NP-MRD: Showing NP-Card for Melianthusigenin (NP0084201)

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Record Information

Version

2.0

Created at

2022-04-29 05:00:09 UTC

Updated at

2022-04-29 05:00:09 UTC

NP-MRD ID

NP0084201

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Melianthusigenin

Description

Melianthusigenin belongs to the class of organic compounds known as bufanolides and derivatives. These are steroid lactones containing a pyran-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative. Melianthusigenin is found in Melianthus major . Based on a literature review very few articles have been published on Melianthusigenin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292207002D          

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M  END

     RDKit          3D

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  4  6  1  6  0  0  0
  4  7  1  0  0  0  0
  8  7  1  6  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 11 19  1  0  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 17 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 24 29  1  0  0  0  0
 27 30  2  0  0  0  0
  8 31  1  0  0  0  0
  2 31  1  0  0  0  0
  8 32  1  0  0  0  0
 13 32  1  0  0  0  0
 32 33  1  1  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 35 37  2  0  0  0  0
 32 38  1  0  0  0  0
  5 38  1  0  0  0  0
 38 39  1  1  0  0  0
 38 40  1  0  0  0  0
  2 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0084201

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12C[C@@]3([H])OC(C)(O1)O[C@@]1(CC[C@]4([H])[C@]([H])(CC[C@]5(C)[C@H](CC[C@]45O)C4=COC(=O)C=C4)[C@@]31COC(C)=O)C2

> <INCHI_IDENTIFIER>
InChI=1S/C28H36O8/c1-16(29)33-15-27-20-6-9-24(2)19(17-4-5-23(30)32-14-17)8-11-28(24,31)21(20)7-10-26(27)13-18-12-22(27)35-25(3,34-18)36-26/h4-5,14,18-22,31H,6-13,15H2,1-3H3/t18-,19+,20-,21+,22+,24+,25?,26-,27-,28-/m0/s1

> <INCHI_KEY>
RRDZJCCZVWCHID-WAJAMXMFSA-N

> <FORMULA>
C28H36O8

> <MOLECULAR_WEIGHT>
500.588

> <EXACT_MASS>
500.241018119

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
52.349574947836665

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1S,4R,5S,8S,9R,12S,13R,14R,18S)-5-hydroxy-9,16-dimethyl-8-(2-oxo-2H-pyran-5-yl)-15,17,20-trioxahexacyclo[14.3.1.1^{14,18}.0^{1,13}.0^{4,12}.0^{5,9}]henicosan-13-yl]methyl acetate

> <ALOGPS_LOGP>
2.50

> <JCHEM_LOGP>
2.451240984333332

> <ALOGPS_LOGS>
-5.04

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
0.26895959812310777

> <JCHEM_POLAR_SURFACE_AREA>
100.52

> <JCHEM_REFRACTIVITY>
127.77579999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.52e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,4R,5S,8S,9R,12S,13R,14R,18S)-5-hydroxy-9,16-dimethyl-8-(6-oxopyran-3-yl)-15,17,20-trioxahexacyclo[14.3.1.1^{14,18}.0^{1,13}.0^{4,12}.0^{5,9}]henicosan-13-yl]methyl 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  C   UNK     0      -0.227  -0.607   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.035   0.572   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.442   1.083   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.784   2.084   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.489   3.565   0.000  0.00  0.00           C+0
HETATM    6  H   UNK     0      -0.428   3.035   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0       2.190   1.012   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.596   0.327   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.592  -1.118   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.268  -0.205   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.653   1.322   0.000  0.00  0.00           C+0
HETATM   12  H   UNK     0       7.110   2.793   0.000  0.00  0.00           H+0
HETATM   13  C   UNK     0       5.608   2.453   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0       4.493   3.516   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0       6.064   3.924   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.566   4.264   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.612   3.133   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.116   4.759   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.155   1.662   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       8.330  -0.061   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       9.413   0.773   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.646   1.695   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.151   3.153   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.040   4.411   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      12.574   4.270   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      13.462   5.528   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      12.818   6.926   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      11.284   7.067   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      10.395   5.809   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      13.755   8.219   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       2.215  -0.534   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.104   1.907   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.456   1.277   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       4.975  -0.239   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       5.897  -1.645   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       7.598  -1.117   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       5.931  -3.310   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       3.042   3.135   0.000  0.00  0.00           C+0
HETATM   39  H   UNK     0       3.053   4.675   0.000  0.00  0.00           H+0
HETATM   40  O   UNK     0       1.939   2.060   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   31   40                                             
CONECT    3    2    4                                                       
CONECT    4    3    5    6    7                                             
CONECT    5    4   38                                                       
CONECT    6    4                                                            
CONECT    7    4    8                                                       
CONECT    8    7    9   31   32                                             
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   19                                             
CONECT   12   11                                                            
CONECT   13   11   14   15   32                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19   23                                             
CONECT   18   17                                                            
CONECT   19   17   11   20   21                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   17   24                                                  
CONECT   24   23   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   30                                                  
CONECT   28   27   29                                                       
CONECT   29   28   24                                                       
CONECT   30   27                                                            
CONECT   31    8    2                                                       
CONECT   32    8   13   33   38                                             
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35                                                            
CONECT   38   32    5   39   40                                             
CONECT   39   38                                                            
CONECT   40   38    2                                                       
MASTER        0    0    0    0    0    0    0    0   40    0   92    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₆O₈

