NP-MRD: Showing NP-Card for methyl (1r,2s,4ar,4bs,7e,8r,8as,10ar)-7-{[(2-hydroxyethyl)(methyl)carbamoyl]methylidene}-1,4a,8-trimethyl-2-{[(2e)-2-methylbut-2-enoyl]oxy}-9-oxo-decahydrophenanthrene-1-carboxylate (NP0259624)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-08 01:33:29 UTC

Updated at

2022-09-08 01:33:29 UTC

NP-MRD ID

NP0259624

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (1r,2s,4ar,4bs,7e,8r,8as,10ar)-7-{[(2-hydroxyethyl)(methyl)carbamoyl]methylidene}-1,4a,8-trimethyl-2-{[(2e)-2-methylbut-2-enoyl]oxy}-9-oxo-decahydrophenanthrene-1-carboxylate

Description

(5Alpha,8beta,10beta,14alpha)-3beta-(2-Methylcrotonoyloxy)-16-[methyl(2-hydroxyethyl)amino]-7,16-dioxocassa-13(15)-ene-19-oic acid methyl ester belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. methyl (1r,2s,4ar,4bs,7e,8r,8as,10ar)-7-{[(2-hydroxyethyl)(methyl)carbamoyl]methylidene}-1,4a,8-trimethyl-2-{[(2e)-2-methylbut-2-enoyl]oxy}-9-oxo-decahydrophenanthrene-1-carboxylate is found in Erythrophleum fordii. Based on a literature review very few articles have been published on (5alpha,8beta,10beta,14alpha)-3beta-(2-Methylcrotonoyloxy)-16-[methyl(2-hydroxyethyl)amino]-7,16-dioxocassa-13(15)-ene-19-oic acid methyl ester.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082203332D          

 37 39  0  0  1  0            999 V2000
   -4.2868    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    5.7750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0013    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   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
   -0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    2.4750    0.0000 C   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    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 C   0  0  2  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
   -3.5724    3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7158    4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.1530    4.2504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5403    4.9212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9774    5.6208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9276    4.1928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7521    4.1640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  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  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 13 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 31 30  1  1  0  0  0
 11 31  1  0  0  0  0
 31 32  1  0  0  0  0
  8 32  1  0  0  0  0
 32 33  1  6  0  0  0
 32 34  1  1  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END

