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Showing NP-Card for Indoline-2-carboxylic acid (NP0331896)

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Record Information
Version2.0
Created at2023-09-28 20:01:11 UTC
Updated at2025-02-11 15:45:23 UTC
NP-MRD IDNP0331896
Natural Product DOIhttps://doi.org/10.57994/1002
Secondary Accession NumbersNone
Natural Product Identification
Common NameIndoline-2-carboxylic acid
DescriptionIndoline-2-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. Indoline-2-carboxylic acid was first documented in 2022 (PMID: 36242553). Based on a literature review a small amount of articles have been published on Indoline-2-carboxylic acid (PMID: 38178981) (PMID: 38170630) (PMID: 37426545) (PMID: 35669118).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0331896 (Indoline-2-carboxylic acid)


  Mrv2104 09282320012D          

 12 13  0  0  0  0            999 V2000
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    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   -1.5229    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
   -0.1712   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837   -1.4124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    0.0165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  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
  1  9  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
M  END
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3D MOL for NP0331896 (Indoline-2-carboxylic acid)

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3D SDF for NP0331896 (Indoline-2-carboxylic acid)

  Mrv2104 09282320012D          

 12 13  0  0  0  0            999 V2000
    1.1387   -1.3654    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -0.0305    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233   -0.2854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.2854    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   -1.5229    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
   -0.1712   -0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837   -1.4124    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5837    0.0165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  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
  1  9  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331896

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)C1CC2=CC=CC=C2N1

> <INCHI_IDENTIFIER>
InChI=1/C9H9NO2/c11-9(12)8-5-6-3-1-2-4-7(6)10-8/h1-4,8,10H,5H2,(H,11,12)

> <INCHI_KEY>
QNRXNRGSOJZINA-UHFFFAOYNA-N

> <FORMULA>
C9H9NO2

> <MOLECULAR_WEIGHT>
163.176

> <EXACT_MASS>
163.063328534

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
16.526146333962757

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,3-dihydro-1H-indole-2-carboxylic acid

> <JCHEM_LOGP>
0.674087922158063

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.37218622553429

> <JCHEM_PKA_STRONGEST_ACIDIC>
2.3272881569015986

> <JCHEM_PKA_STRONGEST_BASIC>
4.713584145027506

> <JCHEM_POLAR_SURFACE_AREA>
49.33

> <JCHEM_REFRACTIVITY>
45.39130000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
2,3-dihydro-1H-indole-2-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0331896 (Indoline-2-carboxylic acid)
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PDB for NP0331896 (Indoline-2-carboxylic acid)
HEADER    PROTEIN                                 28-SEP-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-SEP-23         0                                  
HETATM    1  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM    3  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.320  -1.303   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.090  -2.637   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      -1.090   0.031   0.000  0.00  0.00           O+0
CONECT    1    2    9                                                       
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8    4    1                                                  
CONECT   10    2   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   26    0
END

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3D PDB for NP0331896 (Indoline-2-carboxylic acid)
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SMILES for NP0331896 (Indoline-2-carboxylic acid)
OC(=O)C1CC2=CC=CC=C2N1
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INCHI for NP0331896 (Indoline-2-carboxylic acid)
InChI=1/C9H9NO2/c11-9(12)8-5-6-3-1-2-4-7(6)10-8/h1-4,8,10H,5H2,(H,11,12)
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View in JSmol
Synonyms
ValueSource
Indoline-2-carboxylateGenerator
Chemical FormulaC9H9NO2
Average Mass163.1760 Da
Monoisotopic Mass163.06333 Da
IUPAC Name2,3-dihydro-1H-indole-2-carboxylic acid
Traditional Name2,3-dihydro-1H-indole-2-carboxylic acid
CAS Registry NumberNot Available
SMILES
OC(=O)C1CC2=CC=CC=C2N1
InChI Identifier
InChI=1/C9H9NO2/c11-9(12)8-5-6-3-1-2-4-7(6)10-8/h1-4,8,10H,5H2,(H,11,12)
InChI KeyQNRXNRGSOJZINA-UHFFFAOYNA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
Predicted Spectra
Not Available
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600, CD3OD, simulated)bgnzk@missouri.eduSumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USADr. Bharat Goel2024-05-09View Spectrum
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as indolecarboxylic acids. These 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
    • 

  • Alpha-amino acid
    • 

  • Alpha-amino acid or derivatives
    • 

  • Dihydroindole
    • 

  • Aralkylamine
    • 

  • Secondary aliphatic/aromatic amine
    • 

  • Benzenoid
    • 

  • Amino acid or derivatives
    • 

  • Amino acid
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Azacycle
    • 

  • Secondary amine
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organic nitrogen compound
    • 

  • Organonitrogen compound
    • 

  • Organooxygen compound
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Carbonyl group
    • 

  • Organopnictogen compound
    • 

  • Amine
    • 

  • Organic oxygen compound
    • 

  • 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
logP0.67ChemAxon
pKa (Strongest Acidic)2.33ChemAxon
pKa (Strongest Basic)4.71ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area49.33 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity45.39 m³·mol⁻¹ChemAxon
Polarizability16.53 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Deng C, Zhao L, Gao MY, Darwish S, Song BQ, Sensharma D, Lusi M, Peng YL, Mukherjee S, Zaworotko MJ: Ultramicroporous Lonsdaleite Topology MOF with High Propane Uptake and Propane/Methane Selectivity for Propane Capture from Simulated Natural Gas. ACS Mater Lett. 2023 Dec 1;6(1):56-65. doi: 10.1021/acsmaterialslett.3c01157.  eCollection 2024 Jan 1. [PubMed:38178981  ] 
  2. Song JR, Li XJ, Shi J, Chi Q, Wu W, Ren H: Direct synthesis of N-functionalized indoles through isomerization of azomethine ylides. Org Biomol Chem. 2024 Jan 24;22(4):741-744. doi: 10.1039/d3ob01393f. [PubMed:38170630  ] 
  3. Deng C, Song BQ, Lusi M, Bezrukov AA, Haskins MM, Gao MY, Peng YL, Ma JG, Cheng P, Mukherjee S, Zaworotko MJ: Crystal Engineering of a Chiral Crystalline Sponge That Enables Absolute Structure Determination and Enantiomeric Separation. Cryst Growth Des. 2023 May 16;23(7):5211-5220. doi: 10.1021/acs.cgd.3c00446.  eCollection 2023 Jul 5. [PubMed:37426545  ] 
  4. Pollastrini M, Pasquinelli L, Gorecki M, Balzano F, Cupellini L, Lipparini F, Uccello Barretta G, Marchetti F, Pescitelli G, Angelici G: A Unique and Stable Polyproline I Helix Sorted out from Conformational Equilibrium by Solvent Polarity. J Org Chem. 2022 Nov 4;87(21):13715-13725. doi: 10.1021/acs.joc.2c01377. Epub  2022 Oct 15. [PubMed:36242553  ] 
  5. Chen Z, Wu S, Zeng Y, Chen Z, Li X, Li J, He L, Chen M: FuZhengHuaYuJiangZhuTongLuoFang Prescription Modulates Gut Microbiota and Gut-Derived Metabolites in UUO Rats. Front Cell Infect Microbiol. 2022 May 20;12:837205. doi:  10.3389/fcimb.2022.837205. eCollection 2022. [PubMed:35669118  ]