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Showing NP-Card for Threonic acid (NP0000924)

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Record Information
Version2.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-06-29 00:46:44 UTC
NP-MRD IDNP0000924
Secondary Accession NumbersNone
Natural Product Identification
Common NameThreonic acid
DescriptionThreonic acid, also known as threonate, belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. Threonic acid is a sugar acid derived from threose. The L-isomer is a metabolite of ascorbic acid (vitamin C). One study suggested that because L-threonate inhibits DKK1 expression in vitro, it may have potential in the treatment of androgenic alopecia (PMID: 21034532 ). Threonic acid is probably derived from glycated proteins or from degradation of ascorbic acid. It is a normal component in aqueous humour and blood (PMID: 10420182 ). Threonic acid is a substrate of L-threonate 3-dehydrogenase (EC 1.1.1.129) In the ascorbate and aldarate metabolism pathway (KEGG). It has been found to be a microbial metabolite (PMID: 20615997 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000924 (Threonic acid)


  Mrv1652303062020122D          

  9  8  0  0  0  0            999 V2000
 9992.1939 9992.3189    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9992.9079 9992.7309    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9993.6226 9992.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.3375 9992.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.9079 9993.5562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.4784 9992.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.7628 9992.3189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.4784 9993.5562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.1939 9991.4942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1  9  1  1  0  0  0
  2  3  1  0  0  0  0
  2  5  1  1  0  0  0
  3  4  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
M  END
Download

3D MOL for NP0000924 (Threonic acid)

HMDB0000943
     RDKit          3D
Threonic acid
 17 16  0  0  0  0  0  0  0  0999 V2000
    1.9325   -1.6479   -0.9063 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5930   -0.4834   -0.5723 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0352    0.5915   -1.3216 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7367   -0.2673    0.5998 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4008   -1.4650    1.2167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4938    0.5546    0.2888 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0575    1.7408   -0.3309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4244   -0.1252   -0.6624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9339   -1.3156   -0.1784 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8767    1.1157   -1.1034 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3363    0.3418    1.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0614   -1.3592    2.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0206    0.8121    1.2296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3113    2.5369    0.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8613   -0.3643   -1.5884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2625    0.5487   -0.8727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6072   -1.2142    0.5244 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  3 10  1  0
  4 11  1  1
  5 12  1  0
  6 13  1  1
  7 14  1  0
  8 15  1  0
  8 16  1  0
  9 17  1  0
M  END
Download

3D SDF for NP0000924 (Threonic acid)


  Mrv1652303062020122D          

  9  8  0  0  0  0            999 V2000
 9992.1939 9992.3189    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9992.9079 9992.7309    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
 9993.6226 9992.3189    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.3375 9992.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.9079 9993.5562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.4784 9992.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.7628 9992.3189    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9991.4784 9993.5562    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9992.1939 9991.4942    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  1  9  1  1  0  0  0
  2  3  1  0  0  0  0
  2  5  1  1  0  0  0
  3  4  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0000924

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC[C@H](O)[C@@H](O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C4H8O5/c5-1-2(6)3(7)4(8)9/h2-3,5-7H,1H2,(H,8,9)/t2-,3+/m0/s1

> <INCHI_KEY>
JPIJQSOTBSSVTP-STHAYSLISA-N

> <FORMULA>
C4H8O5

> <MOLECULAR_WEIGHT>
136.1033

> <EXACT_MASS>
136.037173366

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
11.609117870375558

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S)-2,3,4-trihydroxybutanoic acid

> <ALOGPS_LOGP>
-2.11

> <JCHEM_LOGP>
-2.149074426666667

> <ALOGPS_LOGS>
0.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
13.025178139889814

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.4007287139451505

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981778620620938

> <JCHEM_POLAR_SURFACE_AREA>
97.99

> <JCHEM_REFRACTIVITY>
26.345999999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.88e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
threonate

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0000924 (Threonic acid)

