NP-MRD: Showing NP-Card for methyl (4ar,5r,6s,7s,8r,8ar)-7,8-dihydroxy-5,6,8a-trimethyl-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate (NP0209235)

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Record Information

Version

2.0

Created at

2022-09-05 06:33:42 UTC

Updated at

2022-09-05 06:33:43 UTC

NP-MRD ID

NP0209235

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (4ar,5r,6s,7s,8r,8ar)-7,8-dihydroxy-5,6,8a-trimethyl-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate

Description

5Alpha,6alpha,8aalpha-Trimethyl-5-[2-(5-oxo-2,5-dihydrofuran-3-yl)ethyl]-7alpha,8alpha-dihydroxy-3,4,4abeta,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid methyl ester belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. Based on a literature review very few articles have been published on 5alpha,6alpha,8aalpha-Trimethyl-5-[2-(5-oxo-2,5-dihydrofuran-3-yl)ethyl]-7alpha,8alpha-dihydroxy-3,4,4abeta,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid methyl ester.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052208332D          

 27 29  0  0  1  0            999 V2000
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   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
    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  2  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3276    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1060    1.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6363    2.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4367    2.8397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1364    3.2769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1939    4.0999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7684    2.7466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4593    1.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    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
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
 10 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
  5 26  1  0  0  0  0
  9 26  1  0  0  0  0
 26 27  1  6  0  0  0
M  END

     RDKit          3D

 57 59  0  0  0  0  0  0  0  0999 V2000
    5.2520    2.0342   -2.4257 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1475    2.1012   -1.5673 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5515    0.9543   -1.0077 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0965   -0.1150   -1.3466 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4177    1.0406   -0.1280 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9421    2.2551    0.1365 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8025    2.5783    0.9984 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2193    1.3114    1.5682 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3116    0.2289    0.5232 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7345   -0.7927    0.5786 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1716   -1.2100    1.9566 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9768   -0.3764   -0.1899 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6553    0.8534    0.2406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8714    1.1051   -0.6170 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2870    0.3398   -1.6205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4879    0.9020   -2.2056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1269    0.4288   -3.1616 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7872    2.0474   -1.5126 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8270    2.2279   -0.5188 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2892   -2.0202   -0.2248 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3064   -3.1210   -0.1748 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0618   -2.4909    0.0994 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2466   -3.0485    1.3399 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0908   -1.4142   -0.2144 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3449   -1.8694    0.2406 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7559   -0.1628    0.4934 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3834   -0.2462    1.8735 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9760    2.8288   -2.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9442    2.1862   -3.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750    1.0619   -2.2695 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4433    3.1150   -0.3309 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0017    3.0149    0.3303 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0500    3.3144    1.7941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7941    1.4826    1.9734 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8373    1.0704    2.4574 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1268    0.7762   -0.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2418   -1.5547    1.8874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6329   -2.1143    2.3387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1672   -0.3844    2.6637 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6934   -0.3269   -1.2828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7380   -1.2138   -0.1685 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9929    0.9126    1.2625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9878    1.7268   -0.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8067   -0.5636   -1.9528 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3421    3.2122   -0.6998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3628    2.2136    0.4617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2659   -1.6613   -1.2966 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0542   -3.0126   -1.0071 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8134   -4.1028   -0.3627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8467   -3.2103    0.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2926   -3.3199   -0.6378 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8087   -3.9328    1.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1301   -1.3460   -1.3178 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4008   -2.8546    0.2227 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7613   -0.6825    2.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3103   -0.8981    1.8464 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7787    0.7219    2.2400 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  1
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 10 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 22 24  1  0
 24 25  1  0
 24 26  1  0
 26 27  1  1
 26  5  1  0
 26  9  1  0
 19 14  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  6 31  1  0
  7 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  6
 11 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 15 44  1  0
 19 45  1  0
 19 46  1  0
 20 47  1  6
 21 48  1  0
 21 49  1  0
 21 50  1  0
 22 51  1  6
 23 52  1  0
 24 53  1  6
 25 54  1  0
 27 55  1  0
 27 56  1  0
 27 57  1  0
M  END


  Mrv1652309052208332D          

 27 29  0  0  1  0            999 V2000
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 O   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
    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  2  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3276    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3882    0.6320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1060    1.4072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6363    2.0392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4367    2.8397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1364    3.2769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1939    4.0999    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7684    2.7466    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4593    1.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    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
  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 10 12  1  1  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
 10 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
  5 26  1  0  0  0  0
  9 26  1  0  0  0  0
 26 27  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0209235

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C1=CCC[C@@H]2[C@@](C)(CCC3=CC(=O)OC3)[C@H](C)[C@H](O)[C@H](O)[C@@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C21H30O6/c1-12-17(23)18(24)21(3)14(19(25)26-4)6-5-7-15(21)20(12,2)9-8-13-10-16(22)27-11-13/h6,10,12,15,17-18,23-24H,5,7-9,11H2,1-4H3/t12-,15-,17+,18+,20+,21+/m1/s1

> <INCHI_KEY>
WHHJYCIHDIOTJN-QTMFJGDTSA-N

> <FORMULA>
C21H30O6

> <MOLECULAR_WEIGHT>
378.465

> <EXACT_MASS>
378.204238686

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
57

> <JCHEM_AVERAGE_POLARIZABILITY>
41.00735915464259

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
methyl (4aR,5R,6S,7S,8R,8aR)-7,8-dihydroxy-5,6,8a-trimethyl-5-[2-(5-oxo-2,5-dihydrofuran-3-yl)ethyl]-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate

> <JCHEM_LOGP>
2.381843659666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.478097843151826

