NP-MRD: Showing NP-Card for 4-[(1'R,2'R,5'S)-1',2',5'-trihydroxy-2',6',6'-trimethyl-1'-cyclohexyl]-3E+ (NP0038832)

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Record Information

Version

2.0

Created at

2021-06-20 21:25:16 UTC

Updated at

2021-06-30 00:11:49 UTC

NP-MRD ID

NP0038832

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-[(1'R,2'R,5'S)-1',2',5'-trihydroxy-2',6',6'-trimethyl-1'-cyclohexyl]-3E+

Provided By

JEOL Database JEOL Logo

Description

Trihydroxy-beta-ionone belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 4-[(1'R,2'R,5'S)-1',2',5'-trihydroxy-2',6',6'-trimethyl-1'-cyclohexyl]-3E+ is found in Rehmannia glutinosa and Rehmannia glutinosa var. hueichingensis.. 4-[(1'R,2'R,5'S)-1',2',5'-trihydroxy-2',6',6'-trimethyl-1'-cyclohexyl]-3E+ was first documented in 2015 (PMID: 25232801). Based on a literature review very few articles have been published on Trihydroxy-beta-ionone.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306202123253D          

 39 39  0  0  0  0            999 V2000
   -0.1805   -0.3470   -5.7300 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7983   -0.2110   -4.5941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0078   -0.1038   -4.7926 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3086   -0.2150   -3.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9648   -0.4413   -2.8245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5231   -0.4575   -1.4017 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4144   -0.5245   -0.4796 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3091    0.8801   -1.0689 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3466    2.1023   -1.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4311    1.2106   -2.0864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8974    0.7698    0.3697 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6927    1.9171    0.6793 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7582   -0.4756    0.5777 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9969   -1.7555    0.2598 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4072   -1.7562   -1.1645 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6138   -3.0631   -1.3576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4916   -1.8043   -2.1037 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3500   -0.2249   -6.6794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9440    0.4329   -5.6675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6377   -1.3395   -5.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0830    0.0021   -2.4583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7161   -0.6339   -3.5889 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1866   -1.2284   -0.7763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9088    2.2580   -2.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8721    3.0277   -0.8227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5262    1.9844   -0.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8991    2.1759   -1.8589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2339    0.4711   -2.0909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0425    1.2904   -3.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0757    0.7542    1.0973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9352    1.8603    1.6193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6739   -0.4142   -0.0225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1043   -0.5085    1.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1976   -1.8877    1.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6872   -2.5997    0.3830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2184   -3.1440   -2.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7844   -3.1555   -0.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2669   -3.9337   -1.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0550   -2.5665   -1.8820 H   0  0  0  0  0  0  0  0  0  0  0  0
 11  8  1  0  0  0  0
 15 17  1  6  0  0  0
 13 14  1  0  0  0  0
  6  7  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15  6  1  0  0  0  0
  8 10  1  6  0  0  0
  6  8  1  0  0  0  0
  5  4  2  0  0  0  0
  4  2  1  0  0  0  0
  6  5  1  0  0  0  0
  2  1  1  0  0  0  0
 11 13  1  0  0  0  0
  2  3  2  0  0  0  0
  8  9  1  0  0  0  0
 11 12  1  0  0  0  0
 11 30  1  1  0  0  0
 13 32  1  0  0  0  0
 13 33  1  0  0  0  0
 14 34  1  0  0  0  0
 14 35  1  0  0  0  0
  5 22  1  0  0  0  0
  9 24  1  0  0  0  0
  9 25  1  0  0  0  0
  9 26  1  0  0  0  0
 17 39  1  0  0  0  0
  7 23  1  0  0  0  0
 16 36  1  0  0  0  0
 16 37  1  0  0  0  0
 16 38  1  0  0  0  0
 10 27  1  0  0  0  0
 10 28  1  0  0  0  0
 10 29  1  0  0  0  0
  4 21  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
 12 31  1  0  0  0  0
M  END

