NP-MRD: Showing NP-Card for Metaplexigenin 3-O-α-L-cymaropyranosyl-β-D-cymaropyranosyl-(1→4)-α-L-diginopyranosyl-β-D-cymaropyranoside (NP0331634)

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Record Information

Version

2.0

Created at

2023-05-18 04:00:15 UTC

Updated at

2024-09-03 04:16:20 UTC

NP-MRD ID

NP0331634

Natural Product DOI

https://doi.org/10.57994/0622

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Metaplexigenin 3-O-α-L-cymaropyranosyl-β-D-cymaropyranosyl-(1→4)-α-L-diginopyranosyl-β-D-cymaropyranoside

Description

Metaplexigenin 3-O-α-L-cymaropyranosyl-β-D-cymaropyranosyl-(1→4)-α-L-diginopyranosyl-β-D-cymaropyranoside belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton. Metaplexigenin 3-O-α-L-cymaropyranosyl-β-D-cymaropyranosyl-(1→4)-α-L-diginopyranosyl-β-D-cymaropyranoside was first documented in 2023 (PMID: 37178131). Based on a literature review very few articles have been published on Metaplexigenin 3-O-α-L-cymaropyranosyl-β-D-cymaropyranosyl-(1→4)-α-L-diginopyranosyl-β-D-cymaropyranoside.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305182306002D          

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M  END


  Mrv1652305182306002D          

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 44 45  1  0  0  0  0
 43 46  1  0  0  0  0
  7 46  1  0  0  0  0
  5 47  1  0  0  0  0
 47 48  1  0  0  0  0
  2 48  1  0  0  0  0
  3 49  2  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  1  0  0  0
 51 53  1  0  0  0  0
  2 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 56  1  1  0  0  0
 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
 57 59  2  0  0  0  0
 55 60  1  0  0  0  0
 60 61  1  1  0  0  0
 60 62  1  0  0  0  0
 51 62  1  0  0  0  0
 62 63  1  1  0  0  0
 62 64  1  0  0  0  0
 64 65  1  0  0  0  0
 65 66  1  0  0  0  0
 60 66  1  0  0  0  0
 66 67  1  6  0  0  0
 67 68  1  0  0  0  0
 67 69  2  0  0  0  0
 66 70  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0331634

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1C[C@H](O[C@@H]2[C@@H](C)O[C@H](C[C@@H]2OC)O[C@@H]2[C@H](C)O[C@H](C[C@@H]2OC)O[C@@H]2[C@@H](C)O[C@H](C[C@@H]2OC)O[C@H]2CC[C@]3(C)C4C[C@@H](OC(C)=O)[C@]5(C)[C@@](O)(CC[C@]5(O)[C@]4(O)CC=C3C2)C(C)=O)O[C@@H](C)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C51H82O19/c1-25-43(54)33(58-9)20-40(62-25)68-45-27(3)64-42(22-35(45)60-11)70-46-28(4)65-41(23-36(46)61-12)69-44-26(2)63-39(21-34(44)59-10)67-32-14-15-47(7)31(19-32)13-16-50(56)37(47)24-38(66-30(6)53)48(8)49(55,29(5)52)17-18-51(48,50)57/h13,25-28,32-46,54-57H,14-24H2,1-12H3/t25-,26+,27+,28-,32-,33+,34-,35-,36-,37?,38+,39-,40-,41-,42-,43-,44+,45+,46+,47-,48+,49+,50-,51+/m0/s1

> <INCHI_KEY>
LEQNEABVKZQJMW-XEJOKSESSA-N

> <FORMULA>
C51H82O19

> <MOLECULAR_WEIGHT>
999.198

> <EXACT_MASS>
998.54503042

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_ATOM_COUNT>
152

> <JCHEM_AVERAGE_POLARIZABILITY>
106.5814718252916

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,5S,10S,11R,14S,15S,16R)-14-acetyl-10,11,14-trihydroxy-5-{[(2R,4S,5R,6R)-5-{[(2S,4S,5R,6S)-5-{[(2S,4S,5R,6R)-5-{[(2S,4R,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-16-yl acetate

