NP-MRD: Showing NP-Card for (3,4,5,6-tetrahydroxyoxan-2-yl)methyl 3,4-dihydroxybenzoate (NP0329381)

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Record Information

Version

2.0

Created at

2022-09-12 13:42:36 UTC

Updated at

2022-09-12 13:42:36 UTC

NP-MRD ID

NP0329381

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3,4,5,6-tetrahydroxyoxan-2-yl)methyl 3,4-dihydroxybenzoate

Description

(3,4,5,6-Tetrahydroxyoxan-2-yl)methyl 3,4-dihydroxybenzoate belongs to the class of organic compounds known as p-hydroxybenzoic acid alkyl esters. (3,4,5,6-tetrahydroxyoxan-2-yl)methyl 3,4-dihydroxybenzoate is found in Salvinia molesta. These are aromatic compounds containing a benzoic acid, which is esterified with an alkyl group and para-substituted with a hydroxyl group (3,4,5,6-tetrahydroxyoxan-2-yl)methyl 3,4-dihydroxybenzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 38 39  0  0  0  0  0  0  0  0999 V2000
    0.5439    1.2543   -0.6374 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3392    0.5307   -0.0002 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8432   -0.3243    0.9326 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4856   -0.5339    1.3081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3983   -1.0340    0.2301 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5522   -0.2475   -0.8579 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6200    0.5899   -0.9198 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4723    1.7475   -0.1212 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9583   -0.0401   -0.6856 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.7312    0.7393    0.2012 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8634   -1.4162   -0.0998 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.0084   -1.7165    0.6224 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6900   -1.5162    0.8587 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9618   -0.8661    2.0674 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7824    0.6239   -0.2761 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2659    1.4904   -1.2191 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6228    1.5865   -1.4870 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5286    0.8027   -0.8024 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9071    0.8832   -1.0572 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0541   -0.0683    0.1440 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9560   -0.8554    0.8325 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6967   -0.1529    0.4004 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8421    0.4118    1.7695 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4466   -1.2560    2.1750 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9012   -1.9832   -0.1463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6507    0.9998   -1.9747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0337    2.4557   -0.5139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5795   -0.1118   -1.6168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2596    1.4163   -0.2717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6847   -2.1349   -0.9258 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6311   -2.3099    0.1082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6367   -2.6117    1.1355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8381    0.0942    2.0424 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5321    2.1016   -1.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9548    2.2787   -2.2336 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2389    1.5306   -1.7580 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6241   -1.5091    1.5399 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3556   -0.8487    1.1517 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  0
  2 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 18 20  1  0
 20 21  1  0
 20 22  2  0
  5 13  1  0
 13 14  1  0
 13 11  1  0
 11 12  1  0
 11  9  1  0
  9 10  1  0
  9  7  1  0
 22 15  1  0
  8 27  1  0
  7 26  1  6
  5 25  1  6
  4 23  1  0
  4 24  1  0
 16 34  1  0
 17 35  1  0
 19 36  1  0
 21 37  1  0
 22 38  1  0
 13 32  1  1
 14 33  1  0
 11 30  1  6
 12 31  1  0
  9 28  1  6
 10 29  1  0
M  END


  Mrv1533004231522482D          

 22 23  0  0  0  0            999 V2000
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -8.6625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -7.8375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
  9 16  1  0  0  0  0
  4 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
  2 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0329381

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1OC(COC(=O)C2=CC=C(O)C(O)=C2)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C13H16O9/c14-6-2-1-5(3-7(6)15)12(19)21-4-8-9(16)10(17)11(18)13(20)22-8/h1-3,8-11,13-18,20H,4H2

> <INCHI_KEY>
JBLVGFKMCLXCOP-UHFFFAOYSA-N

> <FORMULA>
C13H16O9

> <MOLECULAR_WEIGHT>
316.262

> <EXACT_MASS>
316.079432095

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
29.423110457549342

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3,4,5,6-tetrahydroxyoxan-2-yl)methyl 3,4-dihydroxybenzoate

