NP-MRD: Showing NP-Card for [(1s,4ar,6s,7s,7as)-6-(acetyloxy)-7-(chloromethyl)-4a,7-dihydroxy-1-[(3-methylbutanoyl)oxy]-1h,5h,6h,7ah-cyclopenta[c]pyran-4-yl]methyl (2r)-3-methyl-2-[(3-methylbutanoyl)oxy]butanoate (NP0224641)

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Record Information

Version

2.0

Created at

2022-09-06 03:07:22 UTC

Updated at

2022-09-06 03:07:22 UTC

NP-MRD ID

NP0224641

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1s,4ar,6s,7s,7as)-6-(acetyloxy)-7-(chloromethyl)-4a,7-dihydroxy-1-[(3-methylbutanoyl)oxy]-1h,5h,6h,7ah-cyclopenta[c]pyran-4-yl]methyl (2r)-3-methyl-2-[(3-methylbutanoyl)oxy]butanoate

Description

VOLVALTRATE B, also known as volvaltric acid b, belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups. [(1s,4ar,6s,7s,7as)-6-(acetyloxy)-7-(chloromethyl)-4a,7-dihydroxy-1-[(3-methylbutanoyl)oxy]-1h,5h,6h,7ah-cyclopenta[c]pyran-4-yl]methyl (2r)-3-methyl-2-[(3-methylbutanoyl)oxy]butanoate is found in Valeriana officinalis. [(1s,4ar,6s,7s,7as)-6-(acetyloxy)-7-(chloromethyl)-4a,7-dihydroxy-1-[(3-methylbutanoyl)oxy]-1h,5h,6h,7ah-cyclopenta[c]pyran-4-yl]methyl (2r)-3-methyl-2-[(3-methylbutanoyl)oxy]butanoate was first documented in 2010 (PMID: 20853876). Based on a literature review very few articles have been published on VOLVALTRATE B (PMID: 23036722).

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309062205072D          

 39 40  0  0  1  0            999 V2000
   -6.1899   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3649   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9524   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9524   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1274   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6425   -1.3951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9441   -0.8295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   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   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6425   -2.7299    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4794   -3.5387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2498   -3.2884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0370   -3.0417    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 14 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
  9 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 27 35  1  0  0  0  0
 35  7  1  6  0  0  0
 35 36  1  0  0  0  0
  5 36  1  0  0  0  0
 36 37  1  6  0  0  0
 36 38  1  1  0  0  0
 38 39  1  0  0  0  0
M  END


  Mrv1652309062205072D          

 39 40  0  0  1  0            999 V2000
   -6.1899   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3649   -1.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9524   -0.6336    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9524   -2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1274   -2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6425   -1.3951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9441   -0.8295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   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   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   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
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -2.8875    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.6425   -2.7299    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4794   -3.5387    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2498   -3.2884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0370   -3.0417    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  1  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  1  0  0  0  0
 14 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
  9 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  1  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 27 35  1  0  0  0  0
 35  7  1  6  0  0  0
 35 36  1  0  0  0  0
  5 36  1  0  0  0  0
 36 37  1  6  0  0  0
 36 38  1  1  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0224641

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CC(=O)O[C@H](C(C)C)C(=O)OCC1=CO[C@@H](OC(=O)CC(C)C)[C@@H]2[C@@](O)(CCl)[C@H](C[C@]12O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C27H41ClO11/c1-14(2)8-20(30)38-22(16(5)6)24(32)35-11-18-12-36-25(39-21(31)9-15(3)4)23-26(18,33)10-19(37-17(7)29)27(23,34)13-28/h12,14-16,19,22-23,25,33-34H,8-11,13H2,1-7H3/t19-,22+,23-,25-,26-,27+/m0/s1

> <INCHI_KEY>
OEVPPNBQSYOUCV-PXKJKYEHSA-N

> <FORMULA>
C27H41ClO11

> <MOLECULAR_WEIGHT>
577.06

> <EXACT_MASS>
576.2337398

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
59.24735990448414

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1S,4aR,6S,7S,7aS)-6-(acetyloxy)-7-(chloromethyl)-4a,7-dihydroxy-1-[(3-methylbutanoyl)oxy]-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-yl]methyl (2R)-3-methyl-2-[(3-methylbutanoyl)oxy]butanoate

