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Showing NP-Card for Dihydroxyacetone (NP0001189)

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Record Information
Version1.0
Created at2006-02-28 09:34:34 UTC
Updated at2021-08-19 23:58:53 UTC
NP-MRD IDNP0001189
Secondary Accession NumbersNone
Natural Product Identification
Common NameDihydroxyacetone
DescriptionDihydroxyacetone (also known as DHA) is a ketotriose compound. Its addition to blood preservation solutions results in better maintenance of 2,3-diphosphoglycerate levels during storage. It is readily phosphorylated to dihydroxyacetone phosphate by triokinase in erythrocytes. In combination with naphthoquinones, it acts as a sunscreening agent. Dihydroxyacetone is the simplest of all ketoses and, having no chiral centre, is the only one that has no optical activity. Dihydroxyacetone is a simple non-toxic sugar. It is often derived from plant sources such as sugar beets and sugar cane, by the fermentation of glycerin. Dihydroxyacetone is a white crystalline powder which is water soluble.
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0001189 (Dihydroxyacetone)

      
  Mrv1652305271900092D          

  6  5  0  0  0  0            999 V2000
   -0.1914   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -1.1270    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
    1.2376    0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6666   -0.7145    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
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
M  END
Download

3D MOL for NP0001189 (Dihydroxyacetone)

HMDB0001882
     RDKit          3D
Dihydroxyacetone
 12 11  0  0  0  0  0  0  0  0999 V2000
    0.2333    1.4452   -0.2158 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0528    0.2538   -0.0400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3228   -0.2613   -0.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2280    0.7782   -0.2174 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2578   -0.5976    0.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4192    0.1258    0.0801 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5119   -0.9844   -0.8669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5398   -0.7663    0.9611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1459    1.3864    0.5579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2367   -1.3644   -0.6864 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2351   -1.1162    1.1425 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3136    1.1008    0.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  2  5  1  0
  5  6  1  0
  3  7  1  0
  3  8  1  0
  4  9  1  0
  5 10  1  0
  5 11  1  0
  6 12  1  0
M  END
Download

3D SDF for NP0001189 (Dihydroxyacetone)

      
  Mrv1652305271900092D          

  6  5  0  0  0  0            999 V2000
   -0.1914   -0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230   -1.1270    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
    1.2376    0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520   -1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6666   -0.7145    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
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001189

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OCC(=O)CO

> <INCHI_IDENTIFIER>
InChI=1S/C3H6O3/c4-1-3(6)2-5/h4-5H,1-2H2

> <INCHI_KEY>
RXKJFZQQPQGTFL-UHFFFAOYSA-N

> <FORMULA>
C3H6O3

> <MOLECULAR_WEIGHT>
90.0779

> <EXACT_MASS>
90.031694058

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
8.104016589966427

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,3-dihydroxypropan-2-one

> <ALOGPS_LOGP>
-1.65

> <JCHEM_LOGP>
-1.5282162836666666

> <ALOGPS_LOGS>
0.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.20569157000131

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.491443966912374

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3219094004199308

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
19.599199999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.38e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dihydroxyacetone

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for NP0001189 (Dihydroxyacetone)

HMDB0001882
     RDKit          3D
Dihydroxyacetone
 12 11  0  0  0  0  0  0  0  0999 V2000
    0.2333    1.4452   -0.2158 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0528    0.2538   -0.0400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3228   -0.2613   -0.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2280    0.7782   -0.2174 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2578   -0.5976    0.1423 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4192    0.1258    0.0801 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5119   -0.9844   -0.8669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5398   -0.7663    0.9611 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1459    1.3864    0.5579 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2367   -1.3644   -0.6864 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2351   -1.1162    1.1425 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3136    1.1008    0.2147 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  2  5  1  0
  5  6  1  0
  3  7  1  0
  3  8  1  0
  4  9  1  0
  5 10  1  0
  5 11  1  0
  6 12  1  0
M  END
Download

PDB for NP0001189 (Dihydroxyacetone)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  O   UNK     0      -0.357  -1.334   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       0.976  -2.104   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.310   0.206   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       3.644  -2.104   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.978  -1.334   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5                                                            
MASTER        0    0    0    0    0    0    0    0    6    0   10    0
END
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3D PDB for NP0001189 (Dihydroxyacetone)

COMPND    HMDB0001882
HETATM    1  O1  UNL     1       0.233   1.445  -0.216  1.00  0.00           O  
HETATM    2  C1  UNL     1       0.053   0.254  -0.040  1.00  0.00           C  
HETATM    3  C2  UNL     1      -1.323  -0.261  -0.019  1.00  0.00           C  
HETATM    4  O2  UNL     1      -2.228   0.778  -0.217  1.00  0.00           O  
HETATM    5  C3  UNL     1       1.258  -0.598   0.142  1.00  0.00           C  
HETATM    6  O3  UNL     1       2.419   0.126   0.080  1.00  0.00           O  
HETATM    7  H1  UNL     1      -1.512  -0.984  -0.867  1.00  0.00           H  
HETATM    8  H2  UNL     1      -1.540  -0.766   0.961  1.00  0.00           H  
HETATM    9  H3  UNL     1      -2.146   1.386   0.558  1.00  0.00           H  
HETATM   10  H4  UNL     1       1.237  -1.364  -0.686  1.00  0.00           H  
HETATM   11  H5  UNL     1       1.235  -1.116   1.143  1.00  0.00           H  
HETATM   12  H6  UNL     1       2.314   1.101   0.215  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    5
CONECT    3    4    7    8
CONECT    4    9
CONECT    5    6   10   11
CONECT    6   12
END
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SMILES for NP0001189 (Dihydroxyacetone)