> <ALOGPS_LOGP>
-1.27

> <JCHEM_LOGP>
-1.0443700126666666

> <ALOGPS_LOGS>
-1.26

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.243771317059512

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.558285828070103

> <JCHEM_PKA_STRONGEST_BASIC>
-3.649083918273866

> <JCHEM_POLAR_SURFACE_AREA>
156.91

> <JCHEM_REFRACTIVITY>
69.70720000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.74e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3,4,5,6-tetrahydroxyoxan-2-yl)methyl 3,4-dihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       9.336 -10.010   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      10.669  -9.240   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       9.336 -11.550   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       9.336 -14.630   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       9.336 -16.170   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       8.002 -13.860   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.668 -14.630   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   21                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   17                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14    9                                                       
CONECT   17    4   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19    2   22                                                  
CONECT   22   21                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

View in JSmol

Synonyms

Value	Source
(3,4,5,6-Tetrahydroxyoxan-2-yl)methyl 3,4-dihydroxybenzoic acid	Generator

Chemical Formula

C₁₃H₁₆O₉

Average Mass

316.2620 Da

Monoisotopic Mass

316.07943 Da

IUPAC Name

(3,4,5,6-tetrahydroxyoxan-2-yl)methyl 3,4-dihydroxybenzoate

Traditional Name

(3,4,5,6-tetrahydroxyoxan-2-yl)methyl 3,4-dihydroxybenzoate

CAS Registry Number

Not Available

SMILES

OC1OC(COC(=O)C2=CC=C(O)C(O)=C2)C(O)C(O)C1O

InChI Identifier

InChI=1S/C13H16O9/c14-6-2-1-5(3-7(6)15)12(19)21-4-8-9(16)10(17)11(18)13(20)22-8/h1-3,8-11,13-18,20H,4H2

InChI Key

JBLVGFKMCLXCOP-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
Salvinia molesta	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as p-hydroxybenzoic acid alkyl esters. These are aromatic compounds containing a benzoic acid, which is esterified with an alkyl group and para-substituted with a hydroxyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

p-Hydroxybenzoic acid alkyl esters

Alternative Parents

Substituents

P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
Dihydroxybenzoic acid
Benzoyl
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monosaccharide
Oxane
Carboxylic acid ester
Hemiacetal
Secondary alcohol
Oxacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organoheterocyclic compound
Polyol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Alcohol
Organic oxygen compound
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	-1.3	ALOGPS
logP	-1	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Acidic)	8.56	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	156.91 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	69.71 m³·mol⁻¹	ChemAxon
Polarizability	29.42 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

74323795

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3,4,5,6-tetrahydroxyoxan-2-yl)methyl 3,4-dihydroxybenzoate (NP0329381)

MOL for NP0329381 ((3,4,5,6-tetrahydroxyoxan-2-yl)methyl 3,4-dihydroxybenzoate)

3D MOL for NP0329381 ((3,4,5,6-tetrahydroxyoxan-2-yl)methyl 3,4-dihydroxybenzoate)

3D SDF for NP0329381 ((3,4,5,6-tetrahydroxyoxan-2-yl)methyl 3,4-dihydroxybenzoate)

3D-SDF for NP0329381 ((3,4,5,6-tetrahydroxyoxan-2-yl)methyl 3,4-dihydroxybenzoate)

PDB for NP0329381 ((3,4,5,6-tetrahydroxyoxan-2-yl)methyl 3,4-dihydroxybenzoate)

3D PDB for NP0329381 ((3,4,5,6-tetrahydroxyoxan-2-yl)methyl 3,4-dihydroxybenzoate)

SMILES for NP0329381 ((3,4,5,6-tetrahydroxyoxan-2-yl)methyl 3,4-dihydroxybenzoate)

INCHI for NP0329381 ((3,4,5,6-tetrahydroxyoxan-2-yl)methyl 3,4-dihydroxybenzoate)

Structure for NP0329381 ((3,4,5,6-tetrahydroxyoxan-2-yl)methyl 3,4-dihydroxybenzoate)

3D Structure for NP0329381 ((3,4,5,6-tetrahydroxyoxan-2-yl)methyl 3,4-dihydroxybenzoate)