NP-MRD: Showing NP-Card for [(1r,2s,4r,5r,6s,7s,9r,10s,11s,12s,13s,14s,15r,22r,23r,25r)-12-(benzoyloxy)-10,11,22-trihydroxy-9-(hydroxymethyl)-13,15-dimethyl-4-(prop-1-en-2-yl)-8,24,26,27-tetraoxaheptacyclo[12.10.1.1⁴,²³.1⁵,²³.0¹,⁶.0⁷,⁹.0¹¹,²⁵]heptacosan-2-yl]methyl benzoate (NP0210320)

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Record Information

Version

2.0

Created at

2022-09-05 08:04:28 UTC

Updated at

2022-09-05 08:04:28 UTC

NP-MRD ID

NP0210320

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1r,2s,4r,5r,6s,7s,9r,10s,11s,12s,13s,14s,15r,22r,23r,25r)-12-(benzoyloxy)-10,11,22-trihydroxy-9-(hydroxymethyl)-13,15-dimethyl-4-(prop-1-en-2-yl)-8,24,26,27-tetraoxaheptacyclo[12.10.1.1⁴,²³.1⁵,²³.0¹,⁶.0⁷,⁹.0¹¹,²⁵]heptacosan-2-yl]methyl benzoate

Description

Gnidimacrin belongs to the class of organic compounds known as rhamnofolane and daphnane diterpenoids. These are diterpenoids with a structure based on one the rhamnofolane or daphnane skeleton. The rhamnofolane and daphnane skeletons are closely related, being formally derived from casbane by two cyclizations (6,10 and 5,14) followed by cleavage of the 1,15 (daphnane) or 2,15 (rhamnofolane) cyclopropane bonds. [(1r,2s,4r,5r,6s,7s,9r,10s,11s,12s,13s,14s,15r,22r,23r,25r)-12-(benzoyloxy)-10,11,22-trihydroxy-9-(hydroxymethyl)-13,15-dimethyl-4-(prop-1-en-2-yl)-8,24,26,27-tetraoxaheptacyclo[12.10.1.1⁴,²³.1⁵,²³.0¹,⁶.0⁷,⁹.0¹¹,²⁵]heptacosan-2-yl]methyl benzoate is found in Pimelea ligustrina and Stellera chamaejasme. [(1r,2s,4r,5r,6s,7s,9r,10s,11s,12s,13s,14s,15r,22r,23r,25r)-12-(benzoyloxy)-10,11,22-trihydroxy-9-(hydroxymethyl)-13,15-dimethyl-4-(prop-1-en-2-yl)-8,24,26,27-tetraoxaheptacyclo[12.10.1.1⁴,²³.1⁵,²³.0¹,⁶.0⁷,⁹.0¹¹,²⁵]heptacosan-2-yl]methyl benzoate was first documented in 2018 (PMID: 29541372). Based on a literature review a small amount of articles have been published on Gnidimacrin (PMID: 35786172) (PMID: 35113551) (PMID: 31680527) (PMID: 31343875).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052210042D          

 56 64  0  0  1  0            999 V2000
    2.6412    0.3424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  4 21  1  0  0  0  0
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M  END

     RDKit          2D

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M  END


  Mrv1652309052210042D          

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 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
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 32 42  1  0  0  0  0
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 44 45  1  0  0  0  0
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 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
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 19 53  1  0  0  0  0
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 55 44  1  6  0  0  0
 30 55  1  0  0  0  0
 17 55  1  0  0  0  0
 19 56  1  0  0  0  0
  4 56  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0210320

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@H]1[C@H](OC(=O)C2=CC=CC=C2)[C@]2(O)[C@H]3[C@H]1[C@H](C)CCCCCC[C@@H](O)[C@@]14O[C@@H]5[C@H]([C@@H]6O[C@]6(CO)[C@H]2O)[C@]3(O1)[C@H](COC(=O)C1=CC=CC=C1)C[C@@]5(O4)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C44H54O12/c1-24(2)40-21-29(22-51-37(47)27-16-10-7-11-17-27)43-32-35(40)54-44(55-40,56-43)30(46)20-14-6-5-9-15-25(3)31-26(4)34(52-38(48)28-18-12-8-13-19-28)42(50,33(31)43)39(49)41(23-45)36(32)53-41/h7-8,10-13,16-19,25-26,29-36,39,45-46,49-50H,1,5-6,9,14-15,20-23H2,2-4H3/t25-,26+,29+,30-,31+,32-,33-,34+,35-,36+,39-,40-,41+,42-,43-,44+/m1/s1

