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Showing metabocard for D-Malic acid (HMDB0031518)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2012-09-11 17:43:47 UTC
Update Date2022-03-07 02:53:00 UTC
HMDB IDHMDB0031518
Secondary Accession Numbers
  • HMDB31518
Metabolite Identification
Common NameD-Malic acid
DescriptionD-Malic acid, also known as D-malate, belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. D-Malic acid exists in all living organisms, ranging from bacteria to humans. D-Malic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on D-Malic acid.
Structure
Data?1563862135
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0031518 (D-Malic acid)


  Mrv1652309042000372D          

  9  8  0  0  1  0            999 V2000
    1.9520    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  2  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
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
M  END
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3D MOL for HMDB0031518 (D-Malic acid)

HMDB0031518
     RDKit          3D
D-Malic acid
 15 14  0  0  0  0  0  0  0  0999 V2000
    2.0504    0.7596    1.1777 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8937   -0.0449    0.2252 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0371   -0.5643   -0.3634 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5269   -0.4093   -0.2334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5027    0.3175    0.6025 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3496    1.6988    0.4911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8655   -0.0597    0.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6927    0.8055   -0.1350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2942   -1.3801    0.2406 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6754    0.0445   -0.8819 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4150   -0.2139   -1.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3767   -1.4995   -0.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3047    0.0747    1.6749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7878    2.0657   -0.3069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1780   -1.5946    0.7012 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
  5  7  1  0
  7  8  2  0
  7  9  1  0
  3 10  1  0
  4 11  1  0
  4 12  1  0
  5 13  1  1
  6 14  1  0
  9 15  1  0
M  END
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3D SDF for HMDB0031518 (D-Malic acid)


  Mrv1652309042000372D          

  9  8  0  0  1  0            999 V2000
    1.9520    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    1.1270    0.0000 C   0  0  2  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
    0.5230    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.7145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5230    1.9520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3809    1.1270    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6664   -0.1105    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031518

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/t2-/m1/s1

> <INCHI_KEY>
BJEPYKJPYRNKOW-UWTATZPHSA-N

> <FORMULA>
C4H6O5

> <MOLECULAR_WEIGHT>
134.0874

> <EXACT_MASS>
134.021523302

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
10.926494198525464

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-2-hydroxybutanedioic acid

> <ALOGPS_LOGP>
-0.87

> <JCHEM_LOGP>
-1.1136414279999998

> <ALOGPS_LOGS>
0.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.127730317344291

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1983571934669475

> <JCHEM_PKA_STRONGEST_BASIC>
-3.913035238851454

> <JCHEM_POLAR_SURFACE_AREA>
94.83000000000001

> <JCHEM_REFRACTIVITY>
24.8752

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.18e+02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
.+-.-malic acid

> <JCHEM_VEBER_RULE>
0

$$$$
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3D-SDF for HMDB0031518 (D-Malic acid)

HMDB0031518
     RDKit          3D
D-Malic acid
 15 14  0  0  0  0  0  0  0  0999 V2000
    2.0504    0.7596    1.1777 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8937   -0.0449    0.2252 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0371   -0.5643   -0.3634 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5269   -0.4093   -0.2334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5027    0.3175    0.6025 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.3496    1.6988    0.4911 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8655   -0.0597    0.2219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6927    0.8055   -0.1350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2942   -1.3801    0.2406 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6754    0.0445   -0.8819 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4150   -0.2139   -1.3055 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3767   -1.4995   -0.0757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3047    0.0747    1.6749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7878    2.0657   -0.3069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1780   -1.5946    0.7012 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
  5  7  1  0
  7  8  2  0
  7  9  1  0
  3 10  1  0
  4 11  1  0
  4 12  1  0
  5 13  1  1
  6 14  1  0
  9 15  1  0
M  END
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PDB for HMDB0031518 (D-Malic acid)

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  O   UNK     0       3.644   3.644   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       3.644   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  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.357   1.334   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       0.976   3.644   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       6.311   2.104   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0       4.977  -0.206   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    2    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for HMDB0031518 (D-Malic acid)

