NP-MRD: Showing NP-Card for (6 S,7E)− 6-hydroxy-4,7-megastigmadien-3,9-dione (S(+)-dehydrovomifoliol) (NP0331773)

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Record Information

Version

2.0

Created at

2023-08-23 04:02:03 UTC

Updated at

2024-09-03 04:16:51 UTC

NP-MRD ID

NP0331773

Natural Product DOI

https://doi.org/10.57994/0833

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6 S,7E)− 6-hydroxy-4,7-megastigmadien-3,9-dione (S(+)-dehydrovomifoliol)

Description

(+)-Dehydrovomifoliol belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Thus, (+)-dehydrovomifoliol is considered to be an isoprenoid. (6 S,7E)− 6-hydroxy-4,7-megastigmadien-3,9-dione (S(+)-dehydrovomifoliol) was first documented in 2019 (PMID: 31542954). Based on a literature review a small amount of articles have been published on (+)-Dehydrovomifoliol (PMID: 33668728) (PMID: 33383824) (PMID: 32627491) (PMID: 31359654).

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202101283D          

 34 34  0  0  0  0            999 V2000
    4.9607    0.2337   -2.8386 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5084   -0.1620   -2.8219 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1030   -1.1415   -3.4440 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5897    0.6678   -1.9952 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2754    0.3906   -1.9424 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2339    1.1504   -1.1414 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8883    2.2506   -0.5047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8067    1.7033   -2.1129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4325    2.9179   -2.9250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0047    1.1188   -2.2985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3886   -0.1233   -1.5851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4937   -0.6164   -1.7960 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3822   -0.7722   -0.6614 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4319    0.2609   -0.0196 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6289   -0.4956    0.8151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2396    1.1215    0.9922 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3419    0.1550   -3.8606 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0935    1.2680   -2.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5237   -0.4304   -2.1781 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0227    1.4924   -1.4414 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9048   -0.4529   -2.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2023    2.8772   -0.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2998    3.7909   -2.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4972    2.7456   -3.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2037    3.1718   -3.6606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7430    1.4977   -2.9974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9363   -1.3093    0.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8312   -1.5194   -1.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1594   -1.0497    1.6365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1784   -1.2273    0.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3559    0.1955    1.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7759    0.4855    1.7065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5818    1.7732    1.5782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9829    1.7574    0.5018 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
 13 14  1  0  0  0  0
  4  2  1  0  0  0  0
 11 10  1  0  0  0  0
  2  1  1  0  0  0  0
 10  8  2  0  0  0  0
 11 12  2  0  0  0  0
  8  6  1  0  0  0  0
  8  9  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
  6  5  1  0  0  0  0
  6  7  1  1  0  0  0
 13 11  1  0  0  0  0
  2  3  2  0  0  0  0
 13 27  1  0  0  0  0
 13 28  1  0  0  0  0
 10 26  1  0  0  0  0
  5 21  1  0  0  0  0
  4 20  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  9 23  1  0  0  0  0
  9 24  1  0  0  0  0
  9 25  1  0  0  0  0
 15 29  1  0  0  0  0
 15 30  1  0  0  0  0
 15 31  1  0  0  0  0
 16 32  1  0  0  0  0
 16 33  1  0  0  0  0
 16 34  1  0  0  0  0
  7 22  1  0  0  0  0
M  END