> <INCHI_KEY>
SSXCVTWCXHGTLK-HVMGVZKSSA-N

> <FORMULA>
C44H54O12

> <MOLECULAR_WEIGHT>
774.904

> <EXACT_MASS>
774.361527179

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
110

> <JCHEM_AVERAGE_POLARIZABILITY>
36.99079143262119

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1R,2S,4R,5R,6S,7S,9R,10S,11S,12S,13S,14S,15R,22R,23R,25R)-12-(benzoyloxy)-10,11,22-trihydroxy-9-(hydroxymethyl)-13,15-dimethyl-4-(prop-1-en-2-yl)-8,24,26,27-tetraoxaheptacyclo[12.10.1.1^{4,23}.1^{5,23}.0^{1,6}.0^{7,9}.0^{11,25}]heptacosan-2-yl]methyl benzoate

> <JCHEM_LOGP>
5.752069425999999

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
9

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.635911846883129

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.052566201138285

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1494109764172826

> <JCHEM_POLAR_SURFACE_AREA>
173.74

> <JCHEM_REFRACTIVITY>
200.1968

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(1R,2S,4R,5R,6S,7S,9R,10S,11S,12S,13S,14S,15R,22R,23R,25R)-12-(benzoyloxy)-10,11,22-trihydroxy-9-(hydroxymethyl)-13,15-dimethyl-4-(prop-1-en-2-yl)-8,24,26,27-tetraoxaheptacyclo[12.10.1.1^{4,23}.1^{5,23}.0^{1,6}.0^{7,9}.0^{11,25}]heptacosan-2-yl]methyl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       4.930   0.639   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.477   0.115   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       7.879   1.281   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.204  -1.825   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.843  -0.781   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.127   0.397   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       9.162   1.327   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       8.405   3.108   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       8.059   4.793   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       9.893   4.984   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.170   5.146   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.148   3.994   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.639   4.303   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.153   5.764   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.175   6.916   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.684   6.607   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.949  -0.526   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       5.351  -1.092   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.107  -2.897   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       6.411  -3.902   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.810  -3.111   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.556  -1.790   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.012  -0.915   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      11.515  -0.579   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      10.473   0.555   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.272   0.782   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      13.798   0.188   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       9.703   1.924   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      11.096   3.015   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       8.158   2.192   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       9.082   3.938   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       7.624   3.675   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       7.133   5.524   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       7.112   7.210   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       5.588   8.352   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       8.489   8.077   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       7.972   9.528   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       8.970  10.701   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      10.485  10.423   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      11.002   8.972   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      10.004   7.800   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       6.078   3.631   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       4.550   4.770   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       5.661   2.122   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       4.158   1.731   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       3.643   0.142   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       2.820   2.503   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       1.458   1.776   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       0.978   0.302   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       0.069  -0.954   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       0.424  -2.457   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0       2.002  -2.527   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0       3.462  -3.233   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0       3.454  -4.862   0.000  0.00  0.00           O+0
HETATM   55  C   UNK     0       6.951   1.182   0.000  0.00  0.00           C+0
HETATM   56  O   UNK     0       5.779  -1.796   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   21   56                                             
CONECT    5    4    6                                                       
CONECT    6    5    7   17                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   11                                                       
CONECT   17    6   18   22   55                                             
CONECT   18   17   19                                                       
CONECT   19   18   20   53   56                                             
CONECT   20   19   21                                                       
CONECT   21   20    4   22                                                  
CONECT   22   21   17   23                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23   25                                                       
CONECT   25   24   23   26   28                                             
CONECT   26   25   27                                                       
CONECT   27   26                                                            
CONECT   28   25   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32   55                                             
CONECT   31   30                                                            
CONECT   32   30   33   42                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37   41                                                  
CONECT   37   36   38                                                       
CONECT   38   37   39                                                       
CONECT   39   38   40                                                       
CONECT   40   39   41                                                       
CONECT   41   40   36                                                       
CONECT   42   32   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45   55                                                  
CONECT   45   44   46   47                                                  
CONECT   46   45                                                            
CONECT   47   45   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   19   54                                                  
CONECT   54   53                                                            
CONECT   55   44   30   17                                                  
CONECT   56   19    4                                                       
MASTER        0    0    0    0    0    0    0    0   56    0  128    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₄₄H₅₄O₁₂

