MiMeDB: Showing metabocard for Indoleglycollic acid (MMDBc0002796)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-05-14 21:02:11 UTC

Update Date

2022-08-31 06:19:49 UTC

Metabolite ID

MMDBc0002796

Metabolite Identification

Common Name

Indoleglycollic acid

Description

Indolelactic acid, also known as indolelactate or 5-IHIPA, belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring. Indolelactic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI

Indolelactic acid.mol
  Mrv1652305271900162D          

 15 16  0  0  0  0            999 V2000
    1.6357    0.3648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4221   -0.4321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6375   -0.6871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0523    0.9481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4326    0.5783    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6430    1.0210    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.1107    0.6855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0244   -0.1350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7826   -0.3065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1951   -1.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0201   -1.0210    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4326   -0.3065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0201    0.4079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1951    0.4079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0352   -0.9841    0.0000 O   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
  1  4  2  0  0  0  0
  1  5  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  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
  6 14  1  0  0  0  0
  9 14  2  0  0  0  0
  3  8  1  0  0  0  0
  2 15  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0002796

> <DATABASE_NAME>
MIME

> <SMILES>
OC(CC1=CNC2=C1C=CC=C2)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C11H11NO3/c13-10(11(14)15)5-7-6-12-9-4-2-1-3-8(7)9/h1-4,6,10,12-13H,5H2,(H,14,15)

> <INCHI_KEY>
XGILAAMKEQUXLS-UHFFFAOYSA-N

> <FORMULA>
C11H11NO3

> <MOLECULAR_WEIGHT>
205.2099

> <EXACT_MASS>
205.073893223

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
20.70172453668004

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-3-(1H-indol-3-yl)propanoic acid

> <ALOGPS_LOGP>
1.33

> <JCHEM_LOGP>
1.2832588426666667

> <ALOGPS_LOGS>
-1.99

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.152490662605057

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.14137302327962

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8533048960573746

> <JCHEM_POLAR_SURFACE_AREA>
73.32

> <JCHEM_REFRACTIVITY>
54.545300000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.12e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
indole-3-lactic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Indolelactic acid.mol                             
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       3.053   0.681   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.655  -0.807   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.190  -1.283   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       1.964   1.770   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       4.541   1.079   0.000  0.00  0.00           O+0
HETATM    6  N   UNK     0      -1.200   1.906   0.000  0.00  0.00           N+0
HETATM    7  C   UNK     0       0.207   1.280   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.046  -0.252   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.461  -0.572   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.231  -1.906   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.771  -1.906   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.541  -0.572   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.771   0.761   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.231   0.761   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.799  -1.837   0.000  0.00  0.00           O+0
CONECT    1    2    4    5                                                  
CONECT    2    1    3   15                                                  
CONECT    3    2    8                                                       
CONECT    4    1                                                            
CONECT    5    1                                                            
CONECT    6    7   14                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9    3                                                  
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13    6    9                                                  
CONECT   15    2                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

Synonyms

Value	Source
alpha-Hydroxy-1H-indole-3-propanoic acid	ChEBI
Indole-3-lactic acid	ChEBI
a-Hydroxy-1H-indole-3-propanoate	Generator
a-Hydroxy-1H-indole-3-propanoic acid	Generator
alpha-Hydroxy-1H-indole-3-propanoate	Generator
Α-hydroxy-1H-indole-3-propanoate	Generator
Α-hydroxy-1H-indole-3-propanoic acid	Generator
Indole-3-lactate	Generator
Indolelactate	Generator
(+)-2-Hydroxy-3-indol-3-yl-propionate	HMDB
(+)-2-Hydroxy-3-indol-3-yl-propionic acid	HMDB
(+)-a-Hydroxy-1H-indole-3-propanoate	HMDB
(+)-a-Hydroxy-1H-indole-3-propanoic acid	HMDB
(+)-a-Hydroxy-1H-indole-3-propionate	HMDB
(+)-a-Hydroxy-1H-indole-3-propionic acid	HMDB
(+)-alpha-Hydroxy-1H-indole-3-propanoate	HMDB
(+)-alpha-Hydroxy-1H-indole-3-propanoic acid	HMDB
(+)-alpha-Hydroxy-1H-indole-3-propionate	HMDB
(+)-alpha-Hydroxy-1H-indole-3-propionic acid	HMDB
(S)-2-Hydroxy-3-indol-3-yl-propionate	HMDB
(S)-2-Hydroxy-3-indol-3-yl-propionic acid	HMDB
2-Hydroxy-3-indol-3-yl-propionate	HMDB
2-Hydroxy-3-indol-3-yl-propionic acid	HMDB
2-Hydroxy-3-indol-3-yl-propionsaeure	HMDB
DL-3-Indolelactate	HMDB
DL-3-Indolelactic acid	HMDB
Indole-3-lactic acid, (+-)-isomer	HMDB
5-Hydroxyindolepropionic acid	HMDB
5-IHIPA	HMDB

