NP-MRD: Showing NP-Card for 3-[(1s,2s,3r,4s,6s)-4-(acetyloxy)-6-methyl-2-{[(2z)-2-methylbut-2-enoyl]oxy}-5-oxo-7-oxabicyclo[4.1.0]heptan-3-yl]-1-(3,3-dimethyloxiran-2-yl)but-3-en-2-yl 2-methylbut-2-enoate (NP0276620)

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Record Information

Version

2.0

Created at

2022-09-09 00:50:54 UTC

Updated at

2022-09-09 00:50:54 UTC

NP-MRD ID

NP0276620

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[(1s,2s,3r,4s,6s)-4-(acetyloxy)-6-methyl-2-{[(2z)-2-methylbut-2-enoyl]oxy}-5-oxo-7-oxabicyclo[4.1.0]heptan-3-yl]-1-(3,3-dimethyloxiran-2-yl)but-3-en-2-yl 2-methylbut-2-enoate

Description

3-[(1s,2s,3r,4s,6s)-4-(acetyloxy)-6-methyl-2-{[(2z)-2-methylbut-2-enoyl]oxy}-5-oxo-7-oxabicyclo[4.1.0]heptan-3-yl]-1-(3,3-dimethyloxiran-2-yl)but-3-en-2-yl 2-methylbut-2-enoate is found in Ligularia altaica.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092202502D          

 36 38  0  0  1  0            999 V2000
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3020    0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  2  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309092202502D          

 36 38  0  0  1  0            999 V2000
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 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 20 22  2  0  0  0  0
 18 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 28 27  1  1  0  0  0
 25 28  1  0  0  0  0
 28 29  1  0  0  0  0
 17 29  1  0  0  0  0
 29 30  1  1  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 31 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  2  0  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0276620

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC=C(C)C(=O)OC(CC1OC1(C)C)C(=C)[C@@H]1[C@H](OC(=O)C(\C)=C/C)[C@@H]2O[C@]2(C)C(=O)[C@H]1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H36O9/c1-10-13(3)24(30)33-17(12-18-26(7,8)35-18)15(5)19-20(32-16(6)28)22(29)27(9)23(36-27)21(19)34-25(31)14(4)11-2/h10-11,17-21,23H,5,12H2,1-4,6-9H3/b13-10?,14-11-/t17?,18?,19-,20-,21-,23-,27+/m0/s1

> <INCHI_KEY>
VMZMBTIZKOPION-NJGZOHAASA-N

> <FORMULA>
C27H36O9

> <MOLECULAR_WEIGHT>
504.576

> <EXACT_MASS>
504.235932739

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
53.080459223774895

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(1S,2S,3R,4S,6S)-4-(acetyloxy)-6-methyl-2-{[(2Z)-2-methylbut-2-enoyl]oxy}-5-oxo-7-oxabicyclo[4.1.0]heptan-3-yl]-1-(3,3-dimethyloxiran-2-yl)but-3-en-2-yl 2-methylbut-2-enoate

> <JCHEM_LOGP>
4.2255700146666655

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.053260911032723

> <JCHEM_PKA_STRONGEST_BASIC>
-3.957605137041963

> <JCHEM_POLAR_SURFACE_AREA>
121.03

> <JCHEM_REFRACTIVITY>
129.38099999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-[(1S,2S,3R,4S,6S)-4-(acetyloxy)-6-methyl-2-{[(2Z)-2-methylbut-2-enoyl]oxy}-5-oxo-7-oxabicyclo[4.1.0]heptan-3-yl]-1-(3,3-dimethyloxiran-2-yl)but-3-en-2-yl 2-methylbut-2-enoate

> <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  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       0.564   0.564   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.104   0.564   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.755   1.959   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.638   0.429   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -2.104  -8.264   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -2.667  -6.160   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   17                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5    7                                                       
CONECT    7    6    5    8    9                                             
CONECT    8    7                                                            
CONECT    9    7                                                            
CONECT   10    3   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15                                                            
CONECT   17    2   18   29                                                  
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   18   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   27   28                                             
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   25   29                                                  
CONECT   29   28   17   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   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

C₂₇H₃₆O₉

Average Mass

504.5760 Da

Monoisotopic Mass

504.23593 Da

IUPAC Name

3-[(1S,2S,3R,4S,6S)-4-(acetyloxy)-6-methyl-2-{[(2Z)-2-methylbut-2-enoyl]oxy}-5-oxo-7-oxabicyclo[4.1.0]heptan-3-yl]-1-(3,3-dimethyloxiran-2-yl)but-3-en-2-yl 2-methylbut-2-enoate

Traditional Name

3-[(1S,2S,3R,4S,6S)-4-(acetyloxy)-6-methyl-2-{[(2Z)-2-methylbut-2-enoyl]oxy}-5-oxo-7-oxabicyclo[4.1.0]heptan-3-yl]-1-(3,3-dimethyloxiran-2-yl)but-3-en-2-yl 2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

