NP-MRD: Showing NP-Card for [(3s,4s)-3,4-dihydroxy-5-oxooxolan-3-yl]methyl 4-hydroxy-3-methoxybenzoate (NP0255221)

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Record Information

Version

2.0

Created at

2022-09-07 19:38:22 UTC

Updated at

2022-09-07 19:38:22 UTC

NP-MRD ID

NP0255221

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(3s,4s)-3,4-dihydroxy-5-oxooxolan-3-yl]methyl 4-hydroxy-3-methoxybenzoate

Description

[(3S,4S)-3,4-dihydroxy-5-oxooxolan-3-yl]methyl 4-hydroxy-3-methoxybenzoate belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group. [(3s,4s)-3,4-dihydroxy-5-oxooxolan-3-yl]methyl 4-hydroxy-3-methoxybenzoate is found in Phellodendron chinense. Based on a literature review very few articles have been published on [(3S,4S)-3,4-dihydroxy-5-oxooxolan-3-yl]methyl 4-hydroxy-3-methoxybenzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 35 36  0  0  0  0  0  0  0  0999 V2000
   -5.5820   -1.3049    1.3058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2664   -0.3127    0.3900 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0255    0.1304    0.0380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8360   -0.3328    0.5346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6063    0.1538    0.1412 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3632   -0.3997    0.7254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4087   -1.3154    1.5831 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8753    0.0762    0.3424 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0921   -0.4332    0.8838 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2627    0.2702    0.2836 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2501    1.6283    0.5160 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4272   -0.0507   -1.1879 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0745   -1.3275   -1.2133 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7493   -1.5108   -0.0204 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4530   -2.5137    0.2535 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5241   -0.3696    0.8726 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.5841    0.5348    0.8629 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5343    1.1595   -0.7998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7145    1.6460   -1.3179 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9384    1.1450   -0.9105 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1131    1.6605   -1.4555 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5712   -1.0619    1.7535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8730   -1.3358    2.1801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6879   -2.3229    0.8612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8802   -1.1202    1.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1886   -1.5140    0.7361 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0646   -0.1912    1.9664 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3401    2.1833   -0.2868 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1203    0.6714   -1.6413 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4393   -0.0746   -1.6564 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3238   -0.6379    1.9208 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0000    0.4899   -0.0327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5853    1.5384   -1.1067 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7170    2.4460   -2.0695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0661    2.3957   -2.1437 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  6
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 20  3  1  0
 16 10  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  4 25  1  0
 18 33  1  0
 19 34  1  0
 21 35  1  0
  9 26  1  0
  9 27  1  0
 11 28  1  0
 12 29  1  0
 12 30  1  0
 16 31  1  1
 17 32  1  0
M  END


  Mrv1652309072221382D          

 21 22  0  0  1  0            999 V2000
   -0.7102   10.1142    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4552    9.3296    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0072    8.7165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7523    7.9318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3043    7.3187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0494    6.5341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2424    6.3626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6014    5.9210    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3465    5.1364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8985    4.5233    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4506    5.1364    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2311    4.0384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4860    3.2538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3110    3.2538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7960    2.5863    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5660    4.0384    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.3506    4.2933    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1113    7.4903    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3663    8.2749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8142    8.8880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0692    9.6726    0.0000 O   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  2  0  0  0  0
  4  5  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
  8  9  1  0  0  0  0
 10  9  1  6  0  0  0
 10 11  1  1  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 10 16  1  0  0  0  0
 16 17  1  1  0  0  0
  5 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
  3 20  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0255221

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1O)C(=O)OC[C@]1(O)COC(=O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C13H14O8/c1-19-9-4-7(2-3-8(9)14)11(16)20-5-13(18)6-21-12(17)10(13)15/h2-4,10,14-15,18H,5-6H2,1H3/t10-,13+/m1/s1

> <INCHI_KEY>
XDFVRGIAOTYYJE-MFKMUULPSA-N

> <FORMULA>
C13H14O8

> <MOLECULAR_WEIGHT>
298.247

> <EXACT_MASS>
298.068867411

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
27.66100357420178

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(3S,4S)-3,4-dihydroxy-5-oxooxolan-3-yl]methyl 4-hydroxy-3-methoxybenzoate

> <JCHEM_LOGP>
-0.21687333899999955

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.349209759126051

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.98952245850669

> <JCHEM_PKA_STRONGEST_BASIC>
-4.105577249239064

> <JCHEM_POLAR_SURFACE_AREA>
122.52000000000001

> <JCHEM_REFRACTIVITY>
67.30180000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(3S,4S)-3,4-dihydroxy-5-oxooxolan-3-yl]methyl 4-hydroxy-3-methoxybenzoate

