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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:37:48 UTC

Update Date

2022-03-07 02:56:07 UTC

HMDB ID

HMDB0039246

Secondary Accession Numbers

HMDB39246

Metabolite Identification

Common Name

6'-Malonyltrifolirhizin

Description

6'-Malonyltrifolirhizin belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids. 6'-Malonyltrifolirhizin has been detected, but not quantified in, pulses. This could make 6'-malonyltrifolirhizin a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on 6'-Malonyltrifolirhizin.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 05061310572D          

 38 43  0  0  0  0            999 V2000
    0.9678    2.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7908    2.3914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0671    0.9086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0288    0.8705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0867    2.5195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1334   -1.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1743    0.3392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5867   -0.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0405    1.6253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6059    1.5926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2519    1.7074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3292    1.3079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5361    1.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8901    0.9659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3582    2.1324    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7573    1.2577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7863    2.0822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7637   -0.0049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4795   -0.6316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0749    1.7647    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5789    0.7938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3182   -2.4013    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.0184   -1.3157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7053    0.1672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.3513    0.2819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9485   -0.8037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5325    0.9754    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.5794    2.3094    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2171    1.5353    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5830    2.4147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4019    0.7365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
 10  1  1  0  0  0  0
 10  3  2  0  0  0  0
 11  2  1  0  0  0  0
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 13  7  1  0  0  0  0
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 16  4  1  0  0  0  0
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 36 25  1  0  0  0  0
 37 15  1  0  0  0  0
 37 24  1  0  0  0  0
 38 18  1  0  0  0  0
 38 25  1  0  0  0  0
M  END

HMDB0039246
     RDKit          3D
6'-Malonyltrifolirhizin
 62 67  0  0  0  0  0  0  0  0999 V2000
   -7.2019    1.0455    0.8321 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6866    0.1030    1.4876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6159    0.0929    2.8663 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3381   -1.0188    0.7890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4610   -1.4368   -0.3366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8631   -2.3265   -1.1097 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2237   -0.8909   -0.5655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4330   -1.3441   -1.6366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0951   -0.5289   -1.5765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5563   -0.7782   -0.3537 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6215    0.1303    0.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5009    0.0969   -0.7779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2287   -0.1198   -0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1466   -0.3700    0.9772 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4848   -0.5748    1.3446 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4703   -0.5255    0.3899 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.4374   -0.3485   -0.1162 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.7306    0.3656    1.4253 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.8568   -0.7338    0.8025 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2808    1.3643    2.3297 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3380    0.5955    1.7719 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8206    0.3076    0.4671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1359    1.5666    0.0829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0443    1.7553    1.1085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7180    1.9607   -1.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0
  2  3  1  0
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  4  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
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 19 20  1  0
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 25 30  1  0
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 31 32  1  0
 11 33  1  0
 33 34  1  0
 33 35  1  0
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 37  9  1  0
 18 13  1  0
 29 21  1  0
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 32 24  1  0
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 37 61  1  0
 38 62  1  0
M  END


  Mrv0541 05061310572D          

 38 43  0  0  0  0            999 V2000
    0.9678    2.3341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7908    2.3914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0671    0.9086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0288    0.8705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0867    2.5195    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1334   -1.6025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1743    0.3392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5867   -0.0623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0405    1.6253    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6059    1.5926    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2519    1.7074    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3292    1.3079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5361    1.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.4019    0.7365    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0  0  0  0
 10  1  1  0  0  0  0
 10  3  2  0  0  0  0
 11  2  1  0  0  0  0
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 13  7  1  0  0  0  0
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 31 23  1  0  0  0  0
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 32 14  1  0  0  0  0
 33  8  1  0  0  0  0
 33 20  1  0  0  0  0
 34  9  1  0  0  0  0
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 35  9  1  0  0  0  0
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M  END
> <DATABASE_ID>
HMDB0039246

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1C(COC(=O)CC(O)=O)OC(OC2=CC3=C(C=C2)C2OC4=CC5=C(OCO5)C=C4C2CO3)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H24O13/c26-19(27)6-20(28)33-8-18-21(29)22(30)23(31)25(38-18)36-10-1-2-11-14(3-10)32-7-13-12-4-16-17(35-9-34-16)5-15(12)37-24(11)13/h1-5,13,18,21-25,29-31H,6-9H2,(H,26,27)

> <INCHI_KEY>
ZHXRWFOBROFZAC-UHFFFAOYSA-N

> <FORMULA>
C25H24O13

> <MOLECULAR_WEIGHT>
532.4503

> <EXACT_MASS>
532.121690854

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_AVERAGE_POLARIZABILITY>
50.96406814622962

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-oxo-3-[(3,4,5-trihydroxy-6-{5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-2,4(8),9,13(18),14,16-hexaen-16-yloxy}oxan-2-yl)methoxy]propanoic acid

