NP-MRD: Showing NP-Card for (6-{[(2s)-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 (NP0329596)

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Record Information

Version

2.0

Created at

2022-09-12 14:07:45 UTC

Updated at

2022-09-12 14:07:45 UTC

NP-MRD ID

NP0329596

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6-{[(2s)-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

Arillatose B belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring. (6-{[(2s)-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 Polygala arillata. (6-{[(2s)-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 was first documented in 2005 (PMID: 16308194). Based on a literature review very few articles have been published on Arillatose B (PMID: 16203607).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122216072D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309122216072D          

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 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
  3 35  1  0  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0329596

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(C=CC(=O)OCC2OC(O[C@]3(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/t13?,14?,16?,17?,18?,19?,20?,21?,22-/m0/s1

> <INCHI_KEY>
XMBZZLUIFFOAHR-JYQQYYBKSA-N

> <FORMULA>
C22H30O14

> <MOLECULAR_WEIGHT>
518.468

> <EXACT_MASS>
518.163555646

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
49.81730823889916

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6-{[(2S)-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_LOGP>
-1.9561808329999995

> <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

> <JCHEM_TRADITIONAL_IUPAC>
(6-{[(2S)-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                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         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

Not Available

Chemical Formula

C₂₂H₃₀O₁₄

Average Mass

518.4680 Da

Monoisotopic Mass

518.16356 Da

IUPAC Name

(6-{[(2S)-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-{[(2S)-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(O[C@]3(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/t13?,14?,16?,17?,18?,19?,20?,21?,22-/m0/s1

InChI Key

XMBZZLUIFFOAHR-JYQQYYBKSA-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
Polygala arillata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as coumaric acids and derivatives. These are aromatic compounds containing Aromatic compounds containing a cinnamic acid moiety (or a derivative thereof) hydroxylated at the C2 (ortho-), C3 (meta-), or C4 (para-) carbon atom of the benzene ring.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Hydroxycinnamic acids and derivatives

Direct Parent

Coumaric acids and derivatives

Alternative Parents

Substituents

Cinnamic acid ester
Coumaric acid or derivatives
O-glycosyl compound
Glycosyl compound
Disaccharide
C-glycosyl compound
Methoxyphenol
Phenoxy compound
Methoxybenzene
Styrene
Phenol ether
Anisole
1-hydroxy-2-unsubstituted benzenoid
Ketal
Phenol
Fatty acid ester
Alkyl aryl ether
Fatty acyl
Benzenoid
Oxane
Monocyclic benzene moiety
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Ether
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
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	-2	ChemAxon
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	49.82 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

C00059783

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

138113913

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Georgopoulou C, Aligiannis N, Fokialakis N, Mitaku S: Acretoside, a new sucrose ester from Aristolochia cretica. J Asian Nat Prod Res. 2005 Dec;7(6):799-803. doi: 10.1080/1028602042000191617. [PubMed:16308194 ]
Georgopoulou C, Aligiannis N, Fokialakis N, Mitaku S: Acretoside, a new sucrose ester from Aristolochia cretica. Nat Prod Res. 2005 Dec;19(8):795-9. doi: 10.1080/14786410500184033. [PubMed:16203607 ]
LOTUS database [Link]

Showing NP-Card for (6-{[(2s)-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 (NP0329596)

MOL for NP0329596 ((6-{[(2s)-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 NP0329596 ((6-{[(2s)-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 NP0329596 ((6-{[(2s)-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 NP0329596 ((6-{[(2s)-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 NP0329596 ((6-{[(2s)-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 NP0329596 ((6-{[(2s)-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 NP0329596 ((6-{[(2s)-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 NP0329596 ((6-{[(2s)-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 NP0329596 ((6-{[(2s)-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 NP0329596 ((6-{[(2s)-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)