NP-MRD: Showing NP-Card for Platycoside M-2 (NP0071657)

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Record Information

Version

2.0

Created at

2022-04-28 17:00:23 UTC

Updated at

2022-04-28 17:00:23 UTC

NP-MRD ID

NP0071657

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Platycoside M-2

Description

(2S,3R,4R,5S)-4,5-dihydroxy-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl (1R,2R,5R,6S,8R,9R,14S,18R,19R,21S,24R)-8-hydroxy-1-(hydroxymethyl)-5,6,12,12,19-pentamethyl-23-oxo-24-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-22-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]Tetracos-15-ene-9-carboxylate belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Platycoside M-2 is found in Platycodon grandiflorum A.DC. and Platycodon grandiflorus. Based on a literature review very few articles have been published on (2S,3R,4R,5S)-4,5-dihydroxy-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl (1R,2R,5R,6S,8R,9R,14S,18R,19R,21S,24R)-8-hydroxy-1-(hydroxymethyl)-5,6,12,12,19-pentamethyl-23-oxo-24-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-22-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]Tetracos-15-ene-9-carboxylate.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282219002D          

 67 75  0  0  1  0            999 V2000
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 66 67  1  0  0  0  0
M  END


  Mrv1652304282219002D          

 67 75  0  0  1  0            999 V2000
    9.0058   -2.8255    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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 38 44  1  6  0  0  0
 37 45  1  6  0  0  0
 33 46  1  6  0  0  0
 32 47  1  1  0  0  0
 11 48  1  1  0  0  0
  8 49  1  6  0  0  0
  5 50  1  6  0  0  0
  3 51  1  0  0  0  0
 51 52  2  0  0  0  0
 51 53  1  0  0  0  0
  1 53  1  6  0  0  0
  3 54  1  6  0  0  0
 54 55  1  0  0  0  0
  2 56  1  1  0  0  0
 57 56  1  1  0  0  0
 57 58  1  0  0  0  0
 58 59  1  0  0  0  0
 59 60  1  0  0  0  0
 60 61  1  0  0  0  0
 61 62  1  0  0  0  0
 57 62  1  0  0  0  0
 62 63  1  6  0  0  0
 61 64  1  1  0  0  0
 60 65  1  6  0  0  0
 59 66  1  1  0  0  0
 66 67  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0071657

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1O[C@@H](O[C@@H]2[C@H](O)[C@@H](O)CO[C@H]2OC(=O)[C@]23CCC(C)(C)C[C@H]2C2=CC[C@@H]4[C@@]5(C)C[C@@H]6OC(=O)[C@](CO)([C@H]6O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)[C@@H]5CC[C@@]4(C)[C@]2(C)C[C@H]3O)[C@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C47H72O20/c1-19-28(52)31(55)33(57)37(62-19)65-35-29(53)22(50)17-61-39(35)67-40(59)46-12-11-42(2,3)13-21(46)20-7-8-25-43(4)14-23-36(66-38-34(58)32(56)30(54)24(16-48)63-38)47(18-49,41(60)64-23)26(43)9-10-44(25,5)45(20,6)15-27(46)51/h7,19,21-39,48-58H,8-18H2,1-6H3/t19-,21-,22-,23-,24+,25+,26+,27+,28-,29+,30+,31+,32-,33+,34+,35+,36-,37-,38-,39-,43+,44+,45+,46+,47-/m0/s1

> <INCHI_KEY>
AMFATATVKIIQQF-OBHJWRFRSA-N

> <FORMULA>
C47H72O20

> <MOLECULAR_WEIGHT>
957.073

> <EXACT_MASS>
956.461694718

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
139

> <JCHEM_AVERAGE_POLARIZABILITY>
89.42707515036103

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
11

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4R,5S)-4,5-dihydroxy-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl (1R,2R,5R,6S,8R,9R,14S,18R,19R,21S,24R)-8-hydroxy-1-(hydroxymethyl)-5,6,12,12,19-pentamethyl-23-oxo-24-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-22-oxahexacyclo[19.2.1.0^{2,19}.0^{5,18}.0^{6,15}.0^{9,14}]tetracos-15-ene-9-carboxylate

