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Showing NP-Card for 3-(imidazol-5-yl)lactic acid (NP0309532)

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Record Information
Version2.0
Created at2022-09-11 04:11:26 UTC
Updated at2022-09-11 04:11:26 UTC
NP-MRD IDNP0309532
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-(imidazol-5-yl)lactic acid
Description 3-(imidazol-5-yl)lactic acid is found in Hippospongia communis. 3-(imidazol-5-yl)lactic acid was first documented in 1954 (PMID: 13220477).
Structure
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MOL3D MOLSDFPDBSMILESInChI

MOL for NP0309532 (3-(imidazol-5-yl)lactic acid)


  Mrv0541 11061211522D          

 11 11  0  0  0  0            999 V2000
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    3.5893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    3.5893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  4  2  2  0  0  0  0
  5  1  1  0  0  0  0
  6  5  1  0  0  0  0
  7  2  1  0  0  0  0
  7  3  2  0  0  0  0
  8  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 11  6  1  0  0  0  0
M  END
Download

3D MOL for NP0309532 (3-(imidazol-5-yl)lactic acid)

     RDKit          3D

 19 19  0  0  0  0  0  0  0  0999 V2000
    2.7223    1.5804   -0.7515 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4506    0.3708   -0.6739 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4566   -0.5545   -0.5428 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0502   -0.0808   -0.7218 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9317   -1.4663   -0.6216 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3659    0.5325    0.5074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0689    0.1480    0.5490 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6031   -0.9580    1.1608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9286   -0.9141    0.9521 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1985    0.1827    0.2359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0597    0.8457   -0.0188 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.0348   -0.5837    0.3006 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5877    0.3060   -1.6536 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0371   -1.8191   -1.5539 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9234    0.2154    1.3975 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4866    1.6296    0.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0451   -1.7346    1.7182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1753    0.5433   -0.1212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9677    1.7566   -0.5703 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0
  4  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  0
 11  7  1  0
  5 14  1  0
  4 13  1  6
  6 15  1  0
  6 16  1  0
  8 17  1  0
 10 18  1  0
 11 19  1  0
  3 12  1  0
M  END
Download

3D SDF for NP0309532 (3-(imidazol-5-yl)lactic acid)


  Mrv0541 11061211522D          

 11 11  0  0  0  0            999 V2000
    0.5678    1.9393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2352    0.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1553   -0.1553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    1.1143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    2.3518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1467    3.1768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9803   -0.1553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0997    0.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    1.9393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8612    3.5893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5678    3.5893    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  4  2  2  0  0  0  0
  5  1  1  0  0  0  0
  6  5  1  0  0  0  0
  7  2  1  0  0  0  0
  7  3  2  0  0  0  0
  8  3  1  0  0  0  0
  8  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 11  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0309532

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(CC1=CN=CN1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H8N2O3/c9-5(6(10)11)1-4-2-7-3-8-4/h2-3,5,9H,1H2,(H,7,8)(H,10,11)

> <INCHI_KEY>
ACZFBYCNAVEFLC-UHFFFAOYSA-N

> <FORMULA>
C6H8N2O3

> <MOLECULAR_WEIGHT>
156.1393

> <EXACT_MASS>
156.053492132

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
14.315680930922305

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxy-3-(1H-imidazol-5-yl)propanoic acid

> <ALOGPS_LOGP>
-0.73

> <JCHEM_LOGP>
-2.061685103802343

> <ALOGPS_LOGS>
-0.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.893788668422076

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.3940572202301884

> <JCHEM_PKA_STRONGEST_BASIC>
6.741900819065868

> <JCHEM_POLAR_SURFACE_AREA>
86.21

> <JCHEM_REFRACTIVITY>
36.4015

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.58e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-(imidazol-5-yl)lactic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0309532 (3-(imidazol-5-yl)lactic acid)

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PDB for NP0309532 (3-(imidazol-5-yl)lactic acid)
HEADER    PROTEIN                                 06-NOV-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-NOV-12         0                                  
HETATM    1  C   UNK     0       1.060   3.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.306   1.175   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.290  -0.290   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.060   2.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.274   4.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.274   5.930   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       1.830  -0.290   0.000  0.00  0.00           N+0
HETATM    8  N   UNK     0      -0.186   1.175   0.000  0.00  0.00           N+0
HETATM    9  O   UNK     0      -1.608   3.620   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -1.608   6.700   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.060   6.700   0.000  0.00  0.00           O+0
CONECT    1    4    5                                                       
CONECT    2    4    7                                                       
CONECT    3    7    8                                                       
CONECT    4    1    2    8                                                  
CONECT    5    1    6    9                                                  
CONECT    6    5   10   11                                                  
CONECT    7    2    3                                                       
CONECT    8    3    4                                                       
CONECT    9    5                                                            
CONECT   10    6                                                            
CONECT   11    6                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   22    0
END

