NP-MRD: Showing NP-Card for (1s,6s,7r,7as)-6-(acetyloxy)-4-[(acetyloxy)methyl]-6,7a-dihydro-1h-spiro[cyclopenta[c]pyran-7,2'-oxiran]-1-yl 3-methylbutanoate (NP0182894)

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Record Information

Version

2.0

Created at

2022-09-03 21:42:26 UTC

Updated at

2022-09-03 21:42:26 UTC

NP-MRD ID

NP0182894

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,6s,7r,7as)-6-(acetyloxy)-4-[(acetyloxy)methyl]-6,7a-dihydro-1h-spiro[cyclopenta[c]pyran-7,2'-oxiran]-1-yl 3-methylbutanoate

Description

Diavaltrate, also known as diavaltric acid, belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open. (1s,6s,7r,7as)-6-(acetyloxy)-4-[(acetyloxy)methyl]-6,7a-dihydro-1h-spiro[cyclopenta[c]pyran-7,2'-oxiran]-1-yl 3-methylbutanoate is found in Valeriana capensis, Valeriana microphylla and Valeriana officinalis. Based on a literature review very few articles have been published on Diavaltrate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032223422D          

 27 29  0  0  1  0            999 V2000
    1.4289    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    5.3625    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
    0.0000    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  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    2.8875    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    4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2136    5.2049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6985    4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5235    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9360    3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5235    3.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7610    3.8230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2136    3.8701    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0420    3.0631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8267    3.3180    0.0000 O   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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
  9 17  1  0  0  0  0
 17 18  1  6  0  0  0
  6 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 20 25  1  0  0  0  0
 17 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 25 27  1  6  0  0  0
M  END

     RDKit          3D

 51 53  0  0  0  0  0  0  0  0999 V2000
    4.7118   -2.2424   -2.6947 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0506   -2.5187   -1.3979 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1672   -3.3811   -1.3155 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4538   -1.7860   -0.3011 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8670   -2.0021    0.9472 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3945   -1.7562    0.9501 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5287   -2.6989    1.2600 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1897   -2.3848    1.2369 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3192   -1.1756    0.6866 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.6496   -1.0551    1.0632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7493   -1.0968    0.2572 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4701   -1.2673   -0.9699 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1521   -0.9626    0.7110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1431   -1.0476   -0.3980 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5306   -0.8943    0.2153 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9543    0.1118   -1.3473 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5739   -0.0264    1.0077 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9487   -0.4145    0.5928 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5306    0.5854   -0.0545 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6347    1.7652   -0.1578 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0576    2.8230    0.6745 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4362    4.0141    0.0729 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8954    5.1831    0.8646 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4043    4.1502   -1.1821 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3197    1.1989    0.2214 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7072    2.2010    0.6862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8156    1.3975   -0.5213 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7110   -2.7514   -2.7097 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8471   -1.1497   -2.8704 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0746   -2.6428   -3.5112 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0233   -3.0518    1.3228 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3016   -1.3483    1.7273 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8265   -3.6914    1.5267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2906   -1.3168   -0.4157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4220   -1.7554    1.4603 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2650   -0.0033    1.2284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1151   -2.0126   -0.9403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2778   -1.5145   -0.2898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8262    0.1879    0.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5145   -1.2189    1.2953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4114    0.9067   -0.8017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9597    0.4703   -1.6999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3786   -0.2143   -2.2268 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6446    0.2152    2.0778 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5546    0.4930   -0.4447 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6714    2.0665   -1.2392 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1258    4.9189    1.9155 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7623    5.6248    0.3381 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0910    5.9497    0.8392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3273    1.8523    1.5279 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5187    3.2661    0.5187 H   0  0  0  0  0  0  0  0  0  0  0  0
 15 14  1  0
 14 16  1  0
 14 13  1  0
 13 11  1  0
 11 12  2  0
 11 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  6  2  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
  6 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
 22 24  2  0
 20 25  1  0
 25 26  1  0
 26 27  1  0
 25 17  1  0
 17  9  1  0
 17 18  1  0
 25 27  1  6
 15 38  1  0
 15 39  1  0
 15 40  1  0
 14 37  1  0
 16 41  1  0
 16 42  1  0
 16 43  1  0
 13 35  1  0
 13 36  1  0
  9 34  1  6
  7 33  1  0
  5 31  1  0
  5 32  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
 19 45  1  0
 20 46  1  6
 23 47  1  0
 23 48  1  0
 23 49  1  0
 26 50  1  0
 26 51  1  0
 17 44  1  1
M  END


