NP-MRD: Showing NP-Card for 15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-6,12-dihydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadeca-4,14-dien-13-yl acetate (NP0222350)

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Record Information

Version

2.0

Created at

2022-09-06 00:10:02 UTC

Updated at

2022-09-06 00:10:02 UTC

NP-MRD ID

NP0222350

Secondary Accession Numbers

None

Natural Product Identification

Common Name

15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-6,12-dihydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadeca-4,14-dien-13-yl acetate

Description

(S)-Menthone 8-thioacetate, also known as 8-acetylthio-p-menthanone-3 or fema 3809, 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. 15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-6,12-dihydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadeca-4,14-dien-13-yl acetate is found in Physalis angulata and Physalis minima. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes (S)-Menthone 8-thioacetate is a flavouring ingredient (S)-Menthone 8-thioacetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241220112D          

 38 43  0  0  0  0            999 V2000
   -3.6064   -1.3614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6064   -2.1878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8915   -2.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1781   -2.1878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1781   -1.3614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8915   -0.9495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4633   -2.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7499   -2.1878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7499   -1.3614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4633   -0.9495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0378   -0.9495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0378   -0.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7499    0.2831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4633   -0.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7429   -1.2030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2236   -0.5377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7429    0.1247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8915   -0.1274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8915   -3.4273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1781   -0.5377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0378   -1.7759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9991   -1.9881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0378    0.6989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7429    0.9497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0267    1.3642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4591    1.3642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1753    0.9497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8902    1.3642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8902    2.1892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1753    2.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4591    2.1892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6064    0.9497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6064    2.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1753    3.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1781   -3.0141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8255   -1.9881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2386   -2.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2386   -1.2719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 19  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  4 35  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  5 20  1  0  0  0  0
  6 18  2  0  0  0  0
  7  8  1  0  0  0  0
  7 35  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 14  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  1  0  0  0  0
 11 21  1  0  0  0  0
 12 13  1  0  0  0  0
 12 17  1  0  0  0  0
 12 23  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 15 22  1  0  0  0  0
 16 17  2  0  0  0  0
 17 24  1  0  0  0  0
 22 36  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 31  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 32  2  0  0  0  0
 29 30  2  0  0  0  0
 29 33  1  0  0  0  0
 30 31  1  0  0  0  0
 30 34  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
M  END


  Mrv0541 02241220112D          

 38 43  0  0  0  0            999 V2000
   -3.6064   -1.3614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6064   -2.1878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8915   -2.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1781   -2.1878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1781   -1.3614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8915   -0.9495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4633   -2.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7499   -2.1878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7499   -1.3614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4633   -0.9495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0378   -0.9495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0378   -0.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7499    0.2831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4633   -0.1274    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7429   -1.2030    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2236   -0.5377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7429    0.1247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8915   -0.1274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8915   -3.4273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1781   -0.5377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0378   -1.7759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9991   -1.9881    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0378    0.6989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7429    0.9497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0267    1.3642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4591    1.3642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1753    0.9497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8902    1.3642    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8902    2.1892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1753    2.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4591    2.1892    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6064    0.9497    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6064    2.6009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1753    3.4273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1781   -3.0141    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8255   -1.9881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2386   -2.7042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2386   -1.2719    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3 19  1  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  4 35  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  5 20  1  0  0  0  0
  6 18  2  0  0  0  0
  7  8  1  0  0  0  0
  7 35  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 10 14  1  0  0  0  0
 11 12  1  0  0  0  0
 11 15  1  0  0  0  0
 11 21  1  0  0  0  0
 12 13  1  0  0  0  0
 12 17  1  0  0  0  0
 12 23  1  0  0  0  0
 13 14  1  0  0  0  0
 15 16  1  0  0  0  0
 15 22  1  0  0  0  0
 16 17  2  0  0  0  0
 17 24  1  0  0  0  0
 22 36  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 31  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 32  2  0  0  0  0
 29 30  2  0  0  0  0
 29 33  1  0  0  0  0
 30 31  1  0  0  0  0
 30 34  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0222350

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C1CC(C)=C(C)C(=O)O1)C1=CC(OC(C)=O)C2(O)C3CC4OC44C(O)C=CC(=O)C4(C)C3CCC12C

> <INCHI_IDENTIFIER>
InChI=1S/C30H38O8/c1-14-11-21(37-26(34)15(14)2)16(3)19-12-24(36-17(4)31)29(35)20-13-25-30(38-25)23(33)8-7-22(32)28(30,6)18(20)9-10-27(19,29)5/h7-8,12,16,18,20-21,23-25,33,35H,9-11,13H2,1-6H3

> <INCHI_KEY>
PLPXOWZTDPJPHC-UHFFFAOYSA-N

> <FORMULA>
C30H38O8

> <MOLECULAR_WEIGHT>
526.6179

> <EXACT_MASS>
526.256668192

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_AVERAGE_POLARIZABILITY>
56.63071121362462

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
15-[1-(4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl]-6,12-dihydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadeca-4,14-dien-13-yl acetate

