NP-MRD: Showing NP-Card for 2,3,4,9-tetrahydro-1h-carbazole-3-carboxylic acid (NP0277035)

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Record Information

Version

2.0

Created at

2022-09-09 01:28:26 UTC

Updated at

2022-09-09 01:28:26 UTC

NP-MRD ID

NP0277035

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,3,4,9-tetrahydro-1h-carbazole-3-carboxylic acid

Description

2,3,4,9-Tetrahydro-1H-carbazole-3-carboxylic acid belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring. 2,3,4,9-tetrahydro-1h-carbazole-3-carboxylic acid is found in Taraxacum formosanum. 2,3,4,9-Tetrahydro-1H-carbazole-3-carboxylic acid is a weakly acidic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 31  0  0  0  0  0  0  0  0999 V2000
   -3.5575    1.8517   -0.1594 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6333    1.0353    0.0742 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8489    1.1284    1.1997 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3611   -0.0685   -0.8755 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5245   -1.3877   -0.1795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4064   -1.7683    0.7135 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1639   -1.0025    0.4827 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9513   -1.0345    1.2575 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8608   -0.2129    0.7325 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1420    0.1132    1.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9118    1.0100    0.4085 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3879    1.5908   -0.7276 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1045    1.2503   -1.1044 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3105    0.3645   -0.4162 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0383   -0.1455   -0.5543 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0191    0.0753   -1.5490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3246    1.3976    2.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1282   -0.0201   -1.6725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4721   -1.3427    0.3986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6765   -2.1877   -0.9416 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2278   -2.8672    0.6599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6916   -1.5755    1.7897 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1211   -1.5940    2.1323 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5941   -0.3211    2.0168 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9123    1.2379    0.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9879    2.2991   -1.3007 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6752    1.6998   -1.9994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9654    1.1144   -1.9366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9969   -0.6400   -2.3960 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7 15  2  0
 15 16  1  0
 15 14  1  0
 14 13  2  0
 13 12  1  0
 12 11  2  0
 11 10  1  0
 10  9  2  0
  9  8  1  0
 16  4  1  0
  9 14  1  0
  8  7  1  0
  3 17  1  0
  4 18  1  6
  5 19  1  0
  5 20  1  0
  6 21  1  0
  6 22  1  0
 16 28  1  0
 16 29  1  0
 13 27  1  0
 12 26  1  0
 11 25  1  0
 10 24  1  0
  8 23  1  0
M  END


  Mrv1533004161522172D          

 16 18  0  0  0  0            999 V2000
    0.6159   -2.2741    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4229   -2.4457    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6778   -3.2303    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9749   -1.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7200   -1.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2720   -0.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0790   -0.6064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7464   -0.1215    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4139   -0.6064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2208   -0.4349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7729   -1.0479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5179   -1.8326    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7110   -2.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1589   -1.3910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3339   -1.3910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7819   -2.0041    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  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
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
  7 15  2  0  0  0  0
 15 16  1  0  0  0  0
  4 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0277035

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1CCC2=C(C1)C1=CC=CC=C1N2

> <INCHI_IDENTIFIER>
InChI=1S/C13H13NO2/c15-13(16)8-5-6-12-10(7-8)9-3-1-2-4-11(9)14-12/h1-4,8,14H,5-7H2,(H,15,16)

> <INCHI_KEY>
CGJLAUQMHSAAMY-UHFFFAOYSA-N

> <FORMULA>
C13H13NO2

> <MOLECULAR_WEIGHT>
215.252

> <EXACT_MASS>
215.094628663

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
29

> <JCHEM_AVERAGE_POLARIZABILITY>
23.304927141504795

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid

> <ALOGPS_LOGP>
2.26

> <JCHEM_LOGP>
2.511100192

> <ALOGPS_LOGS>
-2.66

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.748463045483405

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.680524156309934

> <JCHEM_POLAR_SURFACE_AREA>
53.089999999999996

> <JCHEM_REFRACTIVITY>
60.898100000000014

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.68e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  O   UNK     0       1.150  -4.245   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       2.656  -4.565   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.132  -6.030   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       3.687  -3.421   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.211  -1.956   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.241  -0.812   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.747  -1.132   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       6.993  -0.227   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       8.239  -1.132   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.746  -0.812   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.776  -1.956   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.300  -3.421   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.794  -3.741   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.763  -2.597   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.223  -2.597   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.193  -3.741   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   16                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    9   15                                                  
CONECT   15   14    7   16                                                  
CONECT   16   15    4                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

View in JSmol

Synonyms

Value	Source
2,3,4,9-Tetrahydro-1H-carbazole-3-carboxylate	Generator

Chemical Formula

C₁₃H₁₃NO₂

Average Mass

215.2520 Da

Monoisotopic Mass

215.09463 Da

IUPAC Name

2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid

Traditional Name

2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid

CAS Registry Number

Not Available

SMILES

OC(=O)C1CCC2=C(C1)C1=CC=CC=C1N2

InChI Identifier

InChI=1S/C13H13NO2/c15-13(16)8-5-6-12-10(7-8)9-3-1-2-4-11(9)14-12/h1-4,8,14H,5-7H2,(H,15,16)

InChI Key

CGJLAUQMHSAAMY-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
Taraxacum formosanum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as carbazoles. Carbazoles are compounds containing a three ring system containing a pyrrole ring fused on either side to a benzene ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Carbazoles

Direct Parent

Carbazoles

Alternative Parents

Substituents

Carbazole
3-alkylindole
Indole
Benzenoid
Pyrrole
Heteroaromatic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Azacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen 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	2.26	ALOGPS
logP	2.51	ChemAxon
logS	-2.7	ALOGPS
pKa (Strongest Acidic)	4.68	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	53.09 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	60.9 m³·mol⁻¹	ChemAxon
Polarizability	23.3 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

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

13491214

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,3,4,9-tetrahydro-1h-carbazole-3-carboxylic acid (NP0277035)

MOL for NP0277035 (2,3,4,9-tetrahydro-1h-carbazole-3-carboxylic acid)

3D MOL for NP0277035 (2,3,4,9-tetrahydro-1h-carbazole-3-carboxylic acid)

3D SDF for NP0277035 (2,3,4,9-tetrahydro-1h-carbazole-3-carboxylic acid)

3D-SDF for NP0277035 (2,3,4,9-tetrahydro-1h-carbazole-3-carboxylic acid)

PDB for NP0277035 (2,3,4,9-tetrahydro-1h-carbazole-3-carboxylic acid)

3D PDB for NP0277035 (2,3,4,9-tetrahydro-1h-carbazole-3-carboxylic acid)

SMILES for NP0277035 (2,3,4,9-tetrahydro-1h-carbazole-3-carboxylic acid)

INCHI for NP0277035 (2,3,4,9-tetrahydro-1h-carbazole-3-carboxylic acid)

Structure for NP0277035 (2,3,4,9-tetrahydro-1h-carbazole-3-carboxylic acid)

3D Structure for NP0277035 (2,3,4,9-tetrahydro-1h-carbazole-3-carboxylic acid)