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Showing metabocard for Indole-3-carbinol (HMDB0005785)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
enzymes (1) Show 1 protein
Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2007-01-22 13:00:01 UTC
Update Date2023-02-21 17:17:07 UTC
HMDB IDHMDB0005785
Secondary Accession Numbers
  • HMDB05785
Metabolite Identification
Common NameIndole-3-carbinol
DescriptionIndole-3-carbinol, also known as 3-indolylcarbinol or 1H-indole-3-methanol, belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position. Indole-3-carbinol is a dietary indole present in cruciferous vegetables that has been shown to influence estradiol metabolism in humans and may provide a new chemopreventive approach to estrogen-dependent diseases (PMID:2342128 ). Indole-3-carbinol is produced by members of the family Cruciferae, particularly members of the genus Brassica (e.g. cabbage, radishes, cauliflower, broccoli, Brussels sprouts, and daikon). Indole-3-carbinol is metabolized into a number of products, including the dimeric 3,3'-diindolylmethane. Both 3,3'-diindolylmethane and indole-3-carbinol are thought to have biological effects. Indole-3-carbinol is a natural chemopreventive compound. It has multiple anticarcinogenic and antitumorigenic properties; it can suppress the proliferation of certain cancer cells, including breast cancer, prostate cancer, endometrial cancer, colon cancer, and leukemic cells (PMID:16634522 , 16082211 ).
Structure
Data?1676999827
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0005785 (Indole-3-carbinol)


  Mrv1652301272022212D          

 11 12  0  0  0  0            999 V2000
 9997.0764 9999.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8215 9998.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3735 9998.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1805 9998.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.295810000.3109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8834 9999.5964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4354 9998.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1891 9999.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.102810000.1393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9036 9998.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.6180 9999.3189    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  1  0  0  0  0
M  END
Download

3D MOL for HMDB0005785 (Indole-3-carbinol)

HMDB0005785
     RDKit          3D
Indole-3-carbinol
 20 21  0  0  0  0  0  0  0  0999 V2000
    3.4899    0.0235    0.4371 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3548   -0.6788    0.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1776    0.1991    0.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1712    1.5017    0.6426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1136    1.8969    0.6084 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8991    0.9049    0.1564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2705    0.7817   -0.0705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8351   -0.3809   -0.5525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0317   -1.4733   -0.8264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6724   -1.3703   -0.6081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1258   -0.1997   -0.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7666   -0.3401    1.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2173   -1.6294    0.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4785   -0.8513   -1.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0318    2.1015    0.9676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4391    2.8488    0.8974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8603    1.6593    0.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9056   -0.4144   -0.7077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5099   -2.3682   -1.2033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0245   -2.2110   -0.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  3  1  0
 11  6  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  4 15  1  0
  5 16  1  0
  7 17  1  0
  8 18  1  0
  9 19  1  0
 10 20  1  0
M  END
Download

3D SDF for HMDB0005785 (Indole-3-carbinol)


  Mrv1652301272022212D          

 11 12  0  0  0  0            999 V2000
 9997.0764 9999.4249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8215 9998.6402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3735 9998.0272    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.1805 9998.1986    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.295810000.3109    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9997.8834 9999.5964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.4354 9998.9833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.1891 9999.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.102810000.1393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.9036 9998.9064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.6180 9999.3189    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  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0005785

> <DATABASE_NAME>
hmdb

> <SMILES>
OCC1=CNC2=C1C=CC=C2

> <INCHI_IDENTIFIER>
InChI=1S/C9H9NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-5,10-11H,6H2

> <INCHI_KEY>
IVYPNXXAYMYVSP-UHFFFAOYSA-N

> <FORMULA>
C9H9NO

> <MOLECULAR_WEIGHT>
147.1739

> <EXACT_MASS>
147.068413915

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
20

> <JCHEM_AVERAGE_POLARIZABILITY>
15.870666832234898

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1H-indol-3-yl)methanol

> <ALOGPS_LOGP>
1.66

> <JCHEM_LOGP>
1.3046580416666664

> <ALOGPS_LOGS>
-1.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.34307132623539

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.0959887942937

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7165363605434028

> <JCHEM_POLAR_SURFACE_AREA>
36.019999999999996

> <JCHEM_REFRACTIVITY>
43.9604

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.75e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
indole-3-carbinol

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0005785 (Indole-3-carbinol)