Molecular Formula

C₁₁H₁₁NO₃

Average Mass

205.2099

Monoisotopic Mass

205.073893223

IUPAC Name

2-hydroxy-3-(1H-indol-3-yl)propanoic acid

Traditional Name

indole-3-lactic acid

CAS Registry Number

Not Available

SMILES

OC(CC1=CNC2=C1C=CC=C2)C(O)=O

InChI Identifier

InChI=1S/C11H11NO3/c13-10(11(14)15)5-7-6-12-9-4-2-1-3-8(7)9/h1-4,6,10,12-13H,5H2,(H,14,15)

InChI Key

XGILAAMKEQUXLS-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolyl carboxylic acids and derivatives

Direct Parent

Indolyl carboxylic acids and derivatives

Alternative Parents

Substituents

Indolyl carboxylic acid derivative
3-alkylindole
Indole
Alpha-hydroxy acid
Hydroxy acid
Substituted pyrrole
Benzenoid
Pyrrole
Heteroaromatic compound
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Azacycle
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organonitrogen compound
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Organic nitrogen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

hydroxy monocarboxylic acid (CHEBI:24813 )
indol-3-yl carboxylic acid (CHEBI:24813 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	2.12 g/L	ALOGPS
logP	1.33	ALOGPS
logP	1.28	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	4.14	ChemAxon
pKa (Strongest Basic)	-3.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	73.32 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	54.55 m³·mol⁻¹	ChemAxon
Polarizability	20.7 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-MS (2 TMS)	splash10-001i-0900000000-a73dacebbb4e696069e3	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (3 TMS)	splash10-0udi-0290000000-fabadc12766d82241f9d	2014-06-16	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-001i-0900000000-a73dacebbb4e696069e3	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0udi-0290000000-fabadc12766d82241f9d	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-001i-0900000000-026f2953e75b09c74d71	2017-09-12	View Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0udi-0390000000-f0750c125bcd98a91da9	2017-09-12	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-003u-2900000000-bad34fd0864e785e4e97	2017-09-01	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positive	splash10-0089-5291000000-8b3da0b08dd2ffd4d693	2017-10-06	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0bti-0950000000-59498880ad7081aa3753	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0159-0900000000-6a8d0e31efc5b93545e6	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-015c-2900000000-90fc3496f234f903c6de	2012-07-24	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-00lr-0900000000-887bb7e62bbec731a8f7	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , positive	splash10-01p9-0900000000-a21984d35288538673d9	2017-09-14	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum - , positive	splash10-00lr-0900000000-887bb7e62bbec731a8f7	2017-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-053i-0930000000-fe1fd04d5b4f7d40d608	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01qi-0900000000-7e1de8e44f33e343c791	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f89-0900000000-aa813c26618a596bb9a4	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-2590000000-a93dc0fc781357aff735	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0lzl-0910000000-53a7c659337af61dece2	2017-09-01	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-2900000000-61b91ac21dbc478cbe72	2017-09-01	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)		2012-12-04	View Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)		2012-12-05	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	Metabolic reconstruction

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

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

External Links

HMDB ID

HMDB0000671

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022174

KNApSAcK ID

Not Available

Chemspider ID

83867

KEGG Compound ID

C02043

BioCyc ID

INDOLE_LACTATE

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

5641

PubChem Compound

92904

PDB ID

Not Available

ChEBI ID

24813

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 Indoleglycollic acid (MMDBc0002796)

MOL for #<Metabolite:0x00007fecfcc54040>

3D MOL for #<Metabolite:0x00007fecfcc54040>

3D SDF for #<Metabolite:0x00007fecfcc54040>

3D-SDF for #<Metabolite:0x00007fecfcc54040>

PDB for #<Metabolite:0x00007fecfcc54040>

3D PDB for #<Metabolite:0x00007fecfcc54040>

SMILES for #<Metabolite:0x00007fecfcc54040>

INCHI for #<Metabolite:0x00007fecfcc54040>

Structure for #<Metabolite:0x00007fecfcc54040>

3D Structure for #<Metabolite:0x00007fecfcc54040>