NP-MRD: Showing NP-Card for (1s,5s,6s)-3-(hydroxymethyl)-6-isopropyl-5-{[(2z)-2-methylbut-2-enoyl]oxy}-2-oxocyclohex-3-en-1-yl (2e)-4-hydroxy-2-methylbut-2-enoate (NP0146050)

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Record Information

Version

2.0

Created at

2022-09-02 01:22:27 UTC

Updated at

2022-09-02 01:22:28 UTC

NP-MRD ID

NP0146050

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,5s,6s)-3-(hydroxymethyl)-6-isopropyl-5-{[(2z)-2-methylbut-2-enoyl]oxy}-2-oxocyclohex-3-en-1-yl (2e)-4-hydroxy-2-methylbut-2-enoate

Description

(4S)-2-(Hydroxymethyl)-4alpha,6alpha-dihydroxy-5alpha-isopropyl-2-cyclohexen-1-one 4-[(Z)-2-methyl-2-butenoate]6-[(E)-2-methyl-4-hydroxy-2-butenoate] 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. Based on a literature review very few articles have been published on (4S)-2-(Hydroxymethyl)-4alpha,6alpha-dihydroxy-5alpha-isopropyl-2-cyclohexen-1-one 4-[(Z)-2-methyl-2-butenoate]6-[(E)-2-methyl-4-hydroxy-2-butenoate].

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022203222D          

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

     RDKit          3D

 55 55  0  0  0  0  0  0  0  0999 V2000
   -3.4006    2.1416    3.3512 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5450    2.8700    2.3885 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9085    2.2507    1.4190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0793    3.0915    0.5155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0386    0.8241    1.2790 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7488    0.1495    2.0632 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3792    0.1046    0.2580 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5606   -1.2672    0.1980 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2232   -1.5938   -1.0884 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6009   -2.1351   -2.1193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3566   -2.4265   -3.3718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6814   -2.0593   -3.2489 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1754   -2.4646   -2.0770 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3356   -3.1185   -2.9972 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5998   -1.9815   -0.8980 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.0960   -0.7120   -1.1435 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4618   -0.4808   -1.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1973   -1.4909   -0.8782 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0551    0.8273   -1.3769 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2390    2.0190   -1.6718 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3617    0.9509   -1.3398 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1217    2.2034   -1.5690 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3564    3.3042   -1.8397 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3148   -2.0876    0.2923 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3890   -2.0107    1.6009 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8506   -0.6725    2.0195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5401   -2.6154    2.6571 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8517    1.4187    3.9866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8370    2.8749    4.0902 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2923    1.6624    2.8786 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4537    3.9705    2.5097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6242    2.4240   -0.2204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3380    3.7105    1.0722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7964    3.7515   -0.0471 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2433   -1.6499    1.0136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2708   -1.3754   -1.1831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2119   -3.4960   -3.6290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8961   -1.7628   -4.1598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2349   -2.8764   -3.4426 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4308   -2.6845   -0.7114 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1682    1.6891   -1.6343 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4032    2.4084   -2.6975 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3031    2.8086   -0.8843 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9509    0.0482   -1.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6682    2.4153   -0.6029 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9251    2.0692   -2.3260 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5798    4.1032   -1.2901 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6917   -3.1585    0.2358 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2728   -2.6887    1.5469 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8493   -0.6908    2.5191 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8717    0.0952    1.2472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1479   -0.3013    2.8158 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2060   -1.8727    3.1037 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0537   -3.1065    3.4423 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1875   -3.4065    2.1916 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
 10 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 19 21  2  0
 21 22  1  0
 22 23  1  0
 15 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 24  8  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  4 32  1  0
  4 33  1  0
  4 34  1  0
  8 35  1  1
  9 36  1  0
 11 37  1  0
 11 38  1  0
 12 39  1  0
 15 40  1  1
 20 41  1  0
 20 42  1  0
 20 43  1  0
 21 44  1  0
 22 45  1  0
 22 46  1  0
 23 47  1  0
 24 48  1  6
 25 49  1  0
 26 50  1  0
 26 51  1  0
 26 52  1  0
 27 53  1  0
 27 54  1  0
 27 55  1  0
M  END


  Mrv1652309022203222D          

 27 27  0  0  1  0            999 V2000
    2.8579    3.3000    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
    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
    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
    0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   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
    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 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  1  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
   -0.7145   -1.2375    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
   -1.4289   -1.6500    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
   -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
   -2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  1  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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   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
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 10 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 15 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  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 15 24  1  0  0  0  0
  8 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0146050

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O7/c1-6-12(4)19(24)26-15-9-14(10-22)17(23)18(16(15)11(2)3)27-20(25)13(5)7-8-21/h6-7,9,11,15-16,18,21-22H,8,10H2,1-5H3/b12-6-,13-7+/t15-,16-,18-/m0/s1

> <INCHI_KEY>
CARMWCSYOJNGRD-AAIMVQAFSA-N

> <FORMULA>
C20H28O7

> <MOLECULAR_WEIGHT>
380.437

> <EXACT_MASS>
380.183503242

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
40.46157583733001

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
1.90

> <JCHEM_LOGP>
2.7821407266666665

> <ALOGPS_LOGS>
-3.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.404643391258205

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.71844205146126

> <JCHEM_PKA_STRONGEST_BASIC>
-2.5522277768403345

> <JCHEM_POLAR_SURFACE_AREA>
110.13000000000001

> <JCHEM_REFRACTIVITY>
101.43690000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.98e-01 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0       4.001   3.850   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       5.335  -0.000   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   24                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   13                                                  
CONECT   11   10   12                                                       
CONECT   12   11                                                            
CONECT   13   10   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16   24                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   15    8   25                                                  
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   54    0
END

View in JSmol

Synonyms

Value	Source
(4S)-2-(Hydroxymethyl)-4a,6a-dihydroxy-5a-isopropyl-2-cyclohexen-1-one 4-[(Z)-2-methyl-2-butenoate]6-[(e)-2-methyl-4-hydroxy-2-butenoate]	Generator
(4S)-2-(Hydroxymethyl)-4a,6a-dihydroxy-5a-isopropyl-2-cyclohexen-1-one 4-[(Z)-2-methyl-2-butenoic acid]6-[(e)-2-methyl-4-hydroxy-2-butenoic acid]	Generator
(4S)-2-(Hydroxymethyl)-4alpha,6alpha-dihydroxy-5alpha-isopropyl-2-cyclohexen-1-one 4-[(Z)-2-methyl-2-butenoic acid]6-[(e)-2-methyl-4-hydroxy-2-butenoic acid]	Generator
(4S)-2-(Hydroxymethyl)-4α,6α-dihydroxy-5α-isopropyl-2-cyclohexen-1-one 4-[(Z)-2-methyl-2-butenoate]6-[(e)-2-methyl-4-hydroxy-2-butenoate]	Generator
(4S)-2-(Hydroxymethyl)-4α,6α-dihydroxy-5α-isopropyl-2-cyclohexen-1-one 4-[(Z)-2-methyl-2-butenoic acid]6-[(e)-2-methyl-4-hydroxy-2-butenoic acid]	Generator

Chemical Formula

C₂₀H₂₈O₇

Average Mass

380.4370 Da

Monoisotopic Mass

380.18350 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H28O7/c1-6-12(4)19(24)26-15-9-14(10-22)17(23)18(16(15)11(2)3)27-20(25)13(5)7-8-21/h6-7,9,11,15-16,18,21-22H,8,10H2,1-5H3/b12-6-,13-7+/t15-,16-,18-/m0/s1

InChI Key

CARMWCSYOJNGRD-AAIMVQAFSA-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

Not Available

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
Fatty acid ester
Cyclohexenone
Alpha-acyloxy ketone
Dicarboxylic acid or derivatives
Fatty acyl
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Cyclic ketone
Ketone
Carboxylic acid ester
Carboxylic acid derivative
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
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	1.9	ALOGPS
logP	2.78	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	14.72	ChemAxon
pKa (Strongest Basic)	-2.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	110.13 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	101.44 m³·mol⁻¹	ChemAxon
Polarizability	40.46 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

15699876

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,5s,6s)-3-(hydroxymethyl)-6-isopropyl-5-{[(2z)-2-methylbut-2-enoyl]oxy}-2-oxocyclohex-3-en-1-yl (2e)-4-hydroxy-2-methylbut-2-enoate (NP0146050)

MOL for NP0146050 ((1s,5s,6s)-3-(hydroxymethyl)-6-isopropyl-5-{[(2z)-2-methylbut-2-enoyl]oxy}-2-oxocyclohex-3-en-1-yl (2e)-4-hydroxy-2-methylbut-2-enoate)

3D MOL for NP0146050 ((1s,5s,6s)-3-(hydroxymethyl)-6-isopropyl-5-{[(2z)-2-methylbut-2-enoyl]oxy}-2-oxocyclohex-3-en-1-yl (2e)-4-hydroxy-2-methylbut-2-enoate)

3D SDF for NP0146050 ((1s,5s,6s)-3-(hydroxymethyl)-6-isopropyl-5-{[(2z)-2-methylbut-2-enoyl]oxy}-2-oxocyclohex-3-en-1-yl (2e)-4-hydroxy-2-methylbut-2-enoate)

3D-SDF for NP0146050 ((1s,5s,6s)-3-(hydroxymethyl)-6-isopropyl-5-{[(2z)-2-methylbut-2-enoyl]oxy}-2-oxocyclohex-3-en-1-yl (2e)-4-hydroxy-2-methylbut-2-enoate)

PDB for NP0146050 ((1s,5s,6s)-3-(hydroxymethyl)-6-isopropyl-5-{[(2z)-2-methylbut-2-enoyl]oxy}-2-oxocyclohex-3-en-1-yl (2e)-4-hydroxy-2-methylbut-2-enoate)

3D PDB for NP0146050 ((1s,5s,6s)-3-(hydroxymethyl)-6-isopropyl-5-{[(2z)-2-methylbut-2-enoyl]oxy}-2-oxocyclohex-3-en-1-yl (2e)-4-hydroxy-2-methylbut-2-enoate)

SMILES for NP0146050 ((1s,5s,6s)-3-(hydroxymethyl)-6-isopropyl-5-{[(2z)-2-methylbut-2-enoyl]oxy}-2-oxocyclohex-3-en-1-yl (2e)-4-hydroxy-2-methylbut-2-enoate)

INCHI for NP0146050 ((1s,5s,6s)-3-(hydroxymethyl)-6-isopropyl-5-{[(2z)-2-methylbut-2-enoyl]oxy}-2-oxocyclohex-3-en-1-yl (2e)-4-hydroxy-2-methylbut-2-enoate)

Structure for NP0146050 ((1s,5s,6s)-3-(hydroxymethyl)-6-isopropyl-5-{[(2z)-2-methylbut-2-enoyl]oxy}-2-oxocyclohex-3-en-1-yl (2e)-4-hydroxy-2-methylbut-2-enoate)

3D Structure for NP0146050 ((1s,5s,6s)-3-(hydroxymethyl)-6-isopropyl-5-{[(2z)-2-methylbut-2-enoyl]oxy}-2-oxocyclohex-3-en-1-yl (2e)-4-hydroxy-2-methylbut-2-enoate)