> <ALOGPS_LOGP>
0.36

> <JCHEM_LOGP>
0.35541389266666695

> <ALOGPS_LOGS>
-2.83

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.201707345883293

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.399538612934885

> <JCHEM_PKA_STRONGEST_BASIC>
-3.64910302537729

> <JCHEM_POLAR_SURFACE_AREA>
179.66999999999996

> <JCHEM_REFRACTIVITY>
120.00479999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.92e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-oxo-3-[(3,4,5-trihydroxy-6-{5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-2,4(8),9,13(18),14,16-hexaen-16-yloxy}oxan-2-yl)methoxy]propanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0039246
     RDKit          3D
6'-Malonyltrifolirhizin
 62 67  0  0  0  0  0  0  0  0999 V2000
   -7.2019    1.0455    0.8321 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6866    0.1030    1.4876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6159    0.0929    2.8663 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3381   -1.0188    0.7890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4610   -1.4368   -0.3366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8631   -2.3265   -1.1097 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2237   -0.8909   -0.5655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4330   -1.3441   -1.6366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0951   -0.5289   -1.5765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5563   -0.7782   -0.3537 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6215    0.1303    0.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5009    0.0969   -0.7779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2287   -0.1198   -0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1466   -0.3700    0.9772 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4848   -0.5748    1.3446 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4703   -0.5255    0.3899 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1294   -0.2786   -0.9051 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7991   -0.0780   -1.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1354   -0.2207   -1.9077 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4607    0.1037   -1.4766 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8482   -0.8063   -0.3278 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0934   -0.2851    0.2706 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4374   -0.3485   -0.1162 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4320    0.2290    0.6300 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0801    0.8784    1.7807 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7646    0.9450    2.1691 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7306    0.3656    1.4253 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3613    0.3015    1.6024 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8568   -0.7338    0.8025 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2808    1.3643    2.3297 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3380    0.5955    1.7719 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8206    0.3076    0.4671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1359    1.5666    0.0829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0443    1.7553    1.1085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7180    1.9607   -1.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7353    2.4785   -2.1233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4767    0.8567   -1.9007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2971    1.0147   -3.3018 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9342   -0.5488    3.3027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4702   -1.9052    1.4326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3652   -0.7102    0.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1550   -2.3898   -1.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8432   -1.1302   -2.6399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4835   -1.0088   -2.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3683   -0.0731    1.1365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6090   -0.4125    1.7490 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6564   -0.7675    2.3925 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5286    0.1210   -2.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1944   -0.0048   -2.2761 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4021    1.1603   -1.1618 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9669   -1.8517   -0.6986 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6527   -0.8790   -1.0388 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5180    1.4578    3.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9880   -1.6777    1.3975 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2963    1.1363    1.7301 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3825   -0.3638    2.2894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2608    2.2131    0.2667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7663    2.4465    1.7534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4086    2.8037   -1.0620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1541    1.7232   -2.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5755    1.0071   -1.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6290    0.3581   -3.6108 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  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 25 30  1  0
 30 31  1  0
 31 32  1  0
 11 33  1  0
 33 34  1  0
 33 35  1  0
 35 36  1  0
 35 37  1  0
 37 38  1  0
 37  9  1  0
 18 13  1  0
 29 21  1  0
 29 16  1  0
 27 22  1  0
 32 24  1  0
  3 39  1  0
  4 40  1  0
  4 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
 11 45  1  0
 14 46  1  0
 15 47  1  0
 18 48  1  0
 20 49  1  0
 20 50  1  0
 21 51  1  0
 23 52  1  0
 26 53  1  0
 29 54  1  0
 31 55  1  0
 31 56  1  0
 33 57  1  0
 34 58  1  0
 35 59  1  0
 36 60  1  0
 37 61  1  0
 38 62  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       1.807   4.357   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.343   4.464   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.992   1.696   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.387   1.625   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.495   4.703   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.716  -2.991   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.925   0.633   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.829  -0.116   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.142   3.034   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.131   2.973   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.204   3.187   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.081   2.441   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.601   2.017   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.528   1.803   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.135   3.980   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.747   2.348   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.801   3.887   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.292  -0.009   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -9.252  -3.098   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -7.040  -1.607   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.431  -1.286   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.895  -1.179   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.220   0.205   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.740   3.294   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.081   1.482   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -9.927  -4.482   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0     -10.113  -1.821   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      -7.901  -0.330   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -3.107  -2.670   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -0.034  -2.456   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       1.317   0.312   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       4.389   0.526   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -5.504  -1.500   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      12.194   1.821   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      12.282   4.311   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      -0.405   2.866   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       6.688   4.507   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      -2.617   1.375   0.000  0.00  0.00           O+0
CONECT    1    2   10                                                       
CONECT    2    1   11                                                       
CONECT    3   10   14                                                       
CONECT    4   12   16                                                       
CONECT    5   15   17                                                       
CONECT    6   19   20                                                       
CONECT    7   13   32                                                       
CONECT    8   18   33                                                       
CONECT    9   34   35                                                       
CONECT   10    1    3   36                                                  
CONECT   11    2   14   24                                                  
CONECT   12    4   13   15                                                  
CONECT   13    7   12   24                                                  
CONECT   14    3   11   32                                                  
CONECT   15    5   12   37                                                  
CONECT   16    4   17   34                                                  
CONECT   17    5   16   35                                                  
CONECT   18    8   21   38                                                  
CONECT   19    6   26   27                                                  
CONECT   20    6   28   33                                                  
CONECT   21   18   22   29                                                  
CONECT   22   21   23   30                                                  
CONECT   23   22   25   31                                                  
CONECT   24   11   13   37                                                  
CONECT   25   23   36   38                                                  
CONECT   26   19                                                            
CONECT   27   19                                                            
CONECT   28   20                                                            
CONECT   29   21                                                            
CONECT   30   22                                                            
CONECT   31   23                                                            
CONECT   32    7   14                                                       
CONECT   33    8   20                                                       
CONECT   34    9   16                                                       
CONECT   35    9   17                                                       
CONECT   36   10   25                                                       
CONECT   37   15   24                                                       
CONECT   38   18   25                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   86    0
END