> <JCHEM_LOGP>
2.055805253

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.656689901917591

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.576737794691699

> <JCHEM_PKA_STRONGEST_BASIC>
-3.456794371157117

> <JCHEM_POLAR_SURFACE_AREA>
154.89000000000001

> <JCHEM_REFRACTIVITY>
136.7927

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,4aR,6S,7S,7aS)-6-(acetyloxy)-7-(chloromethyl)-4a,7-dihydroxy-1-[(3-methylbutanoyl)oxy]-1H,5H,6H,7aH-cyclopenta[c]pyran-4-yl]methyl (2R)-3-methyl-2-[(3-methylbutanoyl)oxy]butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0     -11.555  -2.516   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -10.015  -2.516   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -9.245  -1.183   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -9.245  -3.850   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -7.705  -3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.799  -2.604   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      -5.496  -1.548   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -6.799  -5.096   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -6.495  -6.606   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -7.933  -6.138   0.000  0.00  0.00           C+0
HETATM   39 Cl   UNK     0      -9.402  -5.678   0.000  0.00  0.00          Cl+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   36                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8    9   35                                             
CONECT    8    7                                                            
CONECT    9    7   10   25                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   22                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   14   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25    9   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   35                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
CONECT   35   27    7   36                                                  
CONECT   36   35    5   37   38                                             
CONECT   37   36                                                            
CONECT   38   36   39                                                       
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   80    0
END

View in JSmol

Synonyms

Value	Source
VOLVALTRic acid b	Generator

Chemical Formula

C₂₇H₄₁ClO₁₁

Average Mass

577.0600 Da

Monoisotopic Mass

576.23374 Da

IUPAC Name

[(1S,4aR,6S,7S,7aS)-6-(acetyloxy)-7-(chloromethyl)-4a,7-dihydroxy-1-[(3-methylbutanoyl)oxy]-1H,4aH,5H,6H,7H,7aH-cyclopenta[c]pyran-4-yl]methyl (2R)-3-methyl-2-[(3-methylbutanoyl)oxy]butanoate

Traditional Name

[(1S,4aR,6S,7S,7aS)-6-(acetyloxy)-7-(chloromethyl)-4a,7-dihydroxy-1-[(3-methylbutanoyl)oxy]-1H,5H,6H,7aH-cyclopenta[c]pyran-4-yl]methyl (2R)-3-methyl-2-[(3-methylbutanoyl)oxy]butanoate

CAS Registry Number

Not Available

SMILES

CC(C)CC(=O)O[C@H](C(C)C)C(=O)OCC1=CO[C@@H](OC(=O)CC(C)C)[C@@H]2[C@@](O)(CCl)[C@H](C[C@]12O)OC(C)=O

InChI Identifier

InChI=1S/C27H41ClO11/c1-14(2)8-20(30)38-22(16(5)6)24(32)35-11-18-12-36-25(39-21(31)9-15(3)4)23-26(18,33)10-19(37-17(7)29)27(23,34)13-28/h12,14-16,19,22-23,25,33-34H,8-11,13H2,1-7H3/t19-,22+,23-,25-,26-,27+/m0/s1

InChI Key

OEVPPNBQSYOUCV-PXKJKYEHSA-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
Valeriana officinalis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetracarboxylic acids and derivatives. These are carboxylic acids containing exactly four carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tetracarboxylic acids and derivatives

Direct Parent

Tetracarboxylic acids and derivatives

Alternative Parents

Substituents

Tetracarboxylic acid or derivatives
Iridoid-skeleton
Bicyclic monoterpenoid
Monoterpenoid
Fatty acid ester
Fatty acyl
Cyclic alcohol
Tertiary alcohol
Carboxylic acid ester
Chlorohydrin
Halohydrin
Acetal
Organoheterocyclic compound
Oxacycle
Organic oxygen compound
Alcohol
Organic oxide
Carbonyl group
Hydrocarbon derivative
Alkyl halide
Alkyl chloride
Organohalogen compound
Organochloride
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	2.06	ChemAxon
pKa (Strongest Acidic)	12.58	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	154.89 Å²	ChemAxon
Rotatable Bond Count	16	ChemAxon
Refractivity	136.79 m³·mol⁻¹	ChemAxon
Polarizability	59.25 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00048233

Chemspider ID

26361501

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

49831716

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lin S, Zhang ZX, Chen T, Ye J, Dai WX, Shan L, Su J, Shen YH, Li HL, Liu RH, Xu XK, Wang H, Zhang WD: Characterization of chlorinated valepotriates from Valeriana jatamansi. Phytochemistry. 2013 Jan;85:185-93. doi: 10.1016/j.phytochem.2012.08.015. Epub 2012 Oct 1. [PubMed:23036722 ]
Lin S, Shen YH, Zhang ZX, Li HL, Shan L, Liu RH, Xu XK, Zhang WD: Revision of the Structures of 1,5-Dihydroxy-3,8-epoxyvalechlorine, Volvaltrate B, and Valeriotetrate C from Valeriana jatamansi and V. officinalis. J Nat Prod. 2010 Oct 22;73(10):1723-6. doi: 10.1021/np100426j. Epub 2010 Sep 20. [PubMed:20853876 ]
LOTUS database [Link]