     RDKit          3D

 39 39  0  0  0  0  0  0  0  0999 V2000
   -0.1805   -0.3470   -5.7300 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7983   -0.2110   -4.5941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0078   -0.1038   -4.7926 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3086   -0.2150   -3.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9648   -0.4413   -2.8245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5231   -0.4575   -1.4017 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4144   -0.5245   -0.4796 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3091    0.8801   -1.0689 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3466    2.1023   -1.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4311    1.2106   -2.0864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8974    0.7698    0.3697 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6927    1.9171    0.6793 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7582   -0.4756    0.5777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9969   -1.7555    0.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4072   -1.7562   -1.1645 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6138   -3.0631   -1.3576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4916   -1.8043   -2.1037 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3500   -0.2249   -6.6794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9440    0.4329   -5.6675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6377   -1.3395   -5.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0830    0.0021   -2.4583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7161   -0.6339   -3.5889 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1866   -1.2284   -0.7763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9088    2.2580   -2.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8721    3.0277   -0.8227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5262    1.9844   -0.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8991    2.1759   -1.8589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2339    0.4711   -2.0909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0425    1.2904   -3.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0757    0.7542    1.0973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9352    1.8603    1.6193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6739   -0.4142   -0.0225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1043   -0.5085    1.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1976   -1.8877    1.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6872   -2.5997    0.3830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2184   -3.1440   -2.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7844   -3.1555   -0.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2669   -3.9337   -1.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0550   -2.5665   -1.8820 H   0  0  0  0  0  0  0  0  0  0  0  0
 11  8  1  0
 15 17  1  6
 13 14  1  0
  6  7  1  1
 14 15  1  0
 15 16  1  0
 15  6  1  0
  8 10  1  6
  6  8  1  0
  5  4  2  0
  4  2  1  0
  6  5  1  0
  2  1  1  0
 11 13  1  0
  2  3  2  0
  8  9  1  0
 11 12  1  0
 11 30  1  1
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
  5 22  1  0
  9 24  1  0
  9 25  1  0
  9 26  1  0
 17 39  1  0
  7 23  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
 10 27  1  0
 10 28  1  0
 10 29  1  0
  4 21  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
 12 31  1  0
M  END


  Mrv1652306202123253D          

 39 39  0  0  0  0            999 V2000
   -0.1805   -0.3470   -5.7300 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7983   -0.2110   -4.5941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0078   -0.1038   -4.7926 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3086   -0.2150   -3.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9648   -0.4413   -2.8245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5231   -0.4575   -1.4017 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4144   -0.5245   -0.4796 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3091    0.8801   -1.0689 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3466    2.1023   -1.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4311    1.2106   -2.0864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8974    0.7698    0.3697 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6927    1.9171    0.6793 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7582   -0.4756    0.5777 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.9969   -1.7555    0.2598 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4072   -1.7562   -1.1645 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6138   -3.0631   -1.3576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4916   -1.8043   -2.1037 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3500   -0.2249   -6.6794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9440    0.4329   -5.6675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6377   -1.3395   -5.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0830    0.0021   -2.4583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7161   -0.6339   -3.5889 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1866   -1.2284   -0.7763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9088    2.2580   -2.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8721    3.0277   -0.8227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5262    1.9844   -0.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8991    2.1759   -1.8589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2339    0.4711   -2.0909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0425    1.2904   -3.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0757    0.7542    1.0973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9352    1.8603    1.6193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6739   -0.4142   -0.0225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1043   -0.5085    1.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1976   -1.8877    1.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6872   -2.5997    0.3830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2184   -3.1440   -2.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7844   -3.1555   -0.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2669   -3.9337   -1.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0550   -2.5665   -1.8820 H   0  0  0  0  0  0  0  0  0  0  0  0
 11  8  1  0  0  0  0
 15 17  1  6  0  0  0
 13 14  1  0  0  0  0
  6  7  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15  6  1  0  0  0  0
  8 10  1  6  0  0  0
  6  8  1  0  0  0  0
  5  4  2  0  0  0  0
  4  2  1  0  0  0  0
  6  5  1  0  0  0  0
  2  1  1  0  0  0  0
 11 13  1  0  0  0  0
  2  3  2  0  0  0  0
  8  9  1  0  0  0  0
 11 12  1  0  0  0  0
 11 30  1  1  0  0  0
 13 32  1  0  0  0  0
 13 33  1  0  0  0  0
 14 34  1  0  0  0  0
 14 35  1  0  0  0  0
  5 22  1  0  0  0  0
  9 24  1  0  0  0  0
  9 25  1  0  0  0  0
  9 26  1  0  0  0  0
 17 39  1  0  0  0  0
  7 23  1  0  0  0  0
 16 36  1  0  0  0  0
 16 37  1  0  0  0  0
 16 38  1  0  0  0  0
 10 27  1  0  0  0  0
 10 28  1  0  0  0  0
 10 29  1  0  0  0  0
  4 21  1  0  0  0  0
  1 18  1  0  0  0  0
  1 19  1  0  0  0  0
  1 20  1  0  0  0  0
 12 31  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0038832

