NP-MRD: Showing NP-Card for [(2r,3s,4r,5s,6r)-6-{[(3s,4r,4as)-4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate (NP0288758)

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Record Information

Version

2.0

Created at

2022-09-09 18:36:09 UTC

Updated at

2022-09-09 18:36:10 UTC

NP-MRD ID

NP0288758

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2r,3s,4r,5s,6r)-6-{[(3s,4r,4as)-4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate

Description

[(2R,3S,4R,5S,6R)-6-{[(3S,4R,4aS)-4-ethenyl-8-oxo-3H,4H,4aH,5H,6H,8H-pyrano[3,4-c]pyran-3-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups. [(2r,3s,4r,5s,6r)-6-{[(3s,4r,4as)-4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate is found in Ophiorrhiza pumila. Based on a literature review very few articles have been published on [(2R,3S,4R,5S,6R)-6-{[(3S,4R,4aS)-4-ethenyl-8-oxo-3H,4H,4aH,5H,6H,8H-pyrano[3,4-c]pyran-3-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092220362D          

 37 39  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309092220362D          

 37 39  0  0  1  0            999 V2000
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 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  2  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  1  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 21 23  2  0  0  0  0
 19 24  1  0  0  0  0
  6 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
  4 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 37 36  1  1  0  0  0
 31 37  1  0  0  0  0
  3 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0288758

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC[C@H]1O[C@H](O[C@@H]2OC=C3[C@@H](CCOC3=O)[C@H]2C=C)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H30O13/c1-6-15-16-7-8-30-22(29)17(16)9-32-23(15)37-24-21(35-14(5)28)20(34-13(4)27)19(33-12(3)26)18(36-24)10-31-11(2)25/h6,9,15-16,18-21,23-24H,1,7-8,10H2,2-5H3/t15-,16+,18-,19+,20-,21+,23+,24-/m1/s1

> <INCHI_KEY>
AGMGHAAGDJHFPJ-XGJBBONISA-N

> <FORMULA>
C24H30O13

> <MOLECULAR_WEIGHT>
526.491

> <EXACT_MASS>
526.168641026

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
50.747076904968765

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4R,5S,6R)-6-{[(3S,4R,4aS)-4-ethenyl-8-oxo-3H,4H,4aH,5H,6H,8H-pyrano[3,4-c]pyran-3-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate

> <JCHEM_LOGP>
0.6353069110000011

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.088681186972342

> <JCHEM_POLAR_SURFACE_AREA>
159.19

> <JCHEM_REFRACTIVITY>
118.05399999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4R,5S,6R)-6-{[(3S,4R,4aS)-4-ethenyl-8-oxo-3H,4H,4aH,5H,6H-pyrano[3,4-c]pyran-3-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate

> <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       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.334  -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      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   37                                                  
CONECT    4    3    5   29                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   24                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    8   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   14   20   24                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21                                                            
CONECT   24   19    6   25                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29    4   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   32   37                                                  
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35   37                                                       
CONECT   37   36   31    3                                                  
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

View in JSmol

Synonyms

Value	Source
[(2R,3S,4R,5S,6R)-6-{[(3S,4R,4as)-4-ethenyl-8-oxo-3H,4H,4ah,5H,6H,8H-pyrano[3,4-c]pyran-3-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetic acid	Generator

Chemical Formula

C₂₄H₃₀O₁₃

Average Mass

526.4910 Da

Monoisotopic Mass

526.16864 Da

IUPAC Name

[(2R,3S,4R,5S,6R)-6-{[(3S,4R,4aS)-4-ethenyl-8-oxo-3H,4H,4aH,5H,6H,8H-pyrano[3,4-c]pyran-3-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate

Traditional Name

[(2R,3S,4R,5S,6R)-6-{[(3S,4R,4aS)-4-ethenyl-8-oxo-3H,4H,4aH,5H,6H-pyrano[3,4-c]pyran-3-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC[C@H]1O[C@H](O[C@@H]2OC=C3[C@@H](CCOC3=O)[C@H]2C=C)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O

InChI Identifier

InChI=1S/C24H30O13/c1-6-15-16-7-8-30-22(29)17(16)9-32-23(15)37-24-21(35-14(5)28)20(34-13(4)27)19(33-12(3)26)18(36-24)10-31-11(2)25/h6,9,15-16,18-21,23-24H,1,7-8,10H2,2-5H3/t15-,16+,18-,19+,20-,21+,23+,24-/m1/s1

InChI Key

AGMGHAAGDJHFPJ-XGJBBONISA-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
Ophiorrhiza pumila	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pentacarboxylic acids and derivatives. These are carboxylic acids containing exactly five carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Pentacarboxylic acids and derivatives

Direct Parent

Pentacarboxylic acids and derivatives

Alternative Parents

Substituents

Pentacarboxylic acid or derivatives
Glycosyl compound
O-glycosyl compound
Delta valerolactone
Delta_valerolactone
Monosaccharide
Oxane
Vinylogous ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Lactone
Carboxylic acid ester
Organoheterocyclic compound
Oxacycle
Acetal
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	0.64	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	159.19 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	118.05 m³·mol⁻¹	ChemAxon
Polarizability	50.75 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

162847343

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,4r,5s,6r)-6-{[(3s,4r,4as)-4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate (NP0288758)

MOL for NP0288758 ([(2r,3s,4r,5s,6r)-6-{[(3s,4r,4as)-4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

3D MOL for NP0288758 ([(2r,3s,4r,5s,6r)-6-{[(3s,4r,4as)-4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

3D SDF for NP0288758 ([(2r,3s,4r,5s,6r)-6-{[(3s,4r,4as)-4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

3D-SDF for NP0288758 ([(2r,3s,4r,5s,6r)-6-{[(3s,4r,4as)-4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

PDB for NP0288758 ([(2r,3s,4r,5s,6r)-6-{[(3s,4r,4as)-4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

3D PDB for NP0288758 ([(2r,3s,4r,5s,6r)-6-{[(3s,4r,4as)-4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

SMILES for NP0288758 ([(2r,3s,4r,5s,6r)-6-{[(3s,4r,4as)-4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

INCHI for NP0288758 ([(2r,3s,4r,5s,6r)-6-{[(3s,4r,4as)-4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

Structure for NP0288758 ([(2r,3s,4r,5s,6r)-6-{[(3s,4r,4as)-4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)

3D Structure for NP0288758 ([(2r,3s,4r,5s,6r)-6-{[(3s,4r,4as)-4-ethenyl-8-oxo-3h,4h,4ah,5h,6h-pyrano[3,4-c]pyran-3-yl]oxy}-3,4,5-tris(acetyloxy)oxan-2-yl]methyl acetate)