NP-MRD: Showing NP-Card for Withastramonolide A (NP0332981)

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Record Information

Version

1.0

Created at

2024-05-03 03:51:40 UTC

Updated at

2024-05-03 03:59:42 UTC

NP-MRD ID

NP0332981

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Withastramonolide A

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 01152306282D          

 60 66  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  1  0  0  0  0  0  0  0  0  0
   -3.3110   -1.5369    0.0000 H   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  1  0  0  0  0  0  0  0  0  0
   -0.8641   -1.4998    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5838   -2.2757    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1156   -2.9064    0.0000 H   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
    0.5086   -3.1969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.1818    3.3165    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3099    4.1936    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.6335    3.6551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2  1  1  6  0  0  0
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  5  6  1  0  0  0  0
  7  6  1  0  0  0  0
  7  8  1  1  0  0  0
  9  7  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 15 14  1  0  0  0  0
 15 16  1  6  0  0  0
 17 15  1  0  0  0  0
  9 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  0  0  0  0
  7 21  1  0  0  0  0
 21  3  1  0  0  0  0
 21 22  1  6  0  0  0
 14 23  1  0  0  0  0
 23 24  1  0  0  0  0
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 15 26  1  0  0  0  0
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  2 28  1  0  0  0  0
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 40 41  1  0  0  0  0
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 28 59  1  0  0  0  0
 31 60  2  0  0  0  0
M  END


  Mrv2104 01152306282D          

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 21  3  1  0  0  0  0
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 28 59  1  0  0  0  0
 31 60  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0332981

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C=C4CC=CC(=O)[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)[C@@]1([H])CC(C)=C(CO[C@@H]2O[C@H](COC(=O)\C=C\C3=CC=C(O)C=C3)[C@@H](O)C(O)[C@H]2O)C(=O)O1

> <INCHI_IDENTIFIER>
InChI=1S/C43H54O12/c1-22-18-32(23(2)28-13-14-29-36-30(16-17-42(28,29)3)43(4)25(19-31(36)45)6-5-7-34(43)46)54-40(51)27(22)20-53-41-39(50)38(49)37(48)33(55-41)21-52-35(47)15-10-24-8-11-26(44)12-9-24/h5,7-12,15,19,23,28-33,36-39,41,44-45,48-50H,6,13-14,16-18,20-21H2,1-4H3/b15-10+/t23-,28+,29-,30-,31+,32+,33+,36-,37+,38?,39+,41+,42+,43-/m0/s1

> <INCHI_KEY>
XLHUMJNCPFKSNR-PPOKXSMESA-N

> <FORMULA>
C43H54O12

> <MOLECULAR_WEIGHT>
762.893

> <EXACT_MASS>
762.361527179

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
109

> <JCHEM_AVERAGE_POLARIZABILITY>
83.62754714614017

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,5R,6R)-6-{[(6R)-6-[(1S)-1-[(1R,3aS,3bS,4S,9aR,9bS,11aR)-4-hydroxy-9a,11a-dimethyl-9-oxo-1H,2H,3H,3aH,3bH,4H,6H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-yl]ethyl]-4-methyl-2-oxo-5,6-dihydro-2H-pyran-3-yl]methoxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <JCHEM_LOGP>
4.97452299333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.212694417704853

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.39797744319036

> <JCHEM_PKA_STRONGEST_BASIC>
-0.9134358539716048

> <JCHEM_POLAR_SURFACE_AREA>
189.28

> <JCHEM_REFRACTIVITY>
202.8581

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,5R,6R)-6-{[(6R)-6-[(1S)-1-[(1R,3aS,3bS,4S,9aR,9bS,11aR)-4-hydroxy-9a,11a-dimethyl-9-oxo-1H,2H,3H,3aH,3bH,4H,6H,9bH,10H,11H-cyclopenta[a]phenanthren-1-yl]ethyl]-4-methyl-2-oxo-5,6-dihydropyran-3-yl]methoxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