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H22O4/c1-9(14)5-8-13(17)11(2,3)10(15)6-7-12(13,4)16/h5,8,10,15-17H,6-7H2,1-4H3/b8-5+/t10-,12+,13+/m0/s1

> <INCHI_KEY>
AINWQXGCCNSLLQ-DFCYBAGLSA-N

> <FORMULA>
C13H22O4

> <MOLECULAR_WEIGHT>
242.315

> <EXACT_MASS>
242.151809188

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
26.167623740298428

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3E)-4-[(1R,3S,6R)-1,3,6-trihydroxy-2,2,6-trimethylcyclohexyl]but-3-en-2-one

> <ALOGPS_LOGP>
0.71

> <JCHEM_LOGP>
0.40931156933333357

> <ALOGPS_LOGS>
-1.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.355431306061025

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.824725519483902

> <JCHEM_PKA_STRONGEST_BASIC>
-2.968343814032801

> <JCHEM_POLAR_SURFACE_AREA>
77.76

> <JCHEM_REFRACTIVITY>
65.5794

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.58e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3E)-4-[(1R,3S,6R)-1,3,6-trihydroxy-2,2,6-trimethylcyclohexyl]but-3-en-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 39 39  0  0  0  0  0  0  0  0999 V2000
   -0.1805   -0.3470   -5.7300 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7983   -0.2110   -4.5941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0078   -0.1038   -4.7926 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3086   -0.2150   -3.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9648   -0.4413   -2.8245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5231   -0.4575   -1.4017 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4144   -0.5245   -0.4796 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3091    0.8801   -1.0689 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3466    2.1023   -1.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4311    1.2106   -2.0864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8974    0.7698    0.3697 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6927    1.9171    0.6793 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7582   -0.4756    0.5777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9969   -1.7555    0.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4072   -1.7562   -1.1645 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6138   -3.0631   -1.3576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4916   -1.8043   -2.1037 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3500   -0.2249   -6.6794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9440    0.4329   -5.6675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6377   -1.3395   -5.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0830    0.0021   -2.4583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7161   -0.6339   -3.5889 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1866   -1.2284   -0.7763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9088    2.2580   -2.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8721    3.0277   -0.8227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5262    1.9844   -0.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8991    2.1759   -1.8589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2339    0.4711   -2.0909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0425    1.2904   -3.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0757    0.7542    1.0973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9352    1.8603    1.6193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6739   -0.4142   -0.0225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1043   -0.5085    1.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1976   -1.8877    1.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6872   -2.5997    0.3830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2184   -3.1440   -2.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7844   -3.1555   -0.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2669   -3.9337   -1.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0550   -2.5665   -1.8820 H   0  0  0  0  0  0  0  0  0  0  0  0
 11  8  1  0
 15 17  1  6
 13 14  1  0
  6  7  1  1
 14 15  1  0
 15 16  1  0
 15  6  1  0
  8 10  1  6
  6  8  1  0
  5  4  2  0
  4  2  1  0
  6  5  1  0
  2  1  1  0
 11 13  1  0
  2  3  2  0
  8  9  1  0
 11 12  1  0
 11 30  1  1
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
  5 22  1  0
  9 24  1  0
  9 25  1  0
  9 26  1  0
 17 39  1  0
  7 23  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
 10 27  1  0
 10 28  1  0
 10 29  1  0
  4 21  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
 12 31  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      -0.181  -0.347  -5.730  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.798  -0.211  -4.594  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.008  -0.104  -4.793  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.309  -0.215  -3.188  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.965  -0.441  -2.825  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.523  -0.458  -1.402  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.414  -0.525  -0.480  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.309   0.880  -1.069  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.347   2.102  -1.086  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.431   1.211  -2.086  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.897   0.770   0.370  0.00  0.00           C+0