> <ALOGPS_LOGP>
0.83

> <JCHEM_LOGP>
-1.267983149666667

> <ALOGPS_LOGS>
-2.85

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.343125920984292

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.866432476164

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5268976092683824

> <JCHEM_POLAR_SURFACE_AREA>
321.28000000000003

> <JCHEM_REFRACTIVITY>
226.25280000000012

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.37e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4R,5S)-4,5-dihydroxy-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl (1R,2R,5R,6S,8R,9R,14S,18R,19R,21S,24R)-8-hydroxy-1-(hydroxymethyl)-5,6,12,12,19-pentamethyl-23-oxo-24-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-22-oxahexacyclo[19.2.1.0^{2,19}.0^{5,18}.0^{6,15}.0^{9,14}]tetracos-15-ene-9-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      16.811  -5.274   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      16.476  -7.026   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.005  -8.729   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      15.487  -8.471   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.312  -7.196   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      15.331  -5.701   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.202  -7.095   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.192  -8.450   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.152  -9.762   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      14.477  -9.827   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      10.867  -8.385   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.122  -7.037   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      10.917  -5.718   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      12.457  -5.747   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.583  -7.008   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.788  -8.327   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.533  -9.675   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      10.073  -9.704   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.382 -10.885   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.248  -8.299   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.503  -6.951   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.298  -5.632   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.838  -5.660   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.008  -4.791   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.273  -4.092   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       6.993  -9.646   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       7.738 -10.994   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       5.453  -9.618   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       4.659 -10.937   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       3.119 -10.908   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       2.324 -12.227   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.069 -13.575   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.609 -13.604   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.404 -12.285   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       6.943 -12.313   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       7.688 -13.661   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       9.228 -13.690   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       9.973 -15.038   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       9.178 -16.357   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       7.638 -16.328   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       6.893 -14.980   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       6.844 -17.647   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       9.923 -17.705   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      11.513 -15.067   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      10.023 -12.371   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0       5.354 -14.951   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0       2.274 -14.894   0.000  0.00  0.00           O+0
HETATM   48  C   UNK     0      10.968  -9.842   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      11.458 -10.028   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      13.898  -5.835   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      18.153  -7.703   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      19.576  -8.292   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      18.067  -6.165   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      17.431 -10.209   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      18.926 -10.580   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      14.938  -7.112   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0      14.244  -8.487   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0      12.707  -8.573   0.000  0.00  0.00           O+0
HETATM   59  C   UNK     0      12.013  -9.948   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      12.856 -11.237   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0      14.394 -11.150   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0      15.088  -9.775   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0      16.626  -9.689   0.000  0.00  0.00           O+0
HETATM   64  O   UNK     0      15.238 -12.439   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0      12.162 -12.611   0.000  0.00  0.00           O+0
HETATM   66  C   UNK     0      10.475 -10.035   0.000  0.00  0.00           C+0
HETATM   67  O   UNK     0       9.781 -11.409   0.000  0.00  0.00           O+0
CONECT    1    2    6   53                                                  
CONECT    2    1    3   56                                                  
CONECT    3    2    4   51   54                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   50                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   14                                                  
CONECT    8    7    9   11   49                                             
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8   12   18   48                                             
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13    7                                                       
CONECT   15   12   16   23                                                  
CONECT   16   15   17   20   26                                             
CONECT   17   16   18   19                                                  
CONECT   18   17   11                                                       
CONECT   19   17                                                            
CONECT   20   16   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24   25                                             
CONECT   23   22   15                                                       
CONECT   24   22                                                            
CONECT   25   22                                                            
CONECT   26   16   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29                                                       
CONECT   29   28   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   47                                                  
CONECT   33   32   34   46                                                  
CONECT   34   33   29   35                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   41                                                  
CONECT   37   36   38   45                                                  
CONECT   38   37   39   44                                                  
CONECT   39   38   40   43                                                  
CONECT   40   39   41   42                                                  
CONECT   41   40   36                                                       
CONECT   42   40                                                            
CONECT   43   39                                                            
CONECT   44   38                                                            
CONECT   45   37                                                            
CONECT   46   33                                                            
CONECT   47   32                                                            
CONECT   48   11                                                            
CONECT   49    8                                                            
CONECT   50    5                                                            
CONECT   51    3   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51    1                                                       
CONECT   54    3   55                                                       
CONECT   55   54                                                            
CONECT   56    2   57                                                       
CONECT   57   56   58   62                                                  
CONECT   58   57   59                                                       
CONECT   59   58   60   66                                                  
CONECT   60   59   61   65                                                  
CONECT   61   60   62   64                                                  
CONECT   62   61   57   63                                                  
CONECT   63   62                                                            
CONECT   64   61                                                            
CONECT   65   60                                                            
CONECT   66   59   67                                                       
CONECT   67   66                                                            
MASTER        0    0    0    0    0    0    0    0   67    0  150    0
END