CC=C(C)C(=O)OC(CC1OC1(C)C)C(=C)[C@@H]1[C@H](OC(=O)C(\C)=C/C)[C@@H]2O[C@]2(C)C(=O)[C@H]1OC(C)=O

InChI Identifier

InChI=1S/C27H36O9/c1-10-13(3)24(30)33-17(12-18-26(7,8)35-18)15(5)19-20(32-16(6)28)22(29)27(9)23(36-27)21(19)34-25(31)14(4)11-2/h10-11,17-21,23H,5,12H2,1-4,6-9H3/b13-10?,14-11-/t17?,18?,19-,20-,21-,23-,27+/m0/s1

InChI Key

VMZMBTIZKOPION-NJGZOHAASA-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
Ligularia altaica	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	4.23	ChemAxon
pKa (Strongest Acidic)	14.05	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	121.03 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	129.38 m³·mol⁻¹	ChemAxon
Polarizability	53.08 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

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-[(1s,2s,3r,4s,6s)-4-(acetyloxy)-6-methyl-2-{[(2z)-2-methylbut-2-enoyl]oxy}-5-oxo-7-oxabicyclo[4.1.0]heptan-3-yl]-1-(3,3-dimethyloxiran-2-yl)but-3-en-2-yl 2-methylbut-2-enoate (NP0276620)

MOL for NP0276620 (3-[(1s,2s,3r,4s,6s)-4-(acetyloxy)-6-methyl-2-{[(2z)-2-methylbut-2-enoyl]oxy}-5-oxo-7-oxabicyclo[4.1.0]heptan-3-yl]-1-(3,3-dimethyloxiran-2-yl)but-3-en-2-yl 2-methylbut-2-enoate)

3D MOL for NP0276620 (3-[(1s,2s,3r,4s,6s)-4-(acetyloxy)-6-methyl-2-{[(2z)-2-methylbut-2-enoyl]oxy}-5-oxo-7-oxabicyclo[4.1.0]heptan-3-yl]-1-(3,3-dimethyloxiran-2-yl)but-3-en-2-yl 2-methylbut-2-enoate)

3D SDF for NP0276620 (3-[(1s,2s,3r,4s,6s)-4-(acetyloxy)-6-methyl-2-{[(2z)-2-methylbut-2-enoyl]oxy}-5-oxo-7-oxabicyclo[4.1.0]heptan-3-yl]-1-(3,3-dimethyloxiran-2-yl)but-3-en-2-yl 2-methylbut-2-enoate)

3D-SDF for NP0276620 (3-[(1s,2s,3r,4s,6s)-4-(acetyloxy)-6-methyl-2-{[(2z)-2-methylbut-2-enoyl]oxy}-5-oxo-7-oxabicyclo[4.1.0]heptan-3-yl]-1-(3,3-dimethyloxiran-2-yl)but-3-en-2-yl 2-methylbut-2-enoate)

PDB for NP0276620 (3-[(1s,2s,3r,4s,6s)-4-(acetyloxy)-6-methyl-2-{[(2z)-2-methylbut-2-enoyl]oxy}-5-oxo-7-oxabicyclo[4.1.0]heptan-3-yl]-1-(3,3-dimethyloxiran-2-yl)but-3-en-2-yl 2-methylbut-2-enoate)

3D PDB for NP0276620 (3-[(1s,2s,3r,4s,6s)-4-(acetyloxy)-6-methyl-2-{[(2z)-2-methylbut-2-enoyl]oxy}-5-oxo-7-oxabicyclo[4.1.0]heptan-3-yl]-1-(3,3-dimethyloxiran-2-yl)but-3-en-2-yl 2-methylbut-2-enoate)

SMILES for NP0276620 (3-[(1s,2s,3r,4s,6s)-4-(acetyloxy)-6-methyl-2-{[(2z)-2-methylbut-2-enoyl]oxy}-5-oxo-7-oxabicyclo[4.1.0]heptan-3-yl]-1-(3,3-dimethyloxiran-2-yl)but-3-en-2-yl 2-methylbut-2-enoate)

INCHI for NP0276620 (3-[(1s,2s,3r,4s,6s)-4-(acetyloxy)-6-methyl-2-{[(2z)-2-methylbut-2-enoyl]oxy}-5-oxo-7-oxabicyclo[4.1.0]heptan-3-yl]-1-(3,3-dimethyloxiran-2-yl)but-3-en-2-yl 2-methylbut-2-enoate)

Structure for NP0276620 (3-[(1s,2s,3r,4s,6s)-4-(acetyloxy)-6-methyl-2-{[(2z)-2-methylbut-2-enoyl]oxy}-5-oxo-7-oxabicyclo[4.1.0]heptan-3-yl]-1-(3,3-dimethyloxiran-2-yl)but-3-en-2-yl 2-methylbut-2-enoate)

3D Structure for NP0276620 (3-[(1s,2s,3r,4s,6s)-4-(acetyloxy)-6-methyl-2-{[(2z)-2-methylbut-2-enoyl]oxy}-5-oxo-7-oxabicyclo[4.1.0]heptan-3-yl]-1-(3,3-dimethyloxiran-2-yl)but-3-en-2-yl 2-methylbut-2-enoate)