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Showing metabocard for 2-Hydroxyadipic acid (HMDB0000321)

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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2023-02-21 17:14:42 UTC
HMDB IDHMDB0000321
Secondary Accession Numbers
  • HMDB00321
Metabolite Identification
Common Name2-Hydroxyadipic acid
Description2-Hydroxyadipic acid is a hydroxy-dicarboxylic acid formed by the reduction of 2-ketoadipic acid. A deficiency of 2-ketoadipic dehydrogenase causes 2-ketoadipic acidemia or 2-oxoadipic acidemia (OMIM: 245130 ), a genetic disorder characterized by accumulation and excretion of 2-hydroxyadipic acid (with 2-ketoadipic and 2-aminoadipic) (OMMBID - The Online Metabolic and Molecular Bases of Inherited Disease, CH.95). When present in sufficiently high levels, 2-hydroxyadipic acid can act as an acidogen and a metabotoxin. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of 2-hydroxyadipic acid are associated with at least three inborn errors of metabolism including 2-oxoadipic acidemia, 2-aminoadipic aciduria, and 2-oxoadipic aciduria. 2-Hydroxyadipic acid is an organic acid. Abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic acidosis. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis, the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart abnormalities, kidney abnormalities, liver damage, seizures, coma, and possibly death. These are also the characteristic symptoms of the untreated IEMs mentioned above. Many affected children with organic acidemias experience intellectual disability or delayed development. In adults, acidosis or acidemia is characterized by headaches, confusion, feeling tired, tremors, sleepiness, and seizures.
Structure
Thumb
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0000321 (2-Hydroxyadipic acid)

  Mrv1652305261923542D          

 11 10  0  0  0  0            999 V2000
 9997.5515 9998.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8368 9997.7078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.1221 9998.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.4074 9997.7078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.1221 9998.9445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8368 9996.8826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2654 9997.7078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9809 9998.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6963 9997.7078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.4097 9998.1199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6963 9996.8826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  2  6  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
M  END
Download

3D MOL for HMDB0000321 (2-Hydroxyadipic acid)

HMDB0000321
     RDKit          3D
2-Hydroxyadipic acid
 21 20  0  0  0  0  0  0  0  0999 V2000
   -2.9239    0.3247    1.3623 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7693   -0.0327    0.1608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4798    0.6570   -0.8155 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8476   -1.1542   -0.1256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4763   -0.9051    0.4854 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1018    0.3375   -0.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4750    0.6909    0.4157 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8607    1.8641   -0.2653 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4852   -0.3494    0.1811 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4282   -1.5105    0.6743 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5865   -0.0656   -0.6349 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2409    1.6400   -0.9536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7566   -1.2320   -1.2264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1736   -2.1246    0.2823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1516   -1.7707    0.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5182   -0.8515    1.5840 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1931    0.1836   -1.2346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5586    1.2137    0.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4088    0.8913    1.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7176    1.6401   -1.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3363    0.5532   -0.2929 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
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  0
  5 16  1  0
  6 17  1  0
  6 18  1  0
  7 19  1  0
  8 20  1  0
 11 21  1  0
M  END
Download

3D SDF for HMDB0000321 (2-Hydroxyadipic acid)

  Mrv1652305261923542D          

 11 10  0  0  0  0            999 V2000
 9997.5515 9998.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8368 9997.7078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.1221 9998.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.4074 9997.7078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.1221 9998.9445    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.8368 9996.8826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2654 9997.7078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9809 9998.1199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6963 9997.7078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.4097 9998.1199    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6963 9996.8826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  7  1  0  0  0  0
  2  3  1  0  0  0  0
  2  6  1  0  0  0  0
  3  4  1  0  0  0  0
  3  5  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0000321

> <DATABASE_NAME>
hmdb

> <SMILES>
OC(CCCC(O)=O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C6H10O5/c7-4(6(10)11)2-1-3-5(8)9/h4,7H,1-3H2,(H,8,9)(H,10,11)

