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Showing NP-Card for 1h-indole-4-carbaldehyde (NP0275513)

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Record Information
Version2.0
Created at2022-09-08 23:17:05 UTC
Updated at2022-09-08 23:17:06 UTC
NP-MRD IDNP0275513
Secondary Accession NumbersNone
Natural Product Identification
Common Name1h-indole-4-carbaldehyde
DescriptionIndole-4-carbaldehyde, also known as 4-formyl-1H-indole, belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene to form 2,3-benzopyrrole. A heteroarenecarbaldehyde that is indole in which the hydrogen at position 4 has been replaced by a formyl group. 1h-indole-4-carbaldehyde is found in Limonia acidissima. 1h-indole-4-carbaldehyde was first documented in 2008 (PMID: 18572918). Indole-4-carbaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 28417922).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0275513 (1h-indole-4-carbaldehyde)


  Mrv1533004261514432D          

 11 12  0  0  0  0            999 V2000
    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 C   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 N   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
    2.6378   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.5396    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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  2  0  0  0  0
  1  9  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  2  0  0  0  0
M  END
Download

3D MOL for NP0275513 (1h-indole-4-carbaldehyde)

     RDKit          3D

 18 19  0  0  0  0  0  0  0  0999 V2000
   -2.2624    2.8066   -0.2617 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1299    2.2862   -0.1251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9217    0.8517   -0.1085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9612   -0.0544   -0.2426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7426   -1.4142   -0.2242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4621   -1.9007   -0.0691 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6043   -1.0206    0.0682 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9252   -1.2115    0.2302 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.5070   -0.0106    0.3096 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5557    0.9806    0.1984 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3498    0.3233    0.0453 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2752    2.9334   -0.0155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9612    0.3708   -0.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5857   -2.1116   -0.3328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3138   -2.9720   -0.0576 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4351   -2.1168    0.2874 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5623    0.2028    0.4413 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6764    2.0571    0.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3 11  2  0
 11 10  1  0
 10  9  2  0
  9  8  1  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  2  0
  4  3  1  0
  7 11  1  0
  2 12  1  0
 10 18  1  0
  9 17  1  0
  8 16  1  0
  6 15  1  0
  5 14  1  0
  4 13  1  0
M  END
Download

3D SDF for NP0275513 (1h-indole-4-carbaldehyde)


  Mrv1533004261514432D          

 11 12  0  0  0  0            999 V2000
    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 C   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 N   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
    2.6378   -0.1271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.5396    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
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  8  1  0  0  0  0
  8  9  2  0  0  0  0
  1  9  1  0  0  0  0
  3 10  1  0  0  0  0
 10 11  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0275513

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=CC1=C2C=CNC2=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H7NO/c11-6-7-2-1-3-9-8(7)4-5-10-9/h1-6,10H

> <INCHI_KEY>
JFDDFGLNZWNJTK-UHFFFAOYSA-N

> <FORMULA>
C9H7NO

> <MOLECULAR_WEIGHT>
145.161

> <EXACT_MASS>
145.052763849

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
14.930174599084197

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1H-indole-4-carbaldehyde

> <ALOGPS_LOGP>
1.83

> <JCHEM_LOGP>
1.7845101536666665

> <ALOGPS_LOGS>
-1.76

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.111421987703853

> <JCHEM_PKA_STRONGEST_BASIC>
-7.171352023907458

> <JCHEM_POLAR_SURFACE_AREA>
32.86

> <JCHEM_REFRACTIVITY>
43.7285

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.53e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1H-indole-4-carbaldehyde

> <JCHEM_VEBER_RULE>
1

$$$$
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3D-SDF for NP0275513 (1h-indole-4-carbaldehyde)

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PDB for NP0275513 (1h-indole-4-carbaldehyde)
HEADER    PROTEIN                                 26-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-APR-15         0                                  
HETATM    1  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.126   1.597   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       2.126   4.089   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.924  -0.237   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.258  -1.007   0.000  0.00  0.00           O+0
CONECT    1    2    9                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    4    9                                                  
CONECT    9    8    1                                                       
CONECT   10    3   11                                                       
CONECT   11   10                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   24    0
END

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3D PDB for NP0275513 (1h-indole-4-carbaldehyde)
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SMILES for NP0275513 (1h-indole-4-carbaldehyde)
O=CC1=C2C=CNC2=CC=C1
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INCHI for NP0275513 (1h-indole-4-carbaldehyde)
InChI=1S/C9H7NO/c11-6-7-2-1-3-9-8(7)4-5-10-9/h1-6,10H
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View in JSmol
Synonyms
ValueSource
1H-Indole-4-carboxaldehydeChEBI
4-Formyl-1H-indoleChEBI
4-FormylindoleChEBI
4-Indole-carboxaldehydeChEBI
4-IndolealdehydeChEBI
4-IndolecarbaldehydeChEBI
Indole-4-aldehydeChEBI
Indole-4-carboxaldehydeChEBI
Chemical FormulaC9H7NO
Average Mass145.1610 Da
Monoisotopic Mass145.05276 Da
IUPAC Name1H-indole-4-carbaldehyde
Traditional Name1H-indole-4-carbaldehyde
CAS Registry NumberNot Available
SMILES
O=CC1=C2C=CNC2=CC=C1
InChI Identifier
InChI=1S/C9H7NO/c11-6-7-2-1-3-9-8(7)4-5-10-9/h1-6,10H
InChI KeyJFDDFGLNZWNJTK-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Limonia acidissimaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indoles. Indoles are compounds containing an indole moiety, which consists of pyrrole ring fused to benzene  to form 2,3-benzopyrrole.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassIndoles and derivatives  
Sub ClassIndoles  
Direct ParentIndoles  
Alternative Parents
Substituents
  • Indole
    • 

  • Aryl-aldehyde
    • 

  • Benzenoid
    • 

  • Heteroaromatic compound
    • 

  • Pyrrole
    • 

  • Azacycle
    • 

  • Organic nitrogen compound
    • 

  • Organic oxygen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Aldehyde
    • 

  • 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
logP1.83ALOGPS
logP1.78ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)15.11ChemAxon
pKa (Strongest Basic)-7.2ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area32.86 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity43.73 m³·mol⁻¹ChemAxon
Polarizability14.93 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
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 Compound333703  
PDB IDNot Available
ChEBI ID143235  
Good Scents IDNot Available
References
General References
  1. Kraus GA, Guo H: One-pot synthesis of 2-substituted indoles from 2-aminobenzyl phosphonium salts. A formal total synthesis of arcyriacyanin A. Org Lett. 2008 Jul 17;10(14):3061-3. doi: 10.1021/ol801034x. Epub 2008 Jun 24. [PubMed:18572918  ] 
  2. Kang MC, Ding Y, Kim EA, Choi YK, de Araujo T, Heo SJ, Lee SH: Indole Derivatives Isolated from Brown Alga Sargassum thunbergii Inhibit Adipogenesis through AMPK Activation in 3T3-L1 Preadipocytes. Mar Drugs. 2017 Apr 12;15(4):119. doi: 10.3390/md15040119. [PubMed:28417922  ] 
  3. LOTUS database [Link]