NP-MRD: Showing NP-Card for 16,25-dihydroxy-13(24),17-cheilanthadien-19,25-olide (NP0025536)

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Record Information

Version

1.0

Created at

2021-06-19 17:38:05 UTC

Updated at

2021-06-29 23:50:33 UTC

NP-MRD ID

NP0025536

Secondary Accession Numbers

None

Natural Product Identification

Common Name

16,25-dihydroxy-13(24),17-cheilanthadien-19,25-olide

Provided By

JEOL Database JEOL Logo

Description

16,25-dihydroxy-13(24),17-cheilanthadien-19,25-olide is found in Ircinia and Ircinia sp.. It was first documented in 2001 (Buchanan, M. S., et al.).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306192119383D          

 67 70  0  0  0  0            999 V2000
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M  END

     RDKit          3D

 67 70  0  0  0  0  0  0  0  0999 V2000
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M  END


  Mrv1652306192119383D          

 67 70  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0025536

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@@]([H])(C1=C([H])C(=O)O[C@]1([H])O[H])C([H])([H])[C@]1([H])C(=C([H])[H])C([H])([H])C([H])([H])[C@@]2([H])[C@@]1(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]1([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@]21C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C25H38O4/c1-15-7-8-20-24(4,12-9-19-23(2,3)10-6-11-25(19,20)5)17(15)14-18(26)16-13-21(27)29-22(16)28/h13,17-20,22,26,28H,1,6-12,14H2,2-5H3/t17-,18-,19+,20+,22+,24+,25+/m1/s1

> <INCHI_KEY>
LWTIZOHDKCIZPP-SCHZJEEGSA-N

> <FORMULA>
C25H38O4

> <MOLECULAR_WEIGHT>
402.575

> <EXACT_MASS>
402.277009704

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
45.72313040506532

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5S)-4-[(1R)-2-[(1R,4aR,4bS,8aS,10aS)-4b,8,8,10a-tetramethyl-2-methylidene-tetradecahydrophenanthren-1-yl]-1-hydroxyethyl]-5-hydroxy-2,5-dihydrofuran-2-one

> <ALOGPS_LOGP>
4.07

> <JCHEM_LOGP>
4.801080017000001

> <ALOGPS_LOGS>
-4.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
11.732733903503863

> <JCHEM_PKA_STRONGEST_ACIDIC>
5.579101226112417

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0661223726998017

> <JCHEM_POLAR_SURFACE_AREA>
66.76

> <JCHEM_REFRACTIVITY>
113.72119999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.92e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5S)-4-[(1R)-2-[(1R,4aR,4bS,8aS,10aS)-4b,8,8,10a-tetramethyl-2-methylidene-decahydrophenanthren-1-yl]-1-hydroxyethyl]-5-hydroxy-5H-furan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 67 70  0  0  0  0  0  0  0  0999 V2000
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  7 37  1  0
  7 38  1  0
  7 39  1  0
 18 57  1  0
 18 58  1  0
 18 59  1  0
 22 64  1  0
M  END