> <INCHI_KEY>
OTTXIFWBPRRYOG-UHFFFAOYSA-N

> <FORMULA>
C6H10O5

> <MOLECULAR_WEIGHT>
162.1406

> <EXACT_MASS>
162.05282343

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
14.876466136336678

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxyhexanedioic acid

> <ALOGPS_LOGP>
-0.79

> <JCHEM_LOGP>
-0.3804115579999999

> <ALOGPS_LOGS>
-0.36

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
4.304936769181927

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.435316368213932

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7978986375206967

> <JCHEM_POLAR_SURFACE_AREA>
94.82999999999998

> <JCHEM_REFRACTIVITY>
34.2312

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.03e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-hydroxyadipic acid

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for HMDB0000321 (2-Hydroxyadipic acid)

HMDB0000321
     RDKit          3D
2-Hydroxyadipic acid
 21 20  0  0  0  0  0  0  0  0999 V2000
   -2.9239    0.3247    1.3623 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7693   -0.0327    0.1608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4798    0.6570   -0.8155 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8476   -1.1542   -0.1256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4763   -0.9051    0.4854 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1018    0.3375   -0.1275 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4750    0.6909    0.4157 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8607    1.8641   -0.2653 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4852   -0.3494    0.1811 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4282   -1.5105    0.6743 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5865   -0.0656   -0.6349 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2409    1.6400   -0.9536 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7566   -1.2320   -1.2264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1736   -2.1246    0.2823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1516   -1.7707    0.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5182   -0.8515    1.5840 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1931    0.1836   -1.2346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5586    1.2137    0.1033 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4088    0.8913    1.5084 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7176    1.6401   -1.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3363    0.5532   -0.2929 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
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  2  0
  9 11  1  0
  3 12  1  0
  4 13  1  0
  4 14  1  0
  5 15  1  0
  5 16  1  0
  6 17  1  0
  6 18  1  0
  7 19  1  0
  8 20  1  0
 11 21  1  0
M  END
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PDB for HMDB0000321 (2-Hydroxyadipic 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    8662.0968663.157   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8660.7628662.388   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8659.4288663.157   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0    8658.0948662.388   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8659.4288664.696   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8660.7628660.848   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8663.4298662.388   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8664.7648663.157   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8666.1008662.388   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0    8667.4318663.157   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8666.1008660.848   0.000  0.00  0.00           O+0
CONECT    1    2    7                                                       
CONECT    2    1    3    6                                                  
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    2                                                            
CONECT    7    1    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
MASTER        0    0    0    0    0    0    0    0   11    0   20    0
END
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3D PDB for HMDB0000321 (2-Hydroxyadipic acid)

COMPND    HMDB0000321
HETATM    1  O1  UNL     1      -2.924   0.325   1.362  1.00  0.00           O  
HETATM    2  C1  UNL     1      -2.769  -0.033   0.161  1.00  0.00           C  
HETATM    3  O2  UNL     1      -3.480   0.657  -0.816  1.00  0.00           O  
HETATM    4  C2  UNL     1      -1.848  -1.154  -0.126  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.476  -0.905   0.485  1.00  0.00           C  
HETATM    6  C4  UNL     1       0.102   0.338  -0.128  1.00  0.00           C  
HETATM    7  C5  UNL     1       1.475   0.691   0.416  1.00  0.00           C  
HETATM    8  O3  UNL     1       1.861   1.864  -0.265  1.00  0.00           O  
HETATM    9  C6  UNL     1       2.485  -0.349   0.181  1.00  0.00           C  
HETATM   10  O4  UNL     1       2.428  -1.511   0.674  1.00  0.00           O  
HETATM   11  O5  UNL     1       3.586  -0.066  -0.635  1.00  0.00           O  
HETATM   12  H1  UNL     1      -3.241   1.640  -0.954  1.00  0.00           H  
HETATM   13  H2  UNL     1      -1.757  -1.232  -1.226  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.174  -2.125   0.282  1.00  0.00           H  
HETATM   15  H4  UNL     1       0.152  -1.771   0.204  1.00  0.00           H  
HETATM   16  H5  UNL     1      -0.518  -0.851   1.584  1.00  0.00           H  
HETATM   17  H6  UNL     1       0.193   0.184  -1.235  1.00  0.00           H  
HETATM   18  H7  UNL     1      -0.559   1.214   0.103  1.00  0.00           H  
HETATM   19  H8  UNL     1       1.409   0.891   1.508  1.00  0.00           H  
HETATM   20  H9  UNL     1       1.718   1.640  -1.215  1.00  0.00           H  
HETATM   21  H10 UNL     1       4.336   0.553  -0.293  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   12
CONECT    4    5   13   14
CONECT    5    6   15   16
CONECT    6    7   17   18
CONECT    7    8    9   19
CONECT    8   20
CONECT    9   10   10   11
CONECT   11   21
END
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SMILES for HMDB0000321 (2-Hydroxyadipic acid)