HMDB0005785
     RDKit          3D
Indole-3-carbinol
 20 21  0  0  0  0  0  0  0  0999 V2000
    3.4899    0.0235    0.4371 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3548   -0.6788    0.0395 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1776    0.1991    0.1883 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1712    1.5017    0.6426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1136    1.8969    0.6084 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8991    0.9049    0.1564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2705    0.7817   -0.0705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8351   -0.3809   -0.5525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0317   -1.4733   -0.8264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6724   -1.3703   -0.6081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1258   -0.1997   -0.1258 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7666   -0.3401    1.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2173   -1.6294    0.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4785   -0.8513   -1.0686 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0318    2.1015    0.9676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4391    2.8488    0.8974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8603    1.6593    0.1570 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9056   -0.4144   -0.7077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5099   -2.3682   -1.2033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0245   -2.2110   -0.8150 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  3  1  0
 11  6  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  4 15  1  0
  5 16  1  0
  7 17  1  0
  8 18  1  0
  9 19  1  0
 10 20  1  0
M  END
Download

PDB for HMDB0005785 (Indole-3-carbinol)

HEADER    PROTEIN                                 27-JAN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-JAN-20         0                                  
HETATM    1  C   UNK     0    8661.2098665.593   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8660.7338664.128   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8661.7648662.984   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8663.2708663.304   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0    8663.4858667.247   0.000  0.00  0.00           N+0
HETATM    6  C   UNK     0    8662.7168665.913   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8663.7468664.769   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8665.1538665.395   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8664.9928666.927   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8666.4878664.625   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0    8667.8208665.395   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 HMDB0005785 (Indole-3-carbinol)

COMPND    HMDB0005785
HETATM    1  O1  UNL     1       3.490   0.024   0.437  1.00  0.00           O  
HETATM    2  C1  UNL     1       2.355  -0.679   0.039  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.178   0.199   0.188  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.171   1.502   0.643  1.00  0.00           C  
HETATM    5  N1  UNL     1      -0.114   1.897   0.608  1.00  0.00           N  
HETATM    6  C4  UNL     1      -0.899   0.905   0.156  1.00  0.00           C  
HETATM    7  C5  UNL     1      -2.271   0.782  -0.071  1.00  0.00           C  
HETATM    8  C6  UNL     1      -2.835  -0.381  -0.552  1.00  0.00           C  
HETATM    9  C7  UNL     1      -2.032  -1.473  -0.826  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.672  -1.370  -0.608  1.00  0.00           C  
HETATM   11  C9  UNL     1      -0.126  -0.200  -0.126  1.00  0.00           C  
HETATM   12  H1  UNL     1       3.767  -0.340   1.313  1.00  0.00           H  
HETATM   13  H2  UNL     1       2.217  -1.629   0.571  1.00  0.00           H  
HETATM   14  H3  UNL     1       2.479  -0.851  -1.069  1.00  0.00           H  
HETATM   15  H4  UNL     1       2.032   2.101   0.968  1.00  0.00           H  
HETATM   16  H5  UNL     1      -0.439   2.849   0.897  1.00  0.00           H  
HETATM   17  H6  UNL     1      -2.860   1.659   0.157  1.00  0.00           H  
HETATM   18  H7  UNL     1      -3.906  -0.414  -0.708  1.00  0.00           H  
HETATM   19  H8  UNL     1      -2.510  -2.368  -1.203  1.00  0.00           H  
HETATM   20  H9  UNL     1      -0.025  -2.211  -0.815  1.00  0.00           H  
CONECT    1    2   12
CONECT    2    3   13   14
CONECT    3    4    4   11
CONECT    4    5   15
CONECT    5    6   16
CONECT    6    7    7   11
CONECT    7    8   17
CONECT    8    9    9   18
CONECT    9   10   19
CONECT   10   11   11   20
END
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SMILES for HMDB0005785 (Indole-3-carbinol)

OCC1=CNC2=C1C=CC=C2
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INCHI for HMDB0005785 (Indole-3-carbinol)