HEADER    PROTEIN                                 19-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-JUN-21         0                                  
HETATM    1  C   UNK     0      -3.501   1.217  -2.293  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.462   1.576  -1.519  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.488   2.625  -1.996  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.079   2.040  -2.107  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.373   1.363  -0.788  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.906   0.948  -0.743  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.237  -0.106  -1.826  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.788   2.204  -1.020  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.273   2.016  -0.707  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.506   1.539   0.719  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.717   0.260   1.095  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.875   0.080   2.628  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.361  -0.977   0.444  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.205   0.469   0.728  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.280  -0.690   1.138  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.195  -0.286   1.068  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.661   0.258  -0.307  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.794  -0.937  -1.283  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.079   0.973  -0.164  0.00  0.00           C+0
HETATM   20  C   UNK     0      -3.180   0.113   0.513  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.449   0.889   0.921  0.00  0.00           C+0
HETATM   22  O   UNK     0      -5.358  -0.012   1.557  0.00  0.00           O+0
HETATM   23  C   UNK     0      -4.248   2.024   1.862  0.00  0.00           C+0
HETATM   24  C   UNK     0      -4.458   3.314   1.601  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.197   4.034   2.842  0.00  0.00           C+0
HETATM   26  O   UNK     0      -4.296   5.240   2.974  0.00  0.00           O+0
HETATM   27  O   UNK     0      -3.853   3.155   3.818  0.00  0.00           O+0
HETATM   28  C   UNK     0      -3.843   1.845   3.270  0.00  0.00           C+0
HETATM   29  O   UNK     0      -2.532   1.326   3.334  0.00  0.00           O+0
HETATM   30  H   UNK     0      -4.194   0.429  -2.025  0.00  0.00           H+0
HETATM   31  H   UNK     0      -3.673   1.691  -3.256  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.782   3.037  -2.969  0.00  0.00           H+0
HETATM   33  H   UNK     0      -1.491   3.465  -1.290  0.00  0.00           H+0
HETATM   34  H   UNK     0      -0.047   1.336  -2.944  0.00  0.00           H+0
HETATM   35  H   UNK     0       0.593   2.864  -2.368  0.00  0.00           H+0
HETATM   36  H   UNK     0       0.293   2.165  -0.035  0.00  0.00           H+0
HETATM   37  H   UNK     0       1.619   0.013  -2.719  0.00  0.00           H+0
HETATM   38  H   UNK     0       2.116  -1.131  -1.475  0.00  0.00           H+0
HETATM   39  H   UNK     0       3.265  -0.030  -2.187  0.00  0.00           H+0
HETATM   40  H   UNK     0       2.705   2.506  -2.071  0.00  0.00           H+0
HETATM   41  H   UNK     0       2.420   3.049  -0.423  0.00  0.00           H+0
HETATM   42  H   UNK     0       4.788   2.974  -0.850  0.00  0.00           H+0
HETATM   43  H   UNK     0       4.737   1.323  -1.416  0.00  0.00           H+0
HETATM   44  H   UNK     0       4.219   2.354   1.397  0.00  0.00           H+0
HETATM   45  H   UNK     0       5.581   1.382   0.872  0.00  0.00           H+0
HETATM   46  H   UNK     0       4.931   0.114   2.921  0.00  0.00           H+0
HETATM   47  H   UNK     0       3.483  -0.883   2.970  0.00  0.00           H+0
HETATM   48  H   UNK     0       3.357   0.873   3.178  0.00  0.00           H+0
HETATM   49  H   UNK     0       5.374  -1.137   0.834  0.00  0.00           H+0
HETATM   50  H   UNK     0       4.465  -0.888  -0.638  0.00  0.00           H+0
HETATM   51  H   UNK     0       3.790  -1.887   0.655  0.00  0.00           H+0
HETATM   52  H   UNK     0       1.896   1.313   1.369  0.00  0.00           H+0
HETATM   53  H   UNK     0       1.459  -1.582   0.531  0.00  0.00           H+0
HETATM   54  H   UNK     0       1.475  -0.990   2.172  0.00  0.00           H+0
HETATM   55  H   UNK     0      -0.791  -1.159   1.358  0.00  0.00           H+0
HETATM   56  H   UNK     0      -0.370   0.479   1.835  0.00  0.00           H+0
HETATM   57  H   UNK     0      -0.987  -0.623  -2.312  0.00  0.00           H+0
HETATM   58  H   UNK     0      -1.615  -1.599  -0.988  0.00  0.00           H+0
HETATM   59  H   UNK     0       0.091  -1.572  -1.298  0.00  0.00           H+0
HETATM   60  H   UNK     0      -1.918   1.825   0.512  0.00  0.00           H+0
HETATM   61  H   UNK     0      -3.476  -0.719  -0.138  0.00  0.00           H+0
HETATM   62  H   UNK     0      -2.791  -0.376   1.411  0.00  0.00           H+0
HETATM   63  H   UNK     0      -4.967   1.255   0.028  0.00  0.00           H+0
HETATM   64  H   UNK     0      -5.553  -0.720   0.918  0.00  0.00           H+0
HETATM   65  H   UNK     0      -4.775   3.787   0.690  0.00  0.00           H+0
HETATM   66  H   UNK     0      -4.535   1.206   3.829  0.00  0.00           H+0
HETATM   67  H   UNK     0      -2.396   1.105   4.270  0.00  0.00           H+0
CONECT    1    2   30   31                                                  
CONECT    2    1   19    3                                                  
CONECT    3    2    4   32   33                                             
CONECT    4    5    3   34   35                                             
CONECT    5    6   17   36    4                                             
CONECT    6    5    8   14    7                                             
CONECT    7    6   37   38   39                                             
CONECT    8    6    9   40   41                                             
CONECT    9   10    8   42   43                                             
CONECT   10    9   11   44   45                                             
CONECT   11   14   12   13   10                                             
CONECT   12   11   46   47   48                                             
CONECT   13   11   49   50   51                                             
CONECT   14   15   11    6   52                                             
CONECT   15   14   16   53   54                                             
CONECT   16   15   17   55   56                                             
CONECT   17   16    5   19   18                                             
CONECT   18   17   57   58   59                                             
CONECT   19   20   60   17    2                                             
CONECT   20   19   21   61   62                                             
CONECT   21   20   23   22   63                                             
CONECT   22   21   64                                                       
CONECT   23   21   28   24                                                  
CONECT   24   25   23   65                                                  
CONECT   25   27   24   26                                                  
CONECT   26   25                                                            
CONECT   27   28   25                                                       
CONECT   28   23   27   29   66                                             
CONECT   29   28   67                                                       
CONECT   30    1                                                            
CONECT   31    1                                                            
CONECT   32    3                                                            
CONECT   33    3                                                            
CONECT   34    4                                                            
CONECT   35    4                                                            
CONECT   36    5                                                            
CONECT   37    7                                                            
CONECT   38    7                                                            
CONECT   39    7                                                            
CONECT   40    8                                                            
CONECT   41    8                                                            
CONECT   42    9                                                            
CONECT   43    9                                                            
CONECT   44   10                                                            
CONECT   45   10                                                            
CONECT   46   12                                                            
CONECT   47   12                                                            
CONECT   48   12                                                            
CONECT   49   13                                                            
CONECT   50   13                                                            
CONECT   51   13                                                            
CONECT   52   14                                                            
CONECT   53   15                                                            
CONECT   54   15                                                            
CONECT   55   16                                                            
CONECT   56   16                                                            
CONECT   57   18                                                            
CONECT   58   18                                                            
CONECT   59   18                                                            
CONECT   60   19                                                            
CONECT   61   20                                                            
CONECT   62   20                                                            
CONECT   63   21                                                            
CONECT   64   22                                                            
CONECT   65   24                                                            
CONECT   66   28                                                            
CONECT   67   29                                                            
MASTER        0    0    0    0    0    0    0    0   67    0  140    0
END