HMDB0000943
     RDKit          3D
Threonic acid
 17 16  0  0  0  0  0  0  0  0999 V2000
    1.9325   -1.6479   -0.9063 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5930   -0.4834   -0.5723 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0352    0.5915   -1.3216 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7367   -0.2673    0.5998 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.4008   -1.4650    1.2167 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4938    0.5546    0.2888 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0575    1.7408   -0.3309 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4244   -0.1252   -0.6624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9339   -1.3156   -0.1784 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8767    1.1157   -1.1034 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3363    0.3418    1.3348 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0614   -1.3592    2.1227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0206    0.8121    1.2296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3113    2.5369    0.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8613   -0.3643   -1.5884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2625    0.5487   -0.8727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6072   -1.2142    0.5244 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  3 10  1  0
  4 11  1  1
  5 12  1  0
  6 13  1  1
  7 14  1  0
  8 15  1  0
  8 16  1  0
  9 17  1  0
M  END
Download

PDB for NP0000924 (Threonic acid)

HEADER    PROTEIN                                 06-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAR-20         0                                  
HETATM    1  C   UNK     0    8652.0958652.329   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8653.4288653.098   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8654.7628652.329   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8656.0978653.098   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8653.4288654.638   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8650.7608653.098   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8649.4248652.329   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8650.7608654.638   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0    8652.0958650.789   0.000  0.00  0.00           O+0
CONECT    1    2    6    9                                                  
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3                                                            
CONECT    5    2                                                            
CONECT    6    1    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6                                                            
CONECT    9    1                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
Download

3D PDB for NP0000924 (Threonic acid)

COMPND    HMDB0000943
HETATM    1  O1  UNL     1       1.932  -1.648  -0.906  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.593  -0.483  -0.572  1.00  0.00           C  
HETATM    3  O2  UNL     1       2.035   0.591  -1.322  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.737  -0.267   0.600  1.00  0.00           C  
HETATM    5  O3  UNL     1       0.401  -1.465   1.217  1.00  0.00           O  
HETATM    6  C3  UNL     1      -0.494   0.555   0.289  1.00  0.00           C  
HETATM    7  O4  UNL     1      -0.058   1.741  -0.331  1.00  0.00           O  
HETATM    8  C4  UNL     1      -1.424  -0.125  -0.662  1.00  0.00           C  
HETATM    9  O5  UNL     1      -1.934  -1.316  -0.178  1.00  0.00           O  
HETATM   10  H1  UNL     1       2.877   1.116  -1.103  1.00  0.00           H  
HETATM   11  H2  UNL     1       1.336   0.342   1.335  1.00  0.00           H  
HETATM   12  H3  UNL     1       0.061  -1.359   2.123  1.00  0.00           H  
HETATM   13  H4  UNL     1      -1.021   0.812   1.230  1.00  0.00           H  
HETATM   14  H5  UNL     1      -0.311   2.537   0.220  1.00  0.00           H  
HETATM   15  H6  UNL     1      -0.861  -0.364  -1.588  1.00  0.00           H  
HETATM   16  H7  UNL     1      -2.263   0.549  -0.873  1.00  0.00           H  
HETATM   17  H8  UNL     1      -2.607  -1.214   0.524  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   10
CONECT    4    5    6   11
CONECT    5   12
CONECT    6    7    8   13
CONECT    7   14
CONECT    8    9   15   16
CONECT    9   17
END
Download

SMILES for NP0000924 (Threonic acid)

OC[C@H](O)[C@@H](O)C(O)=O
Download

INCHI for NP0000924 (Threonic acid)

