NP-MRD: Showing NP-Card for methyl (1r,2r,4as,5r,8as)-5-[2-(furan-3-yl)ethyl]-1,4a-dimethyl-6-methylidene-2-[(2-methylpropanoyl)oxy]-hexahydro-2h-naphthalene-1-carboxylate (NP0234615)

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Record Information

Version

2.0

Created at

2022-09-06 16:45:27 UTC

Updated at

2022-09-06 16:45:28 UTC

NP-MRD ID

NP0234615

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1r,2r,4as,5r,8as)-5-[2-(furan-3-yl)ethyl]-1,4a-dimethyl-6-methylidene-2-[(2-methylpropanoyl)oxy]-hexahydro-2h-naphthalene-1-carboxylate

Description

Methyl (1R,2R,4aS,5R,8aS)-5-[2-(furan-3-yl)ethyl]-1,4a-dimethyl-6-methylidene-2-[(2-methylpropanoyl)oxy]-decahydronaphthalene-1-carboxylate belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations. methyl (1r,2r,4as,5r,8as)-5-[2-(furan-3-yl)ethyl]-1,4a-dimethyl-6-methylidene-2-[(2-methylpropanoyl)oxy]-hexahydro-2h-naphthalene-1-carboxylate is found in Gutierrezia sarothrae. Based on a literature review very few articles have been published on methyl (1R,2R,4aS,5R,8aS)-5-[2-(furan-3-yl)ethyl]-1,4a-dimethyl-6-methylidene-2-[(2-methylpropanoyl)oxy]-decahydronaphthalene-1-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062218452D          

 30 32  0  0  1  0            999 V2000
   -1.4289    0.0000    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
   -0.7145   -1.2375    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  1  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  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   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   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   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8163   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0416   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2171   -2.4072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4788   -3.0781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0915   -3.8065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3819    2.5474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    3.3320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020    3.3320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0470    2.5474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 10 17  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  6  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
  6 23  1  0  0  0  0
  2 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 26 30  2  0  0  0  0
M  END

     RDKit          3D

 66 68  0  0  0  0  0  0  0  0999 V2000
   -3.3708   -1.5211   -1.8895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6009   -1.3102   -0.8467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0858   -2.4730   -0.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5788   -2.3952   -0.0424 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0578   -0.9856   -0.2160 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9182    0.1010    0.2769 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1838    0.1709    1.7302 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2702    1.4364   -0.1435 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1007    1.5492    0.4716 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9380    0.4628   -0.2060 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.2889    0.5930    0.0900 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2906    0.9621   -0.7620 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0174    1.2272   -1.9410 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7220    1.0674   -0.3502 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5980    1.4933   -1.4911 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9044    2.0454    0.7903 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4129   -0.8960    0.1349 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7407   -1.2244    1.5666 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1131   -1.8929   -0.7126 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8454   -1.5558   -1.6739 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0043   -3.2637   -0.4992 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6700   -4.2144   -1.3060 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2428    0.0695   -0.4648 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3213    0.7803    0.3240 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6465    0.7578   -0.4055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6469    1.4850    0.4363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9489    2.8304    0.4082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9422    3.0649    1.3663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2011    1.9075    1.9215 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4653    0.9503    1.4081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7373   -0.6881   -2.4618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6668   -2.5132   -2.2164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3608   -3.4394   -0.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5466   -2.5608    0.9429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2331   -3.0529   -0.8978 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2064   -2.9017    0.8660 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0418   -0.8461   -1.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6843    1.1463    1.9691 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8773   -0.6062    2.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3091    0.1385    2.3948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9051    2.2852    0.2237 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2114    1.4805   -1.2672 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0207    1.4065    1.5435 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5252    2.5151    0.1524 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7884    0.6478   -1.2852 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0071    0.0632    0.0315 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3626    2.2207   -1.1328 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1317    0.6230   -1.9235 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9805    2.0302   -2.2416 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0737    1.9630    1.5351 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0180    3.0796    0.4395 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8295    1.7897    1.3642 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6917   -1.7998    1.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0077   -1.8320    2.0917 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0199   -0.2835    2.1313 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8916   -3.8299   -2.3176 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1127   -5.1727   -1.3669 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6363   -4.4385   -0.8089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1214    0.6373   -1.4284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4533    0.3912    1.3497 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0115    1.8415    0.4123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5321    1.2818   -1.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9627   -0.2976   -0.4618 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5030    3.5641   -0.2321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3794    4.0211    1.5742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5188   -0.0861    1.7227 H   0  0  0  0  0  0  0  0  0  0  0  0
 22 21  1  0
 21 19  1  0
 19 20  2  0
 17 19  1  6
 17 18  1  0
 17 10  1  0
 10  9  1  0
  9  8  1  0
  8  6  1  0
  6  7  1  1
  6 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 30  2  0
 30 29  1  0
 29 28  1  0
 28 27  2  0
 23  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
  5 17  1  0
  5  6  1  0
 27 26  1  0
 22 56  1  0
 22 57  1  0
 22 58  1  0
 18 53  1  0
 18 54  1  0
 18 55  1  0
 10 45  1  6
  9 43  1  0
  9 44  1  0
  8 41  1  0
  8 42  1  0
  7 38  1  0
  7 39  1  0
  7 40  1  0
 23 59  1  6
 24 60  1  0
 24 61  1  0
 25 62  1  0
 25 63  1  0
 30 66  1  0
 28 65  1  0
 27 64  1  0
  1 31  1  0
  1 32  1  0
  3 33  1  0
  3 34  1  0
  4 35  1  0
  4 36  1  0
  5 37  1  6
 14 46  1  0
 15 47  1  0
 15 48  1  0
 15 49  1  0
 16 50  1  0
 16 51  1  0
 16 52  1  0
M  END


  Mrv1652309062218452D          

 30 32  0  0  1  0            999 V2000
   -1.4289    0.0000    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
   -0.7145   -1.2375    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  1  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  1  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   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   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   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8163   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0416   -2.3784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2171   -2.4072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4788   -3.0781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0915   -3.8065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    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    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3819    2.5474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270    3.3320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020    3.3320    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0470    2.5474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  1  1  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  1  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 10 17  1  0  0  0  0
  5 17  1  0  0  0  0
 17 18  1  1  0  0  0
 17 19  1  6  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 21 22  1  0  0  0  0
  6 23  1  0  0  0  0
  2 23  1  0  0  0  0
 23 24  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 26 30  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0234615

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@]1(C)[C@@H](CC[C@@]2(C)[C@H](CCC3=COC=C3)C(=C)CC[C@H]12)OC(=O)C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C25H36O5/c1-16(2)22(26)30-21-11-13-24(4)19(9-8-18-12-14-29-15-18)17(3)7-10-20(24)25(21,5)23(27)28-6/h12,14-16,19-21H,3,7-11,13H2,1-2,4-6H3/t19-,20+,21-,24+,25-/m1/s1

> <INCHI_KEY>
HKQIXOUMCBRAQG-DCDJFBNSSA-N

> <FORMULA>
C25H36O5

> <MOLECULAR_WEIGHT>
416.558

> <EXACT_MASS>
416.256274259

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
66

> <JCHEM_AVERAGE_POLARIZABILITY>
47.37972231883419

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1R,2R,4aS,5R,8aS)-5-[2-(furan-3-yl)ethyl]-1,4a-dimethyl-6-methylidene-2-[(2-methylpropanoyl)oxy]-decahydronaphthalene-1-carboxylate

> <JCHEM_LOGP>
5.734977274666668

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7841497970575455

> <JCHEM_POLAR_SURFACE_AREA>
65.74000000000001

> <JCHEM_REFRACTIVITY>
114.6416

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,2R,4aS,5R,8aS)-5-[2-(furan-3-yl)ethyl]-1,4a-dimethyl-6-methylidene-2-[(2-methylpropanoyl)oxy]-hexahydro-2H-naphthalene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -0.770   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       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   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       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.390  -4.440   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.944  -4.440   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       0.405  -4.493   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.760  -5.746   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       2.037  -7.105   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.580   4.755   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.104   6.220   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -0.564   6.220   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -0.088   4.755   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   23                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   17                                                  
CONECT    6    5    7    8   23                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   10    5   18   19                                             
CONECT   18   17                                                            
CONECT   19   17   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21                                                            
CONECT   23    6    2   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   30                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   26                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   64    0
END

View in JSmol

Synonyms

Value	Source
Methyl (1R,2R,4as,5R,8as)-5-[2-(furan-3-yl)ethyl]-1,4a-dimethyl-6-methylidene-2-[(2-methylpropanoyl)oxy]-decahydronaphthalene-1-carboxylic acid	Generator

Chemical Formula

C₂₅H₃₆O₅

Average Mass

416.5580 Da

Monoisotopic Mass

416.25627 Da

IUPAC Name

methyl (1R,2R,4aS,5R,8aS)-5-[2-(furan-3-yl)ethyl]-1,4a-dimethyl-6-methylidene-2-[(2-methylpropanoyl)oxy]-decahydronaphthalene-1-carboxylate

