NP-MRD: Showing NP-Card for Bersaldegenin 1,3,5-orthoacetate (NP0083908)

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Record Information

Version

2.0

Created at

2022-04-29 04:48:20 UTC

Updated at

2022-04-29 04:48:20 UTC

NP-MRD ID

NP0083908

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Bersaldegenin 1,3,5-orthoacetate

Description

Melianthugenin 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. Thus, melianthugenin is considered to be a sterol. Bersaldegenin 1,3,5-orthoacetate is found in Bryophyllum pinnatum and Melianthus major . Based on a literature review very few articles have been published on Melianthugenin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292206482D          

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M  END

     RDKit          3D

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M  END


  Mrv1652304292206482D          

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M  END
> <DATABASE_ID>
NP0083908

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12C[C@@]3([H])O[C@@](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@@]31C=O)C2

> <INCHI_IDENTIFIER>
InChI=1S/C26H32O7/c1-22-8-5-18-19(26(22,29)10-7-17(22)15-3-4-21(28)30-13-15)6-9-24-12-16-11-20(25(18,24)14-27)32-23(2,31-16)33-24/h3-4,13-14,16-20,29H,5-12H2,1-2H3/t16-,17+,18-,19+,20+,22+,23+,24-,25-,26-/m0/s1

> <INCHI_KEY>
QMZMTFLDQTWANC-PYFUVDDASA-N

> <FORMULA>
C26H32O7

> <MOLECULAR_WEIGHT>
456.535

> <EXACT_MASS>
456.21480337

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
47.50121613736506

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,4R,5S,8S,9R,12S,13R,14R,16R,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}]henicosane-13-carbaldehyde

> <ALOGPS_LOGP>
2.36

> <JCHEM_LOGP>
2.323963077333333

> <ALOGPS_LOGS>
-4.56

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
0.2958597974826308

> <JCHEM_POLAR_SURFACE_AREA>
91.29

> <JCHEM_REFRACTIVITY>
117.64139999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.25e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4R,5S,8S,9R,12S,13R,14R,16R,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}]henicosane-13-carbaldehyde

> <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       0.637   1.469   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.880   0.234   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.070   1.345   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       0.376  -0.231   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.599  -1.213   0.000  0.00  0.00           C+0
HETATM    6  H   UNK     0       0.397  -2.176   0.000  0.00  0.00           H+0
HETATM    7  C   UNK     0       2.318  -2.678   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.036  -0.186   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.460   0.502   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.677   2.012   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.141   1.048   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.507  -0.479   0.000  0.00  0.00           C+0
HETATM   13  H   UNK     0       7.959  -1.951   0.000  0.00  0.00           H+0
HETATM   14  C   UNK     0       6.458  -1.606   0.000  0.00  0.00           C+0
HETATM   15  H   UNK     0       5.352  -2.678   0.000  0.00  0.00           H+0
HETATM   16  C   UNK     0       6.910  -3.079   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.411  -3.423   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.460  -2.295   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.974  -3.933   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.008  -0.823   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.047   0.848   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      10.268   0.062   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.499  -0.863   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.000  -2.320   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.885  -3.580   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.236  -4.977   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      12.121  -6.237   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      13.655  -6.101   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.304  -4.704   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.419  -3.444   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      14.540  -7.361   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.948  -1.090   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       6.394  -0.752   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       5.586   0.721   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       3.897  -2.340   0.000  0.00  0.00           C+0
HETATM   36  H   UNK     0       3.884  -3.880   0.000  0.00  0.00           H+0
HETATM   37  O   UNK     0       2.806  -1.258   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4   37                                             
CONECT    3    2    9                                                       
CONECT    4    2    5                                                       
CONECT    5    4    6    7    8                                             
CONECT    6    5                                                            
CONECT    7    5   35                                                       
CONECT    8    5    9                                                       
CONECT    9    8    3   10   32                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   20                                             
CONECT   13   12                                                            
CONECT   14   12   15   16   32                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20   24                                             
CONECT   19   18                                                            
CONECT   20   18   12   21   22                                             
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   18   25                                                  
CONECT   25   24   26   30                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29   25                                                       
CONECT   31   28                                                            
CONECT   32    9   14   33   35                                             
CONECT   33   32   34                                                       
CONECT   34   33                                                            
CONECT   35   32    7   36   37                                             
CONECT   36   35                                                            
CONECT   37   35    2                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₂O₇

Average Mass

456.5350 Da

Monoisotopic Mass

456.21480 Da

IUPAC Name

(1S,4R,5S,8S,9R,12S,13R,14R,16R,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}]henicosane-13-carbaldehyde

Traditional Name

(1S,4R,5S,8S,9R,12S,13R,14R,16R,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}]henicosane-13-carbaldehyde

CAS Registry Number

Not Available

SMILES

[H][C@@]12C[C@@]3([H])O[C@@](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@@]31C=O)C2

InChI Identifier

InChI=1S/C26H32O7/c1-22-8-5-18-19(26(22,29)10-7-17(22)15-3-4-21(28)30-13-15)6-9-24-12-16-11-20(25(18,24)14-27)32-23(2,31-16)33-24/h3-4,13-14,16-20,29H,5-12H2,1-2H3/t16-,17+,18-,19+,20+,22+,23+,24-,25-,26-/m0/s1

InChI Key

QMZMTFLDQTWANC-PYFUVDDASA-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
Kalanchoe pinnata	Plant	KNApSAcK
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
Carboxylic acid orthoester
Pyranone
Ortho ester
Meta-dioxane
Pyran
Heteroaromatic compound
Cyclic alcohol
Tertiary alcohol
Lactone
Orthocarboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Aldehyde
Alcohol
Organooxygen compound
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	2.36	ALOGPS
logP	2.32	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Basic)	0.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	91.29 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	117.64 m³·mol⁻¹	ChemAxon
Polarizability	47.5 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

C00052873

Chemspider ID

62970122

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101717792

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Bersaldegenin 1,3,5-orthoacetate (NP0083908)

MOL for NP0083908 (Bersaldegenin 1,3,5-orthoacetate)

3D MOL for NP0083908 (Bersaldegenin 1,3,5-orthoacetate)

3D SDF for NP0083908 (Bersaldegenin 1,3,5-orthoacetate)

3D-SDF for NP0083908 (Bersaldegenin 1,3,5-orthoacetate)

PDB for NP0083908 (Bersaldegenin 1,3,5-orthoacetate)

3D PDB for NP0083908 (Bersaldegenin 1,3,5-orthoacetate)

SMILES for NP0083908 (Bersaldegenin 1,3,5-orthoacetate)

INCHI for NP0083908 (Bersaldegenin 1,3,5-orthoacetate)

Structure for NP0083908 (Bersaldegenin 1,3,5-orthoacetate)

3D Structure for NP0083908 (Bersaldegenin 1,3,5-orthoacetate)