NP-MRD: Showing NP-Card for methyl (2r)-2-[(3r,6r)-6-{2-[(1r,2s,4as,8as)-1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl]ethyl}-6-methyl-1,2-dioxan-3-yl]propanoate (NP0155446)

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Record Information

Version

2.0

Created at

2022-09-02 12:30:08 UTC

Updated at

2022-09-02 12:30:09 UTC

NP-MRD ID

NP0155446

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (2r)-2-[(3r,6r)-6-{2-[(1r,2s,4as,8as)-1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl]ethyl}-6-methyl-1,2-dioxan-3-yl]propanoate

Description

(+)-Sigmosceptrellin A methyl ester 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 (2r)-2-[(3r,6r)-6-{2-[(1r,2s,4as,8as)-1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl]ethyl}-6-methyl-1,2-dioxan-3-yl]propanoate is found in Diacarnus bismarckensis. Based on a literature review very few articles have been published on (+)-Sigmosceptrellin A methyl ester.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022214302D          

 29 31  0  0  1  0            999 V2000
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -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  2  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  2  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
    1.4289   -1.6500    0.0000 C   0  0  2  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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1702   -3.1357    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8203   -2.6277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6144   -3.3906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7860   -4.1976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1729   -4.7496    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3444   -5.5566    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2687   -6.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1290   -5.8115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7421   -5.2595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3005   -6.6185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6875   -7.1705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6118   -4.4947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7833   -3.6877    0.0000 O   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
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  1  0  0  0
 15 16  1  0  0  0  0
 17 16  1  6  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 21 28  1  0  0  0  0
 28 29  1  0  0  0  0
 17 29  1  0  0  0  0
M  END

     RDKit          3D

 71 73  0  0  0  0  0  0  0  0999 V2000
   -5.1890    2.6444    0.6942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2641    1.7974    1.0617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5454    1.8327    2.3523 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3144    0.4919    2.9672 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0410   -0.5986    1.9434 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6516    0.0979    0.6722 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.8827    0.6893    0.1146 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0767   -0.1995    0.0550 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6746    1.3553   -1.2265 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8895    0.5211   -2.1646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6499    0.0014   -1.5369 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9240   -0.8009   -2.5954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7721   -0.7103   -0.2361 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3580   -2.0902   -0.4045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4380   -0.7177    0.4521 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6833   -1.4426   -0.1278 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9564   -1.3546    0.7395 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7510   -1.9590    2.0877 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4034    0.0745    0.9123 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9107    0.0656    1.2026 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6714   -0.8430    0.2979 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.8356   -0.2299   -0.4070 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.5102   -1.3609   -1.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5057    0.8972   -1.2862 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7820    0.8318   -2.5164 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9027    2.0403   -0.8388 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6111    3.1003   -1.7582 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7373   -1.3783   -0.6240 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9211   -2.1152    0.0613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4897    3.4607    1.3577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6860    2.5731   -0.2646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2110    2.4067    3.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6386    2.4460    2.2501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4417    0.5691    3.6510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1939    0.2164    3.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3794   -1.3789    2.2940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0455   -1.0947    1.7834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0062    0.9759    0.9866 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9028   -1.2330   -0.1976 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7006   -0.1795    0.9930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7662    0.2161   -0.7376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2579    2.3637   -1.1016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7087    1.4718   -1.6664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5458    1.2121   -2.9939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4843   -0.2497   -2.6983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9884    0.8996   -1.3465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0756   -0.2617   -3.0466 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6495   -0.9055   -3.4593 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7310   -1.8455   -2.3059 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9093   -2.3555    0.5065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9715   -2.1040   -1.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5866   -2.8706   -0.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5293   -1.0459    1.5331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1792    0.3811    0.5746 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0231   -0.9017   -1.0652 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5632   -2.4770   -0.4016 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5952   -1.1658    2.8192 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9097   -2.6852    2.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7108   -2.4699    2.3842 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1897    0.6939    0.0383 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9367    0.4507    1.8587 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3315    1.0696    1.1841 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0855   -0.3093    2.2503 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0679   -1.7523    0.8320 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5639    0.0913    0.3545 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4146   -2.2914   -0.5703 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9423   -1.5523   -2.1298 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5852   -1.1344   -1.3771 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6856    2.7295   -2.7997 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6022    3.5028   -1.5531 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3604    3.8933   -1.5692 H   0  0  0  0  0  0  0  0  0  0  0  0
 27 26  1  0
 26 24  1  0
 24 25  2  0
 24 22  1  0
 22 23  1  0
 22 21  1  0
 21 20  1  0
 20 19  1  0
 19 17  1  0
 17 18  1  1
 17 16  1  0
 16 15  1  0
 13 15  1  1
 13 14  1  0
 13 11  1  0
 11 12  1  0
 11 10  1  0
 10  9  1  0
  9  7  1  0
  7  8  1  6
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  3  1  0
  3  2  1  0
  2  1  2  3
 17 29  1  0
 29 28  1  0
 28 21  1  0
  6 13  1  0
  2  7  1  0
 27 69  1  0
 27 70  1  0
 27 71  1  0
 22 65  1  1
 23 66  1  0
 23 67  1  0
 23 68  1  0
 21 64  1  1
 20 62  1  0
 20 63  1  0
 19 60  1  0
 19 61  1  0
 18 57  1  0
 18 58  1  0
 18 59  1  0
 16 55  1  0
 16 56  1  0
 15 53  1  0
 15 54  1  0
 14 50  1  0
 14 51  1  0
 14 52  1  0
 11 46  1  1
 12 47  1  0
 12 48  1  0
 12 49  1  0
 10 44  1  0
 10 45  1  0
  9 42  1  0
  9 43  1  0
  8 39  1  0
  8 40  1  0
  8 41  1  0
  6 38  1  1
  5 36  1  0
  5 37  1  0
  4 34  1  0
  4 35  1  0
  3 32  1  0
  3 33  1  0
  1 30  1  0
  1 31  1  0
M  END