Traditional Name

methyl (1R,2R,4aS,5R,8aS)-5-[2-(furan-3-yl)ethyl]-1,4a-dimethyl-6-methylidene-2-[(2-methylpropanoyl)oxy]-hexahydro-2H-naphthalene-1-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@]1(C)[C@@H](CC[C@@]2(C)[C@H](CCC3=COC=C3)C(=C)CC[C@H]12)OC(=O)C(C)C

InChI Identifier

InChI=1S/C25H36O5/c1-16(2)22(26)30-21-11-13-24(4)19(9-8-18-12-14-29-15-18)17(3)7-10-20(24)25(21,5)23(27)28-6/h12,14-16,19-21H,3,7-11,13H2,1-2,4-6H3/t19-,20+,21-,24+,25-/m1/s1

InChI Key

HKQIXOUMCBRAQG-DCDJFBNSSA-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
Gutierrezia sarothrae	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Colensane and clerodane diterpenoids

Alternative Parents

Substituents

Clerodane diterpenoid
Dicarboxylic acid or derivatives
Heteroaromatic compound
Methyl ester
Furan
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	5.73	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	65.74 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	114.64 m³·mol⁻¹	ChemAxon
Polarizability	47.38 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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

163019606

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (1r,2r,4as,5r,8as)-5-[2-(furan-3-yl)ethyl]-1,4a-dimethyl-6-methylidene-2-[(2-methylpropanoyl)oxy]-hexahydro-2h-naphthalene-1-carboxylate (NP0234615)

MOL for NP0234615 (methyl (1r,2r,4as,5r,8as)-5-[2-(furan-3-yl)ethyl]-1,4a-dimethyl-6-methylidene-2-[(2-methylpropanoyl)oxy]-hexahydro-2h-naphthalene-1-carboxylate)

3D MOL for NP0234615 (methyl (1r,2r,4as,5r,8as)-5-[2-(furan-3-yl)ethyl]-1,4a-dimethyl-6-methylidene-2-[(2-methylpropanoyl)oxy]-hexahydro-2h-naphthalene-1-carboxylate)

3D SDF for NP0234615 (methyl (1r,2r,4as,5r,8as)-5-[2-(furan-3-yl)ethyl]-1,4a-dimethyl-6-methylidene-2-[(2-methylpropanoyl)oxy]-hexahydro-2h-naphthalene-1-carboxylate)

3D-SDF for NP0234615 (methyl (1r,2r,4as,5r,8as)-5-[2-(furan-3-yl)ethyl]-1,4a-dimethyl-6-methylidene-2-[(2-methylpropanoyl)oxy]-hexahydro-2h-naphthalene-1-carboxylate)

PDB for NP0234615 (methyl (1r,2r,4as,5r,8as)-5-[2-(furan-3-yl)ethyl]-1,4a-dimethyl-6-methylidene-2-[(2-methylpropanoyl)oxy]-hexahydro-2h-naphthalene-1-carboxylate)

3D PDB for NP0234615 (methyl (1r,2r,4as,5r,8as)-5-[2-(furan-3-yl)ethyl]-1,4a-dimethyl-6-methylidene-2-[(2-methylpropanoyl)oxy]-hexahydro-2h-naphthalene-1-carboxylate)

SMILES for NP0234615 (methyl (1r,2r,4as,5r,8as)-5-[2-(furan-3-yl)ethyl]-1,4a-dimethyl-6-methylidene-2-[(2-methylpropanoyl)oxy]-hexahydro-2h-naphthalene-1-carboxylate)

INCHI for NP0234615 (methyl (1r,2r,4as,5r,8as)-5-[2-(furan-3-yl)ethyl]-1,4a-dimethyl-6-methylidene-2-[(2-methylpropanoyl)oxy]-hexahydro-2h-naphthalene-1-carboxylate)

Structure for NP0234615 (methyl (1r,2r,4as,5r,8as)-5-[2-(furan-3-yl)ethyl]-1,4a-dimethyl-6-methylidene-2-[(2-methylpropanoyl)oxy]-hexahydro-2h-naphthalene-1-carboxylate)

3D Structure for NP0234615 (methyl (1r,2r,4as,5r,8as)-5-[2-(furan-3-yl)ethyl]-1,4a-dimethyl-6-methylidene-2-[(2-methylpropanoyl)oxy]-hexahydro-2h-naphthalene-1-carboxylate)