> <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      -1.326  18.880   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -0.850  17.415   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -1.880  16.271   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.404  14.806   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.435  13.662   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.959  12.197   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.453  11.877   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -2.989  11.053   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -2.513   9.588   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.544   8.444   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.574   9.588   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.298   7.538   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -2.774   6.074   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -4.314   6.074   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -5.219   4.828   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -4.790   7.538   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -6.254   8.014   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -3.941  13.982   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.417  15.446   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.387  16.591   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -3.862  18.056   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   18                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   16                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   10   17                                                  
CONECT   17   16                                                            
CONECT   18    5   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19    3   21                                                  
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

View in JSmol

Synonyms

Value	Source
[(3S,4S)-3,4-Dihydroxy-5-oxooxolan-3-yl]methyl 4-hydroxy-3-methoxybenzoic acid	Generator

Chemical Formula

C₁₃H₁₄O₈

Average Mass

298.2470 Da

Monoisotopic Mass

298.06887 Da

IUPAC Name

[(3S,4S)-3,4-dihydroxy-5-oxooxolan-3-yl]methyl 4-hydroxy-3-methoxybenzoate

Traditional Name

[(3S,4S)-3,4-dihydroxy-5-oxooxolan-3-yl]methyl 4-hydroxy-3-methoxybenzoate

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1O)C(=O)OC[C@]1(O)COC(=O)[C@H]1O

InChI Identifier

InChI=1S/C13H14O8/c1-19-9-4-7(2-3-8(9)14)11(16)20-5-13(18)6-21-12(17)10(13)15/h2-4,10,14-15,18H,5-6H2,1H3/t10-,13+/m1/s1

InChI Key

XDFVRGIAOTYYJE-MFKMUULPSA-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
Phellodendron chinense	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as m-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 3 of the benzene ring is replaced by a methoxy group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

M-methoxybenzoic acids and derivatives

Alternative Parents

Substituents

P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
M-methoxybenzoic acid or derivatives
Benzoate ester
Methoxyphenol
Phenoxy compound
Anisole
Methoxybenzene
Benzoyl
Phenol ether
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Phenol
Dicarboxylic acid or derivatives
Gamma butyrolactone
Tetrahydrofuran
Tertiary alcohol
1,2-diol
Lactone
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Ether
Alcohol
Organic oxygen compound
Carbonyl group
Organic oxide
Organooxygen compound
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	-0.22	ChemAxon
pKa (Strongest Acidic)	8.99	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	122.52 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	67.3 m³·mol⁻¹	ChemAxon
Polarizability	27.66 Å³	ChemAxon
Number of Rings	2	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

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

162873914

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(3s,4s)-3,4-dihydroxy-5-oxooxolan-3-yl]methyl 4-hydroxy-3-methoxybenzoate (NP0255221)

MOL for NP0255221 ([(3s,4s)-3,4-dihydroxy-5-oxooxolan-3-yl]methyl 4-hydroxy-3-methoxybenzoate)

3D MOL for NP0255221 ([(3s,4s)-3,4-dihydroxy-5-oxooxolan-3-yl]methyl 4-hydroxy-3-methoxybenzoate)

3D SDF for NP0255221 ([(3s,4s)-3,4-dihydroxy-5-oxooxolan-3-yl]methyl 4-hydroxy-3-methoxybenzoate)

3D-SDF for NP0255221 ([(3s,4s)-3,4-dihydroxy-5-oxooxolan-3-yl]methyl 4-hydroxy-3-methoxybenzoate)

PDB for NP0255221 ([(3s,4s)-3,4-dihydroxy-5-oxooxolan-3-yl]methyl 4-hydroxy-3-methoxybenzoate)

3D PDB for NP0255221 ([(3s,4s)-3,4-dihydroxy-5-oxooxolan-3-yl]methyl 4-hydroxy-3-methoxybenzoate)

SMILES for NP0255221 ([(3s,4s)-3,4-dihydroxy-5-oxooxolan-3-yl]methyl 4-hydroxy-3-methoxybenzoate)

INCHI for NP0255221 ([(3s,4s)-3,4-dihydroxy-5-oxooxolan-3-yl]methyl 4-hydroxy-3-methoxybenzoate)

Structure for NP0255221 ([(3s,4s)-3,4-dihydroxy-5-oxooxolan-3-yl]methyl 4-hydroxy-3-methoxybenzoate)

3D Structure for NP0255221 ([(3s,4s)-3,4-dihydroxy-5-oxooxolan-3-yl]methyl 4-hydroxy-3-methoxybenzoate)