COMPND    HMDB0039246
HETATM    1  O1  UNL     1      -7.202   1.046   0.832  1.00  0.00           O  
HETATM    2  C1  UNL     1      -7.687   0.103   1.488  1.00  0.00           C  
HETATM    3  O2  UNL     1      -7.616   0.093   2.866  1.00  0.00           O  
HETATM    4  C2  UNL     1      -8.338  -1.019   0.789  1.00  0.00           C  
HETATM    5  C3  UNL     1      -7.461  -1.437  -0.337  1.00  0.00           C  
HETATM    6  O3  UNL     1      -7.863  -2.326  -1.110  1.00  0.00           O  
HETATM    7  O4  UNL     1      -6.224  -0.891  -0.565  1.00  0.00           O  
HETATM    8  C4  UNL     1      -5.433  -1.344  -1.637  1.00  0.00           C  
HETATM    9  C5  UNL     1      -4.095  -0.529  -1.577  1.00  0.00           C  
HETATM   10  O5  UNL     1      -3.556  -0.778  -0.354  1.00  0.00           O  
HETATM   11  C6  UNL     1      -2.621   0.130   0.043  1.00  0.00           C  
HETATM   12  O6  UNL     1      -1.501   0.097  -0.778  1.00  0.00           O  
HETATM   13  C7  UNL     1      -0.229  -0.120  -0.313  1.00  0.00           C  
HETATM   14  C8  UNL     1       0.147  -0.370   0.977  1.00  0.00           C  
HETATM   15  C9  UNL     1       1.485  -0.575   1.345  1.00  0.00           C  
HETATM   16  C10 UNL     1       2.470  -0.526   0.390  1.00  0.00           C  
HETATM   17  C11 UNL     1       2.129  -0.279  -0.905  1.00  0.00           C  
HETATM   18  C12 UNL     1       0.799  -0.078  -1.260  1.00  0.00           C  
HETATM   19  O7  UNL     1       3.135  -0.221  -1.908  1.00  0.00           O  
HETATM   20  C13 UNL     1       4.461   0.104  -1.477  1.00  0.00           C  
HETATM   21  C14 UNL     1       4.848  -0.806  -0.328  1.00  0.00           C  
HETATM   22  C15 UNL     1       6.093  -0.285   0.271  1.00  0.00           C  
HETATM   23  C16 UNL     1       7.437  -0.349  -0.116  1.00  0.00           C  
HETATM   24  C17 UNL     1       8.432   0.229   0.630  1.00  0.00           C  
HETATM   25  C18 UNL     1       8.080   0.878   1.781  1.00  0.00           C  
HETATM   26  C19 UNL     1       6.765   0.945   2.169  1.00  0.00           C  
HETATM   27  C20 UNL     1       5.731   0.366   1.425  1.00  0.00           C  
HETATM   28  O8  UNL     1       4.361   0.302   1.602  1.00  0.00           O  
HETATM   29  C21 UNL     1       3.857  -0.734   0.802  1.00  0.00           C  
HETATM   30  O9  UNL     1       9.281   1.364   2.330  1.00  0.00           O  
HETATM   31  C22 UNL     1      10.338   0.596   1.772  1.00  0.00           C  
HETATM   32  O10 UNL     1       9.821   0.308   0.467  1.00  0.00           O  
HETATM   33  C23 UNL     1      -3.136   1.567   0.083  1.00  0.00           C  
HETATM   34  O11 UNL     1      -4.044   1.755   1.109  1.00  0.00           O  
HETATM   35  C24 UNL     1      -3.718   1.961  -1.256  1.00  0.00           C  
HETATM   36  O12 UNL     1      -2.735   2.478  -2.123  1.00  0.00           O  
HETATM   37  C25 UNL     1      -4.477   0.857  -1.901  1.00  0.00           C  
HETATM   38  O13 UNL     1      -4.297   1.015  -3.302  1.00  0.00           O  
HETATM   39  H1  UNL     1      -6.934  -0.549   3.303  1.00  0.00           H  
HETATM   40  H2  UNL     1      -8.470  -1.905   1.433  1.00  0.00           H  
HETATM   41  H3  UNL     1      -9.365  -0.710   0.445  1.00  0.00           H  
HETATM   42  H4  UNL     1      -5.155  -2.390  -1.575  1.00  0.00           H  
HETATM   43  H5  UNL     1      -5.843  -1.130  -2.640  1.00  0.00           H  
HETATM   44  H6  UNL     1      -3.484  -1.009  -2.409  1.00  0.00           H  
HETATM   45  H7  UNL     1      -2.368  -0.073   1.136  1.00  0.00           H  
HETATM   46  H8  UNL     1      -0.609  -0.413   1.749  1.00  0.00           H  
HETATM   47  H9  UNL     1       1.656  -0.767   2.392  1.00  0.00           H  
HETATM   48  H10 UNL     1       0.529   0.121  -2.297  1.00  0.00           H  
HETATM   49  H11 UNL     1       5.194  -0.005  -2.276  1.00  0.00           H  
HETATM   50  H12 UNL     1       4.402   1.160  -1.162  1.00  0.00           H  
HETATM   51  H13 UNL     1       4.967  -1.852  -0.699  1.00  0.00           H  
HETATM   52  H14 UNL     1       7.653  -0.879  -1.039  1.00  0.00           H  
HETATM   53  H15 UNL     1       6.518   1.458   3.074  1.00  0.00           H  
HETATM   54  H16 UNL     1       3.988  -1.678   1.398  1.00  0.00           H  
HETATM   55  H17 UNL     1      11.296   1.136   1.730  1.00  0.00           H  
HETATM   56  H18 UNL     1      10.382  -0.364   2.289  1.00  0.00           H  
HETATM   57  H19 UNL     1      -2.261   2.213   0.267  1.00  0.00           H  
HETATM   58  H20 UNL     1      -3.766   2.446   1.753  1.00  0.00           H  
HETATM   59  H21 UNL     1      -4.409   2.804  -1.062  1.00  0.00           H  
HETATM   60  H22 UNL     1      -2.154   1.723  -2.426  1.00  0.00           H  
HETATM   61  H23 UNL     1      -5.575   1.007  -1.700  1.00  0.00           H  
HETATM   62  H24 UNL     1      -3.629   0.358  -3.611  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3    4
CONECT    3   39
CONECT    4    5   40   41
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   42   43
CONECT    9   10   37   44
CONECT   10   11
CONECT   11   12   33   45
CONECT   12   13
CONECT   13   14   14   18
CONECT   14   15   46
CONECT   15   16   16   47
CONECT   16   17   29
CONECT   17   18   18   19
CONECT   18   48
CONECT   19   20
CONECT   20   21   49   50
CONECT   21   22   29   51
CONECT   22   23   23   27
CONECT   23   24   52
CONECT   24   25   25   32
CONECT   25   26   30
CONECT   26   27   27   53
CONECT   27   28
CONECT   28   29
CONECT   29   54
CONECT   30   31
CONECT   31   32   55   56
CONECT   33   34   35   57
CONECT   34   58
CONECT   35   36   37   59
CONECT   36   60
CONECT   37   38   61
CONECT   38   62
END