InChI=1S/C4H8O5/c5-1-2(6)3(7)4(8)9/h2-3,5-7H,1H2,(H,8,9)/t2-,3+/m0/s1
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View in JSmol
Synonyms
ValueSource
L-ThreonateKegg
(2R,3S)-2,3,4-Trihydroxybutanoic acidKegg
L-Threonic acidGenerator
(2R,3S)-2,3,4-TrihydroxybutanoateGenerator
ThreonateGenerator
Threonic acid, (R-(r*,s*))-isomerHMDB
2,3,4-Trihydroxy-(threo)-butanoic acidHMDB
Threonic acid, (r*,r*)-isomerHMDB
2,3,4-Trihydroxybutanoic acidHMDB
2,3,4-Trihydroxybutyric acidHMDB
Threonic acidMeSH, HMDB
Chemical FormulaC4H8O5
Average Mass136.1033 Da
Monoisotopic Mass136.03717 Da
IUPAC Name(2R,3S)-2,3,4-trihydroxybutanoic acid
Traditional Namethreonate
CAS Registry Number3909-12-4
SMILES
OC[C@@H](O)[C@H](O)C(O)=O
InChI Identifier
InChI=1S/C4H8O5/c5-1-2(6)3(7)4(8)9/h2-3,5-7H,1H2,(H,8,9)/t2-,3+/m1/s1
InChI KeyJPIJQSOTBSSVTP-GBXIJSLDSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
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
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, simulated)varshavi.d26@gmail.comNot AvailableNot Available2021-08-08View Spectrum
Species
Species of Origin
Species NameSourceReference
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Averrhoa carambolaPlant
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Cannabis sativaCannabisDB
      Not Available
Capra aegagrus hircusFooDB
Capsicum annuumKNApSAcK Database
CervidaeFooDB
Cervus canadensisFooDB
Chlamydomonas reinhardtiiLOTUS Database
ColumbaFooDB
ColumbidaeFooDB
Daphnia magnaLOTUS Database
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Homo sapiens (Serum)Animalia
Homo sapiens (Urine)Animalia
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Lotus corniculatusLOTUS Database
Lotus glaberLOTUS Database
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
Parthenocissus quinquefoliaLOTUS Database
PhasianidaeFooDB
Phasianus colchicusFooDB
Pycnandra acuminataLOTUS Database
Sebertia acuminataPlant
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Triticum aestivumPlant
Trypanosoma bruceiLOTUS Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentSugar acids and derivatives
Alternative Parents
Substituents
  • Beta-hydroxy acid
  • Short-chain hydroxy acid
  • Sugar acid
  • Alpha-hydroxy acid
  • Hydroxy acid
  • Monosaccharide
  • Fatty acid
  • Secondary alcohol
  • Polyol
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Alcohol
  • Carbonyl group
  • Primary alcohol
  • Hydrocarbon derivative
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility53 mg/mLNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility488 g/LALOGPS
logP-2.1ALOGPS
logP-2.1ChemAxon
logS0.55ALOGPS
pKa (Strongest Acidic)3.4ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area97.99 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity26.35 m³·mol⁻¹ChemAxon
Polarizability11.61 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0000943
DrugBank IDDB11192
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030975
KNApSAcK IDC00053443
Chemspider ID4573940
KEGG Compound IDC01620
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkThreonic_acid
METLIN IDNot Available
PubChem Compound5460407
PDB IDNot Available
ChEBI ID15908
Good Scents IDNot Available
References
General References
  1. Chalmers RA, Lawson AM, Hauschildt S, Watts RW: The urinary excretion of glycollic acid and threonic acid by xylitol-infused patients and their relationship to the possible role of 'active glycoladehyde' in the transketolase reaction in vivo. Biochem Soc Trans. 1975;3(4):518-21. [PubMed:1183712 ]
  2. Harding JJ, Hassett PC, Rixon KC, Bron AJ, Harvey DJ: Sugars including erythronic and threonic acids in human aqueous humour. Curr Eye Res. 1999 Aug;19(2):131-6. [PubMed:10420182 ]
  3. Leveque N, Mac-Mary S, Muret P, Makki S, Aubin F, Kantelip JP, Heusele C, S S, Humbert P: Evaluation of a sunscreen photoprotective effect by ascorbic acid assessment in human dermis using microdialysis and gas chromatography mass spectrometry. Exp Dermatol. 2005 Mar;14(3):176-81. [PubMed:15740589 ]
  4. Watts RW, Hauschildt S, Chalmers RA, Lawson AM: Metabolic investigations during xylitol infusion. Int Z Vitam Ernahrungsforsch Beih. 1976;15:216-25. [PubMed:821885 ]
  5. Kwack MH, Ahn JS, Kim MK, Kim JC, Sung YK: Preventable effect of L-threonate, an ascorbate metabolite, on androgen-driven balding via repression of dihydrotestosterone-induced dickkopf-1 expression in human hair dermal papilla cells. BMB Rep. 2010 Oct;43(10):688-92. doi: 10.5483/BMBRep.2010.43.10.688. [PubMed:21034532 ]