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Showing NP-Card for D-Phenyllactic acid (NP0334602)

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Record Information
Version2.0
Created at2024-09-10 19:06:07 UTC
Updated at2024-09-10 19:06:07 UTC
NP-MRD IDNP0334602
Secondary Accession NumbersNone
Natural Product Identification
Common NameD-Phenyllactic acid
DescriptionD-Phenyllactic acid is also known as D-phenyllactate. D-Phenyllactic acid was first documented in 2023 (PMID: 37738613). Based on a literature review a small amount of articles have been published on D-Phenyllactic acid (PMID: 38357377) (PMID: 38185431) (PMID: 37114909).
Structure
Thumb
MOLSDFPDBSMILESInChI

MOL for NP0334602 (D-Phenyllactic acid)

HFA
  Mrv2104 05252321382D          

 13 13  0  0  0  0            999 V2000
   -0.1575    1.2268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5569    0.8143    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2714    1.2268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2714    2.0518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5569   -0.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1575   -0.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1575   -1.2482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8720   -0.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8720   -1.6607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5865   -0.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5865   -1.2482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9859    0.8143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5569    1.3983    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  2  5  1  0  0  0  0
  2 13  1  1  0  0  0
  3  4  2  0  0  0  0
  3 12  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  2  0  0  0  0
  9 11  2  0  0  0  0
 10 11  1  0  0  0  0
M  END
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3D MOL for NP0334602 (D-Phenyllactic acid)

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3D SDF for NP0334602 (D-Phenyllactic acid)
HFA
  Mrv2104 05252321382D          

 13 13  0  0  0  0            999 V2000
   -0.1575    1.2268    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5569    0.8143    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2714    1.2268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2714    2.0518    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5569   -0.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1575   -0.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1575   -1.2482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8720   -0.0107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8720   -1.6607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5865   -0.4232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5865   -1.2482    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9859    0.8143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5569    1.3983    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  2  5  1  0  0  0  0
  2 13  1  1  0  0  0
  3  4  2  0  0  0  0
  3 12  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  2  0  0  0  0
  9 11  2  0  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334602

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@](O)(CC1=CC=CC=C1)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1/C9H10O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8,10H,6H2,(H,11,12)/t8-/s2

> <INCHI_KEY>
VOXXWSYKYCBWHO-SVGMAFHSNA-N

> <FORMULA>
C9H10O3

> <MOLECULAR_WEIGHT>
166.176

> <EXACT_MASS>
166.062994182

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
22

> <JCHEM_AVERAGE_POLARIZABILITY>
16.69614539230921

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S)-2-hydroxy-3-phenylpropanoic acid

> <JCHEM_LOGP>
1.1844968496666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.19195842902614

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.020980916532307

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8373742935175534

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
43.45880000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
L-3-phenyllactic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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3D-SDF for NP0334602 (D-Phenyllactic acid)
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PDB for NP0334602 (D-Phenyllactic acid)
HEADER    PROTEIN                                 25-MAY-23   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: HFA                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-MAY-23         0                                  
HETATM    1  O   UNK     0      -0.294   2.290   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.040   1.520   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.373   2.290   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       2.373   3.830   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.040  -0.020   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.294  -0.790   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.294  -2.330   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.628  -0.020   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.628  -3.100   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.961  -0.790   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.961  -2.330   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.707   1.520   0.000  0.00  0.00           O+0
HETATM   13  H   UNK     0       1.040   2.610   0.000  0.00  0.00           H+0
CONECT    1    2                                                            
CONECT    2    1    3    5   13                                             
CONECT    3    2    4   12                                                  
CONECT    4    3                                                            
CONECT    5    2    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   11                                                       
CONECT   11    9   10                                                       
CONECT   12    3                                                            
CONECT   13    2                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END