Average Mass

774.9040 Da

Monoisotopic Mass

774.36153 Da

IUPAC Name

[(1R,2S,4R,5R,6S,7S,9R,10S,11S,12S,13S,14S,15R,22R,23R,25R)-12-(benzoyloxy)-10,11,22-trihydroxy-9-(hydroxymethyl)-13,15-dimethyl-4-(prop-1-en-2-yl)-8,24,26,27-tetraoxaheptacyclo[12.10.1.1^{4,23}.1^{5,23}.0^{1,6}.0^{7,9}.0^{11,25}]heptacosan-2-yl]methyl benzoate

Traditional Name

CAS Registry Number

Not Available

SMILES

C[C@@H]1[C@H](OC(=O)C2=CC=CC=C2)[C@]2(O)[C@H]3[C@H]1[C@H](C)CCCCCC[C@@H](O)[C@@]14O[C@@H]5[C@H]([C@@H]6O[C@]6(CO)[C@H]2O)[C@]3(O1)[C@H](COC(=O)C1=CC=CC=C1)C[C@@]5(O4)C(C)=C

InChI Identifier

InChI=1S/C44H54O12/c1-24(2)40-21-29(22-51-37(47)27-16-10-7-11-17-27)43-32-35(40)54-44(55-40,56-43)30(46)20-14-6-5-9-15-25(3)31-26(4)34(52-38(48)28-18-12-8-13-19-28)42(50,33(31)43)39(49)41(23-45)36(32)53-41/h7-8,10-13,16-19,25-26,29-36,39,45-46,49-50H,1,5-6,9,14-15,20-23H2,2-4H3/t25-,26+,29+,30-,31+,32-,33-,34+,35-,36+,39-,40-,41+,42-,43-,44+/m1/s1

InChI Key

SSXCVTWCXHGTLK-HVMGVZKSSA-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

Species Name	Source	Reference
Pimelea ligustrina	LOTUS Database	35616633
Stellera chamaejasme	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as rhamnofolane and daphnane diterpenoids. These are diterpenoids with a structure based on one the rhamnofolane or daphnane skeleton. The rhamnofolane and daphnane skeletons are closely related, being formally derived from casbane by two cyclizations (6,10 and 5,14) followed by cleavage of the 1,15 (daphnane) or 2,15 (rhamnofolane) cyclopropane bonds.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Rhamnofolane and daphnane diterpenoids

Alternative Parents

Substituents

Daphnane diterpenoid
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Ortho ester
Dioxepane
Carboxylic acid orthoester
1,3-dioxepane
Benzenoid
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Meta-dioxane
Tertiary alcohol
Cyclic alcohol
Meta-dioxolane
Secondary alcohol
Orthocarboxylic acid derivative
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
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	5.75	ChemAxon
pKa (Strongest Acidic)	12.05	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	173.74 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	200.2 m³·mol⁻¹	ChemAxon
Polarizability	36.99 Å³	ChemAxon
Number of Rings	9	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102060434