  Mrv1652309022214302D          

 29 31  0  0  1  0            999 V2000
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -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  2  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  2  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
    1.4289   -1.6500    0.0000 C   0  0  2  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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1702   -3.1357    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8203   -2.6277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6144   -3.3906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7860   -4.1976    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1729   -4.7496    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3444   -5.5566    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2687   -6.1086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1290   -5.8115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7421   -5.2595    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3005   -6.6185    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6875   -7.1705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6118   -4.4947    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7833   -3.6877    0.0000 O   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
  4  5  1  0  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  2  7  1  0  0  0  0
  7  8  1  6  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
  6 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  1  0  0  0
 15 16  1  0  0  0  0
 17 16  1  6  0  0  0
 17 18  1  1  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  6  0  0  0
 22 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 21 28  1  0  0  0  0
 28 29  1  0  0  0  0
 17 29  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0155446

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@H](C)[C@H]1CC[C@@](C)(CC[C@]2(C)[C@@H](C)CC[C@@]3(C)[C@H]2CCCC3=C)OO1

> <INCHI_IDENTIFIER>
InChI=1S/C25H42O4/c1-17-9-8-10-21-24(17,5)14-11-18(2)25(21,6)16-15-23(4)13-12-20(28-29-23)19(3)22(26)27-7/h18-21H,1,8-16H2,2-7H3/t18-,19+,20+,21+,23-,24+,25+/m0/s1

> <INCHI_KEY>
XZMSFDWECPXXRJ-UMXWBDOSSA-N

> <FORMULA>
C25H42O4

> <MOLECULAR_WEIGHT>
406.607

> <EXACT_MASS>
406.308309832

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
47.28060706610354

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (2R)-2-[(3R,6R)-6-{2-[(1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-methylidene-decahydronaphthalen-1-yl]ethyl}-6-methyl-1,2-dioxan-3-yl]propanoate

> <ALOGPS_LOGP>
6.05

> <JCHEM_LOGP>
6.269906795333336

> <ALOGPS_LOGS>
-6.40

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.836291166022049

> <JCHEM_POLAR_SURFACE_AREA>
44.760000000000005

> <JCHEM_REFRACTIVITY>
115.08689999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.61e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl (2R)-2-[(3R,6R)-6-{2-[(1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-methylidene-hexahydro-2H-naphthalen-1-yl]ethyl}-6-methyl-1,2-dioxan-3-yl]propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334  -0.770   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       0.000  -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       1.334   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.390  -4.440   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.944  -4.440   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.405  -4.493   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.318  -5.853   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.531  -4.905   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.147  -6.329   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.467  -7.835   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.323  -8.866   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.643 -10.372   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -0.502 -11.403   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.108 -10.848   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       3.252  -9.818   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       2.428 -12.354   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       1.283 -13.385   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.142  -8.390   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -1.462  -6.884   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    2    8    9                                             
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    6   14   15                                             
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19   29                                             
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   28                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26                                                            
CONECT   28   21   29                                                       
CONECT   29   28   17                                                       
MASTER        0    0    0    0    0    0    0    0   29    0   62    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₅H₄₂O₄