InChI=1S/C9H9NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-5,10-11H,6H2
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
3-HydroxymethylindoleChEBI
3-IndolylcarbinolChEBI
1H-Indole-3-methanolMeSH
I3c CPDMeSH
Indole-3-methanolMeSH
1H-indol-3-YlmethanolHMDB
3-(Hydroxymethyl)indoleHMDB
3-IndolecarbinolHMDB
3-IndolylmethanolHMDB
IndinolHMDB
Indole-3-carbinolChEBI
(1H-Indol-3-yl)methanolHMDB
Chemical FormulaC9H9NO
Average Molecular Weight147.1739
Monoisotopic Molecular Weight147.068413915
IUPAC Name(1H-indol-3-yl)methanol
Traditional Nameindole-3-carbinol
CAS Registry Number700-06-1
SMILES
OCC1=CNC2=C1C=CC=C2
InChI Identifier
InChI=1S/C9H9NO/c11-6-7-5-10-9-4-2-1-3-8(7)9/h1-5,10-11H,6H2
InChI KeyIVYPNXXAYMYVSP-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 3-alkylindoles. 3-Alkylindoles are compounds containing an indole moiety that carries an alkyl chain at the 3-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassIndoles
Direct Parent3-alkylindoles
Alternative Parents
Substituents
  • 3-alkylindole
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Azacycle
  • Alcohol
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Aromatic alcohol
  • Organic oxygen compound
  • Organic nitrogen compound
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
ProcessNot Available
Role
Industrial applicationBiological role
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point90 °CNot Available
Boiling Point360.60 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility8339 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP1.366 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility3.75 g/LALOGPS
logP1.66ALOGPS
logP1.3ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)15.1ChemAxon
pKa (Strongest Basic)-2.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area36.02 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity43.96 m³·mol⁻¹ChemAxon
Polarizability15.87 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
DarkChem[M+H]+131.49331661259
DarkChem[M-H]-128.31831661259
DeepCCS[M+H]+129.56730932474
DeepCCS[M-H]-125.96730932474
DeepCCS[M-2H]-163.34630932474
DeepCCS[M+Na]+138.48230932474
AllCCS[M+H]+130.832859911
AllCCS[M+H-H2O]+126.132859911
AllCCS[M+NH4]+135.232859911
AllCCS[M+Na]+136.532859911
AllCCS[M-H]-130.132859911
AllCCS[M+Na-2H]-131.032859911
AllCCS[M+HCOO]-132.032859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.3.71 minutes32390414
Predicted by Siyang on May 30, 202211.2612 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20221.94 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid1722.8 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid394.8 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid129.7 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid234.4 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid290.2 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid389.4 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid353.7 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)202.5 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid887.3 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid357.9 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1185.4 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid372.2 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid308.0 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate427.9 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA305.3 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water119.7 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
Indole-3-carbinolOCC1=CNC2=C1C=CC=C22944.1Standard polar33892256
Indole-3-carbinolOCC1=CNC2=C1C=CC=C21642.5Standard non polar33892256
Indole-3-carbinolOCC1=CNC2=C1C=CC=C21674.0Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Indole-3-carbinol,1TMS,isomer #1C[Si](C)(C)OCC1=C[NH]C2=CC=CC=C121724.7Semi standard non polar33892256
Indole-3-carbinol,1TMS,isomer #2C[Si](C)(C)N1C=C(CO)C2=CC=CC=C211751.7Semi standard non polar33892256
Indole-3-carbinol,2TMS,isomer #1C[Si](C)(C)OCC1=CN([Si](C)(C)C)C2=CC=CC=C121777.9Semi standard non polar33892256
Indole-3-carbinol,2TMS,isomer #1C[Si](C)(C)OCC1=CN([Si](C)(C)C)C2=CC=CC=C121784.8Standard non polar33892256
Indole-3-carbinol,2TMS,isomer #1C[Si](C)(C)OCC1=CN([Si](C)(C)C)C2=CC=CC=C121856.5Standard polar33892256
Indole-3-carbinol,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC1=C[NH]C2=CC=CC=C121990.3Semi standard non polar33892256
Indole-3-carbinol,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C=C(CO)C2=CC=CC=C212001.8Semi standard non polar33892256
Indole-3-carbinol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C122225.8Semi standard non polar33892256
Indole-3-carbinol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C122202.8Standard non polar33892256
Indole-3-carbinol,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=CC=C122129.6Standard polar33892256
Spectra
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not QuantifiedNot QuantifiedAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB12881
Phenol Explorer Compound IDNot Available
FooDB IDFDB000939
KNApSAcK IDC00041598
Chemspider ID3581
KEGG Compound IDNot Available
BioCyc IDCPDQT-428
BiGG IDNot Available
Wikipedia LinkIndole-3-carbinol
METLIN IDNot Available
PubChem Compound3712
PDB IDNot Available
ChEBI ID24814
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1448011
References
Synthesis ReferenceLeete, Edward; Marion, Leo. Hydrogenolysis of 3-(hydroxymethyl)indole and other indole derivatives with lithium aluminum hydride. Canadian Journal of Chemistry (1953), 31 775-84.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Michnovicz JJ, Bradlow HL: Induction of estradiol metabolism by dietary indole-3-carbinol in humans. J Natl Cancer Inst. 1990 Jun 6;82(11):947-9. [PubMed:2342128 ]
  2. Aggarwal BB, Ichikawa H: Molecular targets and anticancer potential of indole-3-carbinol and its derivatives. Cell Cycle. 2005 Sep;4(9):1201-15. Epub 2005 Sep 6. [PubMed:16082211 ]
  3. Rogan EG: The natural chemopreventive compound indole-3-carbinol: state of the science. In Vivo. 2006 Mar-Apr;20(2):221-8. [PubMed:16634522 ]

Enzymes

Enzyme Details
1. Aryl hydrocarbon receptor
General function:
Involved in transcription regulator activity
Specific function:
Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues
Gene Name:
AHR
Uniprot ID:
P35869
Molecular weight:
96146.7