA>
C12H8N2O3

> <MOLECULAR_WEIGHT>
228.207

> <EXACT_MASS>
228.053492126

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
25

> <JCHEM_AVERAGE_POLARIZABILITY>
22.356440511540676

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
0.06656252548510304

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.440690768324826

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.9676387118181351

> <JCHEM_PKA_STRONGEST_BASIC>
5.7343938442112545

> <JCHEM_POLAR_SURFACE_AREA>
86.21

> <JCHEM_REFRACTIVITY>
60.180400000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 04-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-22         0                                  
HETATM    1  O   UNK     0       8.344  -2.479   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       6.838  -2.159   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.808  -3.304   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       6.362  -0.695   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       7.393   0.450   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0       6.917   1.914   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.410   2.235   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.380   1.090   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.856  -0.374   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0       3.610  -1.280   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0       2.364  -0.374   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.858  -0.695   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.173   0.450   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.303   1.914   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -0.727   3.059   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.810   2.235   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.840   1.090   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   17                                                  
CONECT    9    8    4   10                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   17                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   11    8                                                  
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

View in JSmol

Synonyms

Value	Source
6-Hydroxy-b-carboline-1-carboxylate	Generator
6-Hydroxy-b-carboline-1-carboxylic acid	Generator
6-Hydroxy-beta-carboline-1-carboxylate	Generator
6-Hydroxy-β-carboline-1-carboxylate	Generator
6-Hydroxy-β-carboline-1-carboxylic acid	Generator

Chemical Formula

C₁₂H₈N₂O₃

Average Mass

228.2070 Da

Monoisotopic Mass

228.05349 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

OC(=O)C1=NC=CC2=C1NC1=C2C=C(O)C=C1

InChI Identifier

InChI=1S/C12H8N2O3/c15-6-1-2-9-8(5-6)7-3-4-13-11(12(16)17)10(7)14-9/h1-5,14-15H,(H,16,17)

InChI Key

JFYIBBYEVIXFDE-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Picrasma quassioides	LOTUS Database	35616633

Chemical Taxonomy

Description

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.

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
Hydroxyindole
Indole
Indole or derivatives
Pyridine carboxylic acid
Pyridine carboxylic acid or derivatives
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Pyridine
Vinylogous amide
Pyrrole
Heteroaromatic compound
Azacycle
Organoheterocyclic compound
Carboxylic acid
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxide
Organonitrogen compound
Organic nitrogen compound
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Organopnictogen 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

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

45633451

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

84080012

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Wang N, Li ZY, Zheng XL, Li Q, Yang X, Xu H: Quality Assessment of Kumu Injection, a Traditional Chinese Medicine Preparation, Using HPLC Combined with Chemometric Methods and Qualitative and Quantitative Analysis of Multiple Alkaloids by Single Marker. Molecules. 2018 Apr 9;23(4):856. doi: 10.3390/molecules23040856. [PubMed:29642544 ]
Liao HJ, Lai ZQ, Su JY, Yi YY, Li YC, Lai XP, Su ZR, Lin ZX: Fingerprinting and simultaneous determination of alkaloids in Picrasma quassioides from different locations by high performance liquid chromatography with photodiode array detection. J Sep Sci. 2012 Sep;35(17):2193-202. doi: 10.1002/jssc.201200025. Epub 2012 Aug 7. [PubMed:22888096 ]
LOTUS database [Link]

Showing NP-Card for 6-hydroxy-9h-pyrido[3,4-b]indole-1-carboxylic acid (NP0187460)

MOL for NP0187460 (6-hydroxy-9h-pyrido[3,4-b]indole-1-carboxylic acid)

3D MOL for NP0187460 (6-hydroxy-9h-pyrido[3,4-b]indole-1-carboxylic acid)

3D SDF for NP0187460 (6-hydroxy-9h-pyrido[3,4-b]indole-1-carboxylic acid)

3D-SDF for NP0187460 (6-hydroxy-9h-pyrido[3,4-b]indole-1-carboxylic acid)

PDB for NP0187460 (6-hydroxy-9h-pyrido[3,4-b]indole-1-carboxylic acid)

3D PDB for NP0187460 (6-hydroxy-9h-pyrido[3,4-b]indole-1-carboxylic acid)

SMILES for NP0187460 (6-hydroxy-9h-pyrido[3,4-b]indole-1-carboxylic acid)

INCHI for NP0187460 (6-hydroxy-9h-pyrido[3,4-b]indole-1-carboxylic acid)

Structure for NP0187460 (6-hydroxy-9h-pyrido[3,4-b]indole-1-carboxylic acid)

3D Structure for NP0187460 (6-hydroxy-9h-pyrido[3,4-b]indole-1-carboxylic acid)