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ma X, Zhang H, Wang S, Deng R, Luo D, Luo M, Huang Q, Yu S, Pu C, Liu Y, Tong Y, Li R: Recent Advances in the Discovery and Development of Anti-HIV Natural Products. Am J Chin Med. 2022;50(5):1173-1196. doi: 10.1142/S0192415X22500483. Epub 2022 Jul 2. [PubMed:35786172 ]
El-Desoky AHH, Eguchi K, Kishimoto N, Asano T, Kato H, Hitora Y, Kotani S, Nakamura T, Tsuchiya S, Kawahara T, Watanabe M, Wada M, Nakajima M, Watanabe T, Misumi S, Tsukamoto S: Isolation, Synthesis, and Structure-Activity Relationship Study on Daphnane and Tigliane Diterpenes as HIV Latency-Reversing Agents. J Med Chem. 2022 Feb 24;65(4):3460-3472. doi: 10.1021/acs.jmedchem.1c01973. Epub 2022 Feb 3. [PubMed:35113551 ]
Otsuki K, Li W, Asada Y, Chen CH, Lee KH, Koike K: Daphneodorins A-C, Anti-HIV Gnidimacrin Related Macrocyclic Daphnane Orthoesters from Daphne odora. Org Lett. 2020 Jan 3;22(1):11-15. doi: 10.1021/acs.orglett.9b03539. Epub 2019 Nov 4. [PubMed:31680527 ]
Liu Q, Cheng YY, Li W, Huang L, Asada Y, Hsieh MT, Morris-Natschke SL, Chen CH, Koike K, Lee KH: Synthesis and Structure-Activity Relationship Correlations of Gnidimacrin Derivatives as Potent HIV-1 Inhibitors and HIV Latency Reversing Agents. J Med Chem. 2019 Aug 8;62(15):6958-6971. doi: 10.1021/acs.jmedchem.9b00339. Epub 2019 Jul 25. [PubMed:31343875 ]
Huang L, Lai WH, Zhu L, Li W, Wei L, Lee KH, Xie L, Chen CH: Elimination of HIV-1 Latently Infected Cells by Gnidimacrin and a Selective HDAC Inhibitor. ACS Med Chem Lett. 2018 Feb 6;9(3):268-273. doi: 10.1021/acsmedchemlett.8b00012. eCollection 2018 Mar 8. [PubMed:29541372 ]
LOTUS database [Link]

Showing NP-Card for [(1r,2s,4r,5r,6s,7s,9r,10s,11s,12s,13s,14s,15r,22r,23r,25r)-12-(benzoyloxy)-10,11,22-trihydroxy-9-(hydroxymethyl)-13,15-dimethyl-4-(prop-1-en-2-yl)-8,24,26,27-tetraoxaheptacyclo[12.10.1.1⁴,²³.1⁵,²³.0¹,⁶.0⁷,⁹.0¹¹,²⁵]heptacosan-2-yl]methyl benzoate (NP0210320)

MOL for NP0210320 ([(1r,2s,4r,5r,6s,7s,9r,10s,11s,12s,13s,14s,15r,22r,23r,25r)-12-(benzoyloxy)-10,11,22-trihydroxy-9-(hydroxymethyl)-13,15-dimethyl-4-(prop-1-en-2-yl)-8,24,26,27-tetraoxaheptacyclo[12.10.1.1⁴,²³.1⁵,²³.0¹,⁶.0⁷,⁹.0¹¹,²⁵]heptacosan-2-yl]methyl benzoate)

3D MOL for NP0210320 ([(1r,2s,4r,5r,6s,7s,9r,10s,11s,12s,13s,14s,15r,22r,23r,25r)-12-(benzoyloxy)-10,11,22-trihydroxy-9-(hydroxymethyl)-13,15-dimethyl-4-(prop-1-en-2-yl)-8,24,26,27-tetraoxaheptacyclo[12.10.1.1⁴,²³.1⁵,²³.0¹,⁶.0⁷,⁹.0¹¹,²⁵]heptacosan-2-yl]methyl benzoate)

3D SDF for NP0210320 ([(1r,2s,4r,5r,6s,7s,9r,10s,11s,12s,13s,14s,15r,22r,23r,25r)-12-(benzoyloxy)-10,11,22-trihydroxy-9-(hydroxymethyl)-13,15-dimethyl-4-(prop-1-en-2-yl)-8,24,26,27-tetraoxaheptacyclo[12.10.1.1⁴,²³.1⁵,²³.0¹,⁶.0⁷,⁹.0¹¹,²⁵]heptacosan-2-yl]methyl benzoate)

