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Showing NP-Card for 1H-indole-3-carbaldehyde (NP0331194)

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Record Information
Version2.0
Created at2022-11-28 18:06:30 UTC
Updated at2024-09-03 04:21:25 UTC
NP-MRD IDNP0331194
Natural Product DOIhttps://doi.org/10.57994/2478
Secondary Accession NumbersNone
Natural Product Identification
Common Name1H-indole-3-carbaldehyde
Description1H-Indole-3-carboxaldehyde, also known as 3-formylindole or 3-indolealdehyde, 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. 1H-Indole-3-carboxaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, 1H-Indole-3-carboxaldehyde has been detected, but not quantified in, several different foods, such as gram beans, brussel sprouts, cucumbers, cereals and cereal products, and white cabbages. This could make 1H-indole-3-carboxaldehyde a potential biomarker for the consumption of these foods. 1H-indole-3-carbaldehyde was first documented in 2015 (PMID: 25427277). A heteroarenecarbaldehyde that is indole in which the hydrogen at position 3 has been replaced by a formyl group (PMID: 26802249) (PMID: 26939983) (PMID: 26946839) (PMID: 27019553).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0331194 (1H-indole-3-carbaldehyde)


  Mrv1652309042000372D          

 11 12  0  0  0  0            999 V2000
   -1.6433    0.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8982   -0.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3462   -1.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5392   -0.9704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4239    1.1418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8363    0.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2843   -0.1857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4693    0.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3830    0.9702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1838   -0.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8982    0.1498    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
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  8 10  1  0  0  0  0
  4  7  1  0  0  0  0
  6  1  1  0  0  0  0
 10 11  2  0  0  0  0
M  END
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3D MOL for NP0331194 (1H-indole-3-carbaldehyde)

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3D SDF for NP0331194 (1H-indole-3-carbaldehyde)

  Mrv1652309042000372D          

 11 12  0  0  0  0            999 V2000
   -1.6433    0.2558    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8982   -0.5288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3462   -1.1418    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5392   -0.9704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4239    1.1418    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8363    0.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2843   -0.1857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4693    0.1498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3830    0.9702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1838   -0.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8982    0.1498    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
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  5  6  1  0  0  0  0
  5  9  1  0  0  0  0
  8 10  1  0  0  0  0
  4  7  1  0  0  0  0
  6  1  1  0  0  0  0
 10 11  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0331194

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O=CC1=CNC2=C1C=CC=C2

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

> <INCHI_KEY>
OLNJUISKUQQNIM-UHFFFAOYSA-N

> <FORMULA>
C9H7NO

> <MOLECULAR_WEIGHT>
145.158

> <EXACT_MASS>
145.052763851

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
14.996254284774686

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1H-indole-3-carbaldehyde

> <ALOGPS_LOGP>
1.92

> <JCHEM_LOGP>
1.7845101536666665

> <ALOGPS_LOGS>
-1.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.542810230152927

> <JCHEM_PKA_STRONGEST_BASIC>
-7.253462701456542

> <JCHEM_POLAR_SURFACE_AREA>
32.86

> <JCHEM_REFRACTIVITY>
43.7285

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.46e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
indole-3-carboxaldehyde

