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Showing metabocard for Indoline (HMDB0253472)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-11 11:56:12 UTC
Update Date2021-09-26 23:06:43 UTC
HMDB IDHMDB0253472
Secondary Accession NumbersNone
Metabolite Identification
Common NameIndoline
Descriptionindoline, also known as dihydroindole, belongs to the class of organic compounds known as indolines. Indolines are compounds containing an indole moiety, which consists of pyrrolidine ring fused to benzene to form 2,3-dihydroindole. Indoline is an aromatic heterocyclic organic compound with the chemical formula C8H9N. The compound is based on the indole structure, but the 2-3 bond is saturated. indoline is a strong basic compound (based on its pKa). By oxidation/dehydrogenation it can be converted to indoles. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing ring. Indoline was used to make Indocaine. This compound has been identified in human blood as reported by (PMID: 31557052 ). Indoline is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Indoline is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0253472 (Indoline)


  Mrv0541 05041405432D          

  9 10  0  0  0  0            999 V2000
    3.3523    1.1104    0.0000 C   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
    2.6378    0.6979    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
    1.1387    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
    1.9233    1.1104    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
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  5  1  0  0  0  0
  7  3  2  0  0  0  0
  7  5  1  0  0  0  0
  8  4  2  0  0  0  0
  8  7  1  0  0  0  0
  9  6  1  0  0  0  0
  9  8  1  0  0  0  0
M  END
Download

3D MOL for HMDB0253472 (Indoline)

HMDB0253472
     RDKit          3D
Indoline
 18 19  0  0  0  0  0  0  0  0999 V2000
    2.2423   -0.9045   -0.1372 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4408    0.4336    0.1250 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3288    1.2324    0.2115 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0357    0.7661    0.0504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1269   -0.5785   -0.2110 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9769   -1.4245   -0.3068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5913   -0.8363   -0.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2193    0.3412    0.4114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2569    1.3924    0.0943 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1003   -1.5565   -0.2106 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4558    0.8068    0.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4622    2.2805    0.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7934   -2.4650   -0.5123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9355   -0.7396   -1.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8574   -1.7996    0.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1999    0.0710    1.4876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2281    0.5718    0.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4207    2.4088   -0.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  6  1  1  0
  9  4  1  0
  1 10  1  0
  2 11  1  0
  3 12  1  0
  6 13  1  0
  7 14  1  0
  7 15  1  0
  8 16  1  0
  8 17  1  0
  9 18  1  0
M  END
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3D SDF for HMDB0253472 (Indoline)


  Mrv0541 05041405432D          

  9 10  0  0  0  0            999 V2000
    3.3523    1.1104    0.0000 C   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
    2.6378    0.6979    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
    1.1387    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
    1.9233    1.1104    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
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  6  5  1  0  0  0  0
  7  3  2  0  0  0  0
  7  5  1  0  0  0  0
  8  4  2  0  0  0  0
  8  7  1  0  0  0  0
  9  6  1  0  0  0  0
  9  8  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0253472

> <DATABASE_NAME>
hmdb

> <SMILES>
C1CC2=CC=CC=C2N1

> <INCHI_IDENTIFIER>
InChI=1S/C8H9N/c1-2-4-8-7(3-1)5-6-9-8/h1-4,9H,5-6H2

> <INCHI_KEY>
LPAGFVYQRIESJQ-UHFFFAOYSA-N

> <FORMULA>
C8H9N

> <MOLECULAR_WEIGHT>
119.1638

> <EXACT_MASS>
119.073499293

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
13.503774496435954

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
1.73

> <JCHEM_LOGP>
1.4859124496666662

> <ALOGPS_LOGS>
-0.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
4.613151267130663

> <JCHEM_POLAR_SURFACE_AREA>
12.03

> <JCHEM_REFRACTIVITY>
39.561400000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.62e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
indoline

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0253472 (Indoline)

HMDB0253472
     RDKit          3D
Indoline
 18 19  0  0  0  0  0  0  0  0999 V2000
    2.2423   -0.9045   -0.1372 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4408    0.4336    0.1250 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3288    1.2324    0.2115 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0357    0.7661    0.0504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1269   -0.5785   -0.2110 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9769   -1.4245   -0.3068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5913   -0.8363   -0.3427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2193    0.3412    0.4114 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2569    1.3924    0.0943 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1003   -1.5565   -0.2106 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4558    0.8068    0.2528 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4622    2.2805    0.4156 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7934   -2.4650   -0.5123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9355   -0.7396   -1.3993 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8574   -1.7996    0.1083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1999    0.0710    1.4876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2281    0.5718    0.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4207    2.4088   -0.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  6  1  1  0
  9  4  1  0
  1 10  1  0
  2 11  1  0
  3 12  1  0
  6 13  1  0
  7 14  1  0
  7 15  1  0
  8 16  1  0
  8 17  1  0
  9 18  1  0
M  END
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PDB for HMDB0253472 (Indoline)

HEADER    PROTEIN                                 04-MAY-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-MAY-14         0                                  
HETATM    1  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       0.000   0.000   0.000  0.00  0.00           N+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    7                                                       
CONECT    4    2    8                                                       
CONECT    5    6    7                                                       
CONECT    6    5    9                                                       
CONECT    7    3    5    8                                                  
CONECT    8    4    7    9                                                  
CONECT    9    6    8                                                       
MASTER        0    0    0    0    0    0    0    0    9    0   20    0
END
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3D PDB for HMDB0253472 (Indoline)

