NP-MRD: Showing NP-Card for (1s,5r,6r)-3-(hydroxymethyl)-6-isopropyl-5-{[(2z)-2-methylbut-2-enoyl]oxy}-2-oxocyclohex-3-en-1-yl (2r,3r)-2,3-dimethyloxirane-2-carboxylate (NP0303804)

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Record Information

Version

2.0

Created at

2022-09-10 18:27:42 UTC

Updated at

2022-09-10 18:27:42 UTC

NP-MRD ID

NP0303804

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,5r,6r)-3-(hydroxymethyl)-6-isopropyl-5-{[(2z)-2-methylbut-2-enoyl]oxy}-2-oxocyclohex-3-en-1-yl (2r,3r)-2,3-dimethyloxirane-2-carboxylate

Description

CHEMBL4218380 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,5r,6r)-3-(hydroxymethyl)-6-isopropyl-5-{[(2z)-2-methylbut-2-enoyl]oxy}-2-oxocyclohex-3-en-1-yl (2r,3r)-2,3-dimethyloxirane-2-carboxylate is found in Sphaeranthus africanus. Based on a literature review very few articles have been published on CHEMBL4218380.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102220272D          

 27 28  0  0  1  0            999 V2000
    6.3027    9.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5275    9.3218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8955    8.7915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1203    9.0736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0388    7.9790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8140    7.6968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4068    7.4487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5500    6.6362    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3253    6.3541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4685    5.5416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2438    5.2594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8758    5.7897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8366    5.0113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9798    4.1988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0613    5.2935    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4293    4.7632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5726    3.9507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3478    3.6685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9406    3.4204    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3086    3.9507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3531    2.7059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5281    2.7059    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8136    2.2934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9180    6.1059    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1428    6.3881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9995    7.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5108    5.8578    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  6  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
 19 17  1  6  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  6  0  0  0
 15 24  1  0  0  0  0
  8 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
M  END

     RDKit          3D

 55 56  0  0  0  0  0  0  0  0999 V2000
    4.2865    1.3957   -0.8821 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0459    2.7223   -0.3106 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9632    2.9964    0.3724 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7471    4.3799    0.9490 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9344    2.0191    0.6129 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9113    2.3614    1.2883 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9968    0.7102    0.1453 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9612   -0.1742    0.4270 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4264   -1.2567    1.3404 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5732   -2.2284    1.5882 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9859   -3.3256    2.4876 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1604   -3.4226    3.6040 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7466   -2.1644    0.9525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6446   -2.8958    1.4379 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0864   -1.3151   -0.1973 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0580   -0.3415    0.0325 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2745   -0.2765   -0.6370 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4849   -1.1622   -1.4975 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3143    0.7473   -0.4062 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6883    0.3564   -0.9292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9639    2.0764   -0.8366 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2352    1.8216    0.5032 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0940    2.0305    1.4944 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2222   -0.7389   -0.7459 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.9619   -1.8416   -1.4635 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2889   -1.3953   -2.0185 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1516   -2.4099   -2.6037 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3076    0.6395   -0.0627 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5048    1.1777   -1.6318 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2818    1.4042   -1.3902 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7604    3.5373   -0.4308 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7440    4.8625    1.0504 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0839    4.9696    0.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2410    4.2411    1.9144 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1682    0.3681    1.0373 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4007   -1.2123    1.7496 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0096   -3.1567    2.8637 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9908   -4.3094    1.9537 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2716   -4.2953    3.6239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5042   -1.9929   -1.0010 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5612    0.0740   -1.9965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0541   -0.5729   -0.4246 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4214    1.1430   -0.7517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1753    2.3021    0.8524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3002    1.3836    2.3563 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1116    1.9064    1.0315 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1229    3.0851    1.8991 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0012    0.0567   -1.4532 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1583   -2.7077   -0.7735 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0623   -1.2359   -1.2394 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1548   -0.4847   -2.6716 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7067   -2.1662   -2.7301 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4527   -1.6188   -3.1202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4723   -3.2686   -2.2778 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8452   -2.7983   -3.3722 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
 19 17  1  1
 19 20  1  0
 19 21  1  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
 22 19  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  6
 20 41  1  0
 20 42  1  0
 20 43  1  0
 22 44  1  1
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 23 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


  Mrv1652309102220272D          

 27 28  0  0  1  0            999 V2000
    6.3027    9.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5275    9.3218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8955    8.7915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1203    9.0736    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0388    7.9790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8140    7.6968    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4068    7.4487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5500    6.6362    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3253    6.3541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4685    5.5416    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2438    5.2594    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8758    5.7897    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8366    5.0113    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9798    4.1988    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0613    5.2935    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4293    4.7632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5726    3.9507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3478    3.6685    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9406    3.4204    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3086    3.9507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3531    2.7059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5281    2.7059    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8136    2.2934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9180    6.1059    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1428    6.3881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9995    7.2006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5108    5.8578    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  6  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
 19 17  1  6  0  0  0
 19 20  1  1  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  6  0  0  0
 15 24  1  0  0  0  0
  8 24  1  0  0  0  0
 24 25  1  6  0  0  0
 25 26  1  0  0  0  0
 25 27  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0303804

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H28O7/c1-7-11(4)18(23)25-14-8-13(9-21)16(22)17(15(14)10(2)3)26-19(24)20(6)12(5)27-20/h7-8,10,12,14-15,17,21H,9H2,1-6H3/b11-7-/t12-,14-,15-,17+,20-/m1/s1

> <INCHI_KEY>
ABWZXWZSTAKDDW-YSGBXONQSA-N

> <FORMULA>
C20H28O7

> <MOLECULAR_WEIGHT>
380.437

> <EXACT_MASS>
380.183503242

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
55

> <JCHEM_AVERAGE_POLARIZABILITY>
40.111821533777324

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,5R,6R)-3-(hydroxymethyl)-5-{[(2Z)-2-methylbut-2-enoyl]oxy}-2-oxo-6-(propan-2-yl)cyclohex-3-en-1-yl (2R,3R)-2,3-dimethyloxirane-2-carboxylate

> <JCHEM_LOGP>
3.006750771666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.823699556186988

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.822540779726964

> <JCHEM_PKA_STRONGEST_BASIC>
-2.821553411289999

> <JCHEM_POLAR_SURFACE_AREA>
102.43

> <JCHEM_REFRACTIVITY>
98.34570000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,5R,6R)-3-(hydroxymethyl)-6-isopropyl-5-{[(2Z)-2-methylbut-2-enoyl]oxy}-2-oxocyclohex-3-en-1-yl (2R,3R)-2,3-dimethyloxirane-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      11.765  16.874   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.318  17.401   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.138  16.411   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.691  16.937   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.406  14.894   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      10.853  14.367   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0       8.226  13.904   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.493  12.388   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.941  11.861   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.208  10.344   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      11.655   9.818   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      12.835  10.807   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.028   9.354   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       9.296   7.838   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       7.581   9.881   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.401   8.891   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.669   7.375   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.116   6.848   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.489   6.385   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.309   7.375   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.259   5.051   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.719   5.051   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.385   4.281   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.314  11.398   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.867  11.924   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.599  13.441   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.687  10.935   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   22                                             
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   19   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   56    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₀H₂₈O₇

Average Mass

380.4370 Da

Monoisotopic Mass

380.18350 Da

IUPAC Name

(1S,5R,6R)-3-(hydroxymethyl)-5-{[(2Z)-2-methylbut-2-enoyl]oxy}-2-oxo-6-(propan-2-yl)cyclohex-3-en-1-yl (2R,3R)-2,3-dimethyloxirane-2-carboxylate

Traditional Name

(1S,5R,6R)-3-(hydroxymethyl)-6-isopropyl-5-{[(2Z)-2-methylbut-2-enoyl]oxy}-2-oxocyclohex-3-en-1-yl (2R,3R)-2,3-dimethyloxirane-2-carboxylate

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@]2(C)O[C@@H]2C)[C@@H]1C(C)C

InChI Identifier

InChI=1S/C20H28O7/c1-7-11(4)18(23)25-14-8-13(9-21)16(22)17(15(14)10(2)3)26-19(24)20(6)12(5)27-20/h7-8,10,12,14-15,17,21H,9H2,1-6H3/b11-7-/t12-,14-,15-,17+,20-/m1/s1

InChI Key

ABWZXWZSTAKDDW-YSGBXONQSA-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
Sphaeranthus africanus	LOTUS Database	35616633

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
Cyclohexenone
Fatty acid ester
Alpha-acyloxy ketone
Dicarboxylic acid or derivatives
Fatty acyl
Oxirane carboxylic acid
Oxirane carboxylic acid or derivatives
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Ketone
Cyclic ketone
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Carbonyl group
Organic oxide
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Primary alcohol
Aliphatic heteromonocyclic compound

Molecular Framework

Aliphatic heteromonocyclic 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	3.01	ChemAxon
pKa (Strongest Acidic)	14.82	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	102.43 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	98.35 m³·mol⁻¹	ChemAxon
Polarizability	40.11 Å³	ChemAxon
Number of Rings	2	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

28287231

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

145970294

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,5r,6r)-3-(hydroxymethyl)-6-isopropyl-5-{[(2z)-2-methylbut-2-enoyl]oxy}-2-oxocyclohex-3-en-1-yl (2r,3r)-2,3-dimethyloxirane-2-carboxylate (NP0303804)

MOL for NP0303804 ((1s,5r,6r)-3-(hydroxymethyl)-6-isopropyl-5-{[(2z)-2-methylbut-2-enoyl]oxy}-2-oxocyclohex-3-en-1-yl (2r,3r)-2,3-dimethyloxirane-2-carboxylate)

3D MOL for NP0303804 ((1s,5r,6r)-3-(hydroxymethyl)-6-isopropyl-5-{[(2z)-2-methylbut-2-enoyl]oxy}-2-oxocyclohex-3-en-1-yl (2r,3r)-2,3-dimethyloxirane-2-carboxylate)

3D SDF for NP0303804 ((1s,5r,6r)-3-(hydroxymethyl)-6-isopropyl-5-{[(2z)-2-methylbut-2-enoyl]oxy}-2-oxocyclohex-3-en-1-yl (2r,3r)-2,3-dimethyloxirane-2-carboxylate)

3D-SDF for NP0303804 ((1s,5r,6r)-3-(hydroxymethyl)-6-isopropyl-5-{[(2z)-2-methylbut-2-enoyl]oxy}-2-oxocyclohex-3-en-1-yl (2r,3r)-2,3-dimethyloxirane-2-carboxylate)

PDB for NP0303804 ((1s,5r,6r)-3-(hydroxymethyl)-6-isopropyl-5-{[(2z)-2-methylbut-2-enoyl]oxy}-2-oxocyclohex-3-en-1-yl (2r,3r)-2,3-dimethyloxirane-2-carboxylate)

3D PDB for NP0303804 ((1s,5r,6r)-3-(hydroxymethyl)-6-isopropyl-5-{[(2z)-2-methylbut-2-enoyl]oxy}-2-oxocyclohex-3-en-1-yl (2r,3r)-2,3-dimethyloxirane-2-carboxylate)

SMILES for NP0303804 ((1s,5r,6r)-3-(hydroxymethyl)-6-isopropyl-5-{[(2z)-2-methylbut-2-enoyl]oxy}-2-oxocyclohex-3-en-1-yl (2r,3r)-2,3-dimethyloxirane-2-carboxylate)

INCHI for NP0303804 ((1s,5r,6r)-3-(hydroxymethyl)-6-isopropyl-5-{[(2z)-2-methylbut-2-enoyl]oxy}-2-oxocyclohex-3-en-1-yl (2r,3r)-2,3-dimethyloxirane-2-carboxylate)

Structure for NP0303804 ((1s,5r,6r)-3-(hydroxymethyl)-6-isopropyl-5-{[(2z)-2-methylbut-2-enoyl]oxy}-2-oxocyclohex-3-en-1-yl (2r,3r)-2,3-dimethyloxirane-2-carboxylate)

3D Structure for NP0303804 ((1s,5r,6r)-3-(hydroxymethyl)-6-isopropyl-5-{[(2z)-2-methylbut-2-enoyl]oxy}-2-oxocyclohex-3-en-1-yl (2r,3r)-2,3-dimethyloxirane-2-carboxylate)