NP-MRD: Showing NP-Card for [1S-[1alpha(E),3(E),5beta,6alpha]]-5-(acetyloxy)-6-(1-methylethyl)-3-[[(2-methyl-1-oxo-2-butenyl)oxy]methyl]-4-oxo-2-cyclohexen-1-yl ester (NP0057770)

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Record Information

Version

2.0

Created at

2022-04-28 03:10:04 UTC

Updated at

2022-04-28 03:10:04 UTC

NP-MRD ID

NP0057770

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[1S-[1alpha(E),3(E),5beta,6alpha]]-5-(acetyloxy)-6-(1-methylethyl)-3-[[(2-methyl-1-oxo-2-butenyl)oxy]methyl]-4-oxo-2-cyclohexen-1-yl ester

Description

(3S)-4alpha-Isopropyl-3alpha,5beta-dihydroxy-1-[((E)-2-methyl-2-butenoyloxy)methyl]-1-cyclohexen-6-one 3-[(E)-2-methyl-2-butenoate]5-acetate belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. [1S-[1alpha(E),3(E),5beta,6alpha]]-5-(acetyloxy)-6-(1-methylethyl)-3-[[(2-methyl-1-oxo-2-butenyl)oxy]methyl]-4-oxo-2-cyclohexen-1-yl ester is found in Sphaeranthus bullatus . Based on a literature review very few articles have been published on (3S)-4alpha-Isopropyl-3alpha,5beta-dihydroxy-1-[((E)-2-methyl-2-butenoyloxy)methyl]-1-cyclohexen-6-one 3-[(E)-2-methyl-2-butenoate]5-acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282205102D          

 29 29  0  0  1  0            999 V2000
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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    2.0625    0.0000 O   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    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    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
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    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   -1.6500    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   -2.4750    0.0000 C   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
   -0.7145   -3.7125    0.0000 C   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
    2.1434   -0.4125    0.0000 C   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
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    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
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  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
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
  5 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 19 22  1  0  0  0  0
  4 23  1  1  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
  3 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
M  END

     RDKit          3D

 59 59  0  0  0  0  0  0  0  0999 V2000
    7.2939    0.4165    1.0284 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9085   -0.1398    0.9946 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3673   -0.6437   -0.0978 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1792   -0.6529   -1.3411 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9917   -1.1836   -0.0846 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3048   -1.1763    0.9651 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4227   -1.7133   -1.2329 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1089   -2.2212   -1.1908 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1111   -1.2159   -0.7985 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3852   -1.4053    0.2713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6482   -0.4490    0.7500 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9379   -0.9758    0.6393 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7193   -1.2803    1.7291 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2249   -1.0651    2.8691 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0693   -1.8309    1.6139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8477   -2.1327    2.8342 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6179   -2.0684    0.4514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0060   -2.6343    0.3527 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4440    0.8741    0.1152 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5087    1.8919    0.4088 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6295    2.1829    1.8865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8415    1.5235   -0.2007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2413    0.8240   -1.3777 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0045    2.1737   -1.7950 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8144    2.7453   -2.7540 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5922    4.1424   -3.2129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7453    2.0370   -3.2151 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9551   -0.0223   -1.6201 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8366    0.2164   -2.4777 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8983    0.0684    0.1915 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7151    0.1228    2.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1809    1.5231    1.0782 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3060   -0.1383    1.8975 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7015    0.3135   -1.4852 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5549   -0.8611   -2.2291 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9239   -1.4692   -1.2343 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9861   -3.1201   -0.5904 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8654   -2.5167   -2.2523 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5242   -2.3132    0.8709 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4352   -0.3413    1.8542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8273   -1.6175    2.8440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2964   -1.8502    3.7542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0375   -3.2157    2.8758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0704   -1.8565   -0.4395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6598   -1.8290   -0.0547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0594   -3.4810   -0.3368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3653   -2.9535    1.3455 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5135    1.3028    0.5363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1866    2.8300   -0.0888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4661    1.6180    2.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7439    3.2721    2.0192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6594    1.9052    2.3460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5667    1.4380    0.6440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2532    2.3430   -0.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8128    0.6266   -0.8231 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1004    0.3978   -1.9063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1968    4.8381   -2.5793 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4728    4.4384   -3.0177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8866    4.3085   -4.2574 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 15 17  2  0
 17 18  1  0
 11 19  1  0
 19 20  1  0
 20 21  1  0
 20 22  1  0
 19 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  2  0
 23 28  1  0
 28 29  2  0
 28  9  1  0
  1 30  1  0
  1 31  1  0
  1 32  1  0
  2 33  1  0
  4 34  1  0
  4 35  1  0
  4 36  1  0
  8 37  1  0
  8 38  1  0
 10 39  1  0
 11 40  1  1
 16 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  0
 18 45  1  0
 18 46  1  0
 18 47  1  0
 19 48  1  1
 20 49  1  6
 21 50  1  0
 21 51  1  0
 21 52  1  0
 22 53  1  0
 22 54  1  0
 22 55  1  0
 23 56  1  6
 26 57  1  0
 26 58  1  0
 26 59  1  0
M  END