HETATM   12  O   UNK     0      -3.693   1.917   0.679  0.00  0.00           O+0
HETATM   13  C   UNK     0      -3.758  -0.476   0.578  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.997  -1.756   0.260  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.407  -1.756  -1.165  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.614  -3.063  -1.358  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.492  -1.804  -2.104  0.00  0.00           O+0
HETATM   18  H   UNK     0       0.350  -0.225  -6.679  0.00  0.00           H+0
HETATM   19  H   UNK     0      -0.944   0.433  -5.668  0.00  0.00           H+0
HETATM   20  H   UNK     0      -0.638  -1.339  -5.714  0.00  0.00           H+0
HETATM   21  H   UNK     0       1.083   0.002  -2.458  0.00  0.00           H+0
HETATM   22  H   UNK     0      -1.716  -0.634  -3.589  0.00  0.00           H+0
HETATM   23  H   UNK     0       0.187  -1.228  -0.776  0.00  0.00           H+0
HETATM   24  H   UNK     0      -0.909   2.258  -2.077  0.00  0.00           H+0
HETATM   25  H   UNK     0      -1.872   3.028  -0.823  0.00  0.00           H+0
HETATM   26  H   UNK     0      -0.526   1.984  -0.370  0.00  0.00           H+0
HETATM   27  H   UNK     0      -3.899   2.176  -1.859  0.00  0.00           H+0
HETATM   28  H   UNK     0      -4.234   0.471  -2.091  0.00  0.00           H+0
HETATM   29  H   UNK     0      -3.042   1.290  -3.107  0.00  0.00           H+0
HETATM   30  H   UNK     0      -2.076   0.754   1.097  0.00  0.00           H+0
HETATM   31  H   UNK     0      -3.935   1.860   1.619  0.00  0.00           H+0
HETATM   32  H   UNK     0      -4.674  -0.414  -0.023  0.00  0.00           H+0
HETATM   33  H   UNK     0      -4.104  -0.508   1.619  0.00  0.00           H+0
HETATM   34  H   UNK     0      -2.198  -1.888   1.000  0.00  0.00           H+0
HETATM   35  H   UNK     0      -3.687  -2.600   0.383  0.00  0.00           H+0
HETATM   36  H   UNK     0      -1.218  -3.144  -2.376  0.00  0.00           H+0
HETATM   37  H   UNK     0      -0.784  -3.155  -0.650  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.267  -3.934  -1.221  0.00  0.00           H+0
HETATM   39  H   UNK     0      -4.055  -2.567  -1.882  0.00  0.00           H+0
CONECT    1    2   18   19   20                                             
CONECT    2    4    1    3                                                  
CONECT    3    2                                                            
CONECT    4    5    2   21                                                  
CONECT    5    4    6   22                                                  
CONECT    6    7   15    8    5                                             
CONECT    7    6   23                                                       
CONECT    8   11   10    6    9                                             
CONECT    9    8   24   25   26                                             
CONECT   10    8   27   28   29                                             
CONECT   11    8   13   12   30                                             
CONECT   12   11   31                                                       
CONECT   13   14   11   32   33                                             
CONECT   14   13   15   34   35                                             
CONECT   15   17   14   16    6                                             
CONECT   16   15   36   37   38                                             
CONECT   17   15   39                                                       
CONECT   18    1                                                            
CONECT   19    1                                                            
CONECT   20    1                                                            
CONECT   21    4                                                            
CONECT   22    5                                                            
CONECT   23    7                                                            
CONECT   24    9                                                            
CONECT   25    9                                                            
CONECT   26    9                                                            
CONECT   27   10                                                            
CONECT   28   10                                                            
CONECT   29   10                                                            
CONECT   30   11                                                            
CONECT   31   12                                                            
CONECT   32   13                                                            
CONECT   33   13                                                            
CONECT   34   14                                                            
CONECT   35   14                                                            
CONECT   36   16                                                            
CONECT   37   16                                                            
CONECT   38   16                                                            
CONECT   39   17                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   78    0
END