COMPND    HMDB0031518
HETATM    1  O1  UNL     1       2.050   0.760   1.178  1.00  0.00           O  
HETATM    2  C1  UNL     1       1.894  -0.045   0.225  1.00  0.00           C  
HETATM    3  O2  UNL     1       3.037  -0.564  -0.363  1.00  0.00           O  
HETATM    4  C2  UNL     1       0.527  -0.409  -0.233  1.00  0.00           C  
HETATM    5  C3  UNL     1      -0.503   0.318   0.603  1.00  0.00           C  
HETATM    6  O3  UNL     1      -0.350   1.699   0.491  1.00  0.00           O  
HETATM    7  C4  UNL     1      -1.866  -0.060   0.222  1.00  0.00           C  
HETATM    8  O4  UNL     1      -2.693   0.805  -0.135  1.00  0.00           O  
HETATM    9  O5  UNL     1      -2.294  -1.380   0.241  1.00  0.00           O  
HETATM   10  H1  UNL     1       3.675   0.044  -0.882  1.00  0.00           H  
HETATM   11  H2  UNL     1       0.415  -0.214  -1.305  1.00  0.00           H  
HETATM   12  H3  UNL     1       0.377  -1.499  -0.076  1.00  0.00           H  
HETATM   13  H4  UNL     1      -0.305   0.075   1.675  1.00  0.00           H  
HETATM   14  H5  UNL     1      -0.788   2.066  -0.307  1.00  0.00           H  
HETATM   15  H6  UNL     1      -3.178  -1.595   0.701  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   10
CONECT    4    5   11   12
CONECT    5    6    7   13
CONECT    6   14
CONECT    7    8    8    9
CONECT    9   15
END
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SMILES for HMDB0031518 (D-Malic acid)

O[C@H](CC(O)=O)C(O)=O
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INCHI for HMDB0031518 (D-Malic acid)

InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/t2-/m1/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
(+)-D-Malic acidChEBI
(R)-2-Hydroxybutanedioic acidChEBI
2-HYDROXY-succinIC ACIDChEBI
D-MalateKegg
(+)-D-MalateGenerator
(R)-2-HydroxybutanedioateGenerator
2-HYDROXY-succinateGenerator
(R)-MalateHMDB
(R)-Hydroxybutanedioic acidHMDB
D-(+)-Malic acidHMDB
D-Hydroxybutanedioic acidHMDB
Hydroxy-(R)-butanedioic acidHMDB
R-Malic acidHMDB
D-Malic acidChEBI
Chemical FormulaC4H6O5
Average Molecular Weight134.0874
Monoisotopic Molecular Weight134.021523302
IUPAC Name(2R)-2-hydroxybutanedioic acid
Traditional Name.+-.-malic acid
CAS Registry Number636-61-3
SMILES
O[C@H](CC(O)=O)C(O)=O
InChI Identifier
InChI=1S/C4H6O5/c5-2(4(8)9)1-3(6)7/h2,5H,1H2,(H,6,7)(H,8,9)/t2-/m1/s1
InChI KeyBJEPYKJPYRNKOW-UWTATZPHSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassBeta hydroxy acids and derivatives
Direct ParentBeta hydroxy acids and derivatives
Alternative Parents
Substituents
  • Short-chain hydroxy acid
  • Beta-hydroxy acid
  • Fatty acid
  • Dicarboxylic acid or derivatives
  • Alpha-hydroxy acid
  • Secondary alcohol
  • 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
Ontology
Physiological effectNot Available
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Biological roleIndustrial application
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point101 °CNot Available
Boiling Point306.00 to 307.00 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility364 mg/mL at 20 °CNot Available
LogP-1.26Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-Baker120.67930932474
[M-H]-Not Available120.679http://allccs.zhulab.cn/database/detail?ID=AllCCS00001764
Predicted Molecular Properties
PropertyValueSource
Water Solubility218 g/LALOGPS
logP-0.87ALOGPS
logP-1.1ChemAxon
logS0.21ALOGPS
pKa (Strongest Acidic)3.2ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area94.83 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity24.88 m³·mol⁻¹ChemAxon
Polarizability10.93 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+128.01731661259
DarkChem[M-H]-121.64831661259
DeepCCS[M+H]+122.15430932474
DeepCCS[M-H]-118.5630932474
DeepCCS[M-2H]-155.82930932474
DeepCCS[M+Na]+130.86130932474
AllCCS[M+H]+131.932859911
AllCCS[M+H-H2O]+127.832859911
AllCCS[M+NH4]+135.732859911
AllCCS[M+Na]+136.832859911
AllCCS[M-H]-122.732859911
AllCCS[M+Na-2H]-125.332859911
AllCCS[M+HCOO]-128.232859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.1.06 minutes32390414
Predicted by Siyang on May 30, 20229.619 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20225.66 minutes32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid307.2 seconds40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid708.2 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid364.2 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid46.7 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid233.7 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid86.3 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid278.3 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid249.7 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)578.4 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid609.1 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid55.1 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid830.5 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid226.3 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid294.2 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate780.7 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA308.4 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water459.4 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
D-Malic acidO[C@H](CC(O)=O)C(O)=O2199.2Standard polar33892256
D-Malic acidO[C@H](CC(O)=O)C(O)=O1008.0Standard non polar33892256
D-Malic acidO[C@H](CC(O)=O)C(O)=O1328.4Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
D-Malic acid,1TMS,isomer #1C[Si](C)(C)O[C@H](CC(=O)O)C(=O)O1317.5Semi standard non polar33892256
D-Malic acid,1TMS,isomer #2C[Si](C)(C)OC(=O)C[C@@H](O)C(=O)O1311.4Semi standard non polar33892256
D-Malic acid,1TMS,isomer #3C[Si](C)(C)OC(=O)[C@H](O)CC(=O)O1279.0Semi standard non polar33892256
D-Malic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)C[C@@H](O[Si](C)(C)C)C(=O)O1404.0Semi standard non polar33892256
D-Malic acid,2TMS,isomer #2C[Si](C)(C)OC(=O)[C@@H](CC(=O)O)O[Si](C)(C)C1376.6Semi standard non polar33892256
D-Malic acid,2TMS,isomer #3C[Si](C)(C)OC(=O)C[C@@H](O)C(=O)O[Si](C)(C)C1382.5Semi standard non polar33892256
D-Malic acid,3TMS,isomer #1C[Si](C)(C)OC(=O)C[C@@H](O[Si](C)(C)C)C(=O)O[Si](C)(C)C1498.5Semi standard non polar33892256
D-Malic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)O[C@H](CC(=O)O)C(=O)O1572.3Semi standard non polar33892256
D-Malic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)C[C@@H](O)C(=O)O1571.3Semi standard non polar33892256
D-Malic acid,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)[C@H](O)CC(=O)O1555.1Semi standard non polar33892256
D-Malic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O1851.7Semi standard non polar33892256
D-Malic acid,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)[C@@H](CC(=O)O)O[Si](C)(C)C(C)(C)C1836.9Semi standard non polar33892256
D-Malic acid,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)OC(=O)C[C@@H](O)C(=O)O[Si](C)(C)C(C)(C)C1825.4Semi standard non polar33892256
D-Malic acid,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)C[C@@H](O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C2116.5Semi standard non polar33892256
Spectra
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Colorectal cancer		 details
Associated Disorders and Diseases
Disease References
Colorectal cancer
  1. Sinha R, Ahn J, Sampson JN, Shi J, Yu G, Xiong X, Hayes RB, Goedert JJ: Fecal Microbiota, Fecal Metabolome, and Colorectal Cancer Interrelations. PLoS One. 2016 Mar 25;11(3):e0152126. doi: 10.1371/journal.pone.0152126. eCollection 2016. [PubMed:27015276 ]
  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 ]
Associated OMIM IDs
DrugBank IDDB03499
Phenol Explorer Compound IDNot Available
FooDB IDFDB008115
KNApSAcK IDNot Available
Chemspider ID83793
KEGG Compound IDC00497
BioCyc IDCPD-660
BiGG IDNot Available
Wikipedia LinkMalic_acid
METLIN IDNot Available
PubChem Compound92824
PDB IDDMR
ChEBI ID30796
Food Biomarker OntologyNot Available
VMH IDMAL_D
MarkerDB IDNot Available
Good Scents IDrw1107901
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
  3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
  4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
  5. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
  6. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.