> <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  H   UNK     0      -6.181  -2.869   0.000  0.00  0.00           H+0
HETATM    5  C   UNK     0      -5.096  -4.058   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.822  -4.922   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.606  -3.977   0.000  0.00  0.00           C+0
HETATM    8  H   UNK     0      -1.613  -2.800   0.000  0.00  0.00           H+0
HETATM    9  C   UNK     0      -1.090  -4.248   0.000  0.00  0.00           C+0
HETATM   10  H   UNK     0      -2.082  -5.425   0.000  0.00  0.00           H+0
HETATM   11  C   UNK     0      -0.567  -5.696   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -1.559  -6.874   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       0.949  -5.967   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.942  -4.790   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.419  -3.342   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.896  -1.893   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.097  -3.071   0.000  0.00  0.00           C+0
HETATM   18  H   UNK     0       0.426  -4.519   0.000  0.00  0.00           H+0
HETATM   19  C   UNK     0      -0.620  -1.622   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -2.136  -1.351   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -3.129  -2.529   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -3.801  -1.143   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.458  -5.061   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.451  -3.884   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       3.928  -2.436   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.412  -2.164   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       1.888  -0.716   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -5.033   0.064   0.000  0.00  0.00           C+0
HETATM   29  H   UNK     0      -6.559  -0.147   0.000  0.00  0.00           H+0
HETATM   30  O   UNK     0      -5.978   1.280   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -5.398   2.706   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -3.872   2.917   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -3.292   4.343   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -1.766   4.554   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -1.186   5.980   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -2.131   7.196   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -3.657   6.985   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0       0.339   6.191   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       0.920   7.617   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       2.445   7.828   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       3.390   6.612   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       4.916   6.823   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       5.496   8.249   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       4.551   9.465   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       5.131  10.892   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       4.186  12.107   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       4.767  13.534   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       6.292  13.745   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0       6.872  15.171   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0       7.237  12.529   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       6.657  11.102   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0       5.861   5.607   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      -0.025   8.833   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0       0.555  10.260   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0      -1.551   8.623   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0      -2.496   9.838   0.000  0.00  0.00           O+0
HETATM   57  C   UNK     0      -2.927   1.701   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      -1.402   1.911   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      -3.507   0.274   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0      -6.343   3.922   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   28                                                  
CONECT    3    2    4    5   21                                             
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   21                                             
CONECT    8    7                                                            
CONECT    9    7   10   11   17                                             
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   23                                                  
CONECT   15   14   16   17   26                                             
CONECT   16   15                                                            
CONECT   17   15    9   18   19                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20    7    3   22                                             
CONECT   22   21                                                            
CONECT   23   14   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   15   27                                                  
CONECT   27   26                                                            
CONECT   28    2   29   30   59                                             
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32   60                                                  
CONECT   32   31   33   57                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36   38                                                  
CONECT   36   35   37   55                                                  
CONECT   37   36                                                            
CONECT   38   35   39                                                       
CONECT   39   38   40   53                                                  
CONECT   40   39   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43   52                                                  
CONECT   43   42   44                                                       
CONECT   44   43   45                                                       
CONECT   45   44   46   51                                                  
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   51                                                       
CONECT   51   50   45                                                       
CONECT   52   42                                                            
CONECT   53   39   54   55                                                  
CONECT   54   53                                                            
CONECT   55   53   36   56                                                  
CONECT   56   55                                                            
CONECT   57   32   58   59                                                  
CONECT   58   57                                                            
CONECT   59   57   28                                                       
CONECT   60   31                                                            
MASTER        0    0    0    0    0    0    0    0   60    0  132    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₃H₅₄O₁₂

Average Mass

762.8930 Da

Monoisotopic Mass

762.36153 Da

IUPAC Name

[(2R,3S,5R,6R)-6-{[(6R)-6-[(1S)-1-[(1R,3aS,3bS,4S,9aR,9bS,11aR)-4-hydroxy-9a,11a-dimethyl-9-oxo-1H,2H,3H,3aH,3bH,4H,6H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-yl]ethyl]-4-methyl-2-oxo-5,6-dihydro-2H-pyran-3-yl]methoxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

Traditional Name

[(2R,3S,5R,6R)-6-{[(6R)-6-[(1S)-1-[(1R,3aS,3bS,4S,9aR,9bS,11aR)-4-hydroxy-9a,11a-dimethyl-9-oxo-1H,2H,3H,3aH,3bH,4H,6H,9bH,10H,11H-cyclopenta[a]phenanthren-1-yl]ethyl]-4-methyl-2-oxo-5,6-dihydropyran-3-yl]methoxy}-3,4,5-trihydroxyoxan-2-yl]methyl (2E)-3-(4-hydroxyphenyl)prop-2-enoate

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC[C@@]2([H])[C@]3([H])[C@H](O)C=C4CC=CC(=O)[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)[C@@]1([H])CC(C)=C(CO[C@@H]2O[C@H](COC(=O)\C=C\C3=CC=C(O)C=C3)[C@@H](O)C(O)[C@H]2O)C(=O)O1

InChI Identifier

InChI=1S/C43H54O12/c1-22-18-32(23(2)28-13-14-29-36-30(16-17-42(28,29)3)43(4)25(19-31(36)45)6-5-7-34(43)46)54-40(51)27(22)20-53-41-39(50)38(49)37(48)33(55-41)21-52-35(47)15-10-24-8-11-26(44)12-9-24/h5,7-12,15,19,23,28-33,36-39,41,44-45,48-50H,6,13-14,16-18,20-21H2,1-4H3/b15-10+/t23-,28+,29-,30-,31+,32+,33+,36-,37+,38?,39+,41+,42+,43-/m0/s1

InChI Key

XLHUMJNCPFKSNR-PPOKXSMESA-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	4.97	ChemAxon
pKa (Strongest Acidic)	9.4	ChemAxon
pKa (Strongest Basic)	-0.91	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	189.28 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	202.86 m³·mol⁻¹	ChemAxon
Polarizability	83.63 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	Yes	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 Withastramonolide A (NP0332981)

MOL for NP0332981 (Withastramonolide A)

3D MOL for NP0332981 (Withastramonolide A)

3D SDF for NP0332981 (Withastramonolide A)

3D-SDF for NP0332981 (Withastramonolide A)

PDB for NP0332981 (Withastramonolide A)

3D PDB for NP0332981 (Withastramonolide A)

SMILES for NP0332981 (Withastramonolide A)

INCHI for NP0332981 (Withastramonolide A)

Structure for NP0332981 (Withastramonolide A)

3D Structure for NP0332981 (Withastramonolide A)