     RDKit          3D

 80 82  0  0  0  0  0  0  0  0999 V2000
   -9.5106    1.3190    0.0037 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1146    1.5825   -0.4542 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1013    0.9756    0.1396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4143    0.0480    1.2503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7181    1.2226   -0.2979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5223    2.0211   -1.2458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6374    0.6221    0.2808 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2926    0.8365   -0.1149 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5584    1.4321    1.0442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0792    1.3957    0.9360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5374    0.0240    0.5744 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7739   -0.8910    1.7225 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9356    0.1138    0.2867 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7309    0.8477    1.3081 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1339    1.0510    0.7739 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6643   -0.0843    0.0202 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9111   -0.0631   -0.4483 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8039    1.0613   -0.2465 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4757    2.0920    0.3783 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1183    0.9950   -0.7827 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5511   -0.1739   -1.5152 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0445    2.0973   -0.6035 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8565    1.9286    0.6699 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7127    3.0261    0.7583 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8910   -1.3351   -0.2905 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.0286   -1.6175   -1.7624 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4785   -1.2920    0.1894 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5899   -2.0755   -0.6876 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8493   -3.2582   -0.8285 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5806   -1.5377   -1.4014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2283   -0.3739   -0.7098 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.7187   -0.4715   -0.5910 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2625   -0.6657   -2.0124 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2072   -1.6154    0.2009 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9232   -1.3646    1.2030 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9431   -2.9427   -0.0676 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4821   -3.9312    0.7834 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0554    0.6665   -0.7067 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.0200    2.3258    0.0107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.5423    0.9551    1.0404 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9215    2.2649   -1.2675 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4832   -0.4455    1.5975 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1040   -0.7689    0.9551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8203    0.5905    2.1233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2767    1.5589   -0.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9486    0.9474    1.9801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8702    2.4963    1.1242 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7498    2.1660    0.2115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6615    1.6779    1.9369 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1334   -0.8362    2.3953 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8787   -1.9363    1.4370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6014   -0.5256    2.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0726    0.5918   -0.6847 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7831    0.3531    2.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3059    1.8849    1.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7998    1.1909    1.6762 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1767    2.0154    0.1958 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2850   -0.9323   -1.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.5356    0.0105   -1.9899 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6415   -1.0778   -0.8510 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8001   -0.4624   -2.2948 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7633    2.1794   -1.4499 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4937    3.0476   -0.5287 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.5087    1.0224    0.5791 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2249    1.9015    1.5632 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5877    2.7622    1.1796 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4677   -2.1528    0.2352 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8477   -2.3504   -1.9770 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1013   -1.9088   -2.2599 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3667   -0.6771   -2.2861 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4607   -1.8040    1.1928 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2073   -1.2714   -2.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2801   -2.3774   -1.5847 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0613    0.5184   -1.3915 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6126   -1.2664   -2.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2855    0.3613   -2.4827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3078   -1.0815   -1.9513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9558   -4.7677    0.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6511   -4.3247    1.4299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2311   -3.5199    1.4919 H   0  0  0  0  0  0  0  0  0  0  0  0
 37 36  1  0
 36 34  1  0
 34 35  2  0
 32 34  1  1
 32 33  1  0
 32  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  1
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 16 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 28 29  2  0
 28 30  1  0
 30 31  1  0
  8  7  1  0
  7  5  1  0
  5  6  2  0
  5  3  1  0
  3  4  1  0
  3  2  2  0
  2  1  1  0
 31 32  1  0
 31 11  1  0
 27 13  1  0
 37 78  1  0
 37 79  1  0
 37 80  1  0
 33 75  1  0
 33 76  1  0
 33 77  1  0
  8 45  1  6
  9 46  1  0
  9 47  1  0
 10 48  1  0
 10 49  1  0
 12 50  1  0
 12 51  1  0
 12 52  1  0
 13 53  1  6
 14 54  1  0
 14 55  1  0
 15 56  1  0
 15 57  1  0
 17 58  1  0
 21 59  1  0
 21 60  1  0
 21 61  1  0
 22 62  1  0
 22 63  1  0
 23 64  1  0
 23 65  1  0
 24 66  1  0
 25 67  1  1
 26 68  1  0
 26 69  1  0
 26 70  1  0
 27 71  1  1
 30 72  1  0
 30 73  1  0
 31 74  1  6
  4 42  1  0
  4 43  1  0
  4 44  1  0
  2 41  1  0
  1 38  1  0
  1 39  1  0
  1 40  1  0
M  END


  Mrv1652309082203332D          

 37 39  0  0  1  0            999 V2000
   -4.2868    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1447    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4302    6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7158    5.7750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.0013    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5724    5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    3.3000    0.0000 C   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
   -0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    3.3000    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0000    2.4750    0.0000 C   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    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579    3.3000    0.0000 C   0  0  2  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
   -3.5724    3.7125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -4.2868    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    4.5375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -5.7158    4.9500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.1530    4.2504    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5403    4.9212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9774    5.6208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9276    4.1928    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7521    4.1640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  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  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 16 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 13 27  1  0  0  0  0
 27 28  1  6  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 31 30  1  1  0  0  0
 11 31  1  0  0  0  0
 31 32  1  0  0  0  0
  8 32  1  0  0  0  0
 32 33  1  6  0  0  0
 32 34  1  1  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0259624

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)[C@@]1(C)[C@H](CC[C@]2(C)[C@H]3CC\C(=C/C(=O)N(C)CCO)[C@H](C)[C@@H]3C(=O)C[C@@H]12)OC(=O)C(\C)=C\C

> <INCHI_IDENTIFIER>
InChI=1S/C29H43NO7/c1-8-17(2)26(34)37-23-11-12-28(4)20-10-9-19(15-24(33)30(6)13-14-31)18(3)25(20)21(32)16-22(28)29(23,5)27(35)36-7/h8,15,18,20,22-23,25,31H,9-14,16H2,1-7H3/b17-8+,19-15+/t18-,20-,22+,23-,25-,28+,29+/m0/s1

> <INCHI_KEY>
JEPIEBDHKJYZEP-MBEGZSFPSA-N

> <FORMULA>
C29H43NO7

> <MOLECULAR_WEIGHT>
517.663

> <EXACT_MASS>
517.303952729

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
57.55468951421276

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (1R,2S,4aR,4bS,7E,8R,8aS,10aR)-7-{[(2-hydroxyethyl)(methyl)carbamoyl]methylidene}-1,4a,8-trimethyl-2-{[(2E)-2-methylbut-2-enoyl]oxy}-9-oxo-tetradecahydrophenanthrene-1-carboxylate

