NP-MRD: Showing NP-Card for Ghalakinoside (NP0077960)

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Record Information

Version

2.0

Created at

2022-04-28 23:06:47 UTC

Updated at

2022-04-28 23:06:47 UTC

NP-MRD ID

NP0077960

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Ghalakinoside

Description

4-[(1S,3S,5S,7R,9S,10R,12S,14S,15S,17R,18S,19R,22S,23R)-9,10,17,22-tetrahydroxy-7,14-bis(hydroxymethyl)-18-methyl-4,6,11-trioxahexacyclo[12.11.0.0³,¹².0⁵,¹⁰.0¹⁵,²³.0¹⁸,²²]Pentacosan-19-yl]-2,5-dihydrofuran-2-one belongs to the class of organic compounds known as cardenolide glycosides and derivatives. Cardenolide glycosides and derivatives are compounds containing a carbohydrate glycosidically bound to the cardenolide moiety. Ghalakinoside is found in Pergularia tomentosa . Based on a literature review very few articles have been published on 4-[(1S,3S,5S,7R,9S,10R,12S,14S,15S,17R,18S,19R,22S,23R)-9,10,17,22-tetrahydroxy-7,14-bis(hydroxymethyl)-18-methyl-4,6,11-trioxahexacyclo[12.11.0.0³,¹².0⁵,¹⁰.0¹⁵,²³.0¹⁸,²²]Pentacosan-19-yl]-2,5-dihydrofuran-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292201062D          

 40 46  0  0  1  0            999 V2000
    7.0989    2.0657    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.4543    0.7040    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  1  0  0  0
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  5 38  1  1  0  0  0
  2 39  1  6  0  0  0
 39 40  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652304292201062D          

 40 46  0  0  1  0            999 V2000
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    1.1720    2.5802    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9527    2.3135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0126    3.3896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2684    2.1359    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6152    1.3873    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0104    0.8262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6701    2.8565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4892    2.9550    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6487    3.7644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3972    4.1113    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9281    4.1662    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3233    3.6050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3076    2.8257    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7841    0.4062    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7334    2.0468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3547    2.5896    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.5375    2.5991    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0390    0.9896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6603    1.5324    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  4  3  1  1  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  5  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
  4 11  1  0  0  0  0
 10 12  1  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
  9 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 13 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 16 23  1  6  0  0  0
 22 24  1  6  0  0  0
 21 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 20 27  1  0  0  0  0
 25 28  1  6  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 28 33  1  0  0  0  0
 21 34  1  6  0  0  0
 20 35  1  6  0  0  0
 14 36  1  1  0  0  0
 36 37  1  0  0  0  0
  5 38  1  1  0  0  0
  2 39  1  6  0  0  0
 39 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0077960

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]12[C@H](CC[C@]1(O)[C@@H]1CC[C@H]3C[C@@H]4O[C@@H]5O[C@@H](CO)C[C@H](O)[C@@]5(O)O[C@H]4C[C@@]3(CO)[C@H]1C[C@H]2O)C1=CC(=O)OC1

> <INCHI_IDENTIFIER>
InChI=1S/C29H42O11/c1-26-17(14-6-24(34)37-12-14)4-5-28(26,35)18-3-2-15-7-20-21(10-27(15,13-31)19(18)9-22(26)32)40-29(36)23(33)8-16(11-30)38-25(29)39-20/h6,15-23,25,30-33,35-36H,2-5,7-13H2,1H3/t15-,16+,17+,18+,19-,20-,21-,22+,23-,25-,26-,27-,28-,29+/m0/s1

> <INCHI_KEY>
NPHHLSOQKLWOCK-QOSKVSNOSA-N

> <FORMULA>
C29H42O11

> <MOLECULAR_WEIGHT>
566.644

> <EXACT_MASS>
566.272712172

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
59.28295176805693

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[(1S,3S,5S,7R,9S,10R,12S,14S,15S,17R,18S,19R,22S,23R)-9,10,17,22-tetrahydroxy-7,14-bis(hydroxymethyl)-18-methyl-4,6,11-trioxahexacyclo[12.11.0.0^{3,12}.0^{5,10}.0^{15,23}.0^{18,22}]pentacosan-19-yl]-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
-1.02

> <JCHEM_LOGP>
-0.6276526776666665

> <ALOGPS_LOGS>
-2.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.461751615231734

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.148987278456641

> <JCHEM_PKA_STRONGEST_BASIC>
-2.760425451466972

> <JCHEM_POLAR_SURFACE_AREA>
175.36999999999998

> <JCHEM_REFRACTIVITY>
137.56569999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.49e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-[(1S,3S,5S,7R,9S,10R,12S,14S,15S,17R,18S,19R,22S,23R)-9,10,17,22-tetrahydroxy-7,14-bis(hydroxymethyl)-18-methyl-4,6,11-trioxahexacyclo[12.11.0.0^{3,12}.0^{5,10}.0^{15,23}.0^{18,22}]pentacosan-19-yl]-5H-furan-2-one