HMDB0039246
     RDKit          3D
6'-Malonyltrifolirhizin
 62 67  0  0  0  0  0  0  0  0999 V2000
   -7.2019    1.0455    0.8321 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6866    0.1030    1.4876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6159    0.0929    2.8663 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3381   -1.0188    0.7890 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4610   -1.4368   -0.3366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8631   -2.3265   -1.1097 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2237   -0.8909   -0.5655 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4330   -1.3441   -1.6366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0951   -0.5289   -1.5765 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5563   -0.7782   -0.3537 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6215    0.1303    0.0428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5009    0.0969   -0.7779 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2287   -0.1198   -0.3130 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1466   -0.3700    0.9772 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4848   -0.5748    1.3446 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4703   -0.5255    0.3899 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1294   -0.2786   -0.9051 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7991   -0.0780   -1.2596 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1354   -0.2207   -1.9077 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4607    0.1037   -1.4766 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8482   -0.8063   -0.3278 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0934   -0.2851    0.2706 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4374   -0.3485   -0.1162 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4320    0.2290    0.6300 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0801    0.8784    1.7807 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7646    0.9450    2.1691 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7306    0.3656    1.4253 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3613    0.3015    1.6024 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8568   -0.7338    0.8025 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2808    1.3643    2.3297 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3380    0.5955    1.7719 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8206    0.3076    0.4671 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1359    1.5666    0.0829 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0443    1.7553    1.1085 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7180    1.9607   -1.2564 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7353    2.4785   -2.1233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4767    0.8567   -1.9007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2971    1.0147   -3.3018 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9342   -0.5488    3.3027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4702   -1.9052    1.4326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3652   -0.7102    0.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1550   -2.3898   -1.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8432   -1.1302   -2.6399 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4835   -1.0088   -2.4088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3683   -0.0731    1.1365 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6090   -0.4125    1.7490 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6564   -0.7675    2.3925 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5286    0.1210   -2.2973 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1944   -0.0048   -2.2761 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4021    1.1603   -1.1618 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9669   -1.8517   -0.6986 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6527   -0.8790   -1.0388 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5180    1.4578    3.0737 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9880   -1.6777    1.3975 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.2963    1.1363    1.7301 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3825   -0.3638    2.2894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2608    2.2131    0.2667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7663    2.4465    1.7534 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4086    2.8037   -1.0620 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1541    1.7232   -2.4262 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5755    1.0071   -1.6996 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6290    0.3581   -3.6108 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  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  1  0
 25 30  1  0
 30 31  1  0
 31 32  1  0
 11 33  1  0
 33 34  1  0
 33 35  1  0
 35 36  1  0
 35 37  1  0
 37 38  1  0
 37  9  1  0
 18 13  1  0
 29 21  1  0
 29 16  1  0
 27 22  1  0
 32 24  1  0
  3 39  1  0
  4 40  1  0
  4 41  1  0
  8 42  1  0
  8 43  1  0
  9 44  1  0
 11 45  1  0
 14 46  1  0
 15 47  1  0
 18 48  1  0
 20 49  1  0
 20 50  1  0
 21 51  1  0
 23 52  1  0
 26 53  1  0
 29 54  1  0
 31 55  1  0
 31 56  1  0
 33 57  1  0
 34 58  1  0
 35 59  1  0
 36 60  1  0
 37 61  1  0
 38 62  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Ethyl oxo(2-(trifluoromethyl)anilino)acetate	HMDB
Maackiain 3-O-glucosyl-6''-malonate	HMDB
Trifolirhizin 6'-O-malonate	HMDB
3-oxo-3-[(3,4,5-Trihydroxy-6-{5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-2,4(8),9,13(18),14,16-hexaen-16-yloxy}oxan-2-yl)methoxy]propanoate	Generator

