NP-MRD: Showing NP-Card for 6-(acetyloxy)-5-hydroxy-2-isopropyl-4a-methyl-8-methylidene-octahydronaphthalen-1-yl benzoate (NP0219412)

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Record Information

Version

2.0

Created at

2022-09-05 20:23:26 UTC

Updated at

2022-09-05 20:23:26 UTC

NP-MRD ID

NP0219412

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-(acetyloxy)-5-hydroxy-2-isopropyl-4a-methyl-8-methylidene-octahydronaphthalen-1-yl benzoate

Description

6-(Acetyloxy)-5-hydroxy-4a-methyl-8-methylidene-2-(propan-2-yl)-decahydronaphthalen-1-yl benzoate belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton. 6-(acetyloxy)-5-hydroxy-2-isopropyl-4a-methyl-8-methylidene-octahydronaphthalen-1-yl benzoate is found in Iva annua. 6-(Acetyloxy)-5-hydroxy-4a-methyl-8-methylidene-2-(propan-2-yl)-decahydronaphthalen-1-yl benzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004151517372D          

 29 31  0  0  0  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1060   -2.9737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  1  0  0  0  0
  4 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
 11 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
M  END

     RDKit          3D

 61 63  0  0  0  0  0  0  0  0999 V2000
   -0.9302    2.9065    1.2887 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1318    2.3138    0.6897 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3920    3.0752    0.8278 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6418    2.4340    0.3896 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3984    3.3622   -0.3663 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6422    3.7978    0.0437 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4636    4.7624   -0.7146 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0927    3.3440    1.1231 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4479    1.2079   -0.4619 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.1116    1.4962   -1.7673 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3680    0.3087    0.1113 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4055   -0.9646   -0.7041 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6010    0.0103    1.5660 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4465   -0.8189    2.0643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8889   -0.1440    1.8358 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9365   -1.0173    2.4460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0265   -2.4007    1.8911 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2965   -0.3277    2.5231 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1074    0.2441    0.4151 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3098   -0.9140   -0.3573 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3950   -1.2424   -1.1082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3549   -0.4368   -1.1519 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5180   -2.4828   -1.8727 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5133   -3.4357   -1.8724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6537   -4.5958   -2.5948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7975   -4.8771   -3.3590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7842   -3.9170   -3.3466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6320   -2.7491   -2.6126 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0780    1.0552   -0.0375 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7861    3.8665    1.8119 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9191    2.5353    1.3032 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2219    4.0213    0.2174 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4990    3.4247    1.8811 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2670    2.1779    1.2931 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9069    5.5606   -0.0707 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7782    5.3266   -1.4143 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1850    4.2536   -1.3566 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3909    0.6314   -0.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8708    1.8720   -2.2996 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4766   -1.1432   -0.9774 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0791   -1.8610   -0.1882 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8766   -0.8153   -1.6906 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5432   -0.5544    1.7381 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5892    0.9715    2.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5606   -0.8400    3.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4925   -1.8576    1.7512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8496    0.7789    2.4722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6334   -1.1396    3.5299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2801   -2.6719    1.1442 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0038   -3.1930    2.6917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0380   -2.5224    1.4030 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3849    0.2621    3.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0579   -1.1308    2.4545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4375    0.4110    1.7069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0014    0.8623    0.3357 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6126   -3.2390   -1.2814 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8732   -5.3661   -2.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8471   -5.8083   -3.9069 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6686   -4.1155   -3.9280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4332   -2.0153   -2.6267 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0124    1.3234   -1.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 18  1  0
 16 15  1  0
 15 14  1  0
 14 13  1  0
 13 11  1  0
 11 12  1  6
 11  9  1  0
  9 10  1  0
  9  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
  2 29  1  0
 29 19  1  0
 19 20  1  0
 20 21  1  0
 21 22  2  0
 21 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
 19 15  1  0
 28 23  1  0
 29 11  1  0
 17 49  1  0
 17 50  1  0
 17 51  1  0
 16 48  1  0
 18 52  1  0
 18 53  1  0
 18 54  1  0
 15 47  1  1
 14 45  1  0
 14 46  1  0
 13 43  1  0
 13 44  1  0
 12 40  1  0
 12 41  1  0
 12 42  1  0
  9 38  1  6
 10 39  1  0
  4 34  1  1
  3 32  1  0
  3 33  1  0
  1 30  1  0
  1 31  1  0
 29 61  1  6
 19 55  1  1
 24 56  1  0
 25 57  1  0
 26 58  1  0
 27 59  1  0
 28 60  1  0
  7 35  1  0
  7 36  1  0
  7 37  1  0
M  END


  Mrv1533004151517372D          

 29 31  0  0  0  0            999 V2000
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1060   -2.9737    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  1  0  0  0  0
  4 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 20 25  1  0  0  0  0
 11 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0219412