> <JCHEM_LOGP>
3.5527251089999994

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
18.71204312946721

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.573946596473593

> <JCHEM_PKA_STRONGEST_BASIC>
-0.01829747033515783

> <JCHEM_POLAR_SURFACE_AREA>
110.21

> <JCHEM_REFRACTIVITY>
140.69589999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (1R,2S,4aR,4bS,7E,8R,8aS,10aR)-7-{[(2-hydroxyethyl)(methyl)carbamoyl]methylidene}-1,4a,8-trimethyl-2-{[(2E)-2-methylbut-2-enoyl]oxy}-9-oxo-decahydrophenanthrene-1-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -8.002  13.860   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.336  13.090   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -10.669  13.860   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -10.669  15.400   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -12.003  13.090   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0     -13.337  13.860   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0     -12.003  11.550   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0     -10.669  10.780   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -9.336  11.550   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -8.002  10.780   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -8.002   9.240   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -6.668  10.010   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.668   8.470   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      -1.334   8.470   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0      -0.000   6.160   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      -0.000   4.620   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       4.001   6.930   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -8.002   6.160   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -8.002   4.620   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -9.336   6.930   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -9.336   8.470   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0     -10.669   9.240   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -11.486   7.934   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0     -12.208   9.186   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0     -13.025  10.492   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0     -12.931   7.827   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0     -14.471   7.773   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    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9   32                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   31                                             
CONECT   12   11                                                            
CONECT   13   11   14   27                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   25                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23                                                            
CONECT   25   16   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   13   28                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   11   32                                                  
CONECT   32   31    8   33   34                                             
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   37                                                       
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   78    0
END

View in JSmol

Synonyms

Value	Source
(5a,8b,10b,14a)-3b-(2-Methylcrotonoyloxy)-16-[methyl(2-hydroxyethyl)amino]-7,16-dioxocassa-13(15)-ene-19-Oate methyl ester	Generator
(5a,8b,10b,14a)-3b-(2-Methylcrotonoyloxy)-16-[methyl(2-hydroxyethyl)amino]-7,16-dioxocassa-13(15)-ene-19-Oic acid methyl ester	Generator
(5alpha,8beta,10beta,14alpha)-3beta-(2-Methylcrotonoyloxy)-16-[methyl(2-hydroxyethyl)amino]-7,16-dioxocassa-13(15)-ene-19-Oate methyl ester	Generator
(5Α,8β,10β,14α)-3β-(2-methylcrotonoyloxy)-16-[methyl(2-hydroxyethyl)amino]-7,16-dioxocassa-13(15)-ene-19-Oate methyl ester	Generator
(5Α,8β,10β,14α)-3β-(2-methylcrotonoyloxy)-16-[methyl(2-hydroxyethyl)amino]-7,16-dioxocassa-13(15)-ene-19-Oic acid methyl ester	Generator

Chemical Formula

C₂₉H₄₃NO₇

Average Mass

517.6630 Da

Monoisotopic Mass

517.30395 Da

IUPAC Name

methyl (1R,2S,4aR,4bS,7E,8R,8aS,10aR)-7-{[(2-hydroxyethyl)(methyl)carbamoyl]methylidene}-1,4a,8-trimethyl-2-{[(2E)-2-methylbut-2-enoyl]oxy}-9-oxo-tetradecahydrophenanthrene-1-carboxylate

Traditional Name

methyl (1R,2S,4aR,4bS,7E,8R,8aS,10aR)-7-{[(2-hydroxyethyl)(methyl)carbamoyl]methylidene}-1,4a,8-trimethyl-2-{[(2E)-2-methylbut-2-enoyl]oxy}-9-oxo-decahydrophenanthrene-1-carboxylate

CAS Registry Number

Not Available

SMILES

COC(=O)[C@@]1(C)[C@H](CC[C@]2(C)[C@H]3CC\C(=C/C(=O)N(C)CCO)[C@H](C)[C@@H]3C(=O)C[C@@H]12)OC(=O)C(\C)=C\C

InChI Identifier

InChI=1S/C29H43NO7/c1-8-17(2)26(34)37-23-11-12-28(4)20-10-9-19(15-24(33)30(6)13-14-31)18(3)25(20)21(32)16-22(28)29(23,5)27(35)36-7/h8,15,18,20,22-23,25,31H,9-14,16H2,1-7H3/b17-8+,19-15+/t18-,20-,22+,23-,25-,28+,29+/m0/s1

