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Showing NP-Card for 3-Methyl-2-oxopentanoic acid (NP0002698)

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Record Information
Version1.0
Created at2020-11-23 19:38:13 UTC
Updated at2021-08-12 19:51:53 UTC
NP-MRD IDNP0002698
Secondary Accession NumbersNone
Natural Product Identification
Common Name3-Methyl-2-oxopentanoic acid
Provided ByBMRBBMRB logo
Description(R)-3-methyl-2-oxovaleric acid, also known as (R)-2-oxo-3-methylpentanoate or alpha-oxo-beta-methyl-N-valerate, belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms. It was first documented in 1992 (PMID: 1638756). Based on a literature review very few articles have been published on (R)-3-methyl-2-oxovaleric acid (PMID: 17984079) (PMID: 34404060) (PMID: 34404046) (PMID: 34404029) (PMID: 34404018) (PMID: 34404014).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0002698 (3-Methyl-2-oxopentanoic acid)


     RDKit          2D

 19 18  0  0  0  0  0  0  0  0999 V2000
    2.9470    0.2235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5075   -0.1981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0680   -0.6198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3537    0.8197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3715   -1.0415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7261   -2.4990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4564   -0.0057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2471    0.8550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8960   -0.4273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3687   -1.2160    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5254    1.6630    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3865    0.6452    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3640    0.6759    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9292   -1.6376    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4897   -2.0593    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4597    1.1705    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2387    0.7838    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7753    2.2592    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9809    0.6085    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  6
  1 11  1  0
  1 12  1  0
  2 13  1  6
  2 14  1  0
  3 15  1  1
  4 16  1  1
  4 17  1  0
  4 18  1  0
  9 19  1  0
M  END
Download

3D MOL for NP0002698 (3-Methyl-2-oxopentanoic acid)

NP0002698
     RDKit          3D

 19 18  0  0  0  0  0  0  0  0999 V2000
   -1.5933    1.5428    0.6975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4237    0.3916   -0.2408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2811   -0.5130    0.0926 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2522   -1.6182   -0.9498 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0199    0.1870    0.1326 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0312    1.4157   -0.1074 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2595   -0.4801    0.4331 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2683   -1.7057    0.6753 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4475    0.2160    0.4584 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0210    2.4304    0.3587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6841    1.8211    0.7019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3126    1.2456    1.7294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3582   -0.2115   -0.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3472    0.7454   -1.3042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4803   -1.0001    1.0705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2837   -1.9939   -1.0966 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4126   -2.4329   -0.6650 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0788   -1.2324   -1.9408 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5197    1.1922    0.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  3 15  1  1
  4 16  1  0
  4 17  1  0
  4 18  1  0
  9 19  1  0
M  END
Download

3D SDF for NP0002698 (3-Methyl-2-oxopentanoic acid)


     RDKit          2D

 19 18  0  0  0  0  0  0  0  0999 V2000
    2.9470    0.2235    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5075   -0.1981    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0680   -0.6198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3537    0.8197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3715   -1.0415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7261   -2.4990    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4564   -0.0057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2471    0.8550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8960   -0.4273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3687   -1.2160    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5254    1.6630    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3865    0.6452    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3640    0.6759    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9292   -1.6376    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4897   -2.0593    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4597    1.1705    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2387    0.7838    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7753    2.2592    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9809    0.6085    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  6
  1 11  1  0
  1 12  1  0
  2 13  1  6
  2 14  1  0
  3 15  1  1
  4 16  1  1
  4 17  1  0
  4 18  1  0
  9 19  1  0
M  END
> <DATABASE_ID>
NP0002698

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C6H10O3/c1-3-4(2)5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9)/t4-/m1/s1

> <INCHI_KEY>
JVQYSWDUAOAHFM-SCSAIBSYSA-N

> <FORMULA>
C6H10O3

> <MOLECULAR_WEIGHT>
130.143

> <EXACT_MASS>
130.062994182

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
13.105714379015271

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-3-methyl-2-oxopentanoic acid

> <JCHEM_LOGP>
1.7539647436666668

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.5188639238905273

> <JCHEM_PKA_STRONGEST_BASIC>
-9.724255725220358

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
31.7921

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(R)-omv

> <JCHEM_VEBER_RULE>
0

$$$$
Download

3D-SDF for NP0002698 (3-Methyl-2-oxopentanoic acid)

NP0002698
     RDKit          3D

 19 18  0  0  0  0  0  0  0  0999 V2000
   -1.5933    1.5428    0.6975 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4237    0.3916   -0.2408 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2811   -0.5130    0.0926 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2522   -1.6182   -0.9498 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0199    0.1870    0.1326 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0312    1.4157   -0.1074 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2595   -0.4801    0.4331 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2683   -1.7057    0.6753 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4475    0.2160    0.4584 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0210    2.4304    0.3587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6841    1.8211    0.7019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3126    1.2456    1.7294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3582   -0.2115   -0.2098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3472    0.7454   -1.3042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4803   -1.0001    1.0705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2837   -1.9939   -1.0966 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4126   -2.4329   -0.6650 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0788   -1.2324   -1.9408 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5197    1.1922    0.1645 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  2  0
  7  9  1  0
  1 10  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  0
  2 14  1  0
  3 15  1  1
  4 16  1  0
  4 17  1  0
  4 18  1  0
  9 19  1  0
M  END
Download

PDB for NP0002698 (3-Methyl-2-oxopentanoic acid)