3D-SDF for NP0210320 ([(1r,2s,4r,5r,6s,7s,9r,10s,11s,12s,13s,14s,15r,22r,23r,25r)-12-(benzoyloxy)-10,11,22-trihydroxy-9-(hydroxymethyl)-13,15-dimethyl-4-(prop-1-en-2-yl)-8,24,26,27-tetraoxaheptacyclo[12.10.1.1⁴,²³.1⁵,²³.0¹,⁶.0⁷,⁹.0¹¹,²⁵]heptacosan-2-yl]methyl benzoate)

PDB for NP0210320 ([(1r,2s,4r,5r,6s,7s,9r,10s,11s,12s,13s,14s,15r,22r,23r,25r)-12-(benzoyloxy)-10,11,22-trihydroxy-9-(hydroxymethyl)-13,15-dimethyl-4-(prop-1-en-2-yl)-8,24,26,27-tetraoxaheptacyclo[12.10.1.1⁴,²³.1⁵,²³.0¹,⁶.0⁷,⁹.0¹¹,²⁵]heptacosan-2-yl]methyl benzoate)

3D PDB for NP0210320 ([(1r,2s,4r,5r,6s,7s,9r,10s,11s,12s,13s,14s,15r,22r,23r,25r)-12-(benzoyloxy)-10,11,22-trihydroxy-9-(hydroxymethyl)-13,15-dimethyl-4-(prop-1-en-2-yl)-8,24,26,27-tetraoxaheptacyclo[12.10.1.1⁴,²³.1⁵,²³.0¹,⁶.0⁷,⁹.0¹¹,²⁵]heptacosan-2-yl]methyl benzoate)

SMILES for NP0210320 ([(1r,2s,4r,5r,6s,7s,9r,10s,11s,12s,13s,14s,15r,22r,23r,25r)-12-(benzoyloxy)-10,11,22-trihydroxy-9-(hydroxymethyl)-13,15-dimethyl-4-(prop-1-en-2-yl)-8,24,26,27-tetraoxaheptacyclo[12.10.1.1⁴,²³.1⁵,²³.0¹,⁶.0⁷,⁹.0¹¹,²⁵]heptacosan-2-yl]methyl benzoate)

INCHI for NP0210320 ([(1r,2s,4r,5r,6s,7s,9r,10s,11s,12s,13s,14s,15r,22r,23r,25r)-12-(benzoyloxy)-10,11,22-trihydroxy-9-(hydroxymethyl)-13,15-dimethyl-4-(prop-1-en-2-yl)-8,24,26,27-tetraoxaheptacyclo[12.10.1.1⁴,²³.1⁵,²³.0¹,⁶.0⁷,⁹.0¹¹,²⁵]heptacosan-2-yl]methyl benzoate)

Structure for NP0210320 ([(1r,2s,4r,5r,6s,7s,9r,10s,11s,12s,13s,14s,15r,22r,23r,25r)-12-(benzoyloxy)-10,11,22-trihydroxy-9-(hydroxymethyl)-13,15-dimethyl-4-(prop-1-en-2-yl)-8,24,26,27-tetraoxaheptacyclo[12.10.1.1⁴,²³.1⁵,²³.0¹,⁶.0⁷,⁹.0¹¹,²⁵]heptacosan-2-yl]methyl benzoate)

3D Structure for NP0210320 ([(1r,2s,4r,5r,6s,7s,9r,10s,11s,12s,13s,14s,15r,22r,23r,25r)-12-(benzoyloxy)-10,11,22-trihydroxy-9-(hydroxymethyl)-13,15-dimethyl-4-(prop-1-en-2-yl)-8,24,26,27-tetraoxaheptacyclo[12.10.1.1⁴,²³.1⁵,²³.0¹,⁶.0⁷,⁹.0¹¹,²⁵]heptacosan-2-yl]methyl benzoate)