NP-MRD: Showing NP-Card for [(2r,3s,4s,5r,6s)-6-{[(3s,4r,4ar)-4-ethenyl-4a-hydroxy-8-oxo-3h,4h,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 2,3-dihydroxybenzoate (NP0284046)

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Record Information

Version

2.0

Created at

2022-09-09 11:34:34 UTC

Updated at

2022-09-09 11:34:34 UTC

NP-MRD ID

NP0284046

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2r,3s,4s,5r,6s)-6-{[(3s,4r,4ar)-4-ethenyl-4a-hydroxy-8-oxo-3h,4h,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 2,3-dihydroxybenzoate

Description

6''-(2,3-Dihydroxybenzoyl)swertiamarin belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. [(2r,3s,4s,5r,6s)-6-{[(3s,4r,4ar)-4-ethenyl-4a-hydroxy-8-oxo-3h,4h,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 2,3-dihydroxybenzoate is found in Gentiana algida. Based on a literature review very few articles have been published on 6''-(2,3-Dihydroxybenzoyl)swertiamarin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092213342D          

 36 39  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309092213342D          

 36 39  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0284046

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1[C@H](O)[C@@H](COC(=O)C2=CC=CC(O)=C2O)O[C@@H](O[C@@H]2OC=C3C(=O)OCC[C@@]3(O)[C@H]2C=C)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C23H26O13/c1-2-11-21(34-8-12-20(30)32-7-6-23(11,12)31)36-22-18(28)17(27)16(26)14(35-22)9-33-19(29)10-4-3-5-13(24)15(10)25/h2-5,8,11,14,16-18,21-22,24-28,31H,1,6-7,9H2/t11-,14+,16+,17-,18+,21-,22-,23+/m0/s1

> <INCHI_KEY>
RFPJOMPMFRQYIM-JXVMTUIQSA-N

> <FORMULA>
C23H26O13

> <MOLECULAR_WEIGHT>
510.448

> <EXACT_MASS>
510.137340897

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
48.38480882451485

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6S)-6-{[(3S,4R,4aR)-4-ethenyl-4a-hydroxy-8-oxo-3H,4H,4aH,5H,6H,8H-pyrano[3,4-c]pyran-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 2,3-dihydroxybenzoate

> <JCHEM_LOGP>
0.43795985500000023

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.089264122399198

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.271884173252358

> <JCHEM_PKA_STRONGEST_BASIC>
-3.533771358087744

> <JCHEM_POLAR_SURFACE_AREA>
201.67

> <JCHEM_REFRACTIVITY>
116.35549999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6S)-6-{[(3S,4R,4aR)-4-ethenyl-4a-hydroxy-8-oxo-3H,4H,5H,6H-pyrano[3,4-c]pyran-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 2,3-dihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       4.001  -3.850   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   35                                                  
CONECT    4    3    5   27                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   25                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   21                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   19                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   13   20                                                  
CONECT   20   19                                                            
CONECT   21    8   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23    6   26                                                  
CONECT   26   25                                                            
CONECT   27    4   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   35                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   29    3   36                                             
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₃H₂₆O₁₃

Average Mass

510.4480 Da

Monoisotopic Mass

510.13734 Da

IUPAC Name

[(2R,3S,4S,5R,6S)-6-{[(3S,4R,4aR)-4-ethenyl-4a-hydroxy-8-oxo-3H,4H,4aH,5H,6H,8H-pyrano[3,4-c]pyran-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 2,3-dihydroxybenzoate

Traditional Name

[(2R,3S,4S,5R,6S)-6-{[(3S,4R,4aR)-4-ethenyl-4a-hydroxy-8-oxo-3H,4H,5H,6H-pyrano[3,4-c]pyran-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 2,3-dihydroxybenzoate