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C1CCC2(C)C(O)C(CC(=C)C2C1OC(=O)C1=CC=CC=C1)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H32O5/c1-14(2)18-11-12-24(5)20(15(3)13-19(22(24)26)28-16(4)25)21(18)29-23(27)17-9-7-6-8-10-17/h6-10,14,18-22,26H,3,11-13H2,1-2,4-5H3

> <INCHI_KEY>
UEZQKXQUGANOKW-UHFFFAOYSA-N

> <FORMULA>
C24H32O5

> <MOLECULAR_WEIGHT>
400.515

> <EXACT_MASS>
400.22497413

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
43.50985428717239

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-(acetyloxy)-5-hydroxy-4a-methyl-8-methylidene-2-(propan-2-yl)-decahydronaphthalen-1-yl benzoate

> <ALOGPS_LOGP>
4.15

> <JCHEM_LOGP>
4.324788390999999

> <ALOGPS_LOGS>
-5.11

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.706392400868111

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3646239638602875

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
109.9684

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.10e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-(acetyloxy)-5-hydroxy-2-isopropyl-4a-methyl-8-methylidene-octahydronaphthalen-1-yl benzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 15-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-APR-15         0                                  
HETATM    1  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -0.198  -5.551   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      10.669  -0.000   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   16                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   15                                             
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   26                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    7   16                                                  
CONECT   16   15    4   17                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   20                                                       
CONECT   26   11   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

View in JSmol

Synonyms

Value	Source
6-(Acetyloxy)-5-hydroxy-4a-methyl-8-methylidene-2-(propan-2-yl)-decahydronaphthalen-1-yl benzoic acid	Generator

Chemical Formula

C₂₄H₃₂O₅

Average Mass

400.5150 Da

Monoisotopic Mass

400.22497 Da

IUPAC Name

6-(acetyloxy)-5-hydroxy-4a-methyl-8-methylidene-2-(propan-2-yl)-decahydronaphthalen-1-yl benzoate

Traditional Name

6-(acetyloxy)-5-hydroxy-2-isopropyl-4a-methyl-8-methylidene-octahydronaphthalen-1-yl benzoate

CAS Registry Number

Not Available

SMILES

CC(C)C1CCC2(C)C(O)C(CC(=C)C2C1OC(=O)C1=CC=CC=C1)OC(C)=O

InChI Identifier

InChI=1S/C24H32O5/c1-14(2)18-11-12-24(5)20(15(3)13-19(22(24)26)28-16(4)25)21(18)29-23(27)17-9-7-6-8-10-17/h6-10,14,18-22,26H,3,11-13H2,1-2,4-5H3

InChI Key

UEZQKXQUGANOKW-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
Iva annua	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids

Alternative Parents

Substituents

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoid
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Monocyclic benzene moiety
Benzenoid
Dicarboxylic acid or derivatives
Cyclic alcohol
Carboxylic acid ester
Secondary alcohol
Carboxylic acid derivative
Alcohol
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	4.15	ALOGPS
logP	4.32	ChemAxon
logS	-5.1	ALOGPS
pKa (Strongest Acidic)	13.71	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	109.97 m³·mol⁻¹	ChemAxon
Polarizability	43.51 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-(acetyloxy)-5-hydroxy-2-isopropyl-4a-methyl-8-methylidene-octahydronaphthalen-1-yl benzoate (NP0219412)

MOL for NP0219412 (6-(acetyloxy)-5-hydroxy-2-isopropyl-4a-methyl-8-methylidene-octahydronaphthalen-1-yl benzoate)

3D MOL for NP0219412 (6-(acetyloxy)-5-hydroxy-2-isopropyl-4a-methyl-8-methylidene-octahydronaphthalen-1-yl benzoate)

3D SDF for NP0219412 (6-(acetyloxy)-5-hydroxy-2-isopropyl-4a-methyl-8-methylidene-octahydronaphthalen-1-yl benzoate)

3D-SDF for NP0219412 (6-(acetyloxy)-5-hydroxy-2-isopropyl-4a-methyl-8-methylidene-octahydronaphthalen-1-yl benzoate)

PDB for NP0219412 (6-(acetyloxy)-5-hydroxy-2-isopropyl-4a-methyl-8-methylidene-octahydronaphthalen-1-yl benzoate)

3D PDB for NP0219412 (6-(acetyloxy)-5-hydroxy-2-isopropyl-4a-methyl-8-methylidene-octahydronaphthalen-1-yl benzoate)

SMILES for NP0219412 (6-(acetyloxy)-5-hydroxy-2-isopropyl-4a-methyl-8-methylidene-octahydronaphthalen-1-yl benzoate)

INCHI for NP0219412 (6-(acetyloxy)-5-hydroxy-2-isopropyl-4a-methyl-8-methylidene-octahydronaphthalen-1-yl benzoate)

Structure for NP0219412 (6-(acetyloxy)-5-hydroxy-2-isopropyl-4a-methyl-8-methylidene-octahydronaphthalen-1-yl benzoate)

3D Structure for NP0219412 (6-(acetyloxy)-5-hydroxy-2-isopropyl-4a-methyl-8-methylidene-octahydronaphthalen-1-yl benzoate)