NP-MRD: Showing NP-Card for (-)-Rotundifolioside H (NP0071741)

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Record Information

Version

2.0

Created at

2022-04-28 17:05:07 UTC

Updated at

2022-04-28 17:05:07 UTC

NP-MRD ID

NP0071741

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(-)-Rotundifolioside H

Description

(2S,3R,4S,5R)-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3R,4S,5R,6R)-4,5-dihydroxy-2-{[(1S,2R,4S,5R,8R,10S,13S,14R,17R,18R,19S,20R)-2-hydroxy-4,5,9,9,13,19,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]Tetracos-15-en-10-yl]oxy}-6-(hydroxymethyl)oxan-3-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}oxane-3,4,5-triol belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton. (-)-Rotundifolioside H is found in Bupleurum rotundifolium . Based on a literature review very few articles have been published on (2S,3R,4S,5R)-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3R,4S,5R,6R)-4,5-dihydroxy-2-{[(1S,2R,4S,5R,8R,10S,13S,14R,17R,18R,19S,20R)-2-hydroxy-4,5,9,9,13,19,20-heptamethyl-24-oxahexacyclo[15.5.2.0¹,¹⁸.0⁴,¹⁷.0⁵,¹⁴.0⁸,¹³]Tetracos-15-en-10-yl]oxy}-6-(hydroxymethyl)oxan-3-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}oxane-3,4,5-triol.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652304282219052D          

 64 72  0  0  1  0            999 V2000
    4.5860    0.5313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652304282219052D          

 64 72  0  0  1  0            999 V2000
    4.5860    0.5313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0071741

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1CC[C@]23CO[C@]4(C=C[C@@H]5[C@@]6(C)CC[C@H](O[C@@H]7O[C@H](CO)[C@H](O)[C@H](O)[C@H]7O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O[C@@H]7OC[C@@H](O)[C@H](O)[C@H]7O)C(C)(C)[C@@H]6CC[C@@]5(C)[C@]4(C)C[C@H]2O)[C@@H]3[C@H]1C

> <INCHI_IDENTIFIER>
InChI=1S/C47H76O17/c1-21-8-14-46-20-59-47(38(46)22(21)2)15-10-27-43(5)12-11-29(42(3,4)26(43)9-13-44(27,6)45(47,7)16-28(46)51)62-40-36(33(55)31(53)24(17-48)60-40)64-41-37(34(56)32(54)25(18-49)61-41)63-39-35(57)30(52)23(50)19-58-39/h10,15,21-41,48-57H,8-9,11-14,16-20H2,1-7H3/t21-,22+,23-,24-,25-,26+,27-,28-,29+,30+,31+,32-,33+,34+,35-,36-,37-,38-,39+,40+,41+,43+,44-,45+,46+,47-/m1/s1

> <INCHI_KEY>
OERYSJKYOLNHAD-BDJJZTGYSA-N

> <FORMULA>
C47H76O17

> <MOLECULAR_WEIGHT>
913.108

> <EXACT_MASS>
912.508250987

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_ATOM_COUNT>
140

> <JCHEM_AVERAGE_POLARIZABILITY>
101.81698218950535

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5R)-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3R,4S,5R,6R)-4,5-dihydroxy-2-{[(1S,2R,4S,5R,8R,10S,13S,14R,17R,18R,19S,20R)-2-hydroxy-4,5,9,9,13,19,20-heptamethyl-24-oxahexacyclo[15.5.2.0^{1,18}.0^{4,17}.0^{5,14}.0^{8,13}]tetracos-15-en-10-yl]oxy}-6-(hydroxymethyl)oxan-3-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}oxane-3,4,5-triol

> <ALOGPS_LOGP>
0.89

> <JCHEM_LOGP>
0.47628141400000246

> <ALOGPS_LOGS>
-3.70

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.525548365633558

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.01833337271224

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810838020447212

> <JCHEM_POLAR_SURFACE_AREA>
266.90999999999997

> <JCHEM_REFRACTIVITY>
224.60200000000006

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.82e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5R)-2-{[(2S,3R,4S,5S,6R)-2-{[(2R,3R,4S,5R,6R)-4,5-dihydroxy-2-{[(1S,2R,4S,5R,8R,10S,13S,14R,17R,18R,19S,20R)-2-hydroxy-4,5,9,9,13,19,20-heptamethyl-24-oxahexacyclo[15.5.2.0^{1,18}.0^{4,17}.0^{5,14}.0^{8,13}]tetracos-15-en-10-yl]oxy}-6-(hydroxymethyl)oxan-3-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}oxane-3,4,5-triol

