NP-MRD: Showing NP-Card for Retinestatin (NP0332499)

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Record Information

Version

1.0

Created at

2024-02-13 04:00:57 UTC

Updated at

2024-04-19 09:29:55 UTC

NP-MRD ID

NP0332499

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Retinestatin

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 02132404012D          

 37 38  0  0  1  0            999 V2000
   -2.6577   -4.2207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3221   -3.4670    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7346   -2.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1826   -2.1394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0095   -2.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6222   -3.4906    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0594   -4.1902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6721   -4.9186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1093   -5.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7220   -6.3467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1591   -7.0464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7718   -7.7748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2090   -8.4744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8217   -9.2029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2589   -9.9025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7977   -3.5194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3969   -2.0913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5152   -3.2955    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9021   -3.8475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5551   -2.6663    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
  5  4  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  6  0  0  0
 11 10  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 12 15  1  6  0  0  0
 11 16  1  1  0  0  0
 10 17  1  0  0  0  0
 18 17  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  6  0  0  0
 20 19  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  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
 20 30  1  1  0  0  0
 18 31  1  1  0  0  0
  8 32  1  1  0  0  0
  7 33  1  1  0  0  0
  6 34  1  1  0  0  0
  5 35  1  0  0  0  0
 35  2  1  0  0  0  0
 35 36  1  1  0  0  0
  3 37  2  0  0  0  0
M  END


  Mrv2104 02132404012D          

 37 38  0  0  1  0            999 V2000
   -2.6577   -4.2207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3221   -3.4670    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7346   -2.7525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1826   -2.1394    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7145   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7145   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0095   -2.7621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6222   -3.4906    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.0594   -4.1902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6721   -4.9186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1093   -5.6183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7220   -6.3467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1591   -7.0464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7718   -7.7748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2090   -8.4744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8217   -9.2029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2589   -9.9025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7977   -3.5194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3969   -2.0913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5152   -3.2955    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9021   -3.8475    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5551   -2.6663    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
  5  4  1  0  0  0  0
  5  6  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  6  0  0  0
 11 10  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 12 15  1  6  0  0  0
 11 16  1  1  0  0  0
 10 17  1  0  0  0  0
 18 17  1  0  0  0  0
 13 18  1  0  0  0  0
 18 19  1  6  0  0  0
 20 19  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  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
 20 30  1  1  0  0  0
 18 31  1  1  0  0  0
  8 32  1  1  0  0  0
  7 33  1  1  0  0  0
  6 34  1  1  0  0  0
  5 35  1  0  0  0  0
 35  2  1  0  0  0  0
 35 36  1  1  0  0  0
  3 37  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0332499

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC\C=C\C=C\C=C\[C@@H](O)C[C@]1(O)O[C@H](C[C@H](O)[C@@H](O)[C@H](O)[C@H]2OC(=O)[C@@H](C)[C@@H]2O)[C@@H](O)[C@H](O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C25H40O12/c1-3-4-5-6-7-8-9-10-14(26)12-25(35)23(33)21(32)19(30)16(37-25)11-15(27)18(29)20(31)22-17(28)13(2)24(34)36-22/h5-10,13-23,26-33,35H,3-4,11-12H2,1-2H3/b6-5+,8-7+,10-9+/t13-,14+,15-,16+,17-,18+,19+,20-,21-,22-,23-,25-/m0/s1

> <INCHI_KEY>
MRCPQBDIQZUMSK-SZPBRFHXSA-N

> <FORMULA>
C25H40O12

> <MOLECULAR_WEIGHT>
532.583

> <EXACT_MASS>
532.251976728

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
55.54710287114179

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,4S,5S)-4-hydroxy-3-methyl-5-[(1S,2R,3S)-1,2,3-trihydroxy-4-[(2R,3S,4S,5S,6S)-3,4,5,6-tetrahydroxy-6-[(2S,3E,5E,7E)-2-hydroxyundeca-3,5,7-trien-1-yl]oxan-2-yl]butyl]oxolan-2-one

