NP-MRD: Showing NP-Card for methyl 3-(3,4-dihydroxyphenyl)-2-hydroxypropanoate (NP0166040)

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Record Information

Version

2.0

Created at

2022-09-03 01:20:16 UTC

Updated at

2022-09-03 01:20:16 UTC

NP-MRD ID

NP0166040

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 3-(3,4-dihydroxyphenyl)-2-hydroxypropanoate

Description

3,4-Dihydroxyphenyllactic acid methyl ester belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety. methyl 3-(3,4-dihydroxyphenyl)-2-hydroxypropanoate is found in Isodon oresbius, Meehania urticifolia and Ranunculus chinensis. 3,4-Dihydroxyphenyllactic acid methyl ester is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02271201332D          

 15 15  0  0  0  0            999 V2000
   -0.8097    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0953    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6192    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6192    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3337    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3337    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6192   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0953    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0953    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0953    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8097    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6192    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6192   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8097   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8097    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  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
  4  9  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  7 13  1  0  0  0  0
  8 14  1  0  0  0  0
 11 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0166040

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C(O)CC1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C10H12O5/c1-15-10(14)9(13)5-6-2-3-7(11)8(12)4-6/h2-4,9,11-13H,5H2,1H3

> <INCHI_KEY>
NMAOZVAEJYOPOF-UHFFFAOYSA-N

> <FORMULA>
C10H12O5

> <MOLECULAR_WEIGHT>
212.1993

> <EXACT_MASS>
212.068473494

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
20.769804505679794

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl 3-(3,4-dihydroxyphenyl)-2-hydroxypropanoate

> <ALOGPS_LOGP>
0.35

> <JCHEM_LOGP>
0.7232602623333333

> <ALOGPS_LOGS>
-1.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.390964686372879

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.282823394139953

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8389459829146775

> <JCHEM_POLAR_SURFACE_AREA>
86.99000000000001

> <JCHEM_REFRACTIVITY>
52.1897

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.57e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 3-(3,4-dihydroxyphenyl)-2-hydroxypropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  O   UNK     0      -1.511   3.850   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.178   4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.156   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.156   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.490   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.490   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.156  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.178   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.178   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.178   6.160   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.511   6.930   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       1.156   6.930   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.156  -2.310   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      -1.511  -0.770   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.511   8.470   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   13                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8    4                                                       
CONECT   10    2   11   12                                                  
CONECT   11   10   15                                                       
CONECT   12   10                                                            
CONECT   13    7                                                            
CONECT   14    8                                                            
CONECT   15   11                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol

Synonyms

Value	Source
3,4-Dihydroxyphenyllactate methyl ester	Generator
Methyl 3-(3,4-dihydroxyphenyl)-2-hydroxypropanoic acid	Generator

Chemical Formula

C₁₀H₁₂O₅

Average Mass

212.1993 Da

Monoisotopic Mass

212.06847 Da

IUPAC Name

methyl 3-(3,4-dihydroxyphenyl)-2-hydroxypropanoate

Traditional Name

methyl 3-(3,4-dihydroxyphenyl)-2-hydroxypropanoate

CAS Registry Number

Not Available

SMILES

COC(=O)C(O)CC1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C10H12O5/c1-15-10(14)9(13)5-6-2-3-7(11)8(12)4-6/h2-4,9,11-13H,5H2,1H3

InChI Key

NMAOZVAEJYOPOF-UHFFFAOYSA-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
Isodon oresbius	LOTUS Database	35616633
Meehania urticifolia	LOTUS Database	35616633
Ranunculus chinensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as catechols. Catechols are compounds containing a 1,2-benzenediol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Fatty acid ester
Monocyclic benzene moiety
Fatty acyl
Methyl ester
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Alcohol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen 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
logP	0.35	ALOGPS
logP	0.72	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	9.28	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	86.99 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	52.19 m³·mol⁻¹	ChemAxon
Polarizability	20.77 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0041661

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB029819

KNApSAcK ID

Not Available

Chemspider ID

8760010

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10584634

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 3-(3,4-dihydroxyphenyl)-2-hydroxypropanoate (NP0166040)

MOL for NP0166040 (methyl 3-(3,4-dihydroxyphenyl)-2-hydroxypropanoate)

3D MOL for NP0166040 (methyl 3-(3,4-dihydroxyphenyl)-2-hydroxypropanoate)

3D SDF for NP0166040 (methyl 3-(3,4-dihydroxyphenyl)-2-hydroxypropanoate)

3D-SDF for NP0166040 (methyl 3-(3,4-dihydroxyphenyl)-2-hydroxypropanoate)

PDB for NP0166040 (methyl 3-(3,4-dihydroxyphenyl)-2-hydroxypropanoate)

3D PDB for NP0166040 (methyl 3-(3,4-dihydroxyphenyl)-2-hydroxypropanoate)

SMILES for NP0166040 (methyl 3-(3,4-dihydroxyphenyl)-2-hydroxypropanoate)

INCHI for NP0166040 (methyl 3-(3,4-dihydroxyphenyl)-2-hydroxypropanoate)

Structure for NP0166040 (methyl 3-(3,4-dihydroxyphenyl)-2-hydroxypropanoate)

3D Structure for NP0166040 (methyl 3-(3,4-dihydroxyphenyl)-2-hydroxypropanoate)