NP-MRD: Showing NP-Card for (6-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate (NP0320851)

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Record Information

Version

2.0

Created at

2022-09-11 22:44:15 UTC

Updated at

2022-09-11 22:44:15 UTC

NP-MRD ID

NP0320851

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Description

HMS3357M19 belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen. (6-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate is found in Beta vulgaris, Polygala arillata and Veronica pulvinaris. HMS3357M19 is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171513192D          

 36 38  0  0  0  0            999 V2000
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    4.2158   -3.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8989   -1.5675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0920   -1.3960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1533004171513192D          

 36 38  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0320851

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(C=CC(=O)OCC2OC(OC3(CO)OC(CO)C(O)C3O)C(O)C(O)C2O)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O14/c1-32-12-6-10(2-4-11(12)25)3-5-15(26)33-8-14-16(27)18(29)19(30)21(34-14)36-22(9-24)20(31)17(28)13(7-23)35-22/h2-6,13-14,16-21,23-25,27-31H,7-9H2,1H3

> <INCHI_KEY>
XMBZZLUIFFOAHR-UHFFFAOYSA-N

> <FORMULA>
C22H30O14

> <MOLECULAR_WEIGHT>
518.468

> <EXACT_MASS>
518.163555646

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
49.51874246790607

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

> <ALOGPS_LOGP>
-1.27

> <JCHEM_LOGP>
-1.9561808329999995

> <ALOGPS_LOGS>
-1.91

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.84526258643745

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.86320546579753

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981433338188096

> <JCHEM_POLAR_SURFACE_AREA>
225.05999999999997

> <JCHEM_REFRACTIVITY>
116.78590000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
6.40e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      11.358  -8.280   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.852  -7.960   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.376  -6.496   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.869  -6.175   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.394  -4.711   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.887  -4.391   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.411  -2.926   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.905  -2.606   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       2.875  -3.750   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       3.429  -1.141   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       1.923  -0.821   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.447   0.644   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -0.059   0.964   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -0.535   2.428   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.042   2.749   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -3.072   1.604   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -4.103   2.749   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -5.609   2.428   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -1.826   0.699   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.302  -0.766   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.397  -2.012   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.135  -1.851   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -3.842  -0.766   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -4.747  -2.012   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -4.318   0.699   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -5.783   1.175   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.495   3.573   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       0.019   5.037   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.001   3.253   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.032   4.397   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.477   1.788   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       3.984   1.468   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       8.424  -3.566   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       9.930  -3.887   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      10.406  -5.351   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      11.913  -5.671   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   35                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   33                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   31                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   27                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   19   25                                             
CONECT   17   16   18                                                       
CONECT   18   17                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21   23                                                  
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   20   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   16   26                                                  
CONECT   26   25                                                            
CONECT   27   14   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   12   32                                                  
CONECT   32   31                                                            
CONECT   33    5   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34    3   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Value	Source
(6-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid	Generator

Chemical Formula

C₂₂H₃₀O₁₄

Average Mass

518.4680 Da

Monoisotopic Mass

518.16356 Da

IUPAC Name

(6-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

Traditional Name

(6-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

COC1=CC(C=CC(=O)OCC2OC(OC3(CO)OC(CO)C(O)C3O)C(O)C(O)C2O)=CC=C1O

InChI Identifier

InChI=1S/C22H30O14/c1-32-12-6-10(2-4-11(12)25)3-5-15(26)33-8-14-16(27)18(29)19(30)21(34-14)36-22(9-24)20(31)17(28)13(7-23)35-22/h2-6,13-14,16-21,23-25,27-31H,7-9H2,1H3

InChI Key

XMBZZLUIFFOAHR-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
Beta vulgaris	LOTUS Database	35616633
Polygala arillata	LOTUS Database	35616633
Veronica pulvinaris	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrahydrofurans. These are heterocyclic compounds containing a saturated, aliphatic, five-membered ring where a carbon is replaced by an oxygen.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrahydrofurans

Sub Class

Not Available

Direct Parent

Tetrahydrofurans

Alternative Parents

Substituents

Tetrahydrofuran
Secondary alcohol
Oxacycle
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic 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	-2	ChemAxon
logS	-1.9	ALOGPS
pKa (Strongest Acidic)	9.86	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	225.06 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	116.79 m³·mol⁻¹	ChemAxon
Polarizability	49.52 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

73162489

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (6-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate (NP0320851)

MOL for NP0320851 ((6-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D MOL for NP0320851 ((6-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D SDF for NP0320851 ((6-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D-SDF for NP0320851 ((6-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

PDB for NP0320851 ((6-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D PDB for NP0320851 ((6-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

SMILES for NP0320851 ((6-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

INCHI for NP0320851 ((6-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

Structure for NP0320851 ((6-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)

3D Structure for NP0320851 ((6-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate)