NP-MRD: Showing NP-Card for Gephyronic acid A (NP0061467)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-04-28 06:15:09 UTC

Updated at

2022-04-28 06:15:09 UTC

NP-MRD ID

NP0061467

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Gephyronic acid A

Description

(3S,4S,5R,8R,10S,11R,12S,13S,14R)-3,11,12,13-tetrahydroxy-5-methoxy-4,6,6,8,10,12,14,16-octamethyl-7-oxoheptadec-15-enoic acid belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle. Gephyronic acid A is found in Archangium gephyra. Based on a literature review very few articles have been published on (3S,4S,5R,8R,10S,11R,12S,13S,14R)-3,11,12,13-tetrahydroxy-5-methoxy-4,6,6,8,10,12,14,16-octamethyl-7-oxoheptadec-15-enoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282208152D          

 34 33  0  0  1  0            999 V2000
    4.1250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5014    0.8889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9046    1.1589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5282    1.6990    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3077    1.4289    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9314    1.9690    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.7109    1.6990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4905    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6464    0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1141    1.9690    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.8937    1.6990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5173    2.2391    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.2969    1.9690    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.9205    2.5091    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.5442    3.0492    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.3237    2.7792    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.9474    3.3193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7269    3.0492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3505    3.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8828    2.2391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4796    1.9690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3882    3.8593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4606    1.8855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3804    3.1328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4528    1.1589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3614    3.0492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9582    2.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4409    0.9194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9810    2.4785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7755    2.7792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3991    3.3193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4637    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3723    2.5091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9691    2.2391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 16 21  1  1  0  0  0
 15 22  1  1  0  0  0
 14 23  1  6  0  0  0
 14 24  1  6  0  0  0
 13 25  1  6  0  0  0
 12 26  1  6  0  0  0
 10 27  1  6  0  0  0
  7 28  1  0  0  0  0
  7 29  1  0  0  0  0
  6 30  1  1  0  0  0
 30 31  1  0  0  0  0
  5 32  1  1  0  0  0
  4 33  1  6  0  0  0
  1 34  1  0  0  0  0
M  END

     RDKit          3D

 82 81  0  0  0  0  0  0  0  0999 V2000
   -5.4971   -2.8189   -0.5297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3658   -1.5766   -1.1089 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7181   -0.6173   -0.4076 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.5350    0.5826   -0.0241 C   0  0  1  0  0  0  0  0  0  0  0  0
   -6.1213    1.3467   -1.1946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7309    0.1392    0.7743 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.5531   -0.7061    0.0375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4631   -0.3342    2.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8611    0.6781    3.0336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6850    1.8371    2.6365 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5024    0.2746    4.3233 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3641   -0.2493   -1.0390 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.5555    0.2777   -2.4077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7043   -1.6421   -1.2729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4875    0.4173   -0.1056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9598    0.4959    1.0543 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1476    1.0165   -0.2536 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1709    2.0291   -1.3591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0067    0.1458   -0.0476 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3525    0.7552   -0.1941 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6548    1.2684   -1.5758 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4469   -0.2066    0.2102 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.5103   -1.3537   -0.5411 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8230    0.4155    0.3011 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6069    1.7234    1.0918 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3889    0.7608   -0.8747 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6581   -0.4498    1.2336 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.8728   -0.8111    2.3108 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4828   -1.4697    0.6228 C   0  0  2  0  0  0  0  0  0  0  0  0
    6.1017   -2.3811    1.7347 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6574   -1.1224   -0.1813 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3938   -0.0802   -0.3518 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2907    1.2323    0.2796 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5551   -0.2101   -1.3601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5471   -3.3399   -0.2783 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0592   -2.7964    0.4185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0569   -3.5287   -1.1865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4121   -1.0845    0.5772 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9774    1.3040    0.5630 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0958    1.7923   -0.8081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5118    2.2391   -1.3960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4217    0.7435   -2.0419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3626    1.0907    0.8775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9660   -0.1941   -0.7001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4712   -0.5673    2.6088 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8535   -1.2586    2.2085 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6154    0.9065    5.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7095    1.3399   -2.5401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7431   -0.1178   -3.1052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4493   -0.2407   -2.8428 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4304   -2.1928   -1.8956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5239   -2.1380   -0.3177 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7766   -1.5072   -1.8717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0533    1.7403    0.6706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1186    2.6492   -1.1390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3870    2.8148   -1.2853 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3625    1.6549   -2.3602 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0316   -0.7997   -0.6199 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0385   -0.2193    1.0366 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4643    1.6226    0.5152 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5034    0.6521   -2.0330 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9104    2.3295   -1.5651 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8520    1.1061   -2.3198 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2332   -0.5722    1.2720 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9834   -1.2635   -1.4017 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5586    2.0195    1.6227 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8831    1.5631    1.9284 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2687    2.5460    0.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7149    0.0025   -1.4217 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4163    0.2923    1.7314 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7127   -0.0277    2.8867 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8893   -2.2353    0.0327 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5826   -1.7366    2.4713 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7855   -3.1063    1.2432 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2479   -2.9581    2.1433 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9994   -2.0265   -0.8095 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5488    1.1809    1.3895 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3911    1.8156    0.1346 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1344    1.8925   -0.1167 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8282   -1.2807   -1.4282 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4014    0.3954   -1.0141 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2364    0.1315   -2.3460 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 11  1  0
  9 10  2  0
  3 12  1  0
 12 13  1  6
 12 14  1  0
 12 15  1  0
 15 16  2  0
 15 17  1  0
 17 18  1  0
 17 19  1  0
 19 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  6
 24 27  1  0
 27 28  1  0
 27 29  1  0
 29 30  1  0
 29 31  1  0
 31 32  2  3
 32 33  1  0
 32 34  1  0
  1 35  1  0
  1 36  1  0
  1 37  1  0
  3 38  1  1
  4 39  1  1
  5 40  1  0
  5 41  1  0
  5 42  1  0
  6 43  1  1
  7 44  1  0
  8 45  1  0
  8 46  1  0
 11 47  1  0
 13 48  1  0
 13 49  1  0
 13 50  1  0
 14 51  1  0
 14 52  1  0
 14 53  1  0
 17 54  1  1
 18 55  1  0
 18 56  1  0
 18 57  1  0
 19 58  1  0
 19 59  1  0
 20 60  1  1
 21 61  1  0
 21 62  1  0
 21 63  1  0
 22 64  1  1
 23 65  1  0
 25 66  1  0
 25 67  1  0
 25 68  1  0
 26 69  1  0
 27 70  1  1
 28 71  1  0
 29 72  1  6
 30 73  1  0
 30 74  1  0
 30 75  1  0
 31 76  1  0
 33 77  1  0
 33 78  1  0
 33 79  1  0
 34 80  1  0
 34 81  1  0
 34 82  1  0
M  END