     RDKit          3D

 34 34  0  0  0  0  0  0  0  0999 V2000
    4.9607    0.2337   -2.8386 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5084   -0.1620   -2.8219 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1030   -1.1415   -3.4440 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5897    0.6678   -1.9952 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2754    0.3906   -1.9424 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2339    1.1504   -1.1414 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8883    2.2506   -0.5047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8067    1.7033   -2.1129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4325    2.9179   -2.9250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0047    1.1188   -2.2985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3886   -0.1233   -1.5851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4937   -0.6164   -1.7960 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3822   -0.7722   -0.6614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4319    0.2609   -0.0196 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6289   -0.4956    0.8151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2396    1.1215    0.9922 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3419    0.1550   -3.8606 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0935    1.2680   -2.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5237   -0.4304   -2.1781 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0227    1.4924   -1.4414 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9048   -0.4529   -2.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2023    2.8772   -0.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2998    3.7909   -2.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4972    2.7456   -3.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2037    3.1718   -3.6606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7430    1.4977   -2.9974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9363   -1.3093    0.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8312   -1.5194   -1.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1594   -1.0497    1.6365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1784   -1.2273    0.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3559    0.1955    1.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7759    0.4855    1.7065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5818    1.7732    1.5782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9829    1.7574    0.5018 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0
 13 14  1  0
  4  2  1  0
 11 10  1  0
  2  1  1  0
 10  8  2  0
 11 12  2  0
  8  6  1  0
  8  9  1  0
  6 14  1  0
 14 15  1  1
 14 16  1  0
  6  5  1  0
  6  7  1  1
 13 11  1  0
  2  3  2  0
 13 27  1  0
 13 28  1  0
 10 26  1  0
  5 21  1  0
  4 20  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  9 23  1  0
  9 24  1  0
  9 25  1  0
 15 29  1  0
 15 30  1  0
 15 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
  7 22  1  0
M  END


  Mrv1652306202101283D          

 34 34  0  0  0  0            999 V2000
    4.9607    0.2337   -2.8386 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5084   -0.1620   -2.8219 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1030   -1.1415   -3.4440 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5897    0.6678   -1.9952 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2754    0.3906   -1.9424 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2339    1.1504   -1.1414 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8883    2.2506   -0.5047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8067    1.7033   -2.1129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4325    2.9179   -2.9250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0047    1.1188   -2.2985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3886   -0.1233   -1.5851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4937   -0.6164   -1.7960 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3822   -0.7722   -0.6614 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4319    0.2609   -0.0196 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6289   -0.4956    0.8151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2396    1.1215    0.9922 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3419    0.1550   -3.8606 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0935    1.2680   -2.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5237   -0.4304   -2.1781 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0227    1.4924   -1.4414 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9048   -0.4529   -2.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2023    2.8772   -0.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2998    3.7909   -2.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4972    2.7456   -3.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2037    3.1718   -3.6606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7430    1.4977   -2.9974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9363   -1.3093    0.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8312   -1.5194   -1.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1594   -1.0497    1.6365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1784   -1.2273    0.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3559    0.1955    1.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7759    0.4855    1.7065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5818    1.7732    1.5782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9829    1.7574    0.5018 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
 13 14  1  0  0  0  0
  4  2  1  0  0  0  0
 11 10  1  0  0  0  0
  2  1  1  0  0  0  0
 10  8  2  0  0  0  0
 11 12  2  0  0  0  0
  8  6  1  0  0  0  0
  8  9  1  0  0  0  0
  6 14  1  0  0  0  0
 14 15  1  1  0  0  0
 14 16  1  0  0  0  0
  6  5  1  0  0  0  0
  6  7  1  1  0  0  0
 13 11  1  0  0  0  0
  2  3  2  0  0  0  0
 13 27  1  0  0  0  0
 13 28  1  0  0  0  0
 10 26  1  0  0  0  0
  5 21  1  0  0  0  0
  4 20  1  0  0  0  0
  1 17  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  9 23  1  0  0  0  0
  9 24  1  0  0  0  0
  9 25  1  0  0  0  0
 15 29  1  0  0  0  0
 15 30  1  0  0  0  0
 15 31  1  0  0  0  0
 16 32  1  0  0  0  0
 16 33  1  0  0  0  0
 16 34  1  0  0  0  0
  7 22  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0331773