Download
3D PDB for NP0334602 (D-Phenyllactic acid)
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SMILES for NP0334602 (D-Phenyllactic acid)
[H][C@](O)(CC1=CC=CC=C1)C(O)=O
Download
INCHI for NP0334602 (D-Phenyllactic acid)
InChI=1/C9H10O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8,10H,6H2,(H,11,12)/t8-/s2
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View in JSmol
Synonyms
ValueSource
D-PhenyllactateGenerator
Chemical FormulaC9H10O3
Average Mass166.1760 Da
Monoisotopic Mass166.06299 Da
IUPAC Name(2S)-2-hydroxy-3-phenylpropanoic acid
Traditional NameL-3-phenyllactic acid
CAS Registry NumberNot Available
SMILES
[H][C@](O)(CC1=CC=CC=C1)C(O)=O
InChI Identifier
InChI=1/C9H10O3/c10-8(9(11)12)6-7-4-2-1-3-5-7/h1-5,8,10H,6H2,(H,11,12)/t8-/s2
InChI KeyVOXXWSYKYCBWHO-SVGMAFHSNA-N
Experimental Spectra
Not Available
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of OriginNot Available
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpropanoic acids. These are compounds with a structure containing a benzene ring conjugated to a propanoic acid.
KingdomOrganic compounds  
Super ClassPhenylpropanoids and polyketides  
ClassPhenylpropanoic acids  
Sub ClassNot Available
Direct ParentPhenylpropanoic acids  
Alternative Parents
Substituents
  • 3-phenylpropanoic-acid
    • 

  • Alpha-hydroxy acid
    • 

  • Monocyclic benzene moiety
    • 

  • Hydroxy acid
    • 

  • Benzenoid
    • 

  • Secondary alcohol
    • 

  • Carboxylic acid derivative
    • 

  • Carboxylic acid
    • 

  • Monocarboxylic acid or derivatives
    • 

  • Organic oxygen compound
    • 

  • Alcohol
    • 

  • Carbonyl group
    • 

  • Organic oxide
    • 

  • Hydrocarbon derivative
    • 

  • Organooxygen compound
    • 

  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic 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
logP1.18ChemAxon
pKa (Strongest Acidic)4.02ChemAxon
pKa (Strongest Basic)-3.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity43.46 m³·mol⁻¹ChemAxon
Polarizability16.7 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDC00000150  
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI IDNot Available
Good Scents IDNot Available
References
General References
  1. Gao Z, Zhou MC, Lin J, Lu Y, Liu SQ: Metabolomics analysis of okara probiotic beverages fermented with Lactobacillus gasseri and Limosilactobacillus fermentum by LC-QTOF-MS/MS. Food Chem X. 2024 Feb 6;21:101178. doi: 10.1016/j.fochx.2024.101178. eCollection  2024 Mar 30. [PubMed:38357377  ] 
  2. Zhou Y, Sun X, Hu J, Miao Y, Zi X, Luo X, Fu Y: Enhanced catalytic activity and stability of lactate dehydrogenase for cascade catalysis of D-PLA by rational design. J Biotechnol. 2024 Feb 20;382:1-7. doi: 10.1016/j.jbiotec.2024.01.004. Epub 2024  Jan 6. [PubMed:38185431  ] 
  3. Zhang W, Dong H, Wang X, Zhang L, Chen C, Wang P: Engineered Escherichia coli Consortia Function in a Programmable Pattern for Multiple Enzymatic Biosynthesis. ACS Appl Mater Interfaces. 2023 Oct 4;15(39):45886-45894. doi:  10.1021/acsami.3c09123. Epub 2023 Sep 22. [PubMed:37738613  ] 
  4. Wang Y, Sun X, Hu J, Guo Q, Zhang P, Luo X, Shen B, Fu Y: A two-enzyme system in an amorphous metal-organic framework for the synthesis of D-phenyllactic acid. J Mater Chem B. 2023 May 17;11(19):4227-4236. doi: 10.1039/d3tb00126a. [PubMed:37114909  ]