Chemical Formula

C₂₅H₂₄O₁₃

Average Molecular Weight

532.4503

Monoisotopic Molecular Weight

532.121690854

IUPAC Name

3-oxo-3-[(3,4,5-trihydroxy-6-{5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-2,4(8),9,13(18),14,16-hexaen-16-yloxy}oxan-2-yl)methoxy]propanoic acid

Traditional Name

3-oxo-3-[(3,4,5-trihydroxy-6-{5,7,11,19-tetraoxapentacyclo[10.8.0.0²,¹⁰.0⁴,⁸.0¹³,¹⁸]icosa-2,4(8),9,13(18),14,16-hexaen-16-yloxy}oxan-2-yl)methoxy]propanoic acid

CAS Registry Number

135574-57-1

SMILES

OC1C(COC(=O)CC(O)=O)OC(OC2=CC3=C(C=C2)C2OC4=CC5=C(OCO5)C=C4C2CO3)C(O)C1O

InChI Identifier

InChI=1S/C25H24O13/c26-19(27)6-20(28)33-8-18-21(29)22(30)23(31)25(38-18)36-10-1-2-11-14(3-10)32-7-13-12-4-16-17(35-9-34-16)5-15(12)37-24(11)13/h1-5,13,18,21-25,29-31H,6-9H2,(H,26,27)

InChI Key

ZHXRWFOBROFZAC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pterocarpans. These are benzo-pyrano-furano-benzene compounds, containing the 6H-[1]benzofuro[3,2-c]chromene skeleton. They are derivatives of isoflavonoids.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Isoflavonoids