  Mrv1652309032223422D          

 27 29  0  0  1  0            999 V2000
    1.4289    6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    6.6000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    5.3625    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
    0.0000    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.8875    0.0000 C   0  0  0  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    2.8875    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    4.1250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2136    5.2049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6985    4.5375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5235    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9360    3.8230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5235    3.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7610    3.8230    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2136    3.8701    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0420    3.0631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8267    3.3180    0.0000 O   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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
  9 17  1  0  0  0  0
 17 18  1  6  0  0  0
  6 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 20 25  1  0  0  0  0
 17 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 25 27  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0182894

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)CC(=O)O[C@@H]1OC=C(COC(C)=O)C2=C[C@H](OC(C)=O)[C@]3(CO3)[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C19H24O8/c1-10(2)5-16(22)27-18-17-14(13(8-24-18)7-23-11(3)20)6-15(26-12(4)21)19(17)9-25-19/h6,8,10,15,17-18H,5,7,9H2,1-4H3/t15-,17+,18-,19+/m0/s1

> <INCHI_KEY>
OZYPVATWXAXGPT-WZGPROSRSA-N

> <FORMULA>
C19H24O8

> <MOLECULAR_WEIGHT>
380.393

> <EXACT_MASS>
380.147117733

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
51

> <JCHEM_AVERAGE_POLARIZABILITY>
38.48396384865211

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,6S,7R,7aS)-6-(acetyloxy)-4-[(acetyloxy)methyl]-6,7a-dihydro-1H-spiro[cyclopenta[c]pyran-7,2'-oxirane]-1-yl 3-methylbutanoate

> <JCHEM_LOGP>
0.8043998460000001

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.236664800064094

> <JCHEM_PKA_STRONGEST_BASIC>
-4.145698394977996

> <JCHEM_POLAR_SURFACE_AREA>
100.66

> <JCHEM_REFRACTIVITY>
91.47739999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,6S,7R,7aS)-6-(acetyloxy)-4-[(acetyloxy)methyl]-6,7a-dihydro-1H-spiro[cyclopenta[c]pyran-7,2'-oxirane]-1-yl 3-methylbutanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667  12.320   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  11.550   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.334  10.010   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -0.000  12.320   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.334  11.550   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  10.010   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.000   7.700   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -1.334   5.390   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -0.000   3.080   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.334   5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001   5.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.667   7.700   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.132   9.716   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.037   8.470   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -6.577   8.470   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -7.347   7.136   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -6.577   5.803   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -8.887   7.136   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -4.132   7.224   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.812   5.718   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      -5.276   6.194   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   18                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   17                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17    9   18   25                                                  
CONECT   18   17    6   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   20   17   26   27                                             
CONECT   26   25   27                                                       
CONECT   27   26   25                                                       
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Value	Source
Diavaltric acid	Generator

Chemical Formula

C₁₉H₂₄O₈

Average Mass

380.3930 Da

Monoisotopic Mass

380.14712 Da

IUPAC Name

(1S,6S,7R,7aS)-6-(acetyloxy)-4-[(acetyloxy)methyl]-6,7a-dihydro-1H-spiro[cyclopenta[c]pyran-7,2'-oxirane]-1-yl 3-methylbutanoate

Traditional Name

(1S,6S,7R,7aS)-6-(acetyloxy)-4-[(acetyloxy)methyl]-6,7a-dihydro-1H-spiro[cyclopenta[c]pyran-7,2'-oxirane]-1-yl 3-methylbutanoate