> <ALOGPS_LOGP>
2.33

> <JCHEM_LOGP>
2.8979490179999985

> <ALOGPS_LOGS>
-4.21

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.617999867149305

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.962631011294032

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4735902737671163

> <JCHEM_POLAR_SURFACE_AREA>
122.66

> <JCHEM_REFRACTIVITY>
138.0801

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.21e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-6,12-dihydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadeca-4,14-dien-13-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -6.732  -2.541   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.732  -4.084   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.397  -4.855   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.066  -4.084   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.066  -2.541   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.397  -1.772   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.731  -4.855   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.400  -4.084   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.400  -2.541   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.731  -1.772   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.071  -1.772   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.071  -0.238   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.400   0.528   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.731  -0.238   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.387  -2.246   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.284  -1.004   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.387   0.233   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -5.397  -0.238   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -5.397  -6.398   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -4.066  -1.004   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      -0.071  -3.315   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       1.865  -3.711   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      -0.071   1.305   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.387   1.773   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.050   2.547   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.724   2.547   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.061   1.773   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       5.395   2.547   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       5.395   4.087   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       4.061   4.855   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.724   4.087   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       6.732   1.773   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       6.732   4.855   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.061   6.398   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      -4.066  -5.626   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       3.408  -3.711   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.179  -5.048   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       4.179  -2.374   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4   19                                                  
CONECT    4    3    5    7   35                                             
CONECT    5    4    6   10   20                                             
CONECT    6    1    5   18                                                  
CONECT    7    4    8   35                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    5    9   14                                                  
CONECT   11    9   12   15   21                                             
CONECT   12   11   13   17   23                                             
CONECT   13   12   14                                                       
CONECT   14   10   13                                                       
CONECT   15   11   16   22                                                  
CONECT   16   15   17                                                       
CONECT   17   12   16   24                                                  
CONECT   18    6                                                            
CONECT   19    3                                                            
CONECT   20    5                                                            
CONECT   21   11                                                            
CONECT   22   15   36                                                       
CONECT   23   12                                                            
CONECT   24   17   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   32                                                  
CONECT   29   28   30   33                                                  
CONECT   30   29   31   34                                                  
CONECT   31   26   30                                                       
CONECT   32   28                                                            
CONECT   33   29                                                            
CONECT   34   30                                                            
CONECT   35    4    7                                                       
CONECT   36   22   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   86    0
END

View in JSmol

Synonyms

Value	Source
(S)-Menthone 8-thioacetic acid	Generator
8-Acetylthio-p-menthanone-3	HMDB
FEMA 3809	HMDB
Menthone 8-thioacetate	HMDB
15-[1-(4,5-Dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl]-6,12-dihydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadeca-4,14-dien-13-yl acetic acid	Generator

Chemical Formula

C₃₀H₃₈O₈

Average Mass

526.6179 Da

Monoisotopic Mass

526.25667 Da

IUPAC Name

15-[1-(4,5-dimethyl-6-oxo-3,6-dihydro-2H-pyran-2-yl)ethyl]-6,12-dihydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadeca-4,14-dien-13-yl acetate

Traditional Name

15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-6,12-dihydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadeca-4,14-dien-13-yl acetate

CAS Registry Number

Not Available

SMILES

CC(C1CC(C)=C(C)C(=O)O1)C1=CC(OC(C)=O)C2(O)C3CC4OC44C(O)C=CC(=O)C4(C)C3CCC12C

InChI Identifier

InChI=1S/C30H38O8/c1-14-11-21(37-26(34)15(14)2)16(3)19-12-24(36-17(4)31)29(35)20-13-25-30(38-25)23(33)8-7-22(32)28(30,6)18(20)9-10-27(19,29)5/h7-8,12,16,18,20-21,23-25,33,35H,9-11,13H2,1-6H3

InChI Key

PLPXOWZTDPJPHC-UHFFFAOYSA-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
Physalis angulata	LOTUS Database	35616633
Physalis minima	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
Ketone
Thiocarboxylic acid ester
Cyclic ketone
Carbothioic s-ester
Sulfenyl compound
Thiocarboxylic acid or derivatives
Carboxylic acid derivative
Carbonyl group
Organosulfur compound
Organooxygen compound
Organic oxygen compound
Organic oxide
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	2.33	ALOGPS
logP	2.9	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	12.96	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	122.66 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	138.08 m³·mol⁻¹	ChemAxon
Polarizability	56.63 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0037386

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016428

KNApSAcK ID

Not Available

Chemspider ID

83635

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

92649

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-6,12-dihydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadeca-4,14-dien-13-yl acetate (NP0222350)

MOL for NP0222350 (15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-6,12-dihydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadeca-4,14-dien-13-yl acetate)

3D MOL for NP0222350 (15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-6,12-dihydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadeca-4,14-dien-13-yl acetate)

3D SDF for NP0222350 (15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-6,12-dihydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadeca-4,14-dien-13-yl acetate)

3D-SDF for NP0222350 (15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-6,12-dihydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadeca-4,14-dien-13-yl acetate)

PDB for NP0222350 (15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-6,12-dihydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadeca-4,14-dien-13-yl acetate)

3D PDB for NP0222350 (15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-6,12-dihydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadeca-4,14-dien-13-yl acetate)

SMILES for NP0222350 (15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-6,12-dihydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadeca-4,14-dien-13-yl acetate)

INCHI for NP0222350 (15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-6,12-dihydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadeca-4,14-dien-13-yl acetate)

Structure for NP0222350 (15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-6,12-dihydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadeca-4,14-dien-13-yl acetate)

3D Structure for NP0222350 (15-[1-(4,5-dimethyl-6-oxo-2,3-dihydropyran-2-yl)ethyl]-6,12-dihydroxy-2,16-dimethyl-3-oxo-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadeca-4,14-dien-13-yl acetate)