RDKit          3D

39 39  0  0  0  0  0  0  0  0999 V2000
   -0.1805   -0.3470   -5.7300 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7983   -0.2110   -4.5941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0078   -0.1038   -4.7926 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3086   -0.2150   -3.1881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9648   -0.4413   -2.8245 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5231   -0.4575   -1.4017 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4144   -0.5245   -0.4796 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3091    0.8801   -1.0689 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.3466    2.1023   -1.0859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4311    1.2106   -2.0864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8974    0.7698    0.3697 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.6927    1.9171    0.6793 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7582   -0.4756    0.5777 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9969   -1.7555    0.2598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4072   -1.7562   -1.1645 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.6138   -3.0631   -1.3576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4916   -1.8043   -2.1037 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3500   -0.2249   -6.6794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9440    0.4329   -5.6675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6377   -1.3395   -5.7142 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0830    0.0021   -2.4583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7161   -0.6339   -3.5889 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1866   -1.2284   -0.7763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9088    2.2580   -2.0773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8721    3.0277   -0.8227 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5262    1.9844   -0.3701 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8991    2.1759   -1.8589 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2339    0.4711   -2.0909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0425    1.2904   -3.1069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0757    0.7542    1.0973 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9352    1.8603    1.6193 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6739   -0.4142   -0.0225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1043   -0.5085    1.6187 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1976   -1.8877    1.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6872   -2.5997    0.3830 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2184   -3.1440   -2.3757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7844   -3.1555   -0.6502 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2669   -3.9337   -1.2210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0550   -2.5665   -1.8820 H   0  0  0  0  0  0  0  0  0  0  0  0
 11  8  1  0
 15 17  1  6
 13 14  1  0
  6  7  1  1
 14 15  1  0
 15 16  1  0
 15  6  1  0
  8 10  1  6
  6  8  1  0
  5  4  2  0
  4  2  1  0
  6  5  1  0
  2  1  1  0
 11 13  1  0
  2  3  2  0
  8  9  1  0
 11 12  1  0
 11 30  1  1
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
  5 22  1  0
  9 24  1  0
  9 25  1  0
  9 26  1  0
 17 39  1  0
  7 23  1  0
 16 36  1  0
 16 37  1  0
 16 38  1  0
 10 27  1  0
 10 28  1  0
 10 29  1  0
  4 21  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
 12 31  1  0
M  END

View in JSmol

Synonyms

Value	Source
Trihydroxy-b-ionone	Generator
Trihydroxy-β-ionone	Generator

Chemical Formula

C₁₃H₂₂O₄

Average Mass

242.3150 Da

Monoisotopic Mass

242.15181 Da

IUPAC Name

(3E)-4-[(1R,3S,6R)-1,3,6-trihydroxy-2,2,6-trimethylcyclohexyl]but-3-en-2-one

Traditional Name

(3E)-4-[(1R,3S,6R)-1,3,6-trihydroxy-2,2,6-trimethylcyclohexyl]but-3-en-2-one

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C13H22O4/c1-9(14)5-8-13(17)11(2,3)10(15)6-7-12(13,4)16/h5,8,10,15-17H,6-7H2,1-4H3/b8-5+/t10-,12+,13+/m0/s1

