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Showing NP-Card for 2-hydroxypropanoic acid (NP0000172)

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Record Information
Version2.0
Created at2017-09-20 17:02:09 UTC
Updated at2022-02-03 21:45:36 UTC
NP-MRD IDNP0000172
Secondary Accession NumbersNone
Natural Product Identification
Common Name2-hydroxypropanoic acid
Description2-Hydroxypropanoic acid, also known as lactic acid or lactate, belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon. In humans, 2-hydroxypropanoic acid is involved in the metabolic disorder called the glutaminolysis and cancer pathway. 2-Hydroxypropanoic acid is an odorless tasting compound. 2-Hydroxypropanoic acid is found, on average, in the highest concentration in opium poppies. 2-Hydroxypropanoic acid has also been detected, but not quantified, in several different foods, such as black elderberries, potato, common grapes, guava, and sour cherries. In volant animals such as birds and bats, lactic acid may build up in the pectoral muscles.
Structure
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MOLSDFPDBSMILESInChI

MOL for NP0000172 (2-hydroxypropanoic acid)


  Mrv1652305261923542D          

  6  5  0  0  0  0            999 V2000
    0.8250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  6  3  1  0  0  0  0
M  END
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3D MOL for NP0000172 (2-hydroxypropanoic acid)

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3D SDF for NP0000172 (2-hydroxypropanoic acid)

  Mrv1652305261923542D          

  6  5  0  0  0  0            999 V2000
    0.8250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  2  0  0  0  0
  6  3  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000172

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)

> <INCHI_KEY>
JVTAAEKCZFNVCJ-UHFFFAOYSA-N

> <FORMULA>
C3H6O3

> <MOLECULAR_WEIGHT>
90.0779

> <EXACT_MASS>
90.031694058

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
8.051819865737073

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxypropanoic acid

> <ALOGPS_LOGP>
-0.79

> <JCHEM_LOGP>
-0.47182951800000017

> <ALOGPS_LOGS>
0.79

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.593508084825753

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.784942414122652

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6696493832413326

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
18.8398

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.62e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lactic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0000172 (2-hydroxypropanoic acid)
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PDB for NP0000172 (2-hydroxypropanoic acid)
HEADER    PROTEIN                                 26-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-19         0                                  
HETATM    1  C   UNK     0       1.540   2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       3.850   1.334   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0       2.310  -1.334   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2    5    6                                                  
CONECT    4    2                                                            
CONECT    5    3                                                            
CONECT    6    3                                                            
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END

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3D PDB for NP0000172 (2-hydroxypropanoic acid)
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SMILES for NP0000172 (2-hydroxypropanoic acid)
CC(O)C(O)=O
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INCHI for NP0000172 (2-hydroxypropanoic acid)
InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)
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Synonyms
ValueSource
2-Hydroxypropionic acidChEBI
Lactic acidChEBI
LactateKegg
2-HydroxypropionateGenerator
2-HydroxypropanoateGenerator
2 Hydroxypropanoic acidHMDB
2 Hydroxypropionic acidHMDB
Ammonium lactateHMDB
D Lactic acidHMDB
D-Lactic acidHMDB
L Lactic acidHMDB
L-Lactic acidHMDB
Lactate, ammoniumHMDB
Sarcolactic acidHMDB
2-Hydroxypropanoic acidMeSH, KEGG
Chemical FormulaC3H6O3
Average Mass90.0779 Da
Monoisotopic Mass90.03169 Da
IUPAC Name2-hydroxypropanoic acid
Traditional Namelactic acid
CAS Registry NumberNot Available
SMILES
CC(O)C(O)=O
InChI Identifier
InChI=1S/C3H6O3/c1-2(4)3(5)6/h2,4H,1H3,(H,5,6)
InChI KeyJVTAAEKCZFNVCJ-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 700 MHz, H2O, simulated)Ahselim2022-02-03View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, DMSO-d6, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 100.40 MHz, DMSO-d6, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Ammodendron bifoliumLOTUS Database
Arabidopsis thalianaLOTUS Database
Arbutus unedoLOTUS Database
Chlamydomonas reinhardtiiLOTUS Database
Daphnia magnaLOTUS Database
Digitalis purpureaLOTUS Database
Escherichia coliBacteria
Gunnera perpensaLOTUS Database
Leucaena glaucaLOTUS Database
Lotus corniculatusLOTUS Database
Lupinus luteusLOTUS Database
Lymnaea stagnalisLOTUS Database
Panax ginsengLOTUS Database
Papaver somniferumLOTUS Database
Prunus aviumLOTUS Database
Pseudostellaria heterophyllaLOTUS Database
Rhodiola roseaLOTUS Database
Sambucus nigraLOTUS Database
Scolochloa festucaceaLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alpha hydroxy acids and derivatives. These are organic compounds containing a carboxylic acid substituted with a hydroxyl group on the adjacent carbon.
KingdomOrganic compounds  
Super ClassOrganic acids and derivatives  
ClassHydroxy acids and derivatives  
Sub ClassAlpha hydroxy acids and derivatives  
Direct ParentAlpha hydroxy acids and derivatives  
Alternative Parents
Substituents
  • Alpha-hydroxy acid
    • 

  • Secondary alcohol
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Carboxylic acid
    • 

  • Carboxylic acid derivative
    • 

  • Organic oxygen compound
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Carbonyl group
    • 

  • Alcohol
    • 

  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic 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-0.79ALOGPS
logP-0.47ChemAxon
logS0.79ALOGPS
pKa (Strongest Acidic)3.78ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity18.84 m³·mol⁻¹ChemAxon
Polarizability8.05 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0144295  
DrugBank IDDB04398  
Phenol Explorer Compound IDNot Available
FoodDB IDFDB005406  
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC01432  
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkLactic acid  
METLIN IDNot Available
PubChem Compound612  
PDB IDNot Available
ChEBI ID78320  
Good Scents IDNot Available
References
General References
  1. Zhang L, You T, Zhang L, Li M, Xu F: Comprehensive utilization of waste hemicelluloses during ethanol production to increase lactic acid yield: from pretreatment to fermentation. Biotechnol Biofuels. 2014 Dec 31;7(1):494. doi: 10.1186/s13068-014-0189-4. eCollection 2014. [PubMed:25606053  ] 
  2. Djoumbou Feunang, Yannick (2017). Cheminformatics Tools for Enabling Metabolomics, 2017 (PhD thesis). University of Alberta.