NP-MRD: Showing NP-Card for 4-[(1s,3ar,4s,7s,9as,10s,11ar)-4,7,10-trihydroxy-3a,6,6,9a,11a-pentamethyl-3-oxo-1h,2h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]pentanoic acid (NP0210437)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-05 08:14:41 UTC

Updated at

2022-09-05 08:14:41 UTC

NP-MRD ID

NP0210437

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-[(1s,3ar,4s,7s,9as,10s,11ar)-4,7,10-trihydroxy-3a,6,6,9a,11a-pentamethyl-3-oxo-1h,2h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]pentanoic acid

Description

4-[(2S,5S,9S,11R,14S,15R,17S)-5,9,17-trihydroxy-2,6,6,11,15-pentamethyl-12-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-1(10)-en-14-yl]pentanoic acid belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. Based on a literature review very few articles have been published on 4-[(2S,5S,9S,11R,14S,15R,17S)-5,9,17-trihydroxy-2,6,6,11,15-pentamethyl-12-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]Heptadec-1(10)-en-14-yl]pentanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI

  Mrv1652309052210142D          

 33 36  0  0  1  0            999 V2000
    4.9830   -1.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939   -0.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1111   -0.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6175   -1.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4347   -1.2185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9411   -1.8698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7456   -0.4543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -0.1416    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0168    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3072    1.9385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826    0.6076    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4850    1.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705    0.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190   -0.6539    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0872   -1.2846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -0.1684    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3228   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266    0.2673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8069   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.5577    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9098    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2793    1.6026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7182    1.9630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902    1.5287    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1220    2.1594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  2  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
  8 19  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  6  0  0  0
 15 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 27 30  1  0  0  0  0
 21 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 14 32  1  0  0  0  0
 32 33  1  6  0  0  0
M  END

     RDKit          3D

 75 78  0  0  0  0  0  0  0  0999 V2000
    4.2775    0.9241    1.5092 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1333   -0.1625    0.4852 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.4443   -0.2502   -0.2610 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6360   -0.5986    0.5380 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8048   -0.6345   -0.4157 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0124    0.3910   -1.1118 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.6280   -1.7367   -0.5407 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9831   -0.0684   -0.4434 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9085    1.1764   -1.2788 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4564    1.5645   -1.3240 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0081    2.3328   -2.1351 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7803    0.8693   -0.2647 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6659    1.6841    1.0081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5894    0.3377   -0.5352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0719   -0.4603    0.4517 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1837   -1.2361    1.3568 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2464   -2.5899    1.0430 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2678   -0.8235    1.3063 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6298   -0.3917   -0.0715 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1436   -1.5331   -0.9815 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5675   -0.5378    0.6098 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9602   -1.7600    1.4306 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9070    0.6460    1.5331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3638    0.8010    1.7813 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2357    0.5392    0.6117 C   0  0  2  0  0  0  0  0  0  0  0  0
   -6.1397   -0.5306    0.8104 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5254    0.3975   -0.6914 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5588   -0.2130   -1.6608 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2801    1.7812   -1.2410 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3186   -0.4913   -0.6746 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4794   -0.2750   -1.8876 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3279    0.6564   -1.7485 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.5918    0.5279   -2.9464 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8990    1.9107    1.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2987    1.0387    1.9285 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6394    0.7005    2.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1054   -1.1173    1.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5663    0.7710   -0.7372 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3136   -0.9226   -1.1621 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5077   -1.6715    0.8735 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8633   -0.0110    1.4171 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4945   -1.9172   -0.0825 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2886   -0.8609   -1.2568 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2323    1.0679   -2.3276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5033    2.0170   -0.8699 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1636    2.6367    0.6886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0648    1.1899    1.6791 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5723    1.8651    1.5518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4978   -1.0689    2.4355 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8699   -2.8373    0.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8965   -1.7049    1.5769 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4606   -0.0808    2.1057 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4658   -2.5000   -0.5087 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1338   -1.4759   -1.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7795   -1.5096   -1.9225 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9005   -1.5787    1.9982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2054   -2.6226    0.7655 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2314   -2.0881    2.1576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4328    0.3533    2.5180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3858    1.5576    1.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4992    1.8494    2.1910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7342    0.1619    2.6295 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9235    1.4316    0.4985 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8557   -0.2831    1.4468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4289   -1.3056   -1.6775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5787    0.0719   -1.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3926    0.1447   -2.6920 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2934    2.2905   -1.1778 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0404    1.7918   -2.3213 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6244    2.4113   -0.6308 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7465   -1.5386   -0.8147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1693    0.0037   -2.7251 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0500   -1.2595   -2.2490 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5999    1.7272   -1.7166 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0914    1.0256   -3.6322 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
  5  7  1  0
  5  6  2  0
  2  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 10 12  1  0
 12 13  1  1
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 18 19  1  0
 19 20  1  6
 15 21  1  0
 21 22  1  1
 21 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 27 28  1  0
 27 29  1  0
 27 30  1  0
 30 31  1  0
 31 32  1  0
 32 33  1  0
 19  8  1  0
 30 21  1  0
 19 12  1  0
 32 14  1  0
  1 34  1  0
  1 35  1  0
  1 36  1  0
  2 37  1  1
  3 38  1  0
  3 39  1  0
  4 40  1  0
  4 41  1  0
  7 42  1  0
  8 43  1  6
  9 44  1  0
  9 45  1  0
 13 46  1  0
 13 47  1  0
 13 48  1  0
 16 49  1  1
 17 50  1  0
 18 51  1  0
 18 52  1  0
 20 53  1  0
 20 54  1  0
 20 55  1  0
 22 56  1  0
 22 57  1  0
 22 58  1  0
 23 59  1  0
 23 60  1  0
 24 61  1  0
 24 62  1  0
 25 63  1  6
 26 64  1  0
 28 65  1  0
 28 66  1  0
 28 67  1  0
 29 68  1  0
 29 69  1  0
 29 70  1  0
 30 71  1  6
 31 72  1  0
 31 73  1  0
 32 74  1  1
 33 75  1  0
M  END