> <JCHEM_VEBER_RULE>
1

$$$$

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3D-SDF for NP0331194 (1H-indole-3-carbaldehyde)
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PDB for NP0331194 (1H-indole-3-carbaldehyde)
HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  C   UNK     0      -3.067   0.477   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.543  -0.987   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.513  -2.131   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.007  -1.811   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0      -0.791   2.131   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0      -1.561   0.798   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.531  -0.347   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.876   0.280   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.715   1.811   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.210  -0.490   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.543   0.280   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    7                                                       
CONECT    5    6    9                                                       
CONECT    6    7    5    1                                                  
CONECT    7    6    8    4                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8    5                                                       
CONECT   10    8   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 NP0331194 (1H-indole-3-carbaldehyde)
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SMILES for NP0331194 (1H-indole-3-carbaldehyde)
O=CC1=CNC2=C1C=CC=C2
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INCHI for NP0331194 (1H-indole-3-carbaldehyde)
InChI=1S/C9H7NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-6,10H
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View in JSmol
Synonyms
ValueSource
Indole-3-carbaldehydeKEGG
1H-Indole-3-carbaldehydeHMDB
1H-Indole-3-carboxaldehdeHMDB
3-FormylindoleHMDB, ChEBI
3-IndolealdehydeHMDB, ChEBI
3-IndolecarbaldehydeHMDB, ChEBI
3-IndolecarboxaldehydeHMDB, ChEBI
3-IndolemethanalHMDB, MeSH
b-IndolylaldehydeHMDB, Generator
beta-IndolylaldehydeHMDB, ChEBI
indol-3-CarbaldehydHMDB
indol-3-CarbaldehydeHMDB
indol-3-CarboxaldehydeHMDB
Indole-3-aldehydeHMDB, ChEBI
INDOLE-3-carboxyaldehydeHMDB
1H-Indole-3-carboxaldehydeChEBI
I3choChEBI
Indole-3-carboxaldehydeChEBI
β-IndolylaldehydeGenerator
1H-Indol-3-yl carboxaldehydeHMDB
1H-Indole-3-aldehydeHMDB
1H-Indole-3-methanalHMDB
3-Formyl-1H-indoleHMDB
3-IndolylformaldehydeHMDB
I3AHMDB
Indole-3-carboxylaldehydeHMDB
Indole-3-formaldehydeHMDB
Chemical FormulaC9H7NO
Average Mass145.1580 Da
Monoisotopic Mass145.05276 Da
IUPAC Name1H-indole-3-carbaldehyde
Traditional Nameindole-3-carboxaldehyde
CAS Registry NumberNot Available
SMILES
O=CC1=CNC2=C1C=CC=C2
InChI Identifier
InChI=1S/C9H7NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-6,10H
InChI KeyOLNJUISKUQQNIM-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 101 MHz, CD3OD, experimental)hxkuang@hljucm.netNot AvailableNot Available2024-05-11View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 22.53 MHz, DMSO-d6, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
Chemical Shift Submissions
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, simulated)Not AvailableNot AvailableNot Available2024-05-11View Spectrum
Species
Species of Origin
Species NameSourceReference
metel
      Not Available
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
    • 

  • Substituted pyrrole
    • 

  • Benzenoid
    • 

  • Pyrrole
    • 

  • Heteroaromatic compound
    • 

  • Vinylogous amide
    • 

  • Azacycle
    • 

  • Aldehyde
    • 

  • Hydrocarbon derivative
    • 

  • Organic oxide
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Organooxygen compound
    • 

  • Organonitrogen compound
    • 

  • Organic nitrogen compound
    • 

  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
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
logP1.92ALOGPS
logP1.78ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)13.54ChemAxon
pKa (Strongest Basic)-7.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area32.86 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity43.73 m³·mol⁻¹ChemAxon
Polarizability15 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0029737  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000934  
KNApSAcK IDC00000112  
Chemspider ID9838  
KEGG Compound IDC08493  
BioCyc IDINDOLE-3-CARBOXALDEHYDE  
BiGG IDNot Available
Wikipedia LinkIndole-3-carboxaldehyde  
METLIN IDNot Available
PubChem Compound10256  
PDB IDI3A  
ChEBI ID28238  
Good Scents IDNot Available
References
General References
  1. Yap AC, Teoh WY, Chan KG, Sim KS, Choo YM: A new oxathiolane from Enterobacter cloacae. Nat Prod Res. 2015;29(8):722-6. doi: 10.1080/14786419.2014.983507. Epub 2014 Nov  26. [PubMed:25427277  ] 
  2. Stahl E, Bellwon P, Huber S, Schlaeppi K, Bernsdorff F, Vallat-Michel A, Mauch F, Zeier J: Regulatory and Functional Aspects of Indolic Metabolism in Plant Systemic Acquired Resistance. Mol Plant. 2016 May 2;9(5):662-681. doi: 10.1016/j.molp.2016.01.005. Epub 2016 Jan 20. [PubMed:26802249  ] 
  3. Rajalaxmi M, Beema Shafreen R, Iyer PM, Sahaya Vino R, Balamurugan K, Pandian SK: An in silico, in vitro and in vivo investigation of indole-3-carboxaldehyde identified from the seawater bacterium Marinomonas sp. as an anti-biofilm agent against Vibrio cholerae O1. Biofouling. 2016;32(4):1-12. doi: 10.1080/08927014.2016.1154545. [PubMed:26939983  ] 
  4. Ren H, Dong LM, Zhou ZY, Xu QL, Tan JW: [Chemical Constituents from Sphagneticola trilobata]. Zhong Yao Cai. 2015 Jul;38(7):1426-9. [PubMed:26946839  ] 
  5. Xin-Jia Y, Wei L, Ying Z, Ning C, Ying X, Jian W, Tan W, Yue L, Zheng X: A New Biphenyl Neolignan from Leaves of Patrinia villosa (Thunb.) Juss. Pharmacogn Mag. 2016 Jan-Mar;12(45):1-3. doi: 10.4103/0973-1296.175988. [PubMed:27019553  ]