> <JCHEM_LOGP>
3.2388648836666674

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.941194496223403

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.331728963671814

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5080223941569724

> <JCHEM_POLAR_SURFACE_AREA>
235.04999999999998

> <JCHEM_REFRACTIVITY>
245.0893

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,5S,10S,11R,14S,15S,16R)-14-acetyl-10,11,14-trihydroxy-5-{[(2R,4S,5R,6R)-5-{[(2S,4S,5R,6S)-5-{[(2S,4S,5R,6R)-5-{[(2S,4R,5S,6S)-5-hydroxy-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-4-methoxy-6-methyloxan-2-yl]oxy}-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-16-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 18-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   18-MAY-23         0                                  
HETATM    1  C   UNK     0       8.487  -0.949   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.010   0.499   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.533   1.947   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.049   2.218   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.042   1.041   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      13.558   1.312   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      14.551   0.135   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      16.067   0.406   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      17.059  -0.771   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      18.575  -0.500   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.536  -2.220   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      17.529  -3.397   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      17.006  -4.846   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      17.998  -6.023   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      15.490  -5.117   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      14.967  -6.565   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.451  -6.836   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      15.959  -7.742   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      15.436  -9.191   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      16.429 -10.368   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      17.945 -10.097   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      18.937 -11.274   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      20.453 -11.003   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      18.414 -12.723   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      19.407 -13.900   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      18.884 -15.348   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      19.877 -16.526   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      19.353 -17.974   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      20.346 -19.151   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      17.837 -18.245   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      17.314 -19.694   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      16.845 -17.068   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      15.329 -17.339   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      14.336 -16.162   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      17.368 -15.619   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      16.898 -12.994   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      16.375 -14.442   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      14.859 -14.713   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      15.906 -11.816   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      17.475  -7.471   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      18.468  -8.649   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      19.984  -8.378   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      15.020  -2.491   0.000  0.00  0.00           C+0
HETATM   44  O   UNK     0      14.497  -3.939   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      12.981  -4.210   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      14.028  -1.314   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      11.519  -0.407   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      10.003  -0.678   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       8.541   3.125   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       7.025   2.854   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       6.502   1.405   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0       5.509   2.583   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0       7.494   0.228   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       6.971  -1.221   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0       5.455  -1.492   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0       4.932  -2.940   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0       5.925  -4.117   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0       7.441  -3.846   0.000  0.00  0.00           C+0
HETATM   59  O   UNK     0       5.401  -5.566   0.000  0.00  0.00           O+0
HETATM   60  C   UNK     0       4.462  -0.314   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0       3.791  -1.700   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0       4.986   1.134   0.000  0.00  0.00           C+0
HETATM   63  O   UNK     0       4.874   2.670   0.000  0.00  0.00           O+0
HETATM   64  C   UNK     0       3.770   2.079   0.000  0.00  0.00           C+0
HETATM   65  C   UNK     0       2.495   1.215   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0       2.923  -0.264   0.000  0.00  0.00           C+0
HETATM   67  C   UNK     0       1.503  -0.859   0.000  0.00  0.00           C+0
HETATM   68  C   UNK     0       0.277   0.073   0.000  0.00  0.00           C+0
HETATM   69  O   UNK     0       1.308  -2.387   0.000  0.00  0.00           O+0
HETATM   70  O   UNK     0       2.697  -1.787   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   48   53                                             
CONECT    3    2    4   49                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   47                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   46                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   43                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13   40                                                       
CONECT   15   13   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19   40                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   39                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   36                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   35                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   35                                                  
CONECT   33   32   34                                                       
CONECT   34   33                                                            
CONECT   35   32   26                                                       
CONECT   36   24   37   39                                                  
CONECT   37   36   38                                                       
CONECT   38   37                                                            
CONECT   39   36   20                                                       
CONECT   40   18   14   41                                                  
CONECT   41   40   42                                                       
CONECT   42   41                                                            
CONECT   43   11   44   46                                                  
CONECT   44   43   45                                                       
CONECT   45   44                                                            
CONECT   46   43    7                                                       
CONECT   47    5   48                                                       
CONECT   48   47    2                                                       
CONECT   49    3   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   52   53   62                                             
CONECT   52   51                                                            
CONECT   53   51    2   54                                                  
CONECT   54   53   55                                                       
CONECT   55   54   56   60                                                  
CONECT   56   55   57                                                       
CONECT   57   56   58   59                                                  
CONECT   58   57                                                            
CONECT   59   57                                                            
CONECT   60   55   61   62   66                                             
CONECT   61   60                                                            
CONECT   62   60   51   63   64                                             
CONECT   63   62                                                            
CONECT   64   62   65                                                       
CONECT   65   64   66                                                       
CONECT   66   65   60   67   70                                             
CONECT   67   66   68   69                                                  
CONECT   68   67                                                            
CONECT   69   67                                                            
CONECT   70   66                                                            
MASTER        0    0    0    0    0    0    0    0   70    0  154    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₅₁H₈₂O₁₉