CAS Registry Number

Not Available

SMILES

O[C@H]1[C@H](O)[C@@H](COC(=O)C2=CC=CC(O)=C2O)O[C@@H](O[C@@H]2OC=C3C(=O)OCC[C@@]3(O)[C@H]2C=C)[C@@H]1O

InChI Identifier

InChI=1S/C23H26O13/c1-2-11-21(34-8-12-20(30)32-7-6-23(11,12)31)36-22-18(28)17(27)16(26)14(35-22)9-33-19(29)10-4-3-5-13(24)15(10)25/h2-5,8,11,14,16-18,21-22,24-28,31H,1,6-7,9H2/t11-,14+,16+,17-,18+,21-,22-,23+/m0/s1

InChI Key

RFPJOMPMFRQYIM-JXVMTUIQSA-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
Gentiana algida	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-glycosyl compounds

Alternative Parents

Substituents

M-hydroxybenzoic acid ester
O-hydroxybenzoic acid ester
O-glycosyl compound
Benzoate ester
Salicylic acid or derivatives
Benzoic acid or derivatives
Benzoyl
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Delta valerolactone
Delta_valerolactone
Monosaccharide
Dicarboxylic acid or derivatives
Benzenoid
Oxane
Monocyclic benzene moiety
Vinylogous ester
Vinylogous acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Carboxylic acid ester
Lactone
Secondary alcohol
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Oxacycle
Polyol
Alcohol
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic 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	0.44	ChemAxon
pKa (Strongest Acidic)	9.27	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	201.67 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	116.36 m³·mol⁻¹	ChemAxon
Polarizability	48.38 Å³	ChemAxon
Number of Rings	4	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

102094444

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(2r,3s,4s,5r,6s)-6-{[(3s,4r,4ar)-4-ethenyl-4a-hydroxy-8-oxo-3h,4h,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 2,3-dihydroxybenzoate (NP0284046)

MOL for NP0284046 ([(2r,3s,4s,5r,6s)-6-{[(3s,4r,4ar)-4-ethenyl-4a-hydroxy-8-oxo-3h,4h,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 2,3-dihydroxybenzoate)

3D MOL for NP0284046 ([(2r,3s,4s,5r,6s)-6-{[(3s,4r,4ar)-4-ethenyl-4a-hydroxy-8-oxo-3h,4h,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 2,3-dihydroxybenzoate)

3D SDF for NP0284046 ([(2r,3s,4s,5r,6s)-6-{[(3s,4r,4ar)-4-ethenyl-4a-hydroxy-8-oxo-3h,4h,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 2,3-dihydroxybenzoate)

3D-SDF for NP0284046 ([(2r,3s,4s,5r,6s)-6-{[(3s,4r,4ar)-4-ethenyl-4a-hydroxy-8-oxo-3h,4h,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 2,3-dihydroxybenzoate)

PDB for NP0284046 ([(2r,3s,4s,5r,6s)-6-{[(3s,4r,4ar)-4-ethenyl-4a-hydroxy-8-oxo-3h,4h,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 2,3-dihydroxybenzoate)

3D PDB for NP0284046 ([(2r,3s,4s,5r,6s)-6-{[(3s,4r,4ar)-4-ethenyl-4a-hydroxy-8-oxo-3h,4h,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 2,3-dihydroxybenzoate)

SMILES for NP0284046 ([(2r,3s,4s,5r,6s)-6-{[(3s,4r,4ar)-4-ethenyl-4a-hydroxy-8-oxo-3h,4h,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 2,3-dihydroxybenzoate)

INCHI for NP0284046 ([(2r,3s,4s,5r,6s)-6-{[(3s,4r,4ar)-4-ethenyl-4a-hydroxy-8-oxo-3h,4h,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 2,3-dihydroxybenzoate)

Structure for NP0284046 ([(2r,3s,4s,5r,6s)-6-{[(3s,4r,4ar)-4-ethenyl-4a-hydroxy-8-oxo-3h,4h,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 2,3-dihydroxybenzoate)

3D Structure for NP0284046 ([(2r,3s,4s,5r,6s)-6-{[(3s,4r,4ar)-4-ethenyl-4a-hydroxy-8-oxo-3h,4h,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 2,3-dihydroxybenzoate)