NP-MRD: Showing NP-Card for 2'',4''-Di-O-acetylmearnsitrin (NP0085155)

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Record Information

Version

2.0

Created at

2022-04-29 05:45:38 UTC

Updated at

2022-04-29 05:45:38 UTC

NP-MRD ID

NP0085155

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2'',4''-Di-O-acetylmearnsitrin

Description

2'',4''-Di-O-acetylmearnsitrin is found in Myrsine africana . Based on a literature review very few articles have been published on (2S,3R,4R,5R,6S)-5-(acetyloxy)-2-{[2-(3,5-dihydroxy-4-methoxyphenyl)-5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl]oxy}-4-hydroxy-6-methyloxan-3-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292207452D          

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M  END

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  Mrv1652304292207452D          

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 16 18  2  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  6  0  0  0
 19 21  1  0  0  0  0
 21 22  1  1  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  2  0  0  0  0
 21 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 13 28  1  0  0  0  0
 11 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
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 36 37  2  0  0  0  0
 30 37  1  0  0  0  0
 37 38  1  0  0  0  0
 10 38  1  0  0  0  0
 29 39  2  0  0  0  0
  9 40  2  0  0  0  0
  2 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0085155

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(O)C=C(C=C1O)C1OC2=CC(O)=CC(O)=C2C(=O)C1O[C@@H]1O[C@@H](C)[C@H](OC(C)=O)[C@@H](O)[C@H]1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H28O14/c1-9-21(37-10(2)27)20(34)25(38-11(3)28)26(36-9)40-24-19(33)18-14(30)7-13(29)8-17(18)39-22(24)12-5-15(31)23(35-4)16(32)6-12/h5-9,20-22,24-26,29-32,34H,1-4H3/t9-,20+,21-,22?,24?,25+,26-/m0/s1

> <INCHI_KEY>
JZQSQKFVBILRJH-IHAPNPHWSA-N

> <FORMULA>
C26H28O14

> <MOLECULAR_WEIGHT>
564.496

> <EXACT_MASS>
564.147905582

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
68

> <JCHEM_AVERAGE_POLARIZABILITY>
53.556299535064376

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4R,5R,6S)-5-(acetyloxy)-2-{[2-(3,5-dihydroxy-4-methoxyphenyl)-5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl]oxy}-4-hydroxy-6-methyloxan-3-yl acetate

> <ALOGPS_LOGP>
2.34

> <JCHEM_LOGP>
1.8170381439999999

> <ALOGPS_LOGS>
-2.59

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.18004787089999

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.750131281178494

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7061282108564564

> <JCHEM_POLAR_SURFACE_AREA>
207.73999999999995

> <JCHEM_REFRACTIVITY>
130.2447

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.44e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4R,5R,6S)-5-(acetyloxy)-2-{[2-(3,5-dihydroxy-4-methoxyphenyl)-5,7-dihydroxy-4-oxo-2,3-dihydro-1-benzopyran-3-yl]oxy}-4-hydroxy-6-methyloxan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.667   4.620   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       0.000   6.160   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  C   UNK     0       1.334   8.470   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       2.667   6.160   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+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
HETATM   38  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   40                                                  
CONECT    3    2    4    6                                                  
CONECT    4    3    5                                                       
CONECT    5    4                                                            
CONECT    6    3    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   40                                                  
CONECT   10    9   11   38                                                  
CONECT   11   10   12   29                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   28                                                  
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   14   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   26                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   21   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   13                                                       
CONECT   29   11   30   39                                                  
CONECT   30   29   31   37                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36   30   38                                                  
CONECT   38   37   10                                                       
CONECT   39   29                                                            
CONECT   40    9    2                                                       
MASTER        0    0    0    0    0    0    0    0   40    0   86    0
END

View in JSmol

Synonyms

Value	Source
(2S,3R,4R,5R,6S)-5-(Acetyloxy)-2-{[2-(3,5-dihydroxy-4-methoxyphenyl)-5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl]oxy}-4-hydroxy-6-methyloxan-3-yl acetic acid	Generator

Chemical Formula

C₂₆H₂₈O₁₄

Average Mass

564.4960 Da

Monoisotopic Mass

564.14791 Da

IUPAC Name

(2S,3R,4R,5R,6S)-5-(acetyloxy)-2-{[2-(3,5-dihydroxy-4-methoxyphenyl)-5,7-dihydroxy-4-oxo-3,4-dihydro-2H-1-benzopyran-3-yl]oxy}-4-hydroxy-6-methyloxan-3-yl acetate

Traditional Name

(2S,3R,4R,5R,6S)-5-(acetyloxy)-2-{[2-(3,5-dihydroxy-4-methoxyphenyl)-5,7-dihydroxy-4-oxo-2,3-dihydro-1-benzopyran-3-yl]oxy}-4-hydroxy-6-methyloxan-3-yl acetate

CAS Registry Number

Not Available

SMILES

COC1=C(O)C=C(C=C1O)C1OC2=CC(O)=CC(O)=C2C(=O)C1O[C@@H]1O[C@@H](C)[C@H](OC(C)=O)[C@@H](O)[C@H]1OC(C)=O

InChI Identifier

InChI=1S/C26H28O14/c1-9-21(37-10(2)27)20(34)25(38-11(3)28)26(36-9)40-24-19(33)18-14(30)7-13(29)8-17(18)39-22(24)12-5-15(31)23(35-4)16(32)6-12/h5-9,20-22,24-26,29-32,34H,1-4H3/t9-,20+,21-,22?,24?,25+,26-/m0/s1

InChI Key

JZQSQKFVBILRJH-IHAPNPHWSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Myrsine africana	Plant	KNApSAcK

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	2.34	ALOGPS
logP	1.82	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	7.75	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	207.74 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	130.24 m³·mol⁻¹	ChemAxon
Polarizability	53.56 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

C00054896

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

163184131

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for 2'',4''-Di-O-acetylmearnsitrin (NP0085155)

MOL for NP0085155 (2'',4''-Di-O-acetylmearnsitrin)

3D MOL for NP0085155 (2'',4''-Di-O-acetylmearnsitrin)

3D SDF for NP0085155 (2'',4''-Di-O-acetylmearnsitrin)

3D-SDF for NP0085155 (2'',4''-Di-O-acetylmearnsitrin)

PDB for NP0085155 (2'',4''-Di-O-acetylmearnsitrin)

3D PDB for NP0085155 (2'',4''-Di-O-acetylmearnsitrin)

SMILES for NP0085155 (2'',4''-Di-O-acetylmearnsitrin)

INCHI for NP0085155 (2'',4''-Di-O-acetylmearnsitrin)

Structure for NP0085155 (2'',4''-Di-O-acetylmearnsitrin)

3D Structure for NP0085155 (2'',4''-Di-O-acetylmearnsitrin)