OCC(=O)CO
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INCHI for NP0001189 (Dihydroxyacetone)

InChI=1S/C3H6O3/c4-1-3(6)2-5/h4-5H,1-2H2
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View in JSmol
Synonyms
ValueSource
1,3-Dihydroxy-2-propanoneChEBI
1,3-DihydroxyacetoneChEBI
1,3-Dihydroxydimethyl ketoneChEBI
1,3-Dihydroxypropan-2-oneChEBI
1,3-DihydroxypropanoneChEBI
1,3-Propanediol-2-oneChEBI
alpha,Alpha'-dihydroxyacetoneChEBI
Bis(hydroxymethyl) ketoneChEBI
DHAChEBI
GlyceroneChEBI
ChromelinKegg
a,Alpha'-dihydroxyacetoneGenerator
Α,alpha'-dihydroxyacetoneGenerator
a,A'-dihydroxyacetoneHMDB
Aliphatic ketoneHMDB
Dihydroxy-acetoneHMDB
DihyxalHMDB
KetochrominHMDB
OtanHMDB
OxantinHMDB
OxatoneHMDB
ProtosolHMDB
SolealHMDB
TriuloseHMDB
ViticolorHMDB
1,3 Dihydroxy 2 propanoneHMDB
Summers brand OF dihydroxyacetoneHMDB
ICN brand OF dihydroxyacetoneHMDB
VitadyeHMDB
Chemical FormulaC3H6O3
Average Mass90.0779 Da
Monoisotopic Mass90.03169 Da
IUPAC Name1,3-dihydroxypropan-2-one
Traditional Namedihydroxyacetone
CAS Registry Number96-26-4
SMILES
OCC(=O)CO
InChI Identifier
InChI=1S/C3H6O3/c4-1-3(6)2-5/h4-5H,1-2H2
InChI KeyRXKJFZQQPQGTFL-UHFFFAOYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 600 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
Agave americanaLOTUS Database
Anas platyrhynchosFooDB
AnatidaeFooDB
Anser anserFooDB
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
ColumbaFooDB
ColumbidaeFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Gallus gallusFooDB
Homo sapiensLOTUS Database
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Mus musculusLOTUS Database
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
PhasianidaeFooDB
Phasianus colchicusFooDB
Solanum lycopersicumLOTUS Database
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Triticum aestivumKNApSAcK Database
Chemical Taxonomy
Description Belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentMonosaccharides
Alternative Parents
Substituents
  • Glycerone or derivatives
  • Monosaccharide
  • Alpha-hydroxy ketone
  • Ketone
  • Organic oxide
  • Hydrocarbon derivative
  • Primary alcohol
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point90 °CNot Available
Boiling Point212.00 to 214.00 °C. @ 760.00 mm HgThe Good Scents Company Information System
Water Solubility503200 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-0.779 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility838 g/LALOGPS
logP-1.6ALOGPS
logP-1.5ChemAxon
logS0.97ALOGPS
pKa (Strongest Acidic)13.49ChemAxon
pKa (Strongest Basic)-3.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity19.6 m³·mol⁻¹ChemAxon
Polarizability8.1 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001882
DrugBank IDDB01775
Phenol Explorer Compound IDNot Available
FoodDB IDFDB030826
KNApSAcK IDC00053166
Chemspider ID650
KEGG Compound IDC00184
BioCyc IDDIHYDROXYACETONE
BiGG ID34170
Wikipedia LinkDihydroxyacetone
METLIN ID6368
PubChem Compound670
PDB IDNot Available
ChEBI ID16016
Good Scents IDrw1019441
References
General References
  1. Bales JR, Higham DP, Howe I, Nicholson JK, Sadler PJ: Use of high-resolution proton nuclear magnetic resonance spectroscopy for rapid multi-component analysis of urine. Clin Chem. 1984 Mar;30(3):426-32. [PubMed:6321058 ]
  2. Phillipou G, Seaborn CJ, Phillips PJ: Re-evaluation of the fructosamine reaction. Clin Chem. 1988 Aug;34(8):1561-4. [PubMed:3402055 ]
  3. Blake SM, Treble NJ: Popliteus tendon tenosynovitis. Br J Sports Med. 2005 Dec;39(12):e42; discussion e42. [PubMed:16306488 ]
  4. Forest SE, Grothaus JT, Ertel KD, Rader C, Plante J: Fluorescence spectral imaging of dihydroxyacetone on skin in vivo. Photochem Photobiol. 2003 May;77(5):524-30. [PubMed:12812295 ]
  5. Taylor CR, Kwangsukstith C, Wimberly J, Kollias N, Anderson RR: Turbo-PUVA: dihydroxyacetone-enhanced photochemotherapy for psoriasis: a pilot study. Arch Dermatol. 1999 May;135(5):540-4. [PubMed:10328194 ]
  6. Kerr HH, Pantely GA, Metcalfe J, Welch JE: Reduction of human blood O2 affinity using dihydroxyacetone, phosphate, and pyruvate. J Appl Physiol Respir Environ Exerc Physiol. 1979 Sep;47(3):478-81. [PubMed:118143 ]
  7. GOLDMAN L, WITTGENSTEIN E, BLANEY D, GOLDMAN J, SAWYER F: Studies of some physical properties of the dihydroxyacetone color complex. J Invest Dermatol. 1961 Apr;36:233-4. [PubMed:13706567 ]
  8. WITTGENSTEIN E, BERRY HK: Staining of skin with dihydroxyacetone. Science. 1960 Sep 30;132(3431):894-5. [PubMed:13845496 ]
  9. WITTGENSTEIN E, GUEST GM: Biochemical effects of dihydroxyacetone. J Invest Dermatol. 1961 Nov;37:421-6. [PubMed:14007781 ]