NP-MRD: Showing NP-Card for 3-O-sinapoyl makisterone A (NP0331702)

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Record Information

Version

1.0

Created at

2023-06-28 04:03:48 UTC

Updated at

2024-05-14 23:14:03 UTC

NP-MRD ID

NP0331702

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-O-sinapoyl makisterone A

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306282306032D          

 53 57  0  0  1  0            999 V2000
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M  END


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M  END
> <DATABASE_ID>
NP0331702

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CC[C@@]2(O)C3=CC(=O)[C@]4([H])C[C@@H](OC(=O)\C=C\C5=CC(OC)=C(O)C(OC)=C5)[C@@H](O)C[C@]4(C)[C@@]3([H])CC[C@]12C)[C@@](C)(O)[C@H](O)C[C@@H](C)C(C)(C)O

> <INCHI_IDENTIFIER>
InChI=1S/C39H56O11/c1-21(35(2,3)45)15-32(42)38(6,46)31-12-14-39(47)24-18-26(40)25-19-28(27(41)20-36(25,4)23(24)11-13-37(31,39)5)50-33(43)10-9-22-16-29(48-7)34(44)30(17-22)49-8/h9-10,16-18,21,23,25,27-28,31-32,41-42,44-47H,11-15,19-20H2,1-8H3/b10-9+/t21-,23+,25+,27+,28-,31+,32-,36-,37-,38-,39-/m1/s1

> <INCHI_KEY>
TUPUZJZSKGDISE-DMFFTNCLSA-N

> <FORMULA>
C39H56O11

> <MOLECULAR_WEIGHT>
700.866

> <EXACT_MASS>
700.382262623

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
106

> <JCHEM_AVERAGE_POLARIZABILITY>
77.50844042763634

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,4S,5R,7R,11S,14S,15R)-4,11-dihydroxy-2,15-dimethyl-8-oxo-14-[(2R,3R,5R)-2,3,6-trihydroxy-5,6-dimethylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-yl (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate

> <JCHEM_LOGP>
3.389817895999999

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.302067025006288

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.288682936390071

> <JCHEM_PKA_STRONGEST_BASIC>
-2.766854303607209

> <JCHEM_POLAR_SURFACE_AREA>
183.20999999999998

> <JCHEM_REFRACTIVITY>
187.8224

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,4S,5R,7R,11S,14S,15R)-4,11-dihydroxy-2,15-dimethyl-8-oxo-14-[(2R,3R,5R)-2,3,6-trihydroxy-5,6-dimethylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-9-en-5-yl (2E)-3-(4-hydroxy-3,5-dimethoxyphenyl)prop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-JUN-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-JUN-23         0                                  
HETATM    1  O   UNK     0      -1.685  -7.663   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -0.159  -7.873   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.370  -9.399   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.051  -6.348   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.366  -8.084   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.947  -9.510   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.312  -6.868   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.837  -7.079   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       4.417  -8.505   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       4.782  -5.863   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.998  -6.808   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.566  -4.918   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.727  -4.647   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0       4.215  -4.357   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0       5.299  -3.168   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.574  -2.304   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.790  -3.249   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.159  -1.754   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.306  -2.978   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.829  -1.529   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.345  -1.258   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      12.338  -2.436   0.000  0.00  0.00           C+0
HETATM   23  H   UNK     0      13.330  -3.613   0.000  0.00  0.00           H+0
HETATM   24  C   UNK     0      13.854  -2.164   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.846  -3.342   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      16.362  -3.071   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      16.886  -1.622   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      18.402  -1.351   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      18.925   0.097   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      20.441   0.368   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      20.964   1.817   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      22.480   2.088   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      23.003   3.536   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      22.010   4.713   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      23.473   0.910   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      24.989   1.181   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      22.949  -0.538   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      23.942  -1.715   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      23.419  -3.164   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      21.433  -0.809   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      15.893  -0.445   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0      14.323  -4.790   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      15.316  -5.967   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0      12.807  -5.061   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      11.814  -3.884   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      11.291  -5.332   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      10.299  -4.155   0.000  0.00  0.00           C+0
HETATM   48  H   UNK     0       8.783  -4.426   0.000  0.00  0.00           H+0
HETATM   49  C   UNK     0       9.775  -5.603   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       8.259  -5.874   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       7.267  -4.697   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       6.595  -6.083   0.000  0.00  0.00           C+0
HETATM   53  O   UNK     0      11.868   0.190   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4    5                                             
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    2    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   12   13                                             
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   10   14   15   51                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19   51                                             
CONECT   18   17                                                            
CONECT   19   17   20   47                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   53                                                  
CONECT   22   21   23   24   45                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   42                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   41                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   40                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33   35                                                  
CONECT   33   32   34                                                       
CONECT   34   33                                                            
CONECT   35   32   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   40                                                  
CONECT   38   37   39                                                       
CONECT   39   38                                                            
CONECT   40   37   30                                                       
CONECT   41   27                                                            
CONECT   42   25   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45                                                       
CONECT   45   44   22   46   47                                             
CONECT   46   45                                                            
CONECT   47   45   19   48   49                                             
CONECT   48   47                                                            
CONECT   49   47   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   17   13   52                                             
CONECT   52   51                                                            
CONECT   53   21                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  114    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₉H₅₆O₁₁

