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Showing NP-Card for 1h-indole-5-carboxylic acid (NP0226715)

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Record Information
Version2.0
Created at2022-09-06 05:50:43 UTC
Updated at2022-09-06 05:50:43 UTC
NP-MRD IDNP0226715
Secondary Accession NumbersNone
Natural Product Identification
Common Name1h-indole-5-carboxylic acid
DescriptionIndole-5-carboxylic acid belongs to the class of organic compounds known as indolecarboxylic acids. Indolecarboxylic acids are compounds containing a carboxylic acid group linked to an indole. Indole-5-carboxylic acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. 1h-indole-5-carboxylic acid is found in Aloe africana. 1h-indole-5-carboxylic acid was first documented in 2019 (PMID: 31359720). Based on a literature review a small amount of articles have been published on Indole-5-carboxylic acid (PMID: 35901526) (PMID: 35223774) (PMID: 33660086) (PMID: 33075723).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0226715 (1h-indole-5-carboxylic acid)


  Mrv1652309062207502D          

 12 13  0  0  0  0            999 V2000
    4.0668    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    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  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  2  0  0  0  0
  4 12  1  0  0  0  0
M  END
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3D MOL for NP0226715 (1h-indole-5-carboxylic acid)

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3D SDF for NP0226715 (1h-indole-5-carboxylic acid)

  Mrv1652309062207502D          

 12 13  0  0  0  0            999 V2000
    4.0668    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7812    1.9354    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    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  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
  7 11  1  0  0  0  0
 11 12  2  0  0  0  0
  4 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0226715

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1=CC=C2NC=CC2=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H7NO2/c11-9(12)7-1-2-8-6(5-7)3-4-10-8/h1-5,10H,(H,11,12)

> <INCHI_KEY>
IENZCGNHSIMFJE-UHFFFAOYSA-N

> <FORMULA>
C9H7NO2

> <MOLECULAR_WEIGHT>
161.16

> <EXACT_MASS>
161.047678469

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
16.067714606401516

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1H-indole-5-carboxylic acid

> <JCHEM_LOGP>
1.729590717

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
16.631140983943315

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.6314352213711296

> <JCHEM_POLAR_SURFACE_AREA>
53.089999999999996

> <JCHEM_REFRACTIVITY>
44.40070000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
1H-indole-5-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0226715 (1h-indole-5-carboxylic acid)
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PDB for NP0226715 (1h-indole-5-carboxylic acid)
HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  O   UNK     0       7.591   5.923   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       8.925   3.613   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       2.126   1.597   0.000  0.00  0.00           N+0
HETATM    9  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.126   4.089   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   12                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   11                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10    7   12                                                  
CONECT   12   11    4                                                       
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

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3D PDB for NP0226715 (1h-indole-5-carboxylic acid)
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SMILES for NP0226715 (1h-indole-5-carboxylic acid)
OC(=O)C1=CC=C2NC=CC2=C1
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INCHI for NP0226715 (1h-indole-5-carboxylic acid)
InChI=1S/C9H7NO2/c11-9(12)7-1-2-8-6(5-7)3-4-10-8/h1-5,10H,(H,11,12)
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View in JSmol
Synonyms
ValueSource
Indole-5-carboxylateGenerator
5-Indolecarboxylic acidHMDB
Chemical FormulaC9H7NO2
Average Mass161.1600 Da
Monoisotopic Mass161.04768 Da
IUPAC Name1H-indole-5-carboxylic acid
Traditional Name1H-indole-5-carboxylic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C1=CC=C2NC=CC2=C1
InChI Identifier
InChI=1S/C9H7NO2/c11-9(12)7-1-2-8-6(5-7)3-4-10-8/h1-5,10H,(H,11,12)
InChI KeyIENZCGNHSIMFJE-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Aloe africanaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indolecarboxylic acids. Indolecarboxylic acids are compounds containing a carboxylic acid group linked to an indole.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassIndoles and derivatives  
Sub ClassIndolecarboxylic acids and derivatives  
Direct ParentIndolecarboxylic acids  
Alternative Parents
Substituents
  • Indolecarboxylic acid
    • 

  • Indole
    • 

  • Benzenoid
    • 

  • Pyrrole
    • 

  • Heteroaromatic compound
    • 

  • Carboxylic acid derivative
    • 

  • Azacycle
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Organopnictogen compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organic nitrogen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
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
logP1.73ChemAxon
pKa (Strongest Acidic)3.63ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area53.09 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity44.4 m³·mol⁻¹ChemAxon
Polarizability16.07 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0253469  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID66885  
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound74280  
PDB IDNot Available
ChEBI ID131778  
Good Scents IDNot Available
References
General References
  1. Deng H, Huang M, Liu H, Zhang H, Liu L, Gao B, Li X, Li J, Niu Q, Zhang Z, Luan S, Zhang J, Jing Y, Liu D, Zhao L: Development of a series of novel Mcl-1 inhibitors bearing an indole carboxylic acid moiety. Bioorg Chem. 2022 Oct;127:106018. doi: 10.1016/j.bioorg.2022.106018. Epub 2022  Jul 12. [PubMed:35901526  ] 
  2. Wang H, Fan Y, Yang Q, Sun X, Liu H, Chen W, Aziz A, Wang S: Boosting the Electrochemical Performance of PI-5-CA/C-SWCNT Nanohybrid for Sensitive Detection of E. coli O157:H7 From the Real Sample. Front Chem. 2022 Feb 10;10:843859. doi: 10.3389/fchem.2022.843859. eCollection  2022. [PubMed:35223774  ] 
  3. Yang Q, Deng S, Xu J, Farooq U, Yang T, Chen W, Zhou L, Gao M, Wang S: Poly(indole-5-carboxylic acid)/reduced graphene oxide/gold nanoparticles/phage-based electrochemical biosensor for highly specific detection of Yersinia pseudotuberculosis. Mikrochim Acta. 2021 Mar 4;188(4):107. doi: 10.1007/s00604-020-04676-y. [PubMed:33660086  ] 
  4. Gan X, Han D, Wang J, Liu P, Li X, Zheng Q, Yan Y: A highly sensitive electrochemiluminescence immunosensor for h-FABP determination based on self-enhanced luminophore coupled with ultrathin 2D nickel metal-organic framework nanosheets. Biosens Bioelectron. 2021 Jan 1;171:112735. doi: 10.1016/j.bios.2020.112735. Epub  2020 Oct 14. [PubMed:33075723  ] 
  5. Tian DL, Liang CP, Liang J, Chen H: [Synthesis and antitumor activity of novel indole podophyllotoxin derivatives]. Zhongguo Zhong Yao Za Zhi. 2019 Jun;44(12):2532-2537. doi:  10.19540/j.cnki.cjcmm.20190321.207. [PubMed:31359720  ] 
  6. LOTUS database [Link]