  Mrv1652309052210142D          

 33 36  0  0  1  0            999 V2000
    4.9830   -1.5571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2939   -0.7929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1111   -0.6800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6175   -1.3314    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4347   -1.2185    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9411   -1.8698    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7456   -0.4543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7875   -0.1416    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.0168    0.6509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3340    1.1139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3072    1.9385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6826    0.6076    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4850    1.4085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8705    0.7528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3387    0.1221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6190   -0.6539    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.0872   -1.2846    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4311   -0.7991    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9629   -0.1684    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.3228   -0.9107    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5266    0.2673    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8069   -0.5086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9948   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1827   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0976    0.5577    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9098    0.7029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4342    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2793    1.6026    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7182    1.9630    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2463    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7781    1.6739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5902    1.5287    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.1220    2.1594    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  8  2  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  6  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
  8 19  1  0  0  0  0
 12 19  1  0  0  0  0
 19 20  1  6  0  0  0
 15 21  1  0  0  0  0
 21 22  1  6  0  0  0
 21 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 25 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 27 30  1  0  0  0  0
 21 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 14 32  1  0  0  0  0
 32 33  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0210437

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCC(O)=O)[C@@H]1CC(=O)[C@@]2(C)C3=C([C@@H](O)C[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)C1C[C@@H]3O

> <INCHI_IDENTIFIER>
InChI=1S/C27H42O6/c1-14(7-8-21(32)33)15-11-20(31)27(6)23-16(28)12-18-24(2,3)19(30)9-10-25(18,4)22(23)17(29)13-26(15,27)5/h14-19,28-30H,7-13H2,1-6H3,(H,32,33)/t14?,15-,16-,17-,18?,19-,25-,26+,27-/m0/s1

> <INCHI_KEY>
WYUGOKWLBXFMGU-CGAVQWHESA-N

> <FORMULA>
C27H42O6

> <MOLECULAR_WEIGHT>
462.627

> <EXACT_MASS>
462.298139072

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
52.09554394411727

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-[(2S,5S,9S,11R,14S,15R,17S)-5,9,17-trihydroxy-2,6,6,11,15-pentamethyl-12-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-14-yl]pentanoic acid

> <JCHEM_LOGP>
2.486948315666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.249553891332276

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.302782471285278

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8070024856193297

> <JCHEM_POLAR_SURFACE_AREA>
115.06

> <JCHEM_REFRACTIVITY>
125.33370000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-[(2S,5S,9S,11R,14S,15R,17S)-5,9,17-trihydroxy-2,6,6,11,15-pentamethyl-12-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-14-yl]pentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       9.302  -2.907   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.882  -1.480   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.407  -1.269   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.353  -2.485   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.878  -2.275   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      14.823  -3.490   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      14.458  -0.848   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       8.937  -0.264   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.365   1.215   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.090   2.079   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       8.040   3.618   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.874   1.134   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.505   2.629   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.358   1.405   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.366   0.228   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.889  -1.221   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.896  -2.398   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       6.405  -1.492   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       7.398  -0.314   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.069  -1.700   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       2.850   0.499   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.373  -0.949   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.857  -0.678   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.341  -0.407   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -0.182   1.041   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.698   1.312   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       0.810   2.218   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.521   2.992   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.341   3.664   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.326   1.947   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       3.319   3.125   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.835   2.854   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       5.828   4.031   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    2    9   19                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   14   19                                             
CONECT   13   12                                                            
CONECT   14   12   15   32                                                  
CONECT   15   14   16   21                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18    8   12   20                                             
CONECT   20   19                                                            
CONECT   21   15   22   23   30                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   29   30                                             
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   27   21   31                                                  
CONECT   31   30   32                                                       
CONECT   32   31   14   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Value	Source
4-[(2S,5S,9S,11R,14S,15R,17S)-5,9,17-Trihydroxy-2,6,6,11,15-pentamethyl-12-oxotetracyclo[8.7.0.0,.0,]heptadec-1(10)-en-14-yl]pentanoate	Generator