> <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  C   UNK     0      13.251   3.856   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.549   2.345   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      12.389   1.332   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      10.932   1.830   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      10.634   3.341   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      11.794   4.354   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      11.496   5.865   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       9.177   3.838   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.017   2.825   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.315   1.314   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.772   0.816   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.155   0.301   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.698   0.799   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.400   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.560   3.323   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       3.943   2.808   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.783   1.794   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.080   0.283   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.538  -0.214   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.326   2.292   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.028   3.803   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.188   4.816   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.645   4.319   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.890   6.327   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -0.501   3.987   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.148   2.590   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.020   1.542   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.251   5.332   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -2.780   5.516   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -3.077   7.027   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -4.475   7.674   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0      -1.732   7.777   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -0.604   6.729   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.574   5.275   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       1.464   0.758   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       5.102   3.821   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       6.262   4.834   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      10.337   4.852   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      15.006   1.847   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      16.166   2.860   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   39                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6    8   38                                             
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10   15                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10    4                                                       
CONECT   12   10   13                                                       
CONECT   13   12   14   19                                                  
CONECT   14   13   15   16   36                                             
CONECT   15   14    9                                                       
CONECT   16   14   17   23                                                  
CONECT   17   16   18   20                                                  
CONECT   18   17   19                                                       
CONECT   19   18   13                                                       
CONECT   20   17   21   27   35                                             
CONECT   21   20   22   25   34                                             
CONECT   22   21   23   24                                                  
CONECT   23   22   16                                                       
CONECT   24   22                                                            
CONECT   25   21   26   28                                                  
CONECT   26   25   27                                                       
CONECT   27   26   20                                                       
CONECT   28   25   29   33                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33                                                       
CONECT   33   32   28                                                       
CONECT   34   21                                                            
CONECT   35   20                                                            
CONECT   36   14   37                                                       
CONECT   37   36                                                            
CONECT   38    5                                                            
CONECT   39    2   40                                                       
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₂O₁₁

Average Mass

566.6440 Da

Monoisotopic Mass

566.27271 Da

IUPAC Name

4-[(1S,3S,5S,7R,9S,10R,12S,14S,15S,17R,18S,19R,22S,23R)-9,10,17,22-tetrahydroxy-7,14-bis(hydroxymethyl)-18-methyl-4,6,11-trioxahexacyclo[12.11.0.0^{3,12}.0^{5,10}.0^{15,23}.0^{18,22}]pentacosan-19-yl]-2,5-dihydrofuran-2-one

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@@]12[C@H](CC[C@]1(O)[C@@H]1CC[C@H]3C[C@@H]4O[C@@H]5O[C@@H](CO)C[C@H](O)[C@@]5(O)O[C@H]4C[C@@]3(CO)[C@H]1C[C@H]2O)C1=CC(=O)OC1

InChI Identifier

InChI=1S/C29H42O11/c1-26-17(14-6-24(34)37-12-14)4-5-28(26,35)18-3-2-15-7-20-21(10-27(15,13-31)19(18)9-22(26)32)40-29(36)23(33)8-16(11-30)38-25(29)39-20/h6,15-23,25,30-33,35-36H,2-5,7-13H2,1H3/t15-,16+,17+,18+,19-,20-,21-,22+,23-,25-,26-,27-,28-,29+/m0/s1

InChI Key

NPHHLSOQKLWOCK-QOSKVSNOSA-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
Pergularia tomentosa	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cardenolide glycosides and derivatives. Cardenolide glycosides and derivatives are compounds containing a carbohydrate glycosidically bound to the cardenolide moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Cardenolide glycosides and derivatives

Alternative Parents

Substituents

Cardanolide-glycoside
19-hydroxysteroid
Hydroxysteroid
14-hydroxysteroid
12-hydroxysteroid
Oxane
2-furanone
Para-dioxane
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tertiary alcohol
Dihydrofuran
Cyclic alcohol
Secondary alcohol
Lactone
Hemiacetal
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
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	-1	ALOGPS
logP	-0.63	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	7.15	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	175.37 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	137.57 m³·mol⁻¹	ChemAxon
Polarizability	59.28 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

162878840

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Ghalakinoside (NP0077960)

MOL for NP0077960 (Ghalakinoside)

3D MOL for NP0077960 (Ghalakinoside)

3D SDF for NP0077960 (Ghalakinoside)

3D-SDF for NP0077960 (Ghalakinoside)

PDB for NP0077960 (Ghalakinoside)

3D PDB for NP0077960 (Ghalakinoside)

SMILES for NP0077960 (Ghalakinoside)

INCHI for NP0077960 (Ghalakinoside)

Structure for NP0077960 (Ghalakinoside)

3D Structure for NP0077960 (Ghalakinoside)