Average Mass

999.1980 Da

Monoisotopic Mass

998.54503 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

CO[C@@H]1C[C@H](O[C@@H]2[C@@H](C)O[C@H](C[C@@H]2OC)O[C@@H]2[C@H](C)O[C@H](C[C@@H]2OC)O[C@@H]2[C@@H](C)O[C@H](C[C@@H]2OC)O[C@H]2CC[C@]3(C)C4C[C@@H](OC(C)=O)[C@]5(C)[C@@](O)(CC[C@]5(O)[C@]4(O)CC=C3C2)C(C)=O)O[C@@H](C)[C@@H]1O

InChI Identifier

InChI=1S/C51H82O19/c1-25-43(54)33(58-9)20-40(62-25)68-45-27(3)64-42(22-35(45)60-11)70-46-28(4)65-41(23-36(46)61-12)69-44-26(2)63-39(21-34(44)59-10)67-32-14-15-47(7)31(19-32)13-16-50(56)37(47)24-38(66-30(6)53)48(8)49(55,29(5)52)17-18-51(48,50)57/h13,25-28,32-46,54-57H,14-24H2,1-12H3/t25-,26+,27+,28-,32-,33+,34-,35-,36-,37?,38+,39-,40-,41-,42-,43-,44+,45+,46+,47-,48+,49+,50-,51+/m0/s1

InChI Key

LEQNEABVKZQJMW-XEJOKSESSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, C5D5N, experimental)	1458407846@qq.com	Not Available	Not Available	2023-05-18	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, C5D5N, experimental)	1458407846@qq.com	Not Available	Not Available	2023-05-18	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 400.132470802, C5D5deposition_typeN, simulated)	Not Available	Not Available	Not Available	2024-05-14	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
auriculatum		Not Available

Chemical Taxonomy

Description

This compound belongs to the class of organic compounds known as steroidal glycosides. These are sterol lipids containing a carbohydrate moiety glycosidically linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroidal glycosides

Direct Parent

Steroidal glycosides

Alternative Parents

Substituents

Triterpenoid
Steroidal glycoside
Steroid ester
20-oxosteroid
Androstane-skeleton
17-hydroxysteroid
Oxosteroid
Hydroxysteroid
14-hydroxysteroid
Delta-5-steroid
Fatty alcohol ester
Oxane
Monosaccharide
Acyloin
Tertiary alcohol
Cyclic alcohol
Alpha-hydroxy ketone
Secondary alcohol
Ketone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Metaplexigenin 3-O-α-L-cymaropyranosyl-β-D-cymaropyranosyl-(1→4)-α-L-diginopyranosyl-β-D-cymaropyranoside (NP0331634)

MOL for NP0331634 (Metaplexigenin 3-O-α-L-cymaropyranosyl-β-D-cymaropyranosyl-(1→4)-α-L-diginopyranosyl-β-D-cymaropyranoside)

3D MOL for NP0331634 (Metaplexigenin 3-O-α-L-cymaropyranosyl-β-D-cymaropyranosyl-(1→4)-α-L-diginopyranosyl-β-D-cymaropyranoside)

3D SDF for NP0331634 (Metaplexigenin 3-O-α-L-cymaropyranosyl-β-D-cymaropyranosyl-(1→4)-α-L-diginopyranosyl-β-D-cymaropyranoside)

3D-SDF for NP0331634 (Metaplexigenin 3-O-α-L-cymaropyranosyl-β-D-cymaropyranosyl-(1→4)-α-L-diginopyranosyl-β-D-cymaropyranoside)

PDB for NP0331634 (Metaplexigenin 3-O-α-L-cymaropyranosyl-β-D-cymaropyranosyl-(1→4)-α-L-diginopyranosyl-β-D-cymaropyranoside)

3D PDB for NP0331634 (Metaplexigenin 3-O-α-L-cymaropyranosyl-β-D-cymaropyranosyl-(1→4)-α-L-diginopyranosyl-β-D-cymaropyranoside)

SMILES for NP0331634 (Metaplexigenin 3-O-α-L-cymaropyranosyl-β-D-cymaropyranosyl-(1→4)-α-L-diginopyranosyl-β-D-cymaropyranoside)

INCHI for NP0331634 (Metaplexigenin 3-O-α-L-cymaropyranosyl-β-D-cymaropyranosyl-(1→4)-α-L-diginopyranosyl-β-D-cymaropyranoside)

Structure for NP0331634 (Metaplexigenin 3-O-α-L-cymaropyranosyl-β-D-cymaropyranosyl-(1→4)-α-L-diginopyranosyl-β-D-cymaropyranoside)

3D Structure for NP0331634 (Metaplexigenin 3-O-α-L-cymaropyranosyl-β-D-cymaropyranosyl-(1→4)-α-L-diginopyranosyl-β-D-cymaropyranoside)