InChI Key

AINWQXGCCNSLLQ-DFCYBAGLSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
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, 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, 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, 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

Not Available

Species

Species of Origin

Species Name	Source	Reference
Rehmannia glutinosa	LOTUS Database	35616633
Rehmannia glutinosa var. hueichingensis.	JEOL database	Sasaki, H., et al, Phytochemistry 30, 1997 (1991)

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
Cyclohexanol
Cyclitol or derivatives
Acryloyl-group
Cyclic alcohol
Enone
Alpha,beta-unsaturated ketone
Tertiary alcohol
Ketone
Secondary alcohol
Polyol
Organooxygen compound
Organic oxide
Alcohol
Hydrocarbon derivative
Organic oxygen compound
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	0.71	ALOGPS
logP	0.41	ChemAxon
logS	-1.5	ALOGPS
pKa (Strongest Acidic)	12.82	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	77.76 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	65.58 m³·mol⁻¹	ChemAxon
Polarizability	26.17 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

10260682

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15693869

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Feng WS, Li M, Zheng XK, Zhang N, Song K, Wang JC, Kuang HX: Two new ionone glycosides from the roots of Rehmannia glutinosa Libosch. Nat Prod Res. 2015;29(1):59-63. doi: 10.1080/14786419.2014.958735. Epub 2014 Sep 18. [PubMed:25232801 ]
Sasaki, H., et al. (1991). Sasaki, H., et al, Phytochemistry 30, 1997 (1991). Phytochem..

Showing NP-Card for 4-[(1'R,2'R,5'S)-1',2',5'-trihydroxy-2',6',6'-trimethyl-1'-cyclohexyl]-3E+ (NP0038832)

MOL for NP0038832 (4-[(1'R,2'R,5'S)-1',2',5'-trihydroxy-2',6',6'-trimethyl-1'-cyclohexyl]-3E+)

3D MOL for NP0038832 (4-[(1'R,2'R,5'S)-1',2',5'-trihydroxy-2',6',6'-trimethyl-1'-cyclohexyl]-3E+)

3D SDF for NP0038832 (4-[(1'R,2'R,5'S)-1',2',5'-trihydroxy-2',6',6'-trimethyl-1'-cyclohexyl]-3E+)

3D-SDF for NP0038832 (4-[(1'R,2'R,5'S)-1',2',5'-trihydroxy-2',6',6'-trimethyl-1'-cyclohexyl]-3E+)

PDB for NP0038832 (4-[(1'R,2'R,5'S)-1',2',5'-trihydroxy-2',6',6'-trimethyl-1'-cyclohexyl]-3E+)

3D PDB for NP0038832 (4-[(1'R,2'R,5'S)-1',2',5'-trihydroxy-2',6',6'-trimethyl-1'-cyclohexyl]-3E+)

SMILES for NP0038832 (4-[(1'R,2'R,5'S)-1',2',5'-trihydroxy-2',6',6'-trimethyl-1'-cyclohexyl]-3E+)

INCHI for NP0038832 (4-[(1'R,2'R,5'S)-1',2',5'-trihydroxy-2',6',6'-trimethyl-1'-cyclohexyl]-3E+)

Structure for NP0038832 (4-[(1'R,2'R,5'S)-1',2',5'-trihydroxy-2',6',6'-trimethyl-1'-cyclohexyl]-3E+)

3D Structure for NP0038832 (4-[(1'R,2'R,5'S)-1',2',5'-trihydroxy-2',6',6'-trimethyl-1'-cyclohexyl]-3E+)