> <JCHEM_LOGP>
-1.4759700856666669

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.376414866366801

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.913818085044447

> <JCHEM_PKA_STRONGEST_BASIC>
-3.221743522007165

> <JCHEM_POLAR_SURFACE_AREA>
217.59999999999997

> <JCHEM_REFRACTIVITY>
131.3726

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4S,5S)-4-hydroxy-3-methyl-5-[(1S,2R,3S)-1,2,3-trihydroxy-4-[(2R,3S,4S,5S,6S)-3,4,5,6-tetrahydroxy-6-[(2S,3E,5E,7E)-2-hydroxyundeca-3,5,7-trien-1-yl]oxan-2-yl]butyl]oxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 13-FEB-24   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-FEB-24         0                                  
HETATM    1  C   UNK     0      -4.961  -7.879   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.335  -6.472   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.105  -5.138   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      -4.074  -3.994   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.002  -1.540   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       5.335   0.000   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.667  -1.540   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.668  -3.850   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.484  -5.156   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.761  -6.516   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.578  -7.822   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.855  -9.181   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.671 -10.487   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.948 -11.847   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.764 -13.153   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.041 -14.513   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       7.857 -15.819   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       7.134 -17.179   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.950 -18.485   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       5.222  -6.569   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       8.207  -3.904   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0       0.000  -6.160   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -2.828  -6.152   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -1.684  -7.182   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      -6.636  -4.977   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   35                                                  
CONECT    3    2    4   37                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   35                                                  
CONECT    6    5    7   34                                                  
CONECT    7    6    8   33                                                  
CONECT    8    7    9   32                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13   15                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13                                                            
CONECT   15   12                                                            
CONECT   16   11                                                            
CONECT   17   10   18                                                       
CONECT   18   17   13   19   31                                             
CONECT   19   18   20                                                       
CONECT   20   19   21   30                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28                                                            
CONECT   30   20                                                            
CONECT   31   18                                                            
CONECT   32    8                                                            
CONECT   33    7                                                            
CONECT   34    6                                                            
CONECT   35    5    2   36                                                  
CONECT   36   35                                                            
CONECT   37    3                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₄₀O₁₂

Average Mass

532.5830 Da

Monoisotopic Mass

532.25198 Da

IUPAC Name

(3S,4S,5S)-4-hydroxy-3-methyl-5-[(1S,2R,3S)-1,2,3-trihydroxy-4-[(2R,3S,4S,5S,6S)-3,4,5,6-tetrahydroxy-6-[(2S,3E,5E,7E)-2-hydroxyundeca-3,5,7-trien-1-yl]oxan-2-yl]butyl]oxolan-2-one

Traditional Name

(3S,4S,5S)-4-hydroxy-3-methyl-5-[(1S,2R,3S)-1,2,3-trihydroxy-4-[(2R,3S,4S,5S,6S)-3,4,5,6-tetrahydroxy-6-[(2S,3E,5E,7E)-2-hydroxyundeca-3,5,7-trien-1-yl]oxan-2-yl]butyl]oxolan-2-one

CAS Registry Number

Not Available

SMILES

CCC\C=C\C=C\C=C\[C@@H](O)C[C@]1(O)O[C@H](C[C@H](O)[C@@H](O)[C@H](O)[C@H]2OC(=O)[C@@H](C)[C@@H]2O)[C@@H](O)[C@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C25H40O12/c1-3-4-5-6-7-8-9-10-14(26)12-25(35)23(33)21(32)19(30)16(37-25)11-15(27)18(29)20(31)22-17(28)13(2)24(34)36-22/h5-10,13-23,26-33,35H,3-4,11-12H2,1-2H3/b6-5+,8-7+,10-9+/t13-,14+,15-,16+,17-,18+,19+,20-,21-,22-,23-,25-/m0/s1

InChI Key

MRCPQBDIQZUMSK-SZPBRFHXSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

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	-1.5	ChemAxon
pKa (Strongest Acidic)	10.91	ChemAxon
pKa (Strongest Basic)	-3.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	217.6 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	131.37 m³·mol⁻¹	ChemAxon
Polarizability	55.55 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

Not Available

References

General References

Not Available

Showing NP-Card for Retinestatin (NP0332499)

MOL for NP0332499 (Retinestatin)

3D MOL for NP0332499 (Retinestatin)

3D SDF for NP0332499 (Retinestatin)

3D-SDF for NP0332499 (Retinestatin)

PDB for NP0332499 (Retinestatin)

3D PDB for NP0332499 (Retinestatin)

SMILES for NP0332499 (Retinestatin)

INCHI for NP0332499 (Retinestatin)

Structure for NP0332499 (Retinestatin)

3D Structure for NP0332499 (Retinestatin)