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Showing metabocard for D-Arabitol (HMDB0000568)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:14:58 UTC
HMDB IDHMDB0000568
Secondary Accession Numbers
  • HMDB00568
Metabolite Identification
Common NameD-Arabitol
DescriptionD-Arabitol is a polyol. Polyols are sugar alcohols linked to the pentose phosphate pathway (PPP). They are classified on the basis of the number of carbon atoms. Polyols occur in body fluids. A patient with leukoencephalopathy and peripheral neuropathy has been identified as suffering from ribose-5-phosphate isomerase (RPI) deficiency, a defect in the PPP. In this disorder, highly elevated concentrations of the C5 polyols such as D-arabitol are found in body fluids. In addition, transaldolase deficiency, another defect in the PPP, has been diagnosed in a patient with mainly liver problems among others. This patient had increased concentrations of polyols, mainly D-arabitol. So far, the pathophysiological role of polyols is relatively unknown. It is thought that D-arabitol is a metabolic end-product in humans. The strong brain-CSF-plasma gradient of polyols in the patient with RPI deficiency suggested a primary metabolic disorder. The mechanisms of brain and neuronal damage in RPI deficiency remain to be elucidated. A neurotoxic effect due to the accumulation of the polyols may play a role. D-Arabitol is a product of the enzyme D-arabinitol 4-dehydrogenase (EC 1.1.1.11) in the pentose and glucuronate interconversion pathway (PMID: 16435225 , J Inherit Metab Dis. 2005;28(6):1181-3). D-Arabitol has also been found to be a fungal metabolite, urinary D-Arabinitol is a marker for invasive candidiasis or infection by Candida fungal species (PMID: 15183861 ; PMID: 10647119 ). It can also a metabolite in Debaryomyces, Pichia and Zygosaccharomyces (PMID: 25809659 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000568 (D-Arabitol)

ChEBI
  Mrv1652306232021442D          

 10  9  0  0  1  0            999 V2000
    4.4922   -3.0367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2019   -3.4570    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9211   -3.0462    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6310   -3.4664    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3502   -3.0557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7729   -3.4475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2033   -4.2818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9197   -2.2212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6324   -4.2912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3488   -2.2307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  2  1  1  0  0  0  0
  2  7  1  6  0  0  0
  3  2  1  0  0  0  0
  3  8  1  6  0  0  0
  4  3  1  0  0  0  0
  4  9  1  1  0  0  0
  5  4  1  0  0  0  0
 10  5  1  0  0  0  0
M  END
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3D MOL for HMDB0000568 (D-Arabitol)

HMDB0000568
     RDKit          3D
D-Arabitol
 22 21  0  0  0  0  0  0  0  0999 V2000
    2.8495    0.9305    0.7642 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8469   -0.0417    0.5669 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8877    0.5227   -0.4358 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6227    0.7679   -1.6120 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2345   -0.3865   -0.7981 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3332   -1.5687   -1.3102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1411   -0.7736    0.3094 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1188   -1.6297   -0.2591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9055    0.3745    0.9127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1286    1.3222    1.5180 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0210    1.4536   -0.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3571   -0.9528    0.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3839   -0.1852    1.5703 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5668    1.5170   -0.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3656    0.1609   -2.3344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8149    0.0752   -1.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6729   -2.1284   -0.5501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6490   -1.3886    1.0889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4518   -1.1063   -1.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5666    0.8762    0.1783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5994   -0.0828    1.6777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2972    2.2435    1.2602 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  1 11  1  0
  2 12  1  0
  2 13  1  0
  3 14  1  1
  4 15  1  0
  5 16  1  0
  6 17  1  0
  7 18  1  1
  8 19  1  0
  9 20  1  0
  9 21  1  0
 10 22  1  0
M  END
Download

3D SDF for HMDB0000568 (D-Arabitol)

ChEBI
  Mrv1652306232021442D          

 10  9  0  0  1  0            999 V2000
    4.4922   -3.0367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2019   -3.4570    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.9211   -3.0462    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.6310   -3.4664    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    7.3502   -3.0557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7729   -3.4475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2033   -4.2818    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9197   -2.2212    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6324   -4.2912    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3488   -2.2307    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  2  1  1  0  0  0  0
  2  7  1  6  0  0  0
  3  2  1  0  0  0  0
  3  8  1  6  0  0  0
  4  3  1  0  0  0  0
  4  9  1  1  0  0  0
  5  4  1  0  0  0  0
 10  5  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000568

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4-/m1/s1

> <INCHI_KEY>
HEBKCHPVOIAQTA-QWWZWVQMSA-N

> <FORMULA>
C5H12O5

> <MOLECULAR_WEIGHT>
152.1458

> <EXACT_MASS>
152.068473494

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
14.277797496387443

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,4R)-pentane-1,2,3,4,5-pentol

> <ALOGPS_LOGP>
-2.53

> <JCHEM_LOGP>
-3.099683906666666

> <ALOGPS_LOGS>
0.64

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.742189661908146

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.760078510562963

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9742034412471314

> <JCHEM_POLAR_SURFACE_AREA>
101.15

> <JCHEM_REFRACTIVITY>
32.44109999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.64e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
arabitol