> <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       8.561   0.992   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.348   2.315   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.595   3.659   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.055   3.679   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.268   2.355   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.021   1.012   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.728   2.375   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.976   3.719   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.763   5.042   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.303   5.022   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.398   3.777   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.551   2.354   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.407   1.032   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.950   1.034   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.480   3.148   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.890   3.853   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.024   5.198   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.630   5.228   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.710   6.552   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -2.184   3.019   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.110   1.481   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.740   0.776   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.733   1.735   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.639   0.517   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.666  -0.762   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.153   2.221   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.216   1.348   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       3.217   5.081   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.175   5.246   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.481   1.032   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.912   4.458   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       8.669   5.197   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      10.888   2.295   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      11.640   0.952   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      10.853  -0.372   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      11.606  -1.715   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      13.146  -1.735   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      13.933  -0.412   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      13.180   0.932   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      13.967   2.255   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      15.507   2.235   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      16.294   3.559   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      17.834   3.539   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      18.587   2.196   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      17.800   0.872   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0      16.260   0.892   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0      18.552  -0.472   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0      17.765  -1.795   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      20.127   2.176   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      18.622   4.863   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      15.542   4.903   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      16.329   6.226   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      17.869   6.206   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0      18.656   7.530   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      17.904   8.873   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      16.364   8.893   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      15.576   7.570   0.000  0.00  0.00           C+0
HETATM   58  O   UNK     0      14.037   7.590   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0      15.611  10.237   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0      18.691  10.197   0.000  0.00  0.00           O+0
HETATM   61  O   UNK     0      15.473  -0.432   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0      13.898  -3.079   0.000  0.00  0.00           O+0
HETATM   63  C   UNK     0      10.818  -3.039   0.000  0.00  0.00           C+0
HETATM   64  O   UNK     0       9.279  -3.019   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   33                                                  
CONECT    3    2    4   31   32                                             
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7   30                                             
CONECT    6    5    1                                                       
CONECT    7    5    8   14                                                  
CONECT    8    7    9   11   29                                             
CONECT    9    8   10                                                       
CONECT   10    9    4                                                       
CONECT   11    8   12   18   28                                             
CONECT   12   11   13   15   27                                             
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   25                                                  
CONECT   23   22   15   24                                                  
CONECT   24   23                                                            
CONECT   25   22                                                            
CONECT   26   16   27                                                       
CONECT   27   26   12                                                       
CONECT   28   11                                                            
CONECT   29    8                                                            
CONECT   30    5                                                            
CONECT   31    3                                                            
CONECT   32    3                                                            
CONECT   33    2   34                                                       
CONECT   34   33   35   39                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   63                                                  
CONECT   37   36   38   62                                                  
CONECT   38   37   39   61                                                  
CONECT   39   38   34   40                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42   46                                                  
CONECT   42   41   43   51                                                  
CONECT   43   42   44   50                                                  
CONECT   44   43   45   49                                                  
CONECT   45   44   46   47                                                  
CONECT   46   45   41                                                       
CONECT   47   45   48                                                       
CONECT   48   47                                                            
CONECT   49   44                                                            
CONECT   50   43                                                            
CONECT   51   42   52                                                       
CONECT   52   51   53   57                                                  
CONECT   53   52   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54   56   60                                                  
CONECT   56   55   57   59                                                  
CONECT   57   56   52   58                                                  
CONECT   58   57                                                            
CONECT   59   56                                                            
CONECT   60   55                                                            
CONECT   61   38                                                            
CONECT   62   37                                                            
CONECT   63   36   64                                                       
CONECT   64   63                                                            
MASTER        0    0    0    0    0    0    0    0   64    0  144    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₇H₇₆O₁₇

Average Mass

913.1080 Da

Monoisotopic Mass

912.50825 Da

IUPAC Name

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@@H]1CC[C@]23CO[C@]4(C=C[C@@H]5[C@@]6(C)CC[C@H](O[C@@H]7O[C@H](CO)[C@H](O)[C@H](O)[C@H]7O[C@@H]7O[C@H](CO)[C@@H](O)[C@H](O)[C@H]7O[C@@H]7OC[C@@H](O)[C@H](O)[C@H]7O)C(C)(C)[C@@H]6CC[C@@]5(C)[C@]4(C)C[C@H]2O)[C@@H]3[C@H]1C

InChI Identifier

InChI=1S/C47H76O17/c1-21-8-14-46-20-59-47(38(46)22(21)2)15-10-27-43(5)12-11-29(42(3,4)26(43)9-13-44(27,6)45(47,7)16-28(46)51)62-40-36(33(55)31(53)24(17-48)60-40)64-41-37(34(56)32(54)25(18-49)61-41)63-39-35(57)30(52)23(50)19-58-39/h10,15,21-41,48-57H,8-9,11-14,16-20H2,1-7H3/t21-,22+,23-,24-,25-,26+,27-,28-,29+,30+,31+,32-,33+,34+,35-,36-,37-,38-,39+,40+,41+,43+,44-,45+,46+,47-/m1/s1

InChI Key

OERYSJKYOLNHAD-BDJJZTGYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Bupleurum rotundifolium	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpene saponins. These are glycosylated derivatives of triterpene sapogenins. The sapogenin moiety backbone is usually based on the oleanane, ursane, taraxastane, bauerane, lanostane, lupeol, lupane, dammarane, cycloartane, friedelane, hopane, 9b,19-cyclo-lanostane, cycloartane, or cycloartanol skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene glycosides

Direct Parent

Triterpene saponins

Alternative Parents

Substituents

Triterpene saponin
Triterpenoid
Oligosaccharide
O-glycosyl compound
Glycosyl compound
Oxepane
Oxane
Tetrahydrofuran
Cyclic alcohol
Secondary alcohol
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Dialkyl ether
Acetal
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
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
logP	0.89	ALOGPS
logP	0.48	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	12.02	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	266.91 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	224.6 m³·mol⁻¹	ChemAxon
Polarizability	101.82 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

162855152

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for (-)-Rotundifolioside H (NP0071741)

MOL for NP0071741 ((-)-Rotundifolioside H)

3D MOL for NP0071741 ((-)-Rotundifolioside H)

3D SDF for NP0071741 ((-)-Rotundifolioside H)

3D-SDF for NP0071741 ((-)-Rotundifolioside H)

PDB for NP0071741 ((-)-Rotundifolioside H)

3D PDB for NP0071741 ((-)-Rotundifolioside H)

SMILES for NP0071741 ((-)-Rotundifolioside H)

INCHI for NP0071741 ((-)-Rotundifolioside H)

Structure for NP0071741 ((-)-Rotundifolioside H)

3D Structure for NP0071741 ((-)-Rotundifolioside H)