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1(\C([H])=C(/[H])C(=O)C([H])([H])[H])C(=C([H])C(=O)C([H])([H])C1(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C13H18O3/c1-9-7-11(15)8-12(3,4)13(9,16)6-5-10(2)14/h5-7,16H,8H2,1-4H3/b6-5+/t13-/m1/s1

> <INCHI_KEY>
JJRYPZMXNLLZFH-URWSZGRFSA-N

> <FORMULA>
C13H18O3

> <MOLECULAR_WEIGHT>
222.284

> <EXACT_MASS>
222.12559444

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
24.256379452859598

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S)-4-hydroxy-3,5,5-trimethyl-4-[(1E)-3-oxobut-1-en-1-yl]cyclohex-2-en-1-one

> <ALOGPS_LOGP>
1.41

> <JCHEM_LOGP>
1.6523240710000004

> <ALOGPS_LOGS>
-2.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.034527167005127

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.372685613937566

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5105853036630945

> <JCHEM_POLAR_SURFACE_AREA>
54.37

> <JCHEM_REFRACTIVITY>
63.926899999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.53e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dehydrovomifoliol

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 34 34  0  0  0  0  0  0  0  0999 V2000
    4.9607    0.2337   -2.8386 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5084   -0.1620   -2.8219 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1030   -1.1415   -3.4440 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5897    0.6678   -1.9952 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2754    0.3906   -1.9424 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2339    1.1504   -1.1414 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8883    2.2506   -0.5047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8067    1.7033   -2.1129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4325    2.9179   -2.9250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0047    1.1188   -2.2985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3886   -0.1233   -1.5851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4937   -0.6164   -1.7960 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3822   -0.7722   -0.6614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4319    0.2609   -0.0196 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6289   -0.4956    0.8151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2396    1.1215    0.9922 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3419    0.1550   -3.8606 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0935    1.2680   -2.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5237   -0.4304   -2.1781 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0227    1.4924   -1.4414 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9048   -0.4529   -2.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2023    2.8772   -0.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2998    3.7909   -2.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4972    2.7456   -3.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2037    3.1718   -3.6606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7430    1.4977   -2.9974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9363   -1.3093    0.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8312   -1.5194   -1.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1594   -1.0497    1.6365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1784   -1.2273    0.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3559    0.1955    1.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7759    0.4855    1.7065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5818    1.7732    1.5782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9829    1.7574    0.5018 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0
 13 14  1  0
  4  2  1  0
 11 10  1  0
  2  1  1  0
 10  8  2  0
 11 12  2  0
  8  6  1  0
  8  9  1  0
  6 14  1  0
 14 15  1  1
 14 16  1  0
  6  5  1  0
  6  7  1  1
 13 11  1  0
  2  3  2  0
 13 27  1  0
 13 28  1  0
 10 26  1  0
  5 21  1  0
  4 20  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  9 23  1  0
  9 24  1  0
  9 25  1  0
 15 29  1  0
 15 30  1  0
 15 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
  7 22  1  0
M  END

HEADER    PROTEIN                                 20-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-JUN-21         0                                  
HETATM    1  C   UNK     0       4.961   0.234  -2.839  0.00  0.00           C+0
HETATM    2  C   UNK     0       3.508  -0.162  -2.822  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.103  -1.141  -3.444  0.00  0.00           O+0
HETATM    4  C   UNK     0       2.590   0.668  -1.995  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.275   0.391  -1.942  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.234   1.150  -1.141  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.888   2.251  -0.505  0.00  0.00           O+0
HETATM    8  C   UNK     0      -0.807   1.703  -2.113  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.433   2.918  -2.925  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.005   1.119  -2.299  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.389  -0.123  -1.585  0.00  0.00           C+0
HETATM   12  O   UNK     0      -3.494  -0.616  -1.796  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.382  -0.772  -0.661  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.432   0.261  -0.020  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.629  -0.496   0.815  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.240   1.121   0.992  0.00  0.00           C+0
HETATM   17  H   UNK     0       5.342   0.155  -3.861  0.00  0.00           H+0
HETATM   18  H   UNK     0       5.093   1.268  -2.510  0.00  0.00           H+0
HETATM   19  H   UNK     0       5.524  -0.430  -2.178  0.00  0.00           H+0
HETATM   20  H   UNK     0       3.023   1.492  -1.441  0.00  0.00           H+0
HETATM   21  H   UNK     0       0.905  -0.453  -2.525  0.00  0.00           H+0
HETATM   22  H   UNK     0       0.202   2.877  -0.221  0.00  0.00           H+0
HETATM   23  H   UNK     0      -0.300   3.791  -2.279  0.00  0.00           H+0
HETATM   24  H   UNK     0       0.497   2.746  -3.476  0.00  0.00           H+0
HETATM   25  H   UNK     0      -1.204   3.172  -3.661  0.00  0.00           H+0
HETATM   26  H   UNK     0      -2.743   1.498  -2.997  0.00  0.00           H+0
HETATM   27  H   UNK     0      -1.936  -1.309   0.118  0.00  0.00           H+0
HETATM   28  H   UNK     0      -0.831  -1.519  -1.244  0.00  0.00           H+0
HETATM   29  H   UNK     0       0.159  -1.050   1.637  0.00  0.00           H+0
HETATM   30  H   UNK     0       1.178  -1.227   0.214  0.00  0.00           H+0
HETATM   31  H   UNK     0       1.356   0.196   1.256  0.00  0.00           H+0
HETATM   32  H   UNK     0      -1.776   0.486   1.706  0.00  0.00           H+0
HETATM   33  H   UNK     0      -0.582   1.773   1.578  0.00  0.00           H+0
HETATM   34  H   UNK     0      -1.983   1.757   0.502  0.00  0.00           H+0
CONECT    1    2   17   18   19                                             
CONECT    2    4    1    3                                                  
CONECT    3    2                                                            
CONECT    4    5    2   20                                                  
CONECT    5    4    6   21                                                  
CONECT    6    8   14    5    7                                             
CONECT    7    6   22                                                       
CONECT    8   10    6    9                                                  
CONECT    9    8   23   24   25                                             
CONECT   10   11    8   26                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   14   11   27   28                                             
CONECT   14   13    6   15   16                                             
CONECT   15   14   29   30   31                                             
CONECT   16   14   32   33   34                                             
CONECT   17    1                                                            
CONECT   18    1                                                            
CONECT   19    1                                                            
CONECT   20    4                                                            
CONECT   21    5                                                            
CONECT   22    7                                                            
CONECT   23    9                                                            
CONECT   24    9                                                            
CONECT   25    9                                                            
CONECT   26   10                                                            
CONECT   27   13                                                            
CONECT   28   13                                                            
CONECT   29   15                                                            
CONECT   30   15                                                            
CONECT   31   15                                                            
CONECT   32   16                                                            
CONECT   33   16                                                            
CONECT   34   16                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   68    0
END

RDKit          3D

34 34  0  0  0  0  0  0  0  0999 V2000
    4.9607    0.2337   -2.8386 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5084   -0.1620   -2.8219 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1030   -1.1415   -3.4440 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5897    0.6678   -1.9952 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2754    0.3906   -1.9424 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2339    1.1504   -1.1414 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8883    2.2506   -0.5047 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8067    1.7033   -2.1129 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4325    2.9179   -2.9250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0047    1.1188   -2.2985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3886   -0.1233   -1.5851 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4937   -0.6164   -1.7960 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3822   -0.7722   -0.6614 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4319    0.2609   -0.0196 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6289   -0.4956    0.8151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2396    1.1215    0.9922 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3419    0.1550   -3.8606 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0935    1.2680   -2.5099 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5237   -0.4304   -2.1781 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0227    1.4924   -1.4414 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9048   -0.4529   -2.5250 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2023    2.8772   -0.2207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2998    3.7909   -2.2786 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4972    2.7456   -3.4762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2037    3.1718   -3.6606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7430    1.4977   -2.9974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9363   -1.3093    0.1184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8312   -1.5194   -1.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1594   -1.0497    1.6365 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1784   -1.2273    0.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3559    0.1955    1.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7759    0.4855    1.7065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5818    1.7732    1.5782 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9829    1.7574    0.5018 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0
 13 14  1  0
  4  2  1  0
 11 10  1  0
  2  1  1  0
 10  8  2  0
 11 12  2  0
  8  6  1  0
  8  9  1  0
  6 14  1  0
 14 15  1  1
 14 16  1  0
  6  5  1  0
  6  7  1  1
 13 11  1  0
  2  3  2  0
 13 27  1  0
 13 28  1  0
 10 26  1  0
  5 21  1  0
  4 20  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  9 23  1  0
  9 24  1  0
  9 25  1  0
 15 29  1  0
 15 30  1  0
 15 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
  7 22  1  0
M  END

View in JSmol

Synonyms

Value	Source
(4S)-4-Hydroxy-3,5,5-trimethyl-4-[(1E)-3-oxobut-1-enyl]cyclohex-2-en-1-one	ChEBI
(6R)-6-Hydroxy-3-oxo-alpha-ionone	ChEBI
(6S)-6-Hydroxy-3-oxo-alpha-ionone	ChEBI
Dehydrovomifoliol	ChEBI
(6R)-6-Hydroxy-3-oxo-a-ionone	Generator
(6R)-6-Hydroxy-3-oxo-α-ionone	Generator
(6S)-6-Hydroxy-3-oxo-a-ionone	Generator
(6S)-6-Hydroxy-3-oxo-α-ionone	Generator

Chemical Formula

C₁₃H₁₈O₃

Average Mass

222.2840 Da

Monoisotopic Mass

222.12559 Da

IUPAC Name

(4S)-4-hydroxy-3,5,5-trimethyl-4-[(1E)-3-oxobut-1-en-1-yl]cyclohex-2-en-1-one

Traditional Name

dehydrovomifoliol

CAS Registry Number

Not Available

SMILES

[H]O[C@]1(\C([H])=C(/[H])C(=O)C([H])([H])[H])C(=C([H])C(=O)C([H])([H])C1(C([H])([H])[H])C([H])([H])[H])C([H])([H])[H]

InChI Identifier

InChI=1S/C13H18O3/c1-9-7-11(15)8-12(3,4)13(9,16)6-5-10(2)14/h5-7,16H,8H2,1-4H3/b6-5+/t13-/m1/s1

InChI Key

JJRYPZMXNLLZFH-URWSZGRFSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, CDCl3, experimental)	guangxzh@sina.com	Not Available	Not Available	2024-05-09	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl3, experimental)	guangxzh@sina.com	Not Available	Not Available	2024-05-09	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CD₃OD, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 400, CDCl₃, simulated)	Not Available	Not Available	Not Available	2024-05-09	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
orellana		Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Megastigmane sesquiterpenoid
Cyclofarsesane sesquiterpenoid
Ionone derivative
Cyclohexenone
Acryloyl-group
Enone
Alpha,beta-unsaturated ketone
Tertiary alcohol
Ketone
Cyclic ketone
Organic oxide
Organic oxygen compound
Organooxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

dehydrovomifoliol (CHEBI:4372 )
Cyclofarnesane sesquiterpenoids (C02533 )
Cyclofarnesane sesquiterpenoids (LMPR0103050009 )

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	1.41	ALOGPS
logP	1.65	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	13.37	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	63.93 m³·mol⁻¹	ChemAxon
Polarizability	24.26 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