Average Mass

700.8660 Da

Monoisotopic Mass

700.38226 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CC[C@@]2(O)C3=CC(=O)[C@]4([H])C[C@@H](OC(=O)\C=C\C5=CC(OC)=C(O)C(OC)=C5)[C@@H](O)C[C@]4(C)[C@@]3([H])CC[C@]12C)[C@@](C)(O)[C@H](O)C[C@@H](C)C(C)(C)O

InChI Identifier

InChI=1S/C39H56O11/c1-21(35(2,3)45)15-32(42)38(6,46)31-12-14-39(47)24-18-26(40)25-19-28(27(41)20-36(25,4)23(24)11-13-37(31,39)5)50-33(43)10-9-22-16-29(48-7)34(44)30(17-22)49-8/h9-10,16-18,21,23,25,27-28,31-32,41-42,44-47H,11-15,19-20H2,1-8H3/b10-9+/t21-,23+,25+,27+,28-,31+,32-,36-,37-,38-,39-/m1/s1

InChI Key

TUPUZJZSKGDISE-DMFFTNCLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 800 MHz, CD3OD, experimental)	y_kakumu@bio.uni-frankfurt.de	Not Available	Not Available	2023-06-28	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 800 MHz, CD3OD, experimental)	y_kakumu@bio.uni-frankfurt.de	Not Available	Not Available	2023-06-28	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 800 MHz, CD3OD, experimental)	y_kakumu@bio.uni-frankfurt.de	Not Available	Not Available	2023-06-28	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 800 MHz, CD3OD, experimental)	y_kakumu@bio.uni-frankfurt.de	Not Available	Not Available	2023-06-28	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 800 MHz, CD3OD, experimental)	y_kakumu@bio.uni-frankfurt.de	Not Available	Not Available	2023-06-28	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 201 MHz, CD3OD, experimental)	y_kakumu@bio.uni-frankfurt.de	Not Available	Not Available	2023-06-28	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 800.15405836, CD₃OD, simulated)	y_kakumu@bio.uni-frankfurt.de	Goethe University Frankfurt	Yuya Kakumu	2024-05-14	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
recisa		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

External Links

Not Available

References

General References

Kakumu Y, Thi Nguyen MT, Mitsunaga T, Hattori H: Identification of Ecdysteroid Sinapate Esters with COX-2 Inhibitory Effects from Fibraurea recisa Using Molecular Networking and MS2LDA. J Nat Prod. 2023 Aug 25;86(8):1960-1967. doi: 10.1021/acs.jnatprod.3c00371. Epub 2023 Aug 2. [PubMed:37530540 ]

Showing NP-Card for 3-O-sinapoyl makisterone A (NP0331702)

MOL for NP0331702 (3-O-sinapoyl makisterone A)

3D MOL for NP0331702 (3-O-sinapoyl makisterone A)

3D SDF for NP0331702 (3-O-sinapoyl makisterone A)

3D-SDF for NP0331702 (3-O-sinapoyl makisterone A)

PDB for NP0331702 (3-O-sinapoyl makisterone A)

3D PDB for NP0331702 (3-O-sinapoyl makisterone A)

SMILES for NP0331702 (3-O-sinapoyl makisterone A)

INCHI for NP0331702 (3-O-sinapoyl makisterone A)

Structure for NP0331702 (3-O-sinapoyl makisterone A)

3D Structure for NP0331702 (3-O-sinapoyl makisterone A)