NP-MRD: Showing NP-Card for (22R)-27-hydroxy-7α-methoxy-1-oxowitha-3,5,24-trienolide (NP0332991)

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Record Information

Version

1.0

Created at

2024-05-03 03:57:33 UTC

Updated at

2024-05-03 03:59:45 UTC

NP-MRD ID

NP0332991

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(22R)-27-hydroxy-7α-methoxy-1-oxowitha-3,5,24-trienolide

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01152306342D          

 34 38  0  0  1  0            999 V2000
   -3.8244   -0.8429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0071   -0.7301    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5008   -1.3814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7301   -2.1739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0473   -2.6369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3959   -2.1305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5838   -2.2757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3035   -3.0516    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8353   -3.6824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5550   -4.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5086   -3.1969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0404   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7601   -1.7902    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4798   -1.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0520   -1.6450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3323   -0.8691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1444   -0.7239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6762   -1.3546    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0361   -0.6122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8526   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3844   -2.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1041   -1.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2920   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0117   -0.3836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6962    0.0341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2026    0.6855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8917    1.4496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0745    1.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7636    2.3267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2699    2.9780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5681    0.9112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7509    1.0240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8790    0.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3981    2.1010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
 13 12  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  0  0  0  0
 18  6  1  0  0  0  0
 18  3  1  0  0  0  0
 18 19  1  6  0  0  0
 12 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 13 23  1  0  0  0  0
 23 24  2  0  0  0  0
  2 25  1  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  1  0  0  0  0
 29 30  1  0  0  0  0
 28 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 25 33  1  0  0  0  0
 27 34  2  0  0  0  0
M  END


  Mrv2104 01152306342D          

 34 38  0  0  1  0            999 V2000
   -3.8244   -0.8429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0071   -0.7301    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5008   -1.3814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7301   -2.1739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0473   -2.6369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3959   -2.1305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5838   -2.2757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3035   -3.0516    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8353   -3.6824    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5550   -4.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5086   -3.1969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0404   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7601   -1.7902    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4798   -1.0143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0520   -1.6450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3323   -0.8691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1444   -0.7239    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6762   -1.3546    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0361   -0.6122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8526   -2.7114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3844   -2.0807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1041   -1.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2920   -1.1595    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0117   -0.3836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6962    0.0341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2026    0.6855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8917    1.4496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0745    1.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7636    2.3267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2699    2.9780    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5681    0.9112    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7509    1.0240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8790    0.1470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3981    2.1010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  8  7  1  0  0  0  0
  8  9  1  1  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
 13 12  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 17  1  0  0  0  0
 18  6  1  0  0  0  0
 18  3  1  0  0  0  0
 18 19  1  6  0  0  0
 12 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 13 23  1  0  0  0  0
 23 24  2  0  0  0  0
  2 25  1  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  1  0  0  0  0
 29 30  1  0  0  0  0
 28 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 25 33  1  0  0  0  0
 27 34  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0332991

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1C=C2C=CCC(=O)[C@]2(C)C2CC[C@]3(C)C(CCC3C12)[C@H](C)C1CC(C)=C(CO)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C29H40O5/c1-16-13-23(34-27(32)19(16)15-30)17(2)20-9-10-21-26-22(11-12-28(20,21)3)29(4)18(14-24(26)33-5)7-6-8-25(29)31/h6-7,14,17,20-24,26,30H,8-13,15H2,1-5H3/t17-,20?,21?,22?,23?,24+,26?,28+,29-/m0/s1

> <INCHI_KEY>
JOGIQJMBLQWDHC-JXFPPEJYSA-N

> <FORMULA>
C29H40O5

> <MOLECULAR_WEIGHT>
468.634

> <EXACT_MASS>
468.287574388

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
53.748495663336655

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-[(1S)-1-[(4S,9aR,11aR)-4-methoxy-9a,11a-dimethyl-9-oxo-1H,2H,3H,3aH,3bH,4H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-yl]ethyl]-3-(hydroxymethyl)-4-methyl-5,6-dihydro-2H-pyran-2-one

