NP-MRD: Showing NP-Card for (2r,3r)-2-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4-dihydroxy-2-methylbutanoic acid (NP0241510)

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Record Information

Version

2.0

Created at

2022-09-07 01:36:27 UTC

Updated at

2022-09-07 01:36:27 UTC

NP-MRD ID

NP0241510

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,3r)-2-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4-dihydroxy-2-methylbutanoic acid

Description

(2R,3R)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4-dihydroxy-2-methylbutanoic acid belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. (2r,3r)-2-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4-dihydroxy-2-methylbutanoic acid is found in Bidens pilosa. Based on a literature review very few articles have been published on (2R,3R)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4-dihydroxy-2-methylbutanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 38  0  0  0  0  0  0  0  0999 V2000
   -3.0772   -1.8068    0.2351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5451   -0.3901    0.4940 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1985   -0.3088    0.1554 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7050   -0.5638   -1.1027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5156   -0.8904   -1.9935 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7332   -0.4597   -1.4080 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5855   -0.1165   -0.4719 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0053   -0.0056   -0.7411 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5430   -0.2457   -1.9628 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9220   -0.1198   -2.1522 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7492    0.2459   -1.1135 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1143    0.3668   -1.3156 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1871    0.4872    0.1249 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9761    0.8614    1.2161 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8494    0.3638    0.3036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6678   -0.2202    1.9699 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6198   -0.0276    2.6327 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8638   -0.2603    2.6670 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3735    0.6191   -0.2243 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9205    1.8963    0.1139 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8475    0.4669   -0.0331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4855    1.4147   -0.8718 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5579   -1.7965   -0.7744 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2821   -2.5444    0.3353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8819   -2.0604    0.9647 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0575   -0.6656   -2.3869 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2233    0.0910    0.5325 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9592   -0.5360   -2.8234 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3352   -0.3135   -3.1276 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5180    0.1910   -2.2150 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9665    0.9460    1.0572 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4284    0.5583    1.2860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9837   -0.6557    3.5743 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2020    0.5369   -1.3227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4854    2.6027   -0.2897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1830   -0.5171   -0.4191 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2191    0.5575    0.9855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5386    2.2991   -0.4440 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  6
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  1  0
 13 15  2  0
  2 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
  2 16  1  0
 16 18  1  0
 16 17  2  0
 15  8  1  0
  1 23  1  0
  1 24  1  0
  1 25  1  0
  6 26  1  0
  7 27  1  0
  9 28  1  0
 10 29  1  0
 12 30  1  0
 14 31  1  0
 15 32  1  0
 19 34  1  6
 20 35  1  0
 21 36  1  0
 21 37  1  0
 22 38  1  0
 18 33  1  0
M  END


  Mrv1652309072203362D          

 22 22  0  0  1  0            999 V2000
   -0.1105    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    3.8230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9520    5.2520    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    5.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    6.6000    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  6  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
  8 15  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
  2 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0241510

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@](OC(=O)\C=C\C1=CC=C(O)C(O)=C1)([C@H](O)CO)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C14H16O8/c1-14(13(20)21,11(18)7-15)22-12(19)5-3-8-2-4-9(16)10(17)6-8/h2-6,11,15-18H,7H2,1H3,(H,20,21)/b5-3+/t11-,14-/m1/s1

> <INCHI_KEY>
VFNQXFLXWICPJF-UOLJMSNASA-N

> <FORMULA>
C14H16O8

> <MOLECULAR_WEIGHT>
312.274

> <EXACT_MASS>
312.084517475

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
29.455154859199514

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4-dihydroxy-2-methylbutanoic acid

> <JCHEM_LOGP>
0.710451534

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.208575723304113

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.1853899697408234

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9863644529901503

> <JCHEM_POLAR_SURFACE_AREA>
144.52

> <JCHEM_REFRACTIVITY>
74.58880000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4-dihydroxy-2-methylbutanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.206   8.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.874   8.470   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.644   7.136   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       3.644   9.804   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       1.334  10.010   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.000  10.780   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       2.667  10.780   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.667  12.320   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   16   19                                             
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    8                                                       
CONECT   16    2   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19    2   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   44    0
END

View in JSmol

Synonyms

Value	Source
(2R,3R)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4-dihydroxy-2-methylbutanoate	Generator

Chemical Formula

C₁₄H₁₆O₈

Average Mass

312.2740 Da

Monoisotopic Mass

312.08452 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

C[C@@](OC(=O)\C=C\C1=CC=C(O)C(O)=C1)([C@H](O)CO)C(O)=O

InChI Identifier

InChI=1S/C14H16O8/c1-14(13(20)21,11(18)7-15)22-12(19)5-3-8-2-4-9(16)10(17)6-8/h2-6,11,15-18H,7H2,1H3,(H,20,21)/b5-3+/t11-,14-/m1/s1

InChI Key

VFNQXFLXWICPJF-UOLJMSNASA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Bidens pilosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Coumaric acid or derivatives
Cinnamic acid ester
Catechol
Styrene
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Beta-hydroxy acid
Phenol
Hydroxy acid
Monosaccharide
Benzenoid
Dicarboxylic acid or derivatives
Fatty acyl
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
1,2-diol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid
Carboxylic acid derivative
Hydrocarbon derivative
Alcohol
Carbonyl group
Organic oxide
Organic oxygen compound
Primary alcohol
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

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

133554289

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,3r)-2-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4-dihydroxy-2-methylbutanoic acid (NP0241510)

MOL for NP0241510 ((2r,3r)-2-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4-dihydroxy-2-methylbutanoic acid)

3D MOL for NP0241510 ((2r,3r)-2-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4-dihydroxy-2-methylbutanoic acid)

3D SDF for NP0241510 ((2r,3r)-2-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4-dihydroxy-2-methylbutanoic acid)

3D-SDF for NP0241510 ((2r,3r)-2-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4-dihydroxy-2-methylbutanoic acid)

PDB for NP0241510 ((2r,3r)-2-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4-dihydroxy-2-methylbutanoic acid)

3D PDB for NP0241510 ((2r,3r)-2-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4-dihydroxy-2-methylbutanoic acid)

SMILES for NP0241510 ((2r,3r)-2-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4-dihydroxy-2-methylbutanoic acid)

INCHI for NP0241510 ((2r,3r)-2-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4-dihydroxy-2-methylbutanoic acid)

Structure for NP0241510 ((2r,3r)-2-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4-dihydroxy-2-methylbutanoic acid)

3D Structure for NP0241510 ((2r,3r)-2-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3,4-dihydroxy-2-methylbutanoic acid)