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Showing NP-Card for indole-3-lactic acid (NP0270099)

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Record Information
Version2.0
Created at2022-09-08 15:48:12 UTC
Updated at2022-09-08 15:48:12 UTC
NP-MRD IDNP0270099
Secondary Accession NumbersNone
Natural Product Identification
Common Nameindole-3-lactic acid
DescriptionIndolelactic 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. indole-3-lactic acid is found in Agrobacterium tumefaciens, Apis cerana, Daphnia pulex and Malassezia furfur. indole-3-lactic acid was first documented in 1988 (PMID: 16347781). Indolelactic acid is an extremely weak basic (essentially neutral) compound (based on its pKa) (PMID: 21749142) (PMID: 20540569) (PMID: 22372405) (PMID: 23111785).
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0270099 (indole-3-lactic acid)

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
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3D MOL for NP0270099 (indole-3-lactic acid)

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3D SDF for NP0270099 (indole-3-lactic acid)
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>
NP0270099

> <DATABASE_NAME>
NP-MRD

> <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

$$$$

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3D-SDF for NP0270099 (indole-3-lactic acid)
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PDB for NP0270099 (indole-3-lactic acid)
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

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3D PDB for NP0270099 (indole-3-lactic acid)
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SMILES for NP0270099 (indole-3-lactic acid)
OC(CC1=CNC2=C1C=CC=C2)C(O)=O
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INCHI for NP0270099 (indole-3-lactic acid)
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)
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Synonyms
ValueSource
alpha-Hydroxy-1H-indole-3-propanoic acidChEBI
Indole-3-lactic acidChEBI
a-Hydroxy-1H-indole-3-propanoateGenerator
a-Hydroxy-1H-indole-3-propanoic acidGenerator
alpha-Hydroxy-1H-indole-3-propanoateGenerator
Α-hydroxy-1H-indole-3-propanoateGenerator
Α-hydroxy-1H-indole-3-propanoic acidGenerator
Indole-3-lactateGenerator
IndolelactateGenerator
(+)-2-Hydroxy-3-indol-3-yl-propionateHMDB
(+)-2-Hydroxy-3-indol-3-yl-propionic acidHMDB
(+)-a-Hydroxy-1H-indole-3-propanoateHMDB
(+)-a-Hydroxy-1H-indole-3-propanoic acidHMDB
(+)-a-Hydroxy-1H-indole-3-propionateHMDB
(+)-a-Hydroxy-1H-indole-3-propionic acidHMDB
(+)-alpha-Hydroxy-1H-indole-3-propanoateHMDB
(+)-alpha-Hydroxy-1H-indole-3-propanoic acidHMDB
(+)-alpha-Hydroxy-1H-indole-3-propionateHMDB
(+)-alpha-Hydroxy-1H-indole-3-propionic acidHMDB
(S)-2-Hydroxy-3-indol-3-yl-propionateHMDB
(S)-2-Hydroxy-3-indol-3-yl-propionic acidHMDB
2-Hydroxy-3-indol-3-yl-propionateHMDB
2-Hydroxy-3-indol-3-yl-propionic acidHMDB
2-Hydroxy-3-indol-3-yl-propionsaeureHMDB
DL-3-IndolelactateHMDB
DL-3-Indolelactic acidHMDB
Indole-3-lactic acid, (+-)-isomerHMDB
5-Hydroxyindolepropionic acidHMDB
5-IHIPAHMDB
Chemical FormulaC11H11NO3
Average Mass205.2099 Da
Monoisotopic Mass205.07389 Da
IUPAC Name2-hydroxy-3-(1H-indol-3-yl)propanoic acid
Traditional Nameindole-3-lactic acid
CAS Registry NumberNot 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 KeyXGILAAMKEQUXLS-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Agrobacterium tumefaciensLOTUS Database
Apis ceranaLOTUS Database
Daphnia pulexLOTUS Database
Malassezia furfurLOTUS Database
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.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassIndoles and derivatives  
Sub ClassIndolyl carboxylic acids and derivatives  
Direct ParentIndolyl 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 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
logP1.33ALOGPS
logP1.28ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)4.14ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area73.32 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity54.55 m³·mol⁻¹ChemAxon
Polarizability20.7 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000671  
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB022174  
KNApSAcK IDNot Available
Chemspider ID83867  
KEGG Compound IDC02043  
BioCyc IDINDOLE_LACTATE  
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5641  
PubChem Compound92904  
PDB IDNot Available
ChEBI ID24813  
Good Scents IDNot Available
References
General References
  1. Manna SK, Patterson AD, Yang Q, Krausz KW, Idle JR, Fornace AJ, Gonzalez FJ: UPLC-MS-based urine metabolomics reveals indole-3-lactic acid and phenyllactic acid as conserved biomarkers for alcohol-induced liver disease in the Ppara-null mouse model. J Proteome Res. 2011 Sep 2;10(9):4120-33. doi: 10.1021/pr200310s. Epub 2011 Jul 28. [PubMed:21749142  ] 
  2. Crozier A, Arruda P, Jasmim JM, Monteiro AM, Sandberg G: Analysis of Indole-3-Acetic Acid and Related Indoles in Culture Medium from Azospirillum lipoferum and Azospirillum brasilense. Appl Environ Microbiol. 1988 Nov;54(11):2833-7. doi:  10.1128/aem.54.11.2833-2837.1988. [PubMed:16347781  ] 
  3. Manna SK, Patterson AD, Yang Q, Krausz KW, Li H, Idle JR, Fornace AJ Jr, Gonzalez FJ: Identification of noninvasive biomarkers for alcohol-induced liver disease using urinary metabolomics and the Ppara-null mouse. J Proteome Res. 2010 Aug 6;9(8):4176-88. doi: 10.1021/pr100452b. [PubMed:20540569  ] 
  4. Jacobs DM, Fuhrmann JC, van Dorsten FA, Rein D, Peters S, van Velzen EJ, Hollebrands B, Draijer R, van Duynhoven J, Garczarek U: Impact of short-term intake of red wine and grape polyphenol extract on the human metabolome. J Agric Food Chem. 2012 Mar 28;60(12):3078-85. doi: 10.1021/jf2044247. Epub 2012  Mar 13. [PubMed:22372405  ] 
  5. Szkop M, Bielawski W: A simple method for simultaneous RP-HPLC determination of indolic compounds related to bacterial biosynthesis of indole-3-acetic acid. Antonie Van Leeuwenhoek. 2013 Mar;103(3):683-91. doi: 10.1007/s10482-012-9838-4.  Epub 2012 Oct 31. [PubMed:23111785  ] 
  6. LOTUS database [Link]