Sub Class

Furanoisoflavonoids

Direct Parent

Pterocarpans

Alternative Parents

Substituents

Isoflavanol
Pterocarpan
Isoflavan
Phenolic glycoside
Glycosyl compound
O-glycosyl compound
Chromane
Benzopyran
1-benzopyran
Benzodioxole
Coumaran
Benzofuran
Alkyl aryl ether
Dicarboxylic acid or derivatives
Benzenoid
1,3-dicarbonyl compound
Monosaccharide
Oxane
Carboxylic acid ester
Secondary alcohol
Ether
Acetal
Carboxylic acid
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Polyol
Organic oxygen compound
Alcohol
Carbonyl group
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0039246)
Cytoplasm (HMDB: HMDB0039246)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0039246)

Source

Exogenous

Exogenous (HMDB: HMDB0039246)

Food

Food (HMDB: HMDB0039246)

Pulse

Pulses (FooDB: FOOD00867)

Endogenous

Plant

Plant (HMDB: HMDB0039246)
Fabaceae (HMDB: HMDB0039246)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0039246)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.79 g/L	ALOGPS
logP	0.36	ALOGPS
logP	0.36	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	3.4	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	179.67 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	120 m³·mol⁻¹	ChemAxon
Polarizability	50.96 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	222.725	31661259
DarkChem	[M-H]-	213.815	31661259
DeepCCS	[M+H]+	224.261	30932474
DeepCCS	[M-H]-	221.866	30932474
DeepCCS	[M-2H]-	254.75	30932474
DeepCCS	[M+Na]+	230.174	30932474
AllCCS	[M+H]+	216.6	32859911
AllCCS	[M+H-H2O]+	215.0	32859911
AllCCS	[M+NH4]+	218.0	32859911
AllCCS	[M+Na]+	218.4	32859911
AllCCS	[M-H]-	212.0	32859911
AllCCS	[M+Na-2H]-	213.2	32859911
AllCCS	[M+HCOO]-	214.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
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.	6.17 minutes	32390414
Predicted by Siyang on May 30, 2022	11.9787 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.51 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	108.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2027.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	225.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	152.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	191.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	87.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	389.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	504.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	316.7 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	848.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	482.7 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1440.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	328.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	295.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	383.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	233.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	180.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
6'-Malonyltrifolirhizin	OC1C(COC(=O)CC(O)=O)OC(OC2=CC3=C(C=C2)C2OC4=CC5=C(OCO5)C=C4C2CO3)C(O)C1O	5664.7	Standard polar	33892256
6'-Malonyltrifolirhizin	OC1C(COC(=O)CC(O)=O)OC(OC2=CC3=C(C=C2)C2OC4=CC5=C(OCO5)C=C4C2CO3)C(O)C1O	4154.7	Standard non polar	33892256
6'-Malonyltrifolirhizin	OC1C(COC(=O)CC(O)=O)OC(OC2=CC3=C(C=C2)C2OC4=CC5=C(OCO5)C=C4C2CO3)C(O)C1O	4667.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
6'-Malonyltrifolirhizin,1TMS,isomer #1	C[Si](C)(C)OC1C(COC(=O)CC(=O)O)OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O)C1O	4407.4	Semi standard non polar	33892256
6'-Malonyltrifolirhizin,1TMS,isomer #2	C[Si](C)(C)OC(=O)CC(=O)OCC1OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O)C(O)C1O	4400.6	Semi standard non polar	33892256
6'-Malonyltrifolirhizin,1TMS,isomer #3	C[Si](C)(C)OC1C(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)OC(COC(=O)CC(=O)O)C(O)C1O	4445.1	Semi standard non polar	33892256
6'-Malonyltrifolirhizin,1TMS,isomer #4	C[Si](C)(C)OC1C(O)C(COC(=O)CC(=O)O)OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C1O	4454.4	Semi standard non polar	33892256
6'-Malonyltrifolirhizin,2TMS,isomer #1	C[Si](C)(C)OC(=O)CC(=O)OCC1OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O)C(O)C1O[Si](C)(C)C	4353.7	Semi standard non polar	33892256
6'-Malonyltrifolirhizin,2TMS,isomer #2	C[Si](C)(C)OC1C(COC(=O)CC(=O)O)OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O[Si](C)(C)C)C1O	4438.2	Semi standard non polar	33892256
6'-Malonyltrifolirhizin,2TMS,isomer #3	C[Si](C)(C)OC1C(COC(=O)CC(=O)O)OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O)C1O[Si](C)(C)C	4429.3	Semi standard non polar	33892256