View in JSmol

Synonyms

Value	Source
(2S,3R,4R,5S)-4,5-Dihydroxy-3-{[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl (1R,2R,5R,6S,8R,9R,14S,18R,19R,21S,24R)-8-hydroxy-1-(hydroxymethyl)-5,6,12,12,19-pentamethyl-23-oxo-24-{[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-22-oxahexacyclo[19.2.1.0,.0,.0,.0,]tetracos-15-ene-9-carboxylic acid	Generator

Chemical Formula

C₄₇H₇₂O₂₀

Average Mass

957.0730 Da

Monoisotopic Mass

956.46169 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@@H]1O[C@@H](O[C@@H]2[C@H](O)[C@@H](O)CO[C@H]2OC(=O)[C@]23CCC(C)(C)C[C@H]2C2=CC[C@@H]4[C@@]5(C)C[C@@H]6OC(=O)[C@](CO)([C@H]6O[C@@H]6O[C@H](CO)[C@@H](O)[C@H](O)[C@H]6O)[C@@H]5CC[C@@]4(C)[C@]2(C)C[C@H]3O)[C@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C47H72O20/c1-19-28(52)31(55)33(57)37(62-19)65-35-29(53)22(50)17-61-39(35)67-40(59)46-12-11-42(2,3)13-21(46)20-7-8-25-43(4)14-23-36(66-38-34(58)32(56)30(54)24(16-48)63-38)47(18-49,41(60)64-23)26(43)9-10-44(25,5)45(20,6)15-27(46)51/h7,19,21-39,48-58H,8-18H2,1-6H3/t19-,21-,22-,23-,24+,25+,26+,27+,28-,29+,30+,31+,32-,33+,34+,35+,36-,37-,38-,39-,43+,44+,45+,46+,47-/m0/s1

InChI Key

AMFATATVKIIQQF-OBHJWRFRSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Platycodon grandiflorum A.DC.	Plant	KNApSAcK
Platycodon grandiflorus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Steroid
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
O-glycosyl compound
Glycosyl compound
Disaccharide
Caprolactone
Oxepane
Beta-hydroxy acid
Fatty acyl
Oxane
Hydroxy acid
Gamma butyrolactone
Dicarboxylic acid or derivatives
Tetrahydrofuran
Cyclic alcohol
Secondary alcohol
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
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	0.83	ALOGPS
logP	-1.3	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	11.87	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	11	ChemAxon
Polar Surface Area	321.28 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	226.25 m³·mol⁻¹	ChemAxon
Polarizability	89.43 Å³	ChemAxon
Number of Rings	9	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

163051747

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Platycoside M-2 (NP0071657)

MOL for NP0071657 (Platycoside M-2)

3D MOL for NP0071657 (Platycoside M-2)

3D SDF for NP0071657 (Platycoside M-2)

3D-SDF for NP0071657 (Platycoside M-2)

PDB for NP0071657 (Platycoside M-2)

3D PDB for NP0071657 (Platycoside M-2)

SMILES for NP0071657 (Platycoside M-2)

INCHI for NP0071657 (Platycoside M-2)

Structure for NP0071657 (Platycoside M-2)

3D Structure for NP0071657 (Platycoside M-2)