Showing NP-Card for [(1s,4ar,6s,7s,7as)-6-(acetyloxy)-7-(chloromethyl)-4a,7-dihydroxy-1-[(3-methylbutanoyl)oxy]-1h,5h,6h,7ah-cyclopenta[c]pyran-4-yl]methyl (2r)-3-methyl-2-[(3-methylbutanoyl)oxy]butanoate (NP0224641)

MOL for NP0224641 ([(1s,4ar,6s,7s,7as)-6-(acetyloxy)-7-(chloromethyl)-4a,7-dihydroxy-1-[(3-methylbutanoyl)oxy]-1h,5h,6h,7ah-cyclopenta[c]pyran-4-yl]methyl (2r)-3-methyl-2-[(3-methylbutanoyl)oxy]butanoate)

3D MOL for NP0224641 ([(1s,4ar,6s,7s,7as)-6-(acetyloxy)-7-(chloromethyl)-4a,7-dihydroxy-1-[(3-methylbutanoyl)oxy]-1h,5h,6h,7ah-cyclopenta[c]pyran-4-yl]methyl (2r)-3-methyl-2-[(3-methylbutanoyl)oxy]butanoate)

3D SDF for NP0224641 ([(1s,4ar,6s,7s,7as)-6-(acetyloxy)-7-(chloromethyl)-4a,7-dihydroxy-1-[(3-methylbutanoyl)oxy]-1h,5h,6h,7ah-cyclopenta[c]pyran-4-yl]methyl (2r)-3-methyl-2-[(3-methylbutanoyl)oxy]butanoate)

3D-SDF for NP0224641 ([(1s,4ar,6s,7s,7as)-6-(acetyloxy)-7-(chloromethyl)-4a,7-dihydroxy-1-[(3-methylbutanoyl)oxy]-1h,5h,6h,7ah-cyclopenta[c]pyran-4-yl]methyl (2r)-3-methyl-2-[(3-methylbutanoyl)oxy]butanoate)

PDB for NP0224641 ([(1s,4ar,6s,7s,7as)-6-(acetyloxy)-7-(chloromethyl)-4a,7-dihydroxy-1-[(3-methylbutanoyl)oxy]-1h,5h,6h,7ah-cyclopenta[c]pyran-4-yl]methyl (2r)-3-methyl-2-[(3-methylbutanoyl)oxy]butanoate)

3D PDB for NP0224641 ([(1s,4ar,6s,7s,7as)-6-(acetyloxy)-7-(chloromethyl)-4a,7-dihydroxy-1-[(3-methylbutanoyl)oxy]-1h,5h,6h,7ah-cyclopenta[c]pyran-4-yl]methyl (2r)-3-methyl-2-[(3-methylbutanoyl)oxy]butanoate)

SMILES for NP0224641 ([(1s,4ar,6s,7s,7as)-6-(acetyloxy)-7-(chloromethyl)-4a,7-dihydroxy-1-[(3-methylbutanoyl)oxy]-1h,5h,6h,7ah-cyclopenta[c]pyran-4-yl]methyl (2r)-3-methyl-2-[(3-methylbutanoyl)oxy]butanoate)

INCHI for NP0224641 ([(1s,4ar,6s,7s,7as)-6-(acetyloxy)-7-(chloromethyl)-4a,7-dihydroxy-1-[(3-methylbutanoyl)oxy]-1h,5h,6h,7ah-cyclopenta[c]pyran-4-yl]methyl (2r)-3-methyl-2-[(3-methylbutanoyl)oxy]butanoate)

Structure for NP0224641 ([(1s,4ar,6s,7s,7as)-6-(acetyloxy)-7-(chloromethyl)-4a,7-dihydroxy-1-[(3-methylbutanoyl)oxy]-1h,5h,6h,7ah-cyclopenta[c]pyran-4-yl]methyl (2r)-3-methyl-2-[(3-methylbutanoyl)oxy]butanoate)

3D Structure for NP0224641 ([(1s,4ar,6s,7s,7as)-6-(acetyloxy)-7-(chloromethyl)-4a,7-dihydroxy-1-[(3-methylbutanoyl)oxy]-1h,5h,6h,7ah-cyclopenta[c]pyran-4-yl]methyl (2r)-3-methyl-2-[(3-methylbutanoyl)oxy]butanoate)