InChI Key

JEPIEBDHKJYZEP-MBEGZSFPSA-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
Erythrophleum fordii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Cassane diterpenoid
Diterpenoid
Steroid
Hydrophenanthrene
Phenanthrene
Fatty acid ester
Dicarboxylic acid or derivatives
Fatty acyl
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Methyl ester
Tertiary carboxylic acid amide
Carboxamide group
Carboxylic acid ester
Ketone
Carboxylic acid derivative
Alkanolamine
Primary alcohol
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Alcohol
Carbonyl group
Organonitrogen compound
Organooxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic 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	3.55	ChemAxon
pKa (Strongest Acidic)	15.57	ChemAxon
pKa (Strongest Basic)	-0.018	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	110.21 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	140.7 m³·mol⁻¹	ChemAxon
Polarizability	57.55 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

28283381

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

102321187

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,2s,4ar,4bs,7e,8r,8as,10ar)-7-{[(2-hydroxyethyl)(methyl)carbamoyl]methylidene}-1,4a,8-trimethyl-2-{[(2e)-2-methylbut-2-enoyl]oxy}-9-oxo-decahydrophenanthrene-1-carboxylate (NP0259624)

MOL for NP0259624 (methyl (1r,2s,4ar,4bs,7e,8r,8as,10ar)-7-{[(2-hydroxyethyl)(methyl)carbamoyl]methylidene}-1,4a,8-trimethyl-2-{[(2e)-2-methylbut-2-enoyl]oxy}-9-oxo-decahydrophenanthrene-1-carboxylate)

3D MOL for NP0259624 (methyl (1r,2s,4ar,4bs,7e,8r,8as,10ar)-7-{[(2-hydroxyethyl)(methyl)carbamoyl]methylidene}-1,4a,8-trimethyl-2-{[(2e)-2-methylbut-2-enoyl]oxy}-9-oxo-decahydrophenanthrene-1-carboxylate)

3D SDF for NP0259624 (methyl (1r,2s,4ar,4bs,7e,8r,8as,10ar)-7-{[(2-hydroxyethyl)(methyl)carbamoyl]methylidene}-1,4a,8-trimethyl-2-{[(2e)-2-methylbut-2-enoyl]oxy}-9-oxo-decahydrophenanthrene-1-carboxylate)

3D-SDF for NP0259624 (methyl (1r,2s,4ar,4bs,7e,8r,8as,10ar)-7-{[(2-hydroxyethyl)(methyl)carbamoyl]methylidene}-1,4a,8-trimethyl-2-{[(2e)-2-methylbut-2-enoyl]oxy}-9-oxo-decahydrophenanthrene-1-carboxylate)

PDB for NP0259624 (methyl (1r,2s,4ar,4bs,7e,8r,8as,10ar)-7-{[(2-hydroxyethyl)(methyl)carbamoyl]methylidene}-1,4a,8-trimethyl-2-{[(2e)-2-methylbut-2-enoyl]oxy}-9-oxo-decahydrophenanthrene-1-carboxylate)

3D PDB for NP0259624 (methyl (1r,2s,4ar,4bs,7e,8r,8as,10ar)-7-{[(2-hydroxyethyl)(methyl)carbamoyl]methylidene}-1,4a,8-trimethyl-2-{[(2e)-2-methylbut-2-enoyl]oxy}-9-oxo-decahydrophenanthrene-1-carboxylate)

SMILES for NP0259624 (methyl (1r,2s,4ar,4bs,7e,8r,8as,10ar)-7-{[(2-hydroxyethyl)(methyl)carbamoyl]methylidene}-1,4a,8-trimethyl-2-{[(2e)-2-methylbut-2-enoyl]oxy}-9-oxo-decahydrophenanthrene-1-carboxylate)

INCHI for NP0259624 (methyl (1r,2s,4ar,4bs,7e,8r,8as,10ar)-7-{[(2-hydroxyethyl)(methyl)carbamoyl]methylidene}-1,4a,8-trimethyl-2-{[(2e)-2-methylbut-2-enoyl]oxy}-9-oxo-decahydrophenanthrene-1-carboxylate)

Structure for NP0259624 (methyl (1r,2s,4ar,4bs,7e,8r,8as,10ar)-7-{[(2-hydroxyethyl)(methyl)carbamoyl]methylidene}-1,4a,8-trimethyl-2-{[(2e)-2-methylbut-2-enoyl]oxy}-9-oxo-decahydrophenanthrene-1-carboxylate)

3D Structure for NP0259624 (methyl (1r,2s,4ar,4bs,7e,8r,8as,10ar)-7-{[(2-hydroxyethyl)(methyl)carbamoyl]methylidene}-1,4a,8-trimethyl-2-{[(2e)-2-methylbut-2-enoyl]oxy}-9-oxo-decahydrophenanthrene-1-carboxylate)