> <JCHEM_LOGP>
4.298414599999999

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.790707562692488

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.818043340528968

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8538493304385124

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
133.6707

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
6-[(1S)-1-[(4S,9aR,11aR)-4-methoxy-9a,11a-dimethyl-9-oxo-1H,2H,3H,3aH,3bH,4H,8H,9bH,10H,11H-cyclopenta[a]phenanthren-1-yl]ethyl]-3-(hydroxymethyl)-4-methyl-5,6-dihydropyran-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-JAN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-JAN-23         0                                  
HETATM    1  C   UNK     0      -7.139  -1.573   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.613  -1.363   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.668  -2.579   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.096  -4.058   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.822  -4.922   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.606  -3.977   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.090  -4.248   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.567  -5.696   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.559  -6.874   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.036  -8.322   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.949  -5.967   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.942  -4.790   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.419  -3.342   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.896  -1.893   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.097  -3.071   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.620  -1.622   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.136  -1.351   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -3.129  -2.529   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -3.801  -1.143   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.458  -5.061   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.451  -3.884   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.928  -2.436   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.412  -2.164   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.888  -0.716   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -5.033   0.064   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -5.978   1.280   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -5.398   2.706   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -3.872   2.917   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -3.292   4.343   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -4.237   5.559   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -2.927   1.701   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.402   1.911   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -3.507   0.274   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -6.343   3.922   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   25                                                  
CONECT    3    2    4   18                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   18                                                  
CONECT    7    6    8   15                                                  
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12                                                       
CONECT   12   11   13   20                                                  
CONECT   13   12   14   15   23                                             
CONECT   14   13                                                            
CONECT   15   13    7   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17    6    3   19                                             
CONECT   19   18                                                            
CONECT   20   12   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   13   24                                                  
CONECT   24   23                                                            
CONECT   25    2   26   33                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   34                                                  
CONECT   28   27   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   25                                                       
CONECT   34   27                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₀O₅

Average Mass

468.6340 Da

Monoisotopic Mass

468.28757 Da

IUPAC Name

6-[(1S)-1-[(4S,9aR,11aR)-4-methoxy-9a,11a-dimethyl-9-oxo-1H,2H,3H,3aH,3bH,4H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-yl]ethyl]-3-(hydroxymethyl)-4-methyl-5,6-dihydro-2H-pyran-2-one

Traditional Name

6-[(1S)-1-[(4S,9aR,11aR)-4-methoxy-9a,11a-dimethyl-9-oxo-1H,2H,3H,3aH,3bH,4H,8H,9bH,10H,11H-cyclopenta[a]phenanthren-1-yl]ethyl]-3-(hydroxymethyl)-4-methyl-5,6-dihydropyran-2-one

CAS Registry Number

Not Available

SMILES

CO[C@@H]1C=C2C=CCC(=O)[C@]2(C)C2CC[C@]3(C)C(CCC3C12)[C@H](C)C1CC(C)=C(CO)C(=O)O1

InChI Identifier

InChI=1S/C29H40O5/c1-16-13-23(34-27(32)19(16)15-30)17(2)20-9-10-21-26-22(11-12-28(20,21)3)29(4)18(14-24(26)33-5)7-6-8-25(29)31/h6-7,14,17,20-24,26,30H,8-13,15H2,1-5H3/t17-,20?,21?,22?,23?,24+,26?,28+,29-/m0/s1

InChI Key

JOGIQJMBLQWDHC-JXFPPEJYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600, CD₃OD, simulated)	570075670@qq.com	黑龙江中医药大学	Pan juan	2024-05-03	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
stramonium		Not Available

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	4.3	ChemAxon
pKa (Strongest Acidic)	14.82	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	133.67 m³·mol⁻¹	ChemAxon
Polarizability	53.75 Å³	ChemAxon
Number of Rings	5	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

Not Available

References

General References

Pan J, Liu Y, Li XY, Wang SY, Wu JT, Li MM, Guan W, Mohammed Algradi A, Kuang HX, Yang BY: Cytotoxic withanolides from the leaves of Datura stramonium L. Chem Biodivers. 2024 Feb;21(2):e202301655. doi: 10.1002/cbdv.202301655. Epub 2024 Jan 12. [PubMed:38084071 ]

Showing NP-Card for (22R)-27-hydroxy-7α-methoxy-1-oxowitha-3,5,24-trienolide (NP0332991)

MOL for NP0332991 ((22R)-27-hydroxy-7α-methoxy-1-oxowitha-3,5,24-trienolide)

3D MOL for NP0332991 ((22R)-27-hydroxy-7α-methoxy-1-oxowitha-3,5,24-trienolide)

3D SDF for NP0332991 ((22R)-27-hydroxy-7α-methoxy-1-oxowitha-3,5,24-trienolide)

3D-SDF for NP0332991 ((22R)-27-hydroxy-7α-methoxy-1-oxowitha-3,5,24-trienolide)

PDB for NP0332991 ((22R)-27-hydroxy-7α-methoxy-1-oxowitha-3,5,24-trienolide)

3D PDB for NP0332991 ((22R)-27-hydroxy-7α-methoxy-1-oxowitha-3,5,24-trienolide)

SMILES for NP0332991 ((22R)-27-hydroxy-7α-methoxy-1-oxowitha-3,5,24-trienolide)

INCHI for NP0332991 ((22R)-27-hydroxy-7α-methoxy-1-oxowitha-3,5,24-trienolide)

Structure for NP0332991 ((22R)-27-hydroxy-7α-methoxy-1-oxowitha-3,5,24-trienolide)

3D Structure for NP0332991 ((22R)-27-hydroxy-7α-methoxy-1-oxowitha-3,5,24-trienolide)