FDB006379

KNApSAcK ID

Not Available

Chemspider ID

599941

KEGG Compound ID

C02533

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

4372

Good Scents ID

Not Available

References

General References

Yuzikhin OS, Gogoleva NE, Shaposhnikov AI, Konnova TA, Osipova EV, Syrova DS, Ermakova EA, Shevchenko VP, Nagaev IY, Shevchenko KV, Myasoedov NF, Safronova VI, Shavarda AL, Nizhnikov AA, Belimov AA, Gogolev YV: Rhizosphere Bacterium Rhodococcus sp. P1Y Metabolizes Abscisic Acid to Form Dehydrovomifoliol. Biomolecules. 2021 Feb 25;11(3). pii: biom11030345. doi: 10.3390/biom11030345. [PubMed:33668728 ]
Malarz J, Michalska K, Stojakowska A: Stem Lettuce and Its Metabolites: Does the Variety Make Any Difference? Foods. 2020 Dec 29;10(1). pii: foods10010059. doi: 10.3390/foods10010059. [PubMed:33383824 ]
Feng ZY, Ma YX, Wang H, Chen M: [Studies on chemical constituents of stems of Herpetospermum pedunculosum]. Zhongguo Zhong Yao Za Zhi. 2020 Jun;45(11):2571-2577. doi: 10.19540/j.cnki.cjcmm.20200227.201. [PubMed:32627491 ]
Bendjedou H, Barboni L, Maggi F, Bennaceur M, Benamar H: Alkaloids and sesquiterpenes from roots and leaves of Lycium europaeum L. (Solanaceae) with antioxidant and anti-acetylcholinesterase activities. Nat Prod Res. 2019 Sep 23:1-5. doi: 10.1080/14786419.2019.1666386. [PubMed:31542954 ]
Sun DX, Guo XF, A LT, Ma XL, Wei HY, Ma GX, Shi LL, Zhang J: [Chemical constituents from green walnut husks and their antitumor activity in vitro]. Zhongguo Zhong Yao Za Zhi. 2019 Jun;44(11):2278-2282. doi: 10.19540/j.cnki.cjcmm.20190321.201. [PubMed:31359654 ]

Showing NP-Card for (6 S,7E)− 6-hydroxy-4,7-megastigmadien-3,9-dione (S(+)-dehydrovomifoliol) (NP0331773)

MOL for NP0331773 ((6 S,7E)− 6-hydroxy-4,7-megastigmadien-3,9-dione (S(+)-dehydrovomifoliol))

3D MOL for NP0331773 ((6 S,7E)− 6-hydroxy-4,7-megastigmadien-3,9-dione (S(+)-dehydrovomifoliol))

3D SDF for NP0331773 ((6 S,7E)− 6-hydroxy-4,7-megastigmadien-3,9-dione (S(+)-dehydrovomifoliol))

3D-SDF for NP0331773 ((6 S,7E)− 6-hydroxy-4,7-megastigmadien-3,9-dione (S(+)-dehydrovomifoliol))

PDB for NP0331773 ((6 S,7E)− 6-hydroxy-4,7-megastigmadien-3,9-dione (S(+)-dehydrovomifoliol))

3D PDB for NP0331773 ((6 S,7E)− 6-hydroxy-4,7-megastigmadien-3,9-dione (S(+)-dehydrovomifoliol))

SMILES for NP0331773 ((6 S,7E)− 6-hydroxy-4,7-megastigmadien-3,9-dione (S(+)-dehydrovomifoliol))

INCHI for NP0331773 ((6 S,7E)− 6-hydroxy-4,7-megastigmadien-3,9-dione (S(+)-dehydrovomifoliol))

Structure for NP0331773 ((6 S,7E)− 6-hydroxy-4,7-megastigmadien-3,9-dione (S(+)-dehydrovomifoliol))

3D Structure for NP0331773 ((6 S,7E)− 6-hydroxy-4,7-megastigmadien-3,9-dione (S(+)-dehydrovomifoliol))