OC(CCCC(O)=O)C(O)=O
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INCHI for HMDB0000321 (2-Hydroxyadipic acid)

InChI=1S/C6H10O5/c7-4(6(10)11)2-1-3-5(8)9/h4,7H,1-3H2,(H,8,9)(H,10,11)
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
2-HydroxyadipateChEBI
2-Hydroxyhexanedioic acidChEBI
2-HydroxyhexanedioateGenerator
2,3,4-TrideoxyhexarateHMDB
2,3,4-Trideoxyhexaric acidHMDB
2-Hydroxy-adipateHMDB
2-Hydroxy-adipic acidHMDB
2-Hydroxy-hexanedioateHMDB
2-Hydroxy-hexanedioic acidHMDB
a-HydroxyadipateHMDB
a-Hydroxyadipic acidHMDB
alpha-HydroxyadipateHMDB
alpha-Hydroxyadipic acidHMDB
DL-2-HydroxyadipateHMDB
DL-2-Hydroxyadipic acidHMDB
Chemical FormulaC6H10O5
Average Molecular Weight162.1406
Monoisotopic Molecular Weight162.05282343
IUPAC Name2-hydroxyhexanedioic acid
Traditional Nameα-hydroxyadipic acid
CAS Registry Number18294-85-4
SMILES
OC(CCCC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C6H10O5/c7-4(6(10)11)2-1-3-5(8)9/h4,7H,1-3H2,(H,8,9)(H,10,11)
InChI KeyOTTXIFWBPRRYOG-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Hydroxy fatty acid
  • Monosaccharide
  • Hydroxy acid
  • Dicarboxylic acid or derivatives
  • Alpha-hydroxy acid
  • Secondary alcohol
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Alcohol
  • Carbonyl group
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Physiological effect
Health effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological roleIndirect biological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm (predicted from logP)
Biospecimen Locations
  • Blood
  • Feces
  • Urine
Tissue Locations
  • Placenta
Pathways
Normal Concentrations
Abnormal Concentrations
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ]
  2. 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 ]
2-Ketoadipic acidemia
  1. Peng H, Shinka T, Inoue Y, Mitsubuchi H, Ishimatsu J, Yoshino M, Kuhara T: Asymptomatic alpha-ketoadipic aciduria detected during a pilot study of neonatal urine screening. Acta Paediatr. 1999 Aug;88(8):911-4. [PubMed:10503694 ]
  2. G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.
Alpha-aminoadipic aciduria
  1. Gray RG, O'Neill EM, Pollitt RJ: Alpha-aminoadipic aciduria: chemical and enzymatic studies. J Inherit Metab Dis. 1980;2(4):89-92. [PubMed:6796766 ]
Associated OMIM IDs
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021947
KNApSAcK IDNot Available
Chemspider ID167943
KEGG Compound IDC02360
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5310
PubChem Compound193530
PDB IDNot Available
ChEBI ID17023
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDMDB00000145
Good Scents IDNot Available
References
Synthesis ReferenceGriot, Rudolf. a-Hydroxyadipic acid. Helvetica Chimica Acta (1958), 41 2236-41.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. [PubMed:8087979 ]
  2. Sewell AC, Heil M, Podebrad F, Mosandl A: Chiral compounds in metabolism: a look in the molecular mirror. Eur J Pediatr. 1998 Mar;157(3):185-91. [PubMed:9537483 ]
  3. Inoue Y, Shinka T, Ohse M, Kuhara T: Differential chemical diagnosis of primary hyperoxaluria type II. Highly sensitive analysis of optical isomers of glyceric acid by GC/MS as diastereoisomeric derivatives. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Aug 25;823(1):2-6. Epub 2005 Apr 25. [PubMed:16055048 ]
  4. Svendsen JS, Whist JE, Sydnes LK: Absolute configuration of 3-hydroxyadipic acid in human urine. J Chromatogr. 1985 Jan 11;337(1):9-19. [PubMed:3980660 ]
  5. 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 ]