Average Mass

406.6070 Da

Monoisotopic Mass

406.30831 Da

IUPAC Name

methyl (2R)-2-[(3R,6R)-6-{2-[(1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-methylidene-decahydronaphthalen-1-yl]ethyl}-6-methyl-1,2-dioxan-3-yl]propanoate

Traditional Name

methyl (2R)-2-[(3R,6R)-6-{2-[(1R,2S,4aS,8aS)-1,2,4a-trimethyl-5-methylidene-hexahydro-2H-naphthalen-1-yl]ethyl}-6-methyl-1,2-dioxan-3-yl]propanoate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@H](C)[C@H]1CC[C@@](C)(CC[C@]2(C)[C@@H](C)CC[C@@]3(C)[C@H]2CCCC3=C)OO1

InChI Identifier

InChI=1S/C25H42O4/c1-17-9-8-10-21-24(17,5)14-11-18(2)25(21,6)16-15-23(4)13-12-20(28-29-23)19(3)22(26)27-7/h18-21H,1,8-16H2,2-7H3/t18-,19+,20+,21+,23-,24+,25+/m0/s1

InChI Key

XZMSFDWECPXXRJ-UMXWBDOSSA-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
Diacarnus bismarckensis	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
Ortho-dioxane
Methyl ester
Dialkyl peroxide
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	6.05	ALOGPS
logP	6.27	ChemAxon
logS	-6.4	ALOGPS
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	44.76 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	115.09 m³·mol⁻¹	ChemAxon
Polarizability	47.28 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

10471176

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23425804

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (2r)-2-[(3r,6r)-6-{2-[(1r,2s,4as,8as)-1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl]ethyl}-6-methyl-1,2-dioxan-3-yl]propanoate (NP0155446)

MOL for NP0155446 (methyl (2r)-2-[(3r,6r)-6-{2-[(1r,2s,4as,8as)-1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl]ethyl}-6-methyl-1,2-dioxan-3-yl]propanoate)

3D MOL for NP0155446 (methyl (2r)-2-[(3r,6r)-6-{2-[(1r,2s,4as,8as)-1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl]ethyl}-6-methyl-1,2-dioxan-3-yl]propanoate)

3D SDF for NP0155446 (methyl (2r)-2-[(3r,6r)-6-{2-[(1r,2s,4as,8as)-1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl]ethyl}-6-methyl-1,2-dioxan-3-yl]propanoate)

3D-SDF for NP0155446 (methyl (2r)-2-[(3r,6r)-6-{2-[(1r,2s,4as,8as)-1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl]ethyl}-6-methyl-1,2-dioxan-3-yl]propanoate)

PDB for NP0155446 (methyl (2r)-2-[(3r,6r)-6-{2-[(1r,2s,4as,8as)-1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl]ethyl}-6-methyl-1,2-dioxan-3-yl]propanoate)

3D PDB for NP0155446 (methyl (2r)-2-[(3r,6r)-6-{2-[(1r,2s,4as,8as)-1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl]ethyl}-6-methyl-1,2-dioxan-3-yl]propanoate)

SMILES for NP0155446 (methyl (2r)-2-[(3r,6r)-6-{2-[(1r,2s,4as,8as)-1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl]ethyl}-6-methyl-1,2-dioxan-3-yl]propanoate)

INCHI for NP0155446 (methyl (2r)-2-[(3r,6r)-6-{2-[(1r,2s,4as,8as)-1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl]ethyl}-6-methyl-1,2-dioxan-3-yl]propanoate)

Structure for NP0155446 (methyl (2r)-2-[(3r,6r)-6-{2-[(1r,2s,4as,8as)-1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl]ethyl}-6-methyl-1,2-dioxan-3-yl]propanoate)

3D Structure for NP0155446 (methyl (2r)-2-[(3r,6r)-6-{2-[(1r,2s,4as,8as)-1,2,4a-trimethyl-5-methylidene-hexahydro-2h-naphthalen-1-yl]ethyl}-6-methyl-1,2-dioxan-3-yl]propanoate)