CAS Registry Number

Not Available

SMILES

CC(C)CC(=O)O[C@@H]1OC=C(COC(C)=O)C2=C[C@H](OC(C)=O)[C@]3(CO3)[C@@H]12

InChI Identifier

InChI=1S/C19H24O8/c1-10(2)5-16(22)27-18-17-14(13(8-24-18)7-23-11(3)20)6-15(26-12(4)21)19(17)9-25-19/h6,8,10,15,17-18H,5,7,9H2,1-4H3/t15-,17+,18-,19+/m0/s1

InChI Key

OZYPVATWXAXGPT-WZGPROSRSA-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 capensis	LOTUS Database	35616633
Valeriana microphylla	LOTUS Database	35616633
Valeriana officinalis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as iridoids and derivatives. These are monoterpenes containing a skeleton structurally characterized by the presence of a cylopentane fused to a pyran ( forming a 4,7-dimethylcyclopenta[c]pyran), or a derivative where the pentane moiety is open.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Iridoids and derivatives

Alternative Parents

Substituents

Iridoid-skeleton
Bicyclic monoterpenoid
Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acyl
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	0.8	ChemAxon
pKa (Strongest Acidic)	18.24	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	100.66 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	91.48 m³·mol⁻¹	ChemAxon
Polarizability	38.48 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

101656903

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,6s,7r,7as)-6-(acetyloxy)-4-[(acetyloxy)methyl]-6,7a-dihydro-1h-spiro[cyclopenta[c]pyran-7,2'-oxiran]-1-yl 3-methylbutanoate (NP0182894)

MOL for NP0182894 ((1s,6s,7r,7as)-6-(acetyloxy)-4-[(acetyloxy)methyl]-6,7a-dihydro-1h-spiro[cyclopenta[c]pyran-7,2'-oxiran]-1-yl 3-methylbutanoate)

3D MOL for NP0182894 ((1s,6s,7r,7as)-6-(acetyloxy)-4-[(acetyloxy)methyl]-6,7a-dihydro-1h-spiro[cyclopenta[c]pyran-7,2'-oxiran]-1-yl 3-methylbutanoate)

3D SDF for NP0182894 ((1s,6s,7r,7as)-6-(acetyloxy)-4-[(acetyloxy)methyl]-6,7a-dihydro-1h-spiro[cyclopenta[c]pyran-7,2'-oxiran]-1-yl 3-methylbutanoate)

3D-SDF for NP0182894 ((1s,6s,7r,7as)-6-(acetyloxy)-4-[(acetyloxy)methyl]-6,7a-dihydro-1h-spiro[cyclopenta[c]pyran-7,2'-oxiran]-1-yl 3-methylbutanoate)

PDB for NP0182894 ((1s,6s,7r,7as)-6-(acetyloxy)-4-[(acetyloxy)methyl]-6,7a-dihydro-1h-spiro[cyclopenta[c]pyran-7,2'-oxiran]-1-yl 3-methylbutanoate)

3D PDB for NP0182894 ((1s,6s,7r,7as)-6-(acetyloxy)-4-[(acetyloxy)methyl]-6,7a-dihydro-1h-spiro[cyclopenta[c]pyran-7,2'-oxiran]-1-yl 3-methylbutanoate)

SMILES for NP0182894 ((1s,6s,7r,7as)-6-(acetyloxy)-4-[(acetyloxy)methyl]-6,7a-dihydro-1h-spiro[cyclopenta[c]pyran-7,2'-oxiran]-1-yl 3-methylbutanoate)

INCHI for NP0182894 ((1s,6s,7r,7as)-6-(acetyloxy)-4-[(acetyloxy)methyl]-6,7a-dihydro-1h-spiro[cyclopenta[c]pyran-7,2'-oxiran]-1-yl 3-methylbutanoate)

Structure for NP0182894 ((1s,6s,7r,7as)-6-(acetyloxy)-4-[(acetyloxy)methyl]-6,7a-dihydro-1h-spiro[cyclopenta[c]pyran-7,2'-oxiran]-1-yl 3-methylbutanoate)

3D Structure for NP0182894 ((1s,6s,7r,7as)-6-(acetyloxy)-4-[(acetyloxy)methyl]-6,7a-dihydro-1h-spiro[cyclopenta[c]pyran-7,2'-oxiran]-1-yl 3-methylbutanoate)