COMPND    HMDB0253472
HETATM    1  C1  UNL     1       2.242  -0.904  -0.137  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.441   0.434   0.125  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.329   1.232   0.211  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.036   0.766   0.050  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.127  -0.579  -0.211  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.977  -1.425  -0.307  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.591  -0.836  -0.343  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.219   0.341   0.411  1.00  0.00           C  
HETATM    9  N1  UNL     1      -1.257   1.392   0.094  1.00  0.00           N  
HETATM   10  H1  UNL     1       3.100  -1.557  -0.211  1.00  0.00           H  
HETATM   11  H2  UNL     1       3.456   0.807   0.253  1.00  0.00           H  
HETATM   12  H3  UNL     1       1.462   2.280   0.416  1.00  0.00           H  
HETATM   13  H4  UNL     1       0.793  -2.465  -0.512  1.00  0.00           H  
HETATM   14  H5  UNL     1      -1.936  -0.740  -1.399  1.00  0.00           H  
HETATM   15  H6  UNL     1      -1.857  -1.800   0.108  1.00  0.00           H  
HETATM   16  H7  UNL     1      -2.200   0.071   1.488  1.00  0.00           H  
HETATM   17  H8  UNL     1      -3.228   0.572   0.039  1.00  0.00           H  
HETATM   18  H9  UNL     1      -1.421   2.409  -0.076  1.00  0.00           H  
CONECT    1    2    2    6   10
CONECT    2    3   11
CONECT    3    4    4   12
CONECT    4    5    9
CONECT    5    6    6    7
CONECT    6   13
CONECT    7    8   14   15
CONECT    8    9   16   17
CONECT    9   18
END
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SMILES for HMDB0253472 (Indoline)

C1CC2=CC=CC=C2N1
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INCHI for HMDB0253472 (Indoline)

InChI=1S/C8H9N/c1-2-4-8-7(3-1)5-6-9-8/h1-4,9H,5-6H2
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View in JSmolView Stereo Labels
Synonyms
ValueSource
DihydroindoleChEBI
2,3-dihydro-1H-IndoleMeSH
Chemical FormulaC8H9N
Average Molecular Weight119.1638
Monoisotopic Molecular Weight119.073499293
IUPAC Name2,3-dihydro-1H-indole
Traditional Nameindoline
CAS Registry NumberNot Available
SMILES
C1CC2=CC=CC=C2N1
InChI Identifier
InChI=1S/C8H9N/c1-2-4-8-7(3-1)5-6-9-8/h1-4,9H,5-6H2
InChI KeyLPAGFVYQRIESJQ-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as indolines. Indolines are compounds containing an indole moiety, which consists of pyrrolidine ring fused to benzene to form 2,3-dihydroindole.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndolines
Direct ParentIndolines
Alternative Parents
Substituents
  • Dihydroindole
  • Aralkylamine
  • Secondary aliphatic/aromatic amine
  • Benzenoid
  • Azacycle
  • Secondary amine
  • Organic nitrogen compound
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP1.73ALOGPS
logP1.49ChemAxon
logS-0.87ALOGPS
pKa (Strongest Basic)4.61ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity39.56 m³·mol⁻¹ChemAxon
Polarizability13.5 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+123.54330932474
DeepCCS[M-H]-120.35130932474
DeepCCS[M-2H]-157.25330932474
DeepCCS[M+Na]+132.14930932474
AllCCS[M+H]+125.932859911
AllCCS[M+H-H2O]+121.132859911
AllCCS[M+NH4]+130.532859911
AllCCS[M+Na]+131.832859911
AllCCS[M-H]-121.432859911
AllCCS[M+Na-2H]-123.132859911
AllCCS[M+HCOO]-125.032859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
IndolineC1CC2=CC=CC=C2N12147.2Standard polar33892256
IndolineC1CC2=CC=CC=C2N11211.1Standard non polar33892256
IndolineC1CC2=CC=CC=C2N11196.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Indoline,1TMS,isomer #1C[Si](C)(C)N1CCC2=CC=CC=C211442.8Semi standard non polar33892256
Indoline,1TMS,isomer #1C[Si](C)(C)N1CCC2=CC=CC=C211321.7Standard non polar33892256
Indoline,1TMS,isomer #1C[Si](C)(C)N1CCC2=CC=CC=C211577.7Standard polar33892256
Indoline,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CCC2=CC=CC=C211651.5Semi standard non polar33892256
Indoline,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CCC2=CC=CC=C211598.1Standard non polar33892256
Indoline,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1CCC2=CC=CC=C211787.1Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Indoline GC-MS (Non-derivatized) - 70eV, Positivesplash10-0gbc-7900000000-53f722d2ef33b897fc2f2021-09-23Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Indoline GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Indoline 35V, Positive-QTOFsplash10-00di-0900000000-73b16aa480f918ae141b2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indoline 10V, Positive-QTOFsplash10-00di-0900000000-815d21eccf65979ba6162021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indoline 20V, Positive-QTOFsplash10-00di-2900000000-8402e2c99d64540a32102021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indoline 40V, Positive-QTOFsplash10-0f96-9300000000-942fa68823b9cc0be5522021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indoline 10V, Negative-QTOFsplash10-014i-0900000000-027d0d4be6036ac052f52021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indoline 20V, Negative-QTOFsplash10-014i-1900000000-bc8c6e8ea4ad70195dab2021-10-12Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Indoline 40V, Negative-QTOFsplash10-014l-7900000000-3e53cc0aec0b8faf85572021-10-12Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkIndoline
METLIN IDNot Available
PubChem Compound10328
PDB IDNot Available
ChEBI ID43295
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Barupal DK, Fiehn O: Generating the Blood Exposome Database Using a Comprehensive Text Mining and Database Fusion Approach. Environ Health Perspect. 2019 Sep;127(9):97008. doi: 10.1289/EHP4713. Epub 2019 Sep 26. [PubMed:31557052 ]