NP-MRD: Showing NP-Card for daigremontianin (NP0284768)

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Record Information

Version

2.0

Created at

2022-09-09 12:38:13 UTC

Updated at

2022-09-09 12:38:13 UTC

NP-MRD ID

NP0284768

Secondary Accession Numbers

None

Natural Product Identification

Common Name

daigremontianin

Description

Q5209119 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. Based on a literature review very few articles have been published on Q5209119.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092214382D          

 35 41  0  0  1  0            999 V2000
   -0.4980    0.5140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2061   -0.0319    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4392    0.5264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8301   -0.0341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.7214   -0.9917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3827   -1.9052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1740   -1.2799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3831   -0.4659    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    3.0356    0.9201    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4809    1.5803    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5782    1.9870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4097    0.5280    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5460    1.4053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309092214382D          

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M  END
> <DATABASE_ID>
NP0284768

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]12[C@H](CC[C@]1(O)[C@@H]1CCC34C[C@@H]5CC(OC(C)(O5)O3)[C@]4(C=O)[C@H]1[C@H](O)C2=O)C1=COC(=O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H30O9/c1-22-15(13-3-4-18(28)32-11-13)6-8-26(22,31)16-5-7-24-10-14-9-17(34-23(2,33-14)35-24)25(24,12-27)19(16)20(29)21(22)30/h3-4,11-12,14-17,19-20,29,31H,5-10H2,1-2H3/t14-,15+,16+,17?,19+,20-,22-,23?,24?,25+,26-/m0/s1

> <INCHI_KEY>
PHOLEJIIASOWOL-SQBSQXRJSA-N

> <FORMULA>
C26H30O9

> <MOLECULAR_WEIGHT>
486.517

> <EXACT_MASS>
486.188982546

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
48.46071457973166

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(4R,5S,8R,9R,11S,12S,13R,18S)-5,11-dihydroxy-9,16-dimethyl-10-oxo-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

> <JCHEM_LOGP>
0.8635675253333327

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.04137938236897

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.032347763756547

> <JCHEM_PKA_STRONGEST_BASIC>
-3.247615164731249

> <JCHEM_POLAR_SURFACE_AREA>
128.59

> <JCHEM_REFRACTIVITY>
119.74979999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(4R,5S,8R,9R,11S,12S,13R,18S)-5,11-dihydroxy-9,16-dimethyl-10-oxo-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                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.930   0.960   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.385  -0.060   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.132   1.401   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.687   0.983   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.549  -0.064   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.611  -1.531   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.794  -2.650   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.213  -1.851   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.448  -3.556   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.925  -2.389   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.315  -0.870   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.244   0.237   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.666   1.718   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       4.631   2.950   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       7.160   2.092   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.679   3.709   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.231   0.986   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.486   2.623   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.770   1.041   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.630   2.319   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.953   3.702   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      10.813   4.980   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.349   4.875   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      13.208   6.153   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      13.026   3.492   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      12.166   2.214   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.299  -0.405   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       9.087  -1.355   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.809  -0.495   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       7.888  -2.124   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       3.732  -0.280   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       3.868  -2.047   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       3.101  -3.619   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       1.801  -1.115   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      -0.867  -1.003   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   34   35                                             
CONECT    3    2    4                                                       
CONECT    4    3    5   31                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   35                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   31   34                                             
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   29                                                  
CONECT   12   11   13   31                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19   29                                             
CONECT   18   17                                                            
CONECT   19   17   20   27                                                  
CONECT   20   19   21   26                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   20                                                       
CONECT   27   19   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   11   17   30                                             
CONECT   30   29                                                            
CONECT   31   12    4    8   32                                             
CONECT   32   31   33                                                       
CONECT   33   32                                                            
CONECT   34    8    2                                                       
CONECT   35    6    2                                                       
MASTER        0    0    0    0    0    0    0    0   35    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₀O₉

Average Mass

486.5170 Da

Monoisotopic Mass

486.18898 Da

IUPAC Name

(4R,5S,8R,9R,11S,12S,13R,18S)-5,11-dihydroxy-9,16-dimethyl-10-oxo-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

(4R,5S,8R,9R,11S,12S,13R,18S)-5,11-dihydroxy-9,16-dimethyl-10-oxo-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

C[C@@]12[C@H](CC[C@]1(O)[C@@H]1CCC34C[C@@H]5CC(OC(C)(O5)O3)[C@]4(C=O)[C@H]1[C@H](O)C2=O)C1=COC(=O)C=C1

InChI Identifier

InChI=1S/C26H30O9/c1-22-15(13-3-4-18(28)32-11-13)6-8-26(22,31)16-5-7-24-10-14-9-17(34-23(2,33-14)35-24)25(24,12-27)19(16)20(29)21(22)30/h3-4,11-12,14-17,19-20,29,31H,5-10H2,1-2H3/t14-,15+,16+,17?,19+,20-,22-,23?,24?,25+,26-/m0/s1

InChI Key

PHOLEJIIASOWOL-SQBSQXRJSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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
Secondary alcohol
Orthocarboxylic acid derivative
Lactone
Ketone
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
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	0.86	ChemAxon
pKa (Strongest Acidic)	13.03	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	128.59 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	119.75 m³·mol⁻¹	ChemAxon
Polarizability	48.46 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

112839

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

127105

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for daigremontianin (NP0284768)

MOL for NP0284768 (daigremontianin)

3D MOL for NP0284768 (daigremontianin)

3D SDF for NP0284768 (daigremontianin)

3D-SDF for NP0284768 (daigremontianin)

PDB for NP0284768 (daigremontianin)

3D PDB for NP0284768 (daigremontianin)

SMILES for NP0284768 (daigremontianin)

INCHI for NP0284768 (daigremontianin)

Structure for NP0284768 (daigremontianin)

3D Structure for NP0284768 (daigremontianin)