6'-Malonyltrifolirhizin,2TMS,isomer #4	C[Si](C)(C)OC(=O)CC(=O)OCC1OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O[Si](C)(C)C)C(O)C1O	4377.9	Semi standard non polar	33892256
6'-Malonyltrifolirhizin,2TMS,isomer #5	C[Si](C)(C)OC(=O)CC(=O)OCC1OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O)C(O[Si](C)(C)C)C1O	4396.7	Semi standard non polar	33892256
6'-Malonyltrifolirhizin,2TMS,isomer #6	C[Si](C)(C)OC1C(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)OC(COC(=O)CC(=O)O)C(O)C1O[Si](C)(C)C	4433.9	Semi standard non polar	33892256
6'-Malonyltrifolirhizin,3TMS,isomer #1	C[Si](C)(C)OC(=O)CC(=O)OCC1OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O[Si](C)(C)C)C(O)C1O[Si](C)(C)C	4352.6	Semi standard non polar	33892256
6'-Malonyltrifolirhizin,3TMS,isomer #2	C[Si](C)(C)OC(=O)CC(=O)OCC1OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O)C(O[Si](C)(C)C)C1O[Si](C)(C)C	4361.4	Semi standard non polar	33892256
6'-Malonyltrifolirhizin,3TMS,isomer #3	C[Si](C)(C)OC1C(COC(=O)CC(=O)O)OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O[Si](C)(C)C)C1O[Si](C)(C)C	4421.3	Semi standard non polar	33892256
6'-Malonyltrifolirhizin,3TMS,isomer #4	C[Si](C)(C)OC(=O)CC(=O)OCC1OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O	4355.7	Semi standard non polar	33892256
6'-Malonyltrifolirhizin,4TMS,isomer #1	C[Si](C)(C)OC(=O)CC(=O)OCC1OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O[Si](C)(C)C)C(O[Si](C)(C)C)C1O[Si](C)(C)C	4323.5	Semi standard non polar	33892256
6'-Malonyltrifolirhizin,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC1C(COC(=O)CC(=O)O)OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O)C1O	4635.4	Semi standard non polar	33892256
6'-Malonyltrifolirhizin,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CC(=O)OCC1OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O)C(O)C1O	4639.9	Semi standard non polar	33892256
6'-Malonyltrifolirhizin,1TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1C(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)OC(COC(=O)CC(=O)O)C(O)C1O	4687.6	Semi standard non polar	33892256
6'-Malonyltrifolirhizin,1TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC1C(O)C(COC(=O)CC(=O)O)OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C1O	4691.2	Semi standard non polar	33892256
6'-Malonyltrifolirhizin,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC(=O)OCC1OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O)C(O)C1O[Si](C)(C)C(C)(C)C	4808.2	Semi standard non polar	33892256
6'-Malonyltrifolirhizin,2TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC1C(COC(=O)CC(=O)O)OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O[Si](C)(C)C(C)(C)C)C1O	4885.7	Semi standard non polar	33892256
6'-Malonyltrifolirhizin,2TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1C(COC(=O)CC(=O)O)OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O)C1O[Si](C)(C)C(C)(C)C	4887.4	Semi standard non polar	33892256
6'-Malonyltrifolirhizin,2TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)CC(=O)OCC1OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O[Si](C)(C)C(C)(C)C)C(O)C1O	4835.8	Semi standard non polar	33892256
6'-Malonyltrifolirhizin,2TBDMS,isomer #5	CC(C)(C)[Si](C)(C)OC(=O)CC(=O)OCC1OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O)C(O[Si](C)(C)C(C)(C)C)C1O	4841.4	Semi standard non polar	33892256
6'-Malonyltrifolirhizin,2TBDMS,isomer #6	CC(C)(C)[Si](C)(C)OC1C(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)OC(COC(=O)CC(=O)O)C(O)C1O[Si](C)(C)C(C)(C)C	4892.3	Semi standard non polar	33892256
6'-Malonyltrifolirhizin,3TBDMS,isomer #1	CC(C)(C)[Si](C)(C)OC(=O)CC(=O)OCC1OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O[Si](C)(C)C(C)(C)C)C(O)C1O[Si](C)(C)C(C)(C)C	4986.4	Semi standard non polar	33892256
6'-Malonyltrifolirhizin,3TBDMS,isomer #2	CC(C)(C)[Si](C)(C)OC(=O)CC(=O)OCC1OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C	4973.7	Semi standard non polar	33892256
6'-Malonyltrifolirhizin,3TBDMS,isomer #3	CC(C)(C)[Si](C)(C)OC1C(COC(=O)CC(=O)O)OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O[Si](C)(C)C(C)(C)C)C1O[Si](C)(C)C(C)(C)C	5048.3	Semi standard non polar	33892256