  Mrv1652304282205102D          

 29 29  0  0  1  0            999 V2000
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    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    2.0625    0.0000 O   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    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    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
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    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   -1.6500    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   -2.4750    0.0000 C   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
   -0.7145   -3.7125    0.0000 C   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
    2.1434   -0.4125    0.0000 C   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
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    2.0625    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
    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  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
  1  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
  5 16  1  1  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 19 22  1  0  0  0  0
  4 23  1  1  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
  3 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0057770

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(/C)C(=O)OCC1=C[C@H](OC(=O)C(\C)=C\C)[C@H](C(C)C)[C@@H](OC(C)=O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C22H30O7/c1-8-13(5)21(25)27-11-16-10-17(29-22(26)14(6)9-2)18(12(3)4)20(19(16)24)28-15(7)23/h8-10,12,17-18,20H,11H2,1-7H3/b13-8+,14-9+/t17-,18-,20+/m0/s1

> <INCHI_KEY>
VQVOLXGHPXSBKK-ZDKFFNMDSA-N

> <FORMULA>
C22H30O7

> <MOLECULAR_WEIGHT>
406.475

> <EXACT_MASS>
406.199153306

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
44.02980711602476

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
[(3S,4S,5R)-5-(acetyloxy)-3-{[(2E)-2-methylbut-2-enoyl]oxy}-6-oxo-4-(propan-2-yl)cyclohex-1-en-1-yl]methyl (2E)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
3.37

> <JCHEM_LOGP>
4.504037293666666

> <ALOGPS_LOGS>
-4.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.047339177445128

> <JCHEM_PKA_STRONGEST_BASIC>
-6.4088830689106

> <JCHEM_POLAR_SURFACE_AREA>
95.97000000000003

> <JCHEM_REFRACTIVITY>
108.8137

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.66e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(3S,4S,5R)-5-(acetyloxy)-4-isopropyl-3-{[(2E)-2-methylbut-2-enoyl]oxy}-6-oxocyclohex-1-en-1-yl]methyl (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.001   3.850   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.667   4.620   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
CONECT    1    2    3    7                                                  
CONECT    2    1                                                            
CONECT    3    1    4   26                                                  
CONECT    4    3    5   23                                                  
CONECT    5    4    6   16                                                  
CONECT    6    5    7                                                       
CONECT    7    6    1    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12                                                            
CONECT   16    5   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19                                                            
CONECT   23    4   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26    3   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   58    0
END

View in JSmol

Synonyms

Value	Source
(3S)-4a-Isopropyl-3a,5b-dihydroxy-1-[((e)-2-methyl-2-butenoyloxy)methyl]-1-cyclohexen-6-one 3-[(e)-2-methyl-2-butenoate]5-acetate	Generator
(3S)-4a-Isopropyl-3a,5b-dihydroxy-1-[((e)-2-methyl-2-butenoyloxy)methyl]-1-cyclohexen-6-one 3-[(e)-2-methyl-2-butenoic acid]5-acetic acid	Generator
(3S)-4alpha-Isopropyl-3alpha,5beta-dihydroxy-1-[((e)-2-methyl-2-butenoyloxy)methyl]-1-cyclohexen-6-one 3-[(e)-2-methyl-2-butenoic acid]5-acetic acid	Generator
(3S)-4Α-isopropyl-3α,5β-dihydroxy-1-[((e)-2-methyl-2-butenoyloxy)methyl]-1-cyclohexen-6-one 3-[(e)-2-methyl-2-butenoate]5-acetate	Generator
(3S)-4Α-isopropyl-3α,5β-dihydroxy-1-[((e)-2-methyl-2-butenoyloxy)methyl]-1-cyclohexen-6-one 3-[(e)-2-methyl-2-butenoic acid]5-acetic acid	Generator

Chemical Formula

C₂₂H₃₀O₇

Average Mass

406.4750 Da

Monoisotopic Mass

406.19915 Da

IUPAC Name

[(3S,4S,5R)-5-(acetyloxy)-3-{[(2E)-2-methylbut-2-enoyl]oxy}-6-oxo-4-(propan-2-yl)cyclohex-1-en-1-yl]methyl (2E)-2-methylbut-2-enoate