  Mrv1652304282208152D          

 34 33  0  0  1  0            999 V2000
    4.1250    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5014    0.8889    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9046    1.1589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5282    1.6990    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.3077    1.4289    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9314    1.9690    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.7109    1.6990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4905    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6464    0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1141    1.9690    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.8937    1.6990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5173    2.2391    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.2969    1.9690    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   11.9205    2.5091    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.5442    3.0492    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.3237    2.7792    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.9474    3.3193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7269    3.0492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3505    3.5893    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8828    2.2391    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4796    1.9690    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3882    3.8593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.4606    1.8855    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3804    3.1328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4528    1.1589    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3614    3.0492    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9582    2.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4409    0.9194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9810    2.4785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7755    2.7792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3991    3.3193    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4637    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3723    2.5091    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.9691    2.2391    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 16 21  1  1  0  0  0
 15 22  1  1  0  0  0
 14 23  1  6  0  0  0
 14 24  1  6  0  0  0
 13 25  1  6  0  0  0
 12 26  1  6  0  0  0
 10 27  1  6  0  0  0
  7 28  1  0  0  0  0
  7 29  1  0  0  0  0
  6 30  1  1  0  0  0
 30 31  1  0  0  0  0
  5 32  1  1  0  0  0
  4 33  1  6  0  0  0
  1 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0061467

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]([C@@H](C)[C@@H](O)CC(O)=O)C(C)(C)C(=O)[C@H](C)C[C@H](C)[C@@H](O)[C@](C)(O)[C@@H](O)[C@H](C)C=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C26H48O8/c1-14(2)11-15(3)22(31)26(9,33)23(32)17(5)12-16(4)21(30)25(7,8)24(34-10)18(6)19(27)13-20(28)29/h11,15-19,22-24,27,31-33H,12-13H2,1-10H3,(H,28,29)/t15-,16-,17+,18+,19+,22+,23-,24-,26-/m1/s1

> <INCHI_KEY>
QLGNJMNPBNKCBO-CBBMPAPCSA-N

> <FORMULA>
C26H48O8

> <MOLECULAR_WEIGHT>
488.662

> <EXACT_MASS>
488.334918506

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
54.454073095447086

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,4S,5R,8R,10S,11R,12S,13S,14R)-3,11,12,13-tetrahydroxy-5-methoxy-4,6,6,8,10,12,14,16-octamethyl-7-oxoheptadec-15-enoic acid