RDKit          3D

67 70  0  0  0  0  0  0  0  0999 V2000
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 19 20  1  0
  6  5  1  0
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  2  1  2  3
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  6  7  1  6
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  9 42  1  0
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 16 55  1  0
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  3 32  1  0
  3 33  1  0
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  1 30  1  0
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 13 50  1  0
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  7 37  1  0
  7 38  1  0
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 18 57  1  0
 18 58  1  0
 18 59  1  0
 22 64  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₃₈O₄

Average Mass

402.5750 Da

Monoisotopic Mass

402.27701 Da

IUPAC Name

(5S)-4-[(1R)-2-[(1R,4aR,4bS,8aS,10aS)-4b,8,8,10a-tetramethyl-2-methylidene-tetradecahydrophenanthren-1-yl]-1-hydroxyethyl]-5-hydroxy-2,5-dihydrofuran-2-one

Traditional Name

(5S)-4-[(1R)-2-[(1R,4aR,4bS,8aS,10aS)-4b,8,8,10a-tetramethyl-2-methylidene-decahydrophenanthren-1-yl]-1-hydroxyethyl]-5-hydroxy-5H-furan-2-one

CAS Registry Number

Not Available

SMILES

[H]O[C@@]([H])(C1=C([H])C(=O)O[C@]1([H])O[H])C([H])([H])[C@]1([H])C(=C([H])[H])C([H])([H])C([H])([H])[C@@]2([H])[C@@]1(C([H])([H])[H])C([H])([H])C([H])([H])[C@@]1([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])C([H])([H])C([H])([H])[C@]21C([H])([H])[H]

InChI Identifier

InChI=1S/C25H38O4/c1-15-7-8-20-24(4,12-9-19-23(2,3)10-6-11-25(19,20)5)17(15)14-18(26)16-13-21(27)29-22(16)28/h13,17-20,22,26,28H,1,6-12,14H2,2-5H3/t17-,18-,19+,20+,22+,24+,25+/m1/s1

InChI Key

LWTIZOHDKCIZPP-SCHZJEEGSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ircinia	JEOL database	Buchanan, M. S., et al, J. Nat. Prod. 64, 300 (2001)
Ircinia sp.	Animalia	KNApSAcK

Chemical Taxonomy

Classification

Not classified

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	4.07	ALOGPS
logP	4.8	ChemAxon
logS	-4.8	ALOGPS
pKa (Strongest Acidic)	5.58	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	66.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	113.72 m³·mol⁻¹	ChemAxon
Polarizability	45.72 Å³	ChemAxon
Number of Rings	4	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

Not Available

References

General References

Buchanan, M. S., et al. (2001). Buchanan, M. S., et al, J. Nat. Prod. 64, 300 (2001). J. Nat. Prod..

Showing NP-Card for 16,25-dihydroxy-13(24),17-cheilanthadien-19,25-olide (NP0025536)

MOL for NP0025536 (16,25-dihydroxy-13(24),17-cheilanthadien-19,25-olide)

3D MOL for NP0025536 (16,25-dihydroxy-13(24),17-cheilanthadien-19,25-olide)

3D SDF for NP0025536 (16,25-dihydroxy-13(24),17-cheilanthadien-19,25-olide)

3D-SDF for NP0025536 (16,25-dihydroxy-13(24),17-cheilanthadien-19,25-olide)

PDB for NP0025536 (16,25-dihydroxy-13(24),17-cheilanthadien-19,25-olide)

3D PDB for NP0025536 (16,25-dihydroxy-13(24),17-cheilanthadien-19,25-olide)

SMILES for NP0025536 (16,25-dihydroxy-13(24),17-cheilanthadien-19,25-olide)

INCHI for NP0025536 (16,25-dihydroxy-13(24),17-cheilanthadien-19,25-olide)

Structure for NP0025536 (16,25-dihydroxy-13(24),17-cheilanthadien-19,25-olide)

3D Structure for NP0025536 (16,25-dihydroxy-13(24),17-cheilanthadien-19,25-olide)