Chemical Formula

C₂₇H₄₂O₆

Average Mass

462.6270 Da

Monoisotopic Mass

462.29814 Da

IUPAC Name

4-[(2S,5S,9S,11R,14S,15R,17S)-5,9,17-trihydroxy-2,6,6,11,15-pentamethyl-12-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-14-yl]pentanoic acid

Traditional Name

4-[(2S,5S,9S,11R,14S,15R,17S)-5,9,17-trihydroxy-2,6,6,11,15-pentamethyl-12-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-1(10)-en-14-yl]pentanoic acid

CAS Registry Number

Not Available

SMILES

CC(CCC(O)=O)[C@@H]1CC(=O)[C@@]2(C)C3=C([C@@H](O)C[C@]12C)[C@@]1(C)CC[C@H](O)C(C)(C)C1C[C@@H]3O

InChI Identifier

InChI=1S/C27H42O6/c1-14(7-8-21(32)33)15-11-20(31)27(6)23-16(28)12-18-24(2,3)19(30)9-10-25(18,4)22(23)17(29)13-26(15,27)5/h14-19,28-30H,7-13H2,1-6H3,(H,32,33)/t14?,15-,16-,17-,18?,19-,25-,26+,27-/m0/s1

InChI Key

WYUGOKWLBXFMGU-CGAVQWHESA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Trihydroxy bile acid, alcohol, or derivatives
Hydroxy bile acid, alcohol, or derivatives
Bile acid, alcohol, or derivatives
3-hydroxysteroid
Hydroxysteroid
15-oxosteroid
Oxosteroid
14-alpha-methylsteroid
11-beta-hydroxysteroid
11-hydroxysteroid
3-beta-hydroxysteroid
7-alpha-hydroxysteroid
7-hydroxysteroid
Steroid
Cyclic alcohol
Ketone
Secondary alcohol
Monocarboxylic acid or derivatives
Polyol
Carboxylic acid derivative
Carboxylic acid
Organic oxygen compound
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Alcohol
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	2.49	ChemAxon
pKa (Strongest Acidic)	4.3	ChemAxon
pKa (Strongest Basic)	-0.81	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	115.06 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	125.33 m³·mol⁻¹	ChemAxon
Polarizability	52.1 Å³	ChemAxon
Number of Rings	4	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

78438576

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139588461

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-[(1s,3ar,4s,7s,9as,10s,11ar)-4,7,10-trihydroxy-3a,6,6,9a,11a-pentamethyl-3-oxo-1h,2h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]pentanoic acid (NP0210437)

MOL for NP0210437 (4-[(1s,3ar,4s,7s,9as,10s,11ar)-4,7,10-trihydroxy-3a,6,6,9a,11a-pentamethyl-3-oxo-1h,2h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]pentanoic acid)

3D MOL for NP0210437 (4-[(1s,3ar,4s,7s,9as,10s,11ar)-4,7,10-trihydroxy-3a,6,6,9a,11a-pentamethyl-3-oxo-1h,2h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]pentanoic acid)

3D SDF for NP0210437 (4-[(1s,3ar,4s,7s,9as,10s,11ar)-4,7,10-trihydroxy-3a,6,6,9a,11a-pentamethyl-3-oxo-1h,2h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]pentanoic acid)

3D-SDF for NP0210437 (4-[(1s,3ar,4s,7s,9as,10s,11ar)-4,7,10-trihydroxy-3a,6,6,9a,11a-pentamethyl-3-oxo-1h,2h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]pentanoic acid)

PDB for NP0210437 (4-[(1s,3ar,4s,7s,9as,10s,11ar)-4,7,10-trihydroxy-3a,6,6,9a,11a-pentamethyl-3-oxo-1h,2h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]pentanoic acid)

3D PDB for NP0210437 (4-[(1s,3ar,4s,7s,9as,10s,11ar)-4,7,10-trihydroxy-3a,6,6,9a,11a-pentamethyl-3-oxo-1h,2h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]pentanoic acid)

SMILES for NP0210437 (4-[(1s,3ar,4s,7s,9as,10s,11ar)-4,7,10-trihydroxy-3a,6,6,9a,11a-pentamethyl-3-oxo-1h,2h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]pentanoic acid)

INCHI for NP0210437 (4-[(1s,3ar,4s,7s,9as,10s,11ar)-4,7,10-trihydroxy-3a,6,6,9a,11a-pentamethyl-3-oxo-1h,2h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]pentanoic acid)

Structure for NP0210437 (4-[(1s,3ar,4s,7s,9as,10s,11ar)-4,7,10-trihydroxy-3a,6,6,9a,11a-pentamethyl-3-oxo-1h,2h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]pentanoic acid)

3D Structure for NP0210437 (4-[(1s,3ar,4s,7s,9as,10s,11ar)-4,7,10-trihydroxy-3a,6,6,9a,11a-pentamethyl-3-oxo-1h,2h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]pentanoic acid)