> <ALOGPS_LOGP>
2.09

> <JCHEM_LOGP>
3.107390693999999

> <ALOGPS_LOGS>
-3.53

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
12.92208280309103

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.512904911640185

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9690600573150867

> <JCHEM_POLAR_SURFACE_AREA>
144.52

> <JCHEM_REFRACTIVITY>
131.5035

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.43e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4S,5R,8R,10S,11R,12S,13S,14R)-3,11,12,13-tetrahydroxy-5-methoxy-4,6,6,8,10,12,14,16-octamethyl-7-oxoheptadec-15-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0       7.700   2.667   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       6.536   1.659   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       9.155   2.163   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      10.319   3.171   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.774   2.667   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.939   3.676   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.394   3.171   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.849   2.667   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      16.140   1.155   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      17.013   3.676   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.468   3.171   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      19.632   4.180   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      21.088   3.676   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      22.252   4.684   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      23.416   5.692   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      24.871   5.188   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      26.035   6.196   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      27.490   5.692   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      28.654   6.700   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      27.781   4.180   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      25.162   3.676   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      23.125   7.204   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      23.260   3.520   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      21.243   5.848   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      21.379   2.163   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      19.341   5.692   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      16.722   5.188   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.890   1.716   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.898   4.627   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      12.648   5.188   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      13.812   6.196   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      12.065   1.155   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      10.028   4.684   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       7.409   4.180   0.000  0.00  0.00           O+0
CONECT    1    2    3   34                                                  
CONECT    2    1                                                            
CONECT    3    1    4                                                       
CONECT    4    3    5   33                                                  
CONECT    5    4    6   32                                                  
CONECT    6    5    7   30                                                  
CONECT    7    6    8   28   29                                             
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   27                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   26                                                  
CONECT   13   12   14   25                                                  
CONECT   14   13   15   23   24                                             
CONECT   15   14   16   22                                                  
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
CONECT   21   16                                                            
CONECT   22   15                                                            
CONECT   23   14                                                            
CONECT   24   14                                                            
CONECT   25   13                                                            
CONECT   26   12                                                            
CONECT   27   10                                                            
CONECT   28    7                                                            
CONECT   29    7                                                            
CONECT   30    6   31                                                       
CONECT   31   30                                                            
CONECT   32    5                                                            
CONECT   33    4                                                            
CONECT   34    1                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   66    0
END

View in JSmol

Synonyms

Value	Source
(3S,4S,5R,8R,10S,11R,12S,13S,14R)-3,11,12,13-Tetrahydroxy-5-methoxy-4,6,6,8,10,12,14,16-octamethyl-7-oxoheptadec-15-enoate	Generator

Chemical Formula

C₂₆H₄₈O₈

Average Mass

488.6620 Da

Monoisotopic Mass

488.33492 Da

IUPAC Name

(3S,4S,5R,8R,10S,11R,12S,13S,14R)-3,11,12,13-tetrahydroxy-5-methoxy-4,6,6,8,10,12,14,16-octamethyl-7-oxoheptadec-15-enoic acid

Traditional Name

(3S,4S,5R,8R,10S,11R,12S,13S,14R)-3,11,12,13-tetrahydroxy-5-methoxy-4,6,6,8,10,12,14,16-octamethyl-7-oxoheptadec-15-enoic acid

CAS Registry Number

Not Available

SMILES

CO[C@H]([C@@H](C)[C@@H](O)CC(O)=O)C(C)(C)C(=O)[C@H](C)C[C@H](C)[C@@H](O)[C@](C)(O)[C@@H](O)[C@H](C)C=C(C)C

InChI Identifier

InChI=1S/C26H48O8/c1-14(2)11-15(3)22(31)26(9,33)23(32)17(5)12-16(4)21(30)25(7,8)24(34-10)18(6)19(27)13-20(28)29/h11,15-19,22-24,27,31-33H,12-13H2,1-10H3,(H,28,29)/t15-,16-,17+,18+,19+,22+,23-,24-,26-/m1/s1

InChI Key

QLGNJMNPBNKCBO-CBBMPAPCSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Archangium gephyra	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Acyclic diterpenoids

Alternative Parents

Substituents

Acyclic diterpenoid
Long-chain fatty acid
Methyl-branched fatty acid
Hydroxy fatty acid
Branched fatty acid
Beta-hydroxy acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Hydroxy acid
Tertiary alcohol
Secondary alcohol
Ketone
Polyol
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	2.09	ALOGPS
logP	3.11	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	4.51	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	144.52 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	131.5 m³·mol⁻¹	ChemAxon
Polarizability	54.45 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	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

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

163002733

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Gephyronic acid A (NP0061467)

MOL for NP0061467 (Gephyronic acid A)

3D MOL for NP0061467 (Gephyronic acid A)

3D SDF for NP0061467 (Gephyronic acid A)

3D-SDF for NP0061467 (Gephyronic acid A)

PDB for NP0061467 (Gephyronic acid A)

3D PDB for NP0061467 (Gephyronic acid A)

SMILES for NP0061467 (Gephyronic acid A)

INCHI for NP0061467 (Gephyronic acid A)

Structure for NP0061467 (Gephyronic acid A)

3D Structure for NP0061467 (Gephyronic acid A)