HEADER    PROTEIN                                 23-NOV-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-NOV-20         0                                  
HETATM    1  C   UNK     0      -0.357   1.334   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.310  -0.206   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.976   2.104   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.644   2.104   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.977   1.334   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.644   3.644   0.000  0.00  0.00           O+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    3                                                            
CONECT    2    4                                                            
CONECT    3    1    4                                                       
CONECT    4    2    3    5                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    8    9                                                  
CONECT    7    5                                                            
CONECT    8    6                                                            
CONECT    9    6                                                            
MASTER        0    0    0    0    0    0    0    0    9    0   16    0
END
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3D PDB for NP0002698 (3-Methyl-2-oxopentanoic acid)

COMPND    NP0002698
HETATM    1  C1  UNL     1      -1.593   1.543   0.697  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.424   0.392  -0.241  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.281  -0.513   0.093  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.252  -1.618  -0.950  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.020   0.187   0.133  1.00  0.00           C  
HETATM    6  O1  UNL     1       1.031   1.416  -0.107  1.00  0.00           O  
HETATM    7  C6  UNL     1       2.259  -0.480   0.433  1.00  0.00           C  
HETATM    8  O2  UNL     1       2.268  -1.706   0.675  1.00  0.00           O  
HETATM    9  O3  UNL     1       3.447   0.216   0.458  1.00  0.00           O  
HETATM   10  H1  UNL     1      -1.021   2.430   0.359  1.00  0.00           H  
HETATM   11  H2  UNL     1      -2.684   1.821   0.702  1.00  0.00           H  
HETATM   12  H3  UNL     1      -1.313   1.246   1.729  1.00  0.00           H  
HETATM   13  H4  UNL     1      -2.358  -0.212  -0.210  1.00  0.00           H  
HETATM   14  H5  UNL     1      -1.347   0.745  -1.304  1.00  0.00           H  
HETATM   15  H6  UNL     1      -0.480  -1.000   1.070  1.00  0.00           H  
HETATM   16  H7  UNL     1      -1.284  -1.994  -1.097  1.00  0.00           H  
HETATM   17  H8  UNL     1       0.413  -2.433  -0.665  1.00  0.00           H  
HETATM   18  H9  UNL     1       0.079  -1.232  -1.941  1.00  0.00           H  
HETATM   19  H10 UNL     1       3.520   1.192   0.164  1.00  0.00           H  
CONECT    1    2   10   11   12
CONECT    2    3   13   14
CONECT    3    4    5   15
CONECT    4   16   17   18
CONECT    5    6    6    7
CONECT    7    8    8    9
CONECT    9   19
END
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SMILES for NP0002698 (3-Methyl-2-oxopentanoic acid)

CC[C@@H](C)C(=O)C(O)=O
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INCHI for NP0002698 (3-Methyl-2-oxopentanoic acid)

InChI=1S/C6H10O3/c1-3-4(2)5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9)/t4-/m1/s1
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View in JSmol
Synonyms
ValueSource
(3R)-2-oxo-3-Methyl-N-valeric acidChEBI
(3R)-2-OxoisoleucineChEBI
(3R)-3-Methyl-2-oxopentanoic acidChEBI
(R)-2-oxo-3-MethylpentanoateChEBI
(R)-2-oxo-3-Methylpentanoic acidChEBI
(R)-OMVChEBI
alpha-oxo-beta-Methyl-N-valeric acidChEBI
alpha-oxo-beta-Methylvaleric acidChEBI
(3R)-2-oxo-3-Methyl-N-valerateGenerator
(3R)-3-Methyl-2-oxopentanoateGenerator
a-oxo-b-Methyl-N-valerateGenerator
a-oxo-b-Methyl-N-valeric acidGenerator
alpha-oxo-beta-Methyl-N-valerateGenerator
Α-oxo-β-methyl-N-valerateGenerator
Α-oxo-β-methyl-N-valeric acidGenerator
a-oxo-b-MethylvalerateGenerator
a-oxo-b-Methylvaleric acidGenerator
alpha-oxo-beta-MethylvalerateGenerator
Α-oxo-β-methylvalerateGenerator
Α-oxo-β-methylvaleric acidGenerator
(R)-3-Methyl-2-oxovalerateGenerator
2oxo-3R-Methyl-pentanoateGenerator
Chemical FormulaC6H10O3
Average Mass130.1430 Da
Monoisotopic Mass130.06299 Da
IUPAC Name(3R)-3-methyl-2-oxopentanoic acid
Traditional Name(R)-omv
CAS Registry NumberNot Available
SMILES
CC[C@@H](C)C(=O)C(O)=O
InChI Identifier
InChI=1S/C6H10O3/c1-3-4(2)5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9)/t4-/m1/s1
InChI KeyJVQYSWDUAOAHFM-SCSAIBSYSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, simulated)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
Description Belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassShort-chain keto acids and derivatives
Direct ParentShort-chain keto acids and derivatives
Alternative Parents
Substituents
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Short-chain keto acid
  • Alpha-keto acid
  • Fatty acyl
  • Alpha-hydroxy ketone
  • Ketone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.75ChemAxon
pKa (Strongest Acidic)3.52ChemAxon
pKa (Strongest Basic)-9.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity31.79 m³·mol⁻¹ChemAxon
Polarizability13.11 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID389709
KEGG Compound IDC06008
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
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References
General References
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