Average Mass

500.5880 Da

Monoisotopic Mass

500.24102 Da

IUPAC Name

[(1S,4R,5S,8S,9R,12S,13R,14R,18S)-5-hydroxy-9,16-dimethyl-8-(2-oxo-2H-pyran-5-yl)-15,17,20-trioxahexacyclo[14.3.1.1^{14,18}.0^{1,13}.0^{4,12}.0^{5,9}]henicosan-13-yl]methyl acetate

Traditional Name

[(1S,4R,5S,8S,9R,12S,13R,14R,18S)-5-hydroxy-9,16-dimethyl-8-(6-oxopyran-3-yl)-15,17,20-trioxahexacyclo[14.3.1.1^{14,18}.0^{1,13}.0^{4,12}.0^{5,9}]henicosan-13-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

[H][C@@]12C[C@@]3([H])OC(C)(O1)O[C@@]1(CC[C@]4([H])[C@]([H])(CC[C@]5(C)[C@H](CC[C@]45O)C4=COC(=O)C=C4)[C@@]31COC(C)=O)C2

InChI Identifier

InChI=1S/C28H36O8/c1-16(29)33-15-27-20-6-9-24(2)19(17-4-5-23(30)32-14-17)8-11-28(24,31)21(20)7-10-26(27)13-18-12-22(27)35-25(3,34-18)36-26/h4-5,14,18-22,31H,6-13,15H2,1-3H3/t18-,19+,20-,21+,22+,24+,25?,26-,27-,28-/m0/s1

InChI Key

RRDZJCCZVWCHID-WAJAMXMFSA-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
Melianthus major	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as bufanolides and derivatives. These are steroid lactones containing a pyran-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Bufanolides and derivatives

Alternative Parents

Substituents

Bufanolide-skeleton
Pyranone
Ortho ester
Carboxylic acid orthoester
Pyran
Meta-dioxane
Heteroaromatic compound
Tertiary alcohol
Cyclic alcohol
Orthocarboxylic acid derivative
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	2.5	ALOGPS
logP	2.45	ChemAxon
logS	-5	ALOGPS
pKa (Strongest Basic)	0.27	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	100.52 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	127.78 m³·mol⁻¹	ChemAxon
Polarizability	52.35 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	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

C00053467

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

101306864

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Melianthusigenin (NP0084201)

MOL for NP0084201 (Melianthusigenin)

3D MOL for NP0084201 (Melianthusigenin)

3D SDF for NP0084201 (Melianthusigenin)

3D-SDF for NP0084201 (Melianthusigenin)

PDB for NP0084201 (Melianthusigenin)

3D PDB for NP0084201 (Melianthusigenin)

SMILES for NP0084201 (Melianthusigenin)

INCHI for NP0084201 (Melianthusigenin)

Structure for NP0084201 (Melianthusigenin)

3D Structure for NP0084201 (Melianthusigenin)