MiMeDB: Showing metabocard for 2,2-bis(3,3'-indolyl)-isocaproic acid (MMDBc0008878)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-15 01:34:34 UTC

Update Date

2022-08-31 06:29:13 UTC

Metabolite ID

MMDBc0008878

Metabolite Identification

Common Name

2,2-bis(3,3'-indolyl)-isocaproic acid

Description

SCHEMBL17867125 belongs to the class of organic compounds known as indole-3-acetic acid derivatives. Indole-3-acetic acid derivatives are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole. SCHEMBL17867125 is a weakly acidic compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv1533004241502542D          

 26 29  0  0  0  0            999 V2000
   -0.8570   -0.8332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0724   -1.0881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3401   -0.3736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -1.8951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6684   -2.4049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8399   -3.2119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2815   -1.8529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6288   -2.9346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1138   -3.6021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6288   -4.2695    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1558   -4.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8702   -4.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5847   -4.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5847   -3.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8702   -2.7771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1558   -3.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  9 17  1  0  0  0  0
 12 17  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 18 26  1  0  0  0  0
 21 26  1  0  0  0  0
M  END


  Mrv1533004241502542D          

 26 29  0  0  0  0            999 V2000
   -0.8570   -0.8332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0724   -1.0881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3401   -0.3736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -1.8951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838   -2.1500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6684   -2.4049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8399   -3.2119    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2815   -1.8529    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6288   -2.9346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1138   -3.6021    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6288   -4.2695    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1558   -4.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8702   -4.4271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5847   -4.0146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5847   -3.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8702   -2.7771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1558   -3.1896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    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
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  5  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
  9 17  1  0  0  0  0
 12 17  1  0  0  0  0
  5 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 18 26  1  0  0  0  0
 21 26  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0008878

> <DATABASE_NAME>
MIME

> <SMILES>
CC(C)CC(C(O)=O)(C1=CNC2=CC=CC=C12)C1=CNC2=CC=CC=C12

> <INCHI_IDENTIFIER>
InChI=1S/C22H22N2O2/c1-14(2)11-22(21(25)26,17-12-23-19-9-5-3-7-15(17)19)18-13-24-20-10-6-4-8-16(18)20/h3-10,12-14,23-24H,11H2,1-2H3,(H,25,26)

> <INCHI_KEY>
WVXVAVCGGZLUNU-UHFFFAOYSA-N

> <FORMULA>
C22H22N2O2

> <MOLECULAR_WEIGHT>
346.43

> <EXACT_MASS>
346.168127956

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
48

> <JCHEM_AVERAGE_POLARIZABILITY>
37.53887949763388

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,2-bis(1H-indol-3-yl)-4-methylpentanoic acid

> <ALOGPS_LOGP>
4.99

> <JCHEM_LOGP>
5.217479070666666

> <ALOGPS_LOGS>
-5.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
15.740701737045509

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.644649812869954

> <JCHEM_POLAR_SURFACE_AREA>
68.88

> <JCHEM_REFRACTIVITY>
102.33920000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.57e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,2-bis(1H-indol-3-yl)-4-methylpentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -1.600  -1.555   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.135  -2.031   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.635  -0.697   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.185  -3.537   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.650  -4.013   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.114  -4.489   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.435  -5.996   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       4.259  -3.459   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.174  -5.478   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.079  -6.724   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       1.174  -7.970   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      -0.291  -7.494   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.624  -8.264   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.958  -7.494   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.958  -5.954   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.624  -5.184   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.291  -5.954   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.126  -2.549   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.220  -1.303   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0       2.126  -0.057   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0       3.590  -0.533   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.924   0.237   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.258  -0.533   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.258  -2.073   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.924  -2.843   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.590  -2.073   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    9   18                                             
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    5   10   17                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    9   12                                                  
CONECT   18    5   19   26                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   18   21                                                  
MASTER        0    0    0    0    0    0    0    0   26    0   58    0
END

Synonyms

Not Available

Molecular Formula

C₂₂H₂₂N₂O₂

Average Mass

346.43

Monoisotopic Mass

346.168127956

IUPAC Name

2,2-bis(1H-indol-3-yl)-4-methylpentanoic acid

Traditional Name

2,2-bis(1H-indol-3-yl)-4-methylpentanoic acid

CAS Registry Number

Not Available

SMILES

CC(C)CC(C(O)=O)(C1=CNC2=CC=CC=C12)C1=CNC2=CC=CC=C12

InChI Identifier

InChI=1S/C22H22N2O2/c1-14(2)11-22(21(25)26,17-12-23-19-9-5-3-7-15(17)19)18-13-24-20-10-6-4-8-16(18)20/h3-10,12-14,23-24H,11H2,1-2H3,(H,25,26)

InChI Key

WVXVAVCGGZLUNU-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indole-3-acetic acid derivatives. Indole-3-acetic acid derivatives are compounds containing an acetic acid (or a derivative) linked to the C3 carbon atom of an indole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolyl carboxylic acids and derivatives

Direct Parent

Indole-3-acetic acid derivatives

Alternative Parents

Substituents

Indole-3-acetic acid derivative
3-alkylindole
Indole
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Azacycle
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.00086 g/L	ALOGPS
logP	4.99	ALOGPS
logP	5.22	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	4.64	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	68.88 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	102.34 m³·mol⁻¹	ChemAxon
Polarizability	37.54 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2022-08-08	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available	2022-08-09	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available	2022-08-09	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-21	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Not Available

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Metabolic reconstruction

Exposure Sources

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10641320

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

van Santen JA, Poynton EF, Iskakova D, McMann E, Alsup TA, Clark TN, Fergusson CH, Fewer DP, Hughes AH, McCadden CA, Parra J, Soldatou S, Rudolf JD, Janssen EM, Duncan KR, Linington RG: The Natural Products Atlas 2.0: a database of microbially-derived natural products. Nucleic Acids Res. 2022 Jan 7;50(D1):D1317-D1323. doi: 10.1093/nar/gkab941. [PubMed:34718710 ]

Showing metabocard for 2,2-bis(3,3'-indolyl)-isocaproic acid (MMDBc0008878)

MOL for #<Metabolite:0x00007fdb0afe1518>

3D MOL for #<Metabolite:0x00007fdb0afe1518>

3D SDF for #<Metabolite:0x00007fdb0afe1518>

3D-SDF for #<Metabolite:0x00007fdb0afe1518>

PDB for #<Metabolite:0x00007fdb0afe1518>

3D PDB for #<Metabolite:0x00007fdb0afe1518>

SMILES for #<Metabolite:0x00007fdb0afe1518>

INCHI for #<Metabolite:0x00007fdb0afe1518>

Structure for #<Metabolite:0x00007fdb0afe1518>

3D Structure for #<Metabolite:0x00007fdb0afe1518>