Traditional Name

[(3S,4S,5R)-5-(acetyloxy)-4-isopropyl-3-{[(2E)-2-methylbut-2-enoyl]oxy}-6-oxocyclohex-1-en-1-yl]methyl (2E)-2-methylbut-2-enoate

CAS Registry Number

Not Available

SMILES

C\C=C(/C)C(=O)OCC1=C[C@H](OC(=O)C(\C)=C\C)[C@H](C(C)C)[C@@H](OC(C)=O)C1=O

InChI Identifier

InChI=1S/C22H30O7/c1-8-13(5)21(25)27-11-16-10-17(29-22(26)14(6)9-2)18(12(3)4)20(19(16)24)28-15(7)23/h8-10,12,17-18,20H,11H2,1-7H3/b13-8+,14-9+/t17-,18-,20+/m0/s1

InChI Key

VQVOLXGHPXSBKK-ZDKFFNMDSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Sphaeranthus bullatus	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Menthane monoterpenoids

Alternative Parents

Substituents

Monocyclic monoterpenoid
P-menthane monoterpenoid
Tricarboxylic acid or derivatives
Fatty acid ester
Cyclohexenone
Alpha-acyloxy ketone
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Cyclic ketone
Ketone
Carboxylic acid ester
Carboxylic acid derivative
Carbonyl group
Organic oxide
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic 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	3.37	ALOGPS
logP	4.5	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	16.05	ChemAxon
pKa (Strongest Basic)	-6.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	95.97 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	108.81 m³·mol⁻¹	ChemAxon
Polarizability	44.03 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

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

14589112

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for [1S-[1alpha(E),3(E),5beta,6alpha]]-5-(acetyloxy)-6-(1-methylethyl)-3-[[(2-methyl-1-oxo-2-butenyl)oxy]methyl]-4-oxo-2-cyclohexen-1-yl ester (NP0057770)

MOL for NP0057770 ([1S-[1alpha(E),3(E),5beta,6alpha]]-5-(acetyloxy)-6-(1-methylethyl)-3-[[(2-methyl-1-oxo-2-butenyl)oxy]methyl]-4-oxo-2-cyclohexen-1-yl ester)

3D MOL for NP0057770 ([1S-[1alpha(E),3(E),5beta,6alpha]]-5-(acetyloxy)-6-(1-methylethyl)-3-[[(2-methyl-1-oxo-2-butenyl)oxy]methyl]-4-oxo-2-cyclohexen-1-yl ester)

3D SDF for NP0057770 ([1S-[1alpha(E),3(E),5beta,6alpha]]-5-(acetyloxy)-6-(1-methylethyl)-3-[[(2-methyl-1-oxo-2-butenyl)oxy]methyl]-4-oxo-2-cyclohexen-1-yl ester)

3D-SDF for NP0057770 ([1S-[1alpha(E),3(E),5beta,6alpha]]-5-(acetyloxy)-6-(1-methylethyl)-3-[[(2-methyl-1-oxo-2-butenyl)oxy]methyl]-4-oxo-2-cyclohexen-1-yl ester)

PDB for NP0057770 ([1S-[1alpha(E),3(E),5beta,6alpha]]-5-(acetyloxy)-6-(1-methylethyl)-3-[[(2-methyl-1-oxo-2-butenyl)oxy]methyl]-4-oxo-2-cyclohexen-1-yl ester)

3D PDB for NP0057770 ([1S-[1alpha(E),3(E),5beta,6alpha]]-5-(acetyloxy)-6-(1-methylethyl)-3-[[(2-methyl-1-oxo-2-butenyl)oxy]methyl]-4-oxo-2-cyclohexen-1-yl ester)

SMILES for NP0057770 ([1S-[1alpha(E),3(E),5beta,6alpha]]-5-(acetyloxy)-6-(1-methylethyl)-3-[[(2-methyl-1-oxo-2-butenyl)oxy]methyl]-4-oxo-2-cyclohexen-1-yl ester)

INCHI for NP0057770 ([1S-[1alpha(E),3(E),5beta,6alpha]]-5-(acetyloxy)-6-(1-methylethyl)-3-[[(2-methyl-1-oxo-2-butenyl)oxy]methyl]-4-oxo-2-cyclohexen-1-yl ester)

Structure for NP0057770 ([1S-[1alpha(E),3(E),5beta,6alpha]]-5-(acetyloxy)-6-(1-methylethyl)-3-[[(2-methyl-1-oxo-2-butenyl)oxy]methyl]-4-oxo-2-cyclohexen-1-yl ester)

3D Structure for NP0057770 ([1S-[1alpha(E),3(E),5beta,6alpha]]-5-(acetyloxy)-6-(1-methylethyl)-3-[[(2-methyl-1-oxo-2-butenyl)oxy]methyl]-4-oxo-2-cyclohexen-1-yl ester)