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.471522730112549

> <JCHEM_PKA_STRONGEST_BASIC>
-3.268074343050926

> <JCHEM_POLAR_SURFACE_AREA>
93.06000000000002

> <JCHEM_REFRACTIVITY>
100.56250000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
methyl (4aR,5R,6S,7S,8R,8aR)-7,8-dihydroxy-5,6,8a-trimethyl-5-[2-(5-oxo-2H-furan-3-yl)ethyl]-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.345   1.180   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.325   1.180   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.798   2.627   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.788   3.807   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.415   5.301   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.721   6.117   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.829   7.653   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       8.901   5.127   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       8.324   3.699   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   26                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   26                                                  
CONECT   10    9   11   12   20                                             
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   14                                                       
CONECT   20   10   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24    5    9   27                                             
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   58    0
END

View in JSmol

Synonyms

Value	Source
5a,6a,8Aalpha-trimethyl-5-[2-(5-oxo-2,5-dihydrofuran-3-yl)ethyl]-7a,8a-dihydroxy-3,4,4abeta,5,6,7,8,8a-octahydronaphthalene-1-carboxylate methyl ester	Generator
5a,6a,8Aalpha-trimethyl-5-[2-(5-oxo-2,5-dihydrofuran-3-yl)ethyl]-7a,8a-dihydroxy-3,4,4abeta,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid methyl ester	Generator
5alpha,6alpha,8Aalpha-trimethyl-5-[2-(5-oxo-2,5-dihydrofuran-3-yl)ethyl]-7alpha,8alpha-dihydroxy-3,4,4abeta,5,6,7,8,8a-octahydronaphthalene-1-carboxylate methyl ester	Generator
5Α,6α,8aalpha-trimethyl-5-[2-(5-oxo-2,5-dihydrofuran-3-yl)ethyl]-7α,8α-dihydroxy-3,4,4abeta,5,6,7,8,8a-octahydronaphthalene-1-carboxylate methyl ester	Generator
5Α,6α,8aalpha-trimethyl-5-[2-(5-oxo-2,5-dihydrofuran-3-yl)ethyl]-7α,8α-dihydroxy-3,4,4abeta,5,6,7,8,8a-octahydronaphthalene-1-carboxylic acid methyl ester	Generator

Chemical Formula

C₂₁H₃₀O₆

Average Mass

378.4650 Da

Monoisotopic Mass

378.20424 Da

IUPAC Name

methyl (4aR,5R,6S,7S,8R,8aR)-7,8-dihydroxy-5,6,8a-trimethyl-5-[2-(5-oxo-2,5-dihydrofuran-3-yl)ethyl]-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1-carboxylate

Traditional Name

methyl (4aR,5R,6S,7S,8R,8aR)-7,8-dihydroxy-5,6,8a-trimethyl-5-[2-(5-oxo-2H-furan-3-yl)ethyl]-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)C1=CCC[C@@H]2[C@@](C)(CCC3=CC(=O)OC3)[C@H](C)[C@H](O)[C@H](O)[C@@]12C

InChI Identifier

InChI=1S/C21H30O6/c1-12-17(23)18(24)21(3)14(19(25)26-4)6-5-7-15(21)20(12,2)9-8-13-10-16(22)27-11-13/h6,10,12,15,17-18,23-24H,5,7-9,11H2,1-4H3/t12-,15-,17+,18+,20+,21+/m1/s1

InChI Key

WHHJYCIHDIOTJN-QTMFJGDTSA-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Clerodane diterpenoid
Diterpenoid
2-furanone
Dicarboxylic acid or derivatives
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
1,2-diol
Carboxylic acid ester
Secondary alcohol
Lactone
Oxacycle
Carboxylic acid derivative
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic 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	2.38	ChemAxon
pKa (Strongest Acidic)	7.47	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	93.06 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	100.56 m³·mol⁻¹	ChemAxon
Polarizability	41.01 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	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

9660573

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11485754

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (4ar,5r,6s,7s,8r,8ar)-7,8-dihydroxy-5,6,8a-trimethyl-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate (NP0209235)

MOL for NP0209235 (methyl (4ar,5r,6s,7s,8r,8ar)-7,8-dihydroxy-5,6,8a-trimethyl-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate)

3D MOL for NP0209235 (methyl (4ar,5r,6s,7s,8r,8ar)-7,8-dihydroxy-5,6,8a-trimethyl-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate)

3D SDF for NP0209235 (methyl (4ar,5r,6s,7s,8r,8ar)-7,8-dihydroxy-5,6,8a-trimethyl-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate)

3D-SDF for NP0209235 (methyl (4ar,5r,6s,7s,8r,8ar)-7,8-dihydroxy-5,6,8a-trimethyl-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate)

PDB for NP0209235 (methyl (4ar,5r,6s,7s,8r,8ar)-7,8-dihydroxy-5,6,8a-trimethyl-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate)

3D PDB for NP0209235 (methyl (4ar,5r,6s,7s,8r,8ar)-7,8-dihydroxy-5,6,8a-trimethyl-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate)

SMILES for NP0209235 (methyl (4ar,5r,6s,7s,8r,8ar)-7,8-dihydroxy-5,6,8a-trimethyl-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate)

INCHI for NP0209235 (methyl (4ar,5r,6s,7s,8r,8ar)-7,8-dihydroxy-5,6,8a-trimethyl-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate)

Structure for NP0209235 (methyl (4ar,5r,6s,7s,8r,8ar)-7,8-dihydroxy-5,6,8a-trimethyl-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate)

3D Structure for NP0209235 (methyl (4ar,5r,6s,7s,8r,8ar)-7,8-dihydroxy-5,6,8a-trimethyl-5-[2-(5-oxo-2h-furan-3-yl)ethyl]-3,4,4a,6,7,8-hexahydronaphthalene-1-carboxylate)