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0000568 (D-Arabitol)

HMDB0000568
     RDKit          3D
D-Arabitol
 22 21  0  0  0  0  0  0  0  0999 V2000
    2.8495    0.9305    0.7642 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8469   -0.0417    0.5669 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8877    0.5227   -0.4358 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6227    0.7679   -1.6120 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2345   -0.3865   -0.7981 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3332   -1.5687   -1.3102 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1411   -0.7736    0.3094 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1188   -1.6297   -0.2591 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9055    0.3745    0.9127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1286    1.3222    1.5180 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0210    1.4536   -0.0561 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3571   -0.9528    0.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3839   -0.1852    1.5703 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5668    1.5170   -0.0776 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3656    0.1609   -2.3344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8149    0.0752   -1.6076 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6729   -2.1284   -0.5501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6490   -1.3886    1.0889 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4518   -1.1063   -1.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5666    0.8762    0.1783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5994   -0.0828    1.6777 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2972    2.2435    1.2602 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
  1 11  1  0
  2 12  1  0
  2 13  1  0
  3 14  1  1
  4 15  1  0
  5 16  1  0
  6 17  1  0
  7 18  1  1
  8 19  1  0
  9 20  1  0
  9 21  1  0
 10 22  1  0
M  END
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PDB for HMDB0000568 (D-Arabitol)

HEADER    PROTEIN                                 23-JUN-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: ChEBI                                             
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-JUN-20         0                                  
HETATM    1  C   UNK     0       8.385  -5.669   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.710  -6.453   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.053  -5.686   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.378  -6.471   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.720  -5.704   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       7.043  -6.435   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       9.713  -7.993   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      11.050  -4.146   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      12.380  -8.010   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      13.718  -4.164   0.000  0.00  0.00           O+0
CONECT    1    6    2                                                       
CONECT    2    1    7    3                                                  
CONECT    3    2    8    4                                                  
CONECT    4    3    9    5                                                  
CONECT    5    4   10                                                       
CONECT    6    1                                                            
CONECT    7    2                                                            
CONECT    8    3                                                            
CONECT    9    4                                                            
CONECT   10    5                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   18    0
END
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3D PDB for HMDB0000568 (D-Arabitol)

COMPND    HMDB0000568
HETATM    1  O1  UNL     1       2.849   0.930   0.764  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.847  -0.042   0.567  1.00  0.00           C  
HETATM    3  C2  UNL     1       0.888   0.523  -0.436  1.00  0.00           C  
HETATM    4  O2  UNL     1       1.623   0.768  -1.612  1.00  0.00           O  
HETATM    5  C3  UNL     1      -0.234  -0.386  -0.798  1.00  0.00           C  
HETATM    6  O3  UNL     1       0.333  -1.569  -1.310  1.00  0.00           O  
HETATM    7  C4  UNL     1      -1.141  -0.774   0.309  1.00  0.00           C  
HETATM    8  O4  UNL     1      -2.119  -1.630  -0.259  1.00  0.00           O  
HETATM    9  C5  UNL     1      -1.905   0.375   0.913  1.00  0.00           C  
HETATM   10  O5  UNL     1      -1.129   1.322   1.518  1.00  0.00           O  
HETATM   11  H1  UNL     1       3.021   1.454  -0.056  1.00  0.00           H  
HETATM   12  H2  UNL     1       2.357  -0.953   0.250  1.00  0.00           H  
HETATM   13  H3  UNL     1       1.384  -0.185   1.570  1.00  0.00           H  
HETATM   14  H4  UNL     1       0.567   1.517  -0.078  1.00  0.00           H  
HETATM   15  H5  UNL     1       1.366   0.161  -2.334  1.00  0.00           H  
HETATM   16  H6  UNL     1      -0.815   0.075  -1.608  1.00  0.00           H  
HETATM   17  H7  UNL     1       0.673  -2.128  -0.550  1.00  0.00           H  
HETATM   18  H8  UNL     1      -0.649  -1.389   1.089  1.00  0.00           H  
HETATM   19  H9  UNL     1      -2.452  -1.106  -1.056  1.00  0.00           H  
HETATM   20  H10 UNL     1      -2.567   0.876   0.178  1.00  0.00           H  
HETATM   21  H11 UNL     1      -2.599  -0.083   1.678  1.00  0.00           H  
HETATM   22  H12 UNL     1      -1.297   2.244   1.260  1.00  0.00           H  
CONECT    1    2   11
CONECT    2    3   12   13
CONECT    3    4    5   14
CONECT    4   15
CONECT    5    6    7   16
CONECT    6   17
CONECT    7    8    9   18
CONECT    8   19
CONECT    9   10   20   21
CONECT   10   22
END
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SMILES for HMDB0000568 (D-Arabitol)

OC[C@@H](O)C(O)[C@H](O)CO
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INCHI for HMDB0000568 (D-Arabitol)

InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4-/m1/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
D-ArabinolChEBI
D-LyxitolChEBI
D-ArabinitolKegg
Arabitol, (D)-isomerHMDB
ArabitolHMDB
D-(+)-ArabitolHMDB
(+--)-ArabitolHMDB
DL-ArabitolHMDB
Arabino-pentitolHMDB
LyxitolHMDB
D-ArabitolChEBI
Chemical FormulaC5H12O5
Average Molecular Weight152.1458
Monoisotopic Molecular Weight152.068473494
IUPAC Name(2R,4R)-pentane-1,2,3,4,5-pentol
Traditional Namearabitol
CAS Registry Number488-82-4
SMILES
OC[C@@H](O)C(O)[C@H](O)CO
InChI Identifier
InChI=1S/C5H12O5/c6-1-3(8)5(10)4(9)2-7/h3-10H,1-2H2/t3-,4-/m1/s1
InChI KeyHEBKCHPVOIAQTA-QWWZWVQMSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentSugar alcohols
Alternative Parents
Substituents
  • Sugar alcohol
  • Monosaccharide
  • Secondary alcohol
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
Role
Industrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point101 - 104 °CNot Available
Boiling Point494.53 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility729 mg/mLNot Available
LogP-3.774 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Blood
  • Cerebrospinal Fluid (CSF)
  • Feces
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified115 (32 - 198) uMAdolescent (13-18 years old)MaleRibose-5-Phosphate Isomerase Deficiency details
BloodDetected and Quantified39.4 (0.7-788) uMAdult (>18 years old)Both
Invasive candidiasis		 details
Cerebrospinal Fluid (CSF)Detected and Quantified3342-5535 uMAdolescent (13-18 years old)Both
Ribose-5-Phosphate Isomerase Deficiency		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
UrineDetected and Quantified1021 - 1612 umol/mmol creatinineAdult (>18 years old)Both
Ribose-5-Phosphate Isomerase Deficiency		 details
UrineDetected and Quantified63.837 +/- 87.775 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
Eosinophilic esophagitis
    • Analysis of 30 no...
 details
Associated Disorders and Diseases
Disease References
Ribose-5-phosphate isomerase deficiency
  1. Huck JH, Verhoeven NM, Struys EA, Salomons GS, Jakobs C, van der Knaap MS: Ribose-5-phosphate isomerase deficiency: new inborn error in the pentose phosphate pathway associated with a slowly progressive leukoencephalopathy. Am J Hum Genet. 2004 Apr;74(4):745-51. Epub 2004 Feb 25. [PubMed:14988808 ]
Invasive candidiasis
  1. Kiehn TE, Bernard EM, Gold JW, Armstrong D: Candidiasis: detection by gas-liquid chromatography of D-arabinitol, a fungal metabolite, in human serum. Science. 1979 Nov 2;206(4418):577-80. [PubMed:493963 ]
Colorectal cancer
  1. Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Eosinophilic esophagitis
  1. Slae, M., Huynh, H., Wishart, D.S. (2014). Analysis of 30 normal pediatric urine samples via NMR spectroscopy (unpublished work). NA.
Associated OMIM IDs
  • 608611 (Ribose-5-phosphate isomerase deficiency)
  • 114500 (Colorectal cancer)
  • 610247 (Eosinophilic esophagitis)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB001475
KNApSAcK IDC00052193
Chemspider ID84971
KEGG Compound IDC01904
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkD-arabinitol
METLIN ID5551
PubChem Compound94154
PDB IDNot Available
ChEBI ID18333
Food Biomarker OntologyNot Available
VMH IDABT_D
MarkerDB IDMDB00000189
Good Scents IDrw1233671
References
Synthesis ReferenceDelobeau, Didier; Moine, Didier. Process for the preparation of d-arabitol from lactose. Eur. Pat. Appl. (1997), 9 pp.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kiehn TE, Bernard EM, Gold JW, Armstrong D: Candidiasis: detection by gas-liquid chromatography of D-arabinitol, a fungal metabolite, in human serum. Science. 1979 Nov 2;206(4418):577-80. [PubMed:493963 ]
  2. Klusmann A, Fleischer W, Waldhaus A, Siebler M, Mayatepek E: Influence of D-arabitol and ribitol on neuronal network activity. J Inherit Metab Dis. 2005;28(6):1181-3. [PubMed:16435225 ]
  3. Hui M, Cheung SW, Chin ML, Chu KC, Chan RC, Cheng AF: Development and application of a rapid diagnostic method for invasive Candidiasis by the detection of D-/L-arabinitol using gas chromatography/mass spectrometry. Diagn Microbiol Infect Dis. 2004 Jun;49(2):117-23. doi: 10.1016/j.diagmicrobio.2004.02.006. [PubMed:15183861 ]
  4. Christensson B, Sigmundsdottir G, Larsson L: D-arabinitol--a marker for invasive candidiasis. Med Mycol. 1999 Dec;37(6):391-6. [PubMed:10647119 ]
  5. Kordowska-Wiater M: Production of arabitol by yeasts: current status and future prospects. J Appl Microbiol. 2015 Aug;119(2):303-14. doi: 10.1111/jam.12807. Epub 2015 Apr 8. [PubMed:25809659 ]
  6. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]