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3D PDB for NP0309532 (3-(imidazol-5-yl)lactic acid)
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SMILES for NP0309532 (3-(imidazol-5-yl)lactic acid)
OC(CC1=CN=CN1)C(O)=O
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INCHI for NP0309532 (3-(imidazol-5-yl)lactic acid)
InChI=1S/C6H8N2O3/c9-5(6(10)11)1-4-2-7-3-8-4/h2-3,5,9H,1H2,(H,7,8)(H,10,11)
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Synonyms
ValueSource
2-Hydroxy-3-(1H-imidazol-5-yl)-propanoic acidChEBI
2-Hydroxy-3-[4-imidazolyl]-propanoateChEBI
alpha-Hydroxy-1H-imidazolepropanoic acidChEBI
Imidazole lactateChEBI
Imidazole lactic acidChEBI
2-Hydroxy-3-(1H-imidazol-5-yl)-propanoateGenerator
2-Hydroxy-3-[4-imidazolyl]-propanoic acidGenerator
a-Hydroxy-1H-imidazolepropanoateGenerator
a-Hydroxy-1H-imidazolepropanoic acidGenerator
alpha-Hydroxy-1H-imidazolepropanoateGenerator
Α-hydroxy-1H-imidazolepropanoateGenerator
Α-hydroxy-1H-imidazolepropanoic acidGenerator
3-(Imidazol-5-yl)lactateGenerator
Chemical FormulaC6H8N2O3
Average Mass156.1393 Da
Monoisotopic Mass156.05349 Da
IUPAC Name2-hydroxy-3-(1H-imidazol-5-yl)propanoic acid
Traditional Name3-(imidazol-5-yl)lactic acid
CAS Registry NumberNot Available
SMILES
OC(CC1=CN=CN1)C(O)=O
InChI Identifier
InChI=1S/C6H8N2O3/c9-5(6(10)11)1-4-2-7-3-8-4/h2-3,5,9H,1H2,(H,7,8)(H,10,11)
InChI KeyACZFBYCNAVEFLC-UHFFFAOYSA-N
Experimental Spectra
Not Available
Predicted Spectra
Spectrum TypeDescriptionDepositor IDDepositor OrganizationDepositorDeposition DateView
1D NMR13C NMR Spectrum (1D, 25 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 252 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 50 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 75 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 101 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 126 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 151 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 176 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 201 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 226 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, H2O, predicted)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Hippospongia communisLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as imidazolyl carboxylic acids and derivatives. These are organic compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an imidazole ring.
KingdomOrganic compounds  
Super ClassOrganoheterocyclic compounds  
ClassAzoles  
Sub ClassImidazoles  
Direct ParentImidazolyl carboxylic acids and derivatives  
Alternative Parents
Substituents
  • Imidazolyl carboxylic acid derivative
    • 

  • Alpha-hydroxy acid
    • 

  • Hydroxy acid
    • 

  • Heteroaromatic compound
    • 

  • Secondary alcohol
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Azacycle
    • 

  • Organonitrogen compound
    • 

  • Organopnictogen compound
    • 

  • Organic oxygen compound
    • 

  • Organic nitrogen compound
    • 

  • Alcohol
    • 

  • Organooxygen compound
    • 

  • Organic oxide
    • 

  • Carbonyl group
    • 

  • Hydrocarbon derivative
    • 

  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic 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
logP-0.73ALOGPS
logP-2.1ChemAxon
logS-0.53ALOGPS
pKa (Strongest Acidic)3.39ChemAxon
pKa (Strongest Basic)6.74ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area86.21 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity36.4 m³·mol⁻¹ChemAxon
Polarizability14.32 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC05568  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound793  
PDB IDNot Available
ChEBI ID27487  
Good Scents IDNot Available
References
General References
  1. GORIUKHINA TA: [Fermentative conversion of imidazole lactic acid in normal and tumor-bearing rabbits]. Dokl Akad Nauk SSSR. 1954 Oct 1;98(4):619-22. [PubMed:13220477  ] 
  2. Smith I, Rider LJ: Imidazole lactic acid--a component of normal human urine. Proc Soc Exp Biol Med. 1967 Jan;124(1):233-5. doi: 10.3181/00379727-124-31711. [PubMed:6017775  ] 
  3. Sharpan' IuV: [Determination of the antihistaminic properties of histidine derivatives on models of guinea pig T- and B-lymphocyte rosette formation]. Biull Eksp Biol Med. 1984 Oct;98(10):503-5. [PubMed:6333900  ] 
  4. LOTUS database [Link]