6'-Malonyltrifolirhizin,3TBDMS,isomer #4	CC(C)(C)[Si](C)(C)OC(=O)CC(=O)OCC1OC(OC2=CC=C3C(=C2)OCC2C4=CC5=C(C=C4OC32)OCO5)C(O[Si](C)(C)C(C)(C)C)C(O[Si](C)(C)C(C)(C)C)C1O	4969.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 6'-Malonyltrifolirhizin GC-MS (Non-derivatized) - 70eV, Positive	splash10-029i-9370230000-9f9ca5c8d038a0d2c9b9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6'-Malonyltrifolirhizin GC-MS (2 TMS) - 70eV, Positive	splash10-08gi-8954338000-f45731bf49ae86d52761	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6'-Malonyltrifolirhizin GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6'-Malonyltrifolirhizin GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6'-Malonyltrifolirhizin GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6'-Malonyltrifolirhizin GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6'-Malonyltrifolirhizin GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6'-Malonyltrifolirhizin GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6'-Malonyltrifolirhizin GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6'-Malonyltrifolirhizin GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6'-Malonyltrifolirhizin GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6'-Malonyltrifolirhizin GC-MS (TMS_3_1) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6'-Malonyltrifolirhizin GC-MS (TMS_3_2) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6'-Malonyltrifolirhizin GC-MS (TMS_3_3) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6'-Malonyltrifolirhizin GC-MS (TMS_3_4) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6'-Malonyltrifolirhizin GC-MS (TMS_4_1) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6'-Malonyltrifolirhizin GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6'-Malonyltrifolirhizin GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6'-Malonyltrifolirhizin GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6'-Malonyltrifolirhizin GC-MS (TBDMS_1_4) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6'-Malonyltrifolirhizin GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6'-Malonyltrifolirhizin GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6'-Malonyltrifolirhizin GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6'-Malonyltrifolirhizin GC-MS (TBDMS_2_4) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 6'-Malonyltrifolirhizin GC-MS (TBDMS_2_5) - 70eV, Positive	Not Available	2021-10-13	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6'-Malonyltrifolirhizin 10V, Positive-QTOF	splash10-00kr-2093360000-969c2a8c2bd054c66577	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6'-Malonyltrifolirhizin 20V, Positive-QTOF	splash10-000i-1090100000-cd80a1b18d77c8724740	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6'-Malonyltrifolirhizin 40V, Positive-QTOF	splash10-000l-7590000000-38c42d58ddbbbced3f35	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6'-Malonyltrifolirhizin 10V, Negative-QTOF	splash10-001i-9870560000-2bcab3b3e48a3d734cde	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6'-Malonyltrifolirhizin 20V, Negative-QTOF	splash10-0f89-7590210000-364401dc8ac7cbdf7def	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6'-Malonyltrifolirhizin 40V, Negative-QTOF	splash10-0f89-4390000000-1c3958773d04ba181d04	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6'-Malonyltrifolirhizin 10V, Positive-QTOF	splash10-000i-0090010000-cb91e2f4d1fd40a1c27f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6'-Malonyltrifolirhizin 20V, Positive-QTOF	splash10-000i-0090000000-f4fa0fd9677bfb09f0a0	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6'-Malonyltrifolirhizin 40V, Positive-QTOF	splash10-000l-9780100000-db5866c797adec0cfbdb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6'-Malonyltrifolirhizin 10V, Negative-QTOF	splash10-001i-2190410000-8222ff3317d8493d1a5e	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6'-Malonyltrifolirhizin 20V, Negative-QTOF	splash10-053r-6061910000-74f4645f1b1e8ffff3e0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 6'-Malonyltrifolirhizin 40V, Negative-QTOF	splash10-000x-9160000000-e316b3b7412dc39cfbf8	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB018784

KNApSAcK ID

C00019704

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14841223

PDB ID

Not Available

ChEBI ID

191751

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

Enzyme Details

1. Liver carboxylesterase 1

General function:: Lipid transport and metabolism
Specific function:: Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:: CES1
Uniprot ID:: P23141
Molecular weight:: 62520.62

Reactions

6'-Malonyltrifolirhizin → Trifolirhizin	details

Showing metabocard for 6'-Malonyltrifolirhizin (HMDB0039246)

MOL for HMDB0039246 (6'-Malonyltrifolirhizin)

3D MOL for HMDB0039246 (6'-Malonyltrifolirhizin)

3D SDF for HMDB0039246 (6'-Malonyltrifolirhizin)

3D-SDF for HMDB0039246 (6'-Malonyltrifolirhizin)

PDB for HMDB0039246 (6'-Malonyltrifolirhizin)

3D PDB for HMDB0039246 (6'-Malonyltrifolirhizin)

SMILES for HMDB0039246 (6'-Malonyltrifolirhizin)

INCHI for HMDB0039246 (6'-Malonyltrifolirhizin)

Structure for HMDB0039246 (6'-Malonyltrifolirhizin)

3D Structure for HMDB0039246 (6'-Malonyltrifolirhizin)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions