NP-MRD: Showing NP-Card for 3-[(1s,4r,5r,8s,9s,12s,13r)-5-[(2r)-4-(acetyloxy)-6-methylhept-5-en-2-yl]-13-ethyl-4,8-dimethyltetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-12-yl]but-3-enoic acid (NP0300276)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-10 12:35:33 UTC

Updated at

2022-09-10 12:35:34 UTC

NP-MRD ID

NP0300276

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3-[(1s,4r,5r,8s,9s,12s,13r)-5-[(2r)-4-(acetyloxy)-6-methylhept-5-en-2-yl]-13-ethyl-4,8-dimethyltetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-12-yl]but-3-enoic acid

Description

Coccinetane H belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 3-[(1s,4r,5r,8s,9s,12s,13r)-5-[(2r)-4-(acetyloxy)-6-methylhept-5-en-2-yl]-13-ethyl-4,8-dimethyltetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-12-yl]but-3-enoic acid is found in Kadsura coccinea. Based on a literature review very few articles have been published on Coccinetane H.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309102214352D          

 36 39  0  0  1  0            999 V2000
   -2.5659    0.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7375    1.2744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5221    1.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1352    0.9773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9637    0.1704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9198    1.2323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1244    1.8265    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2959    2.6334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6828    3.1855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8982    2.9305    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7267    2.1236    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0580    1.8686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6711    2.4207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4995    3.2276    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3065    3.0561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9844    3.8951    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8094    3.8951    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2219    3.1806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2219    4.6095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0469    4.6095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4594    5.3240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0469    6.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2219    6.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4594    6.7530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4594    3.8951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2844    3.8951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6969    4.6095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6969    3.1806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4995    4.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2851    4.3076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2851    3.4826    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0388    3.8181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5551    1.3166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3398    1.5715    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5947    0.7869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0427    0.1738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  7  2  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  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  6  0  0  0
 14 16  1  0  0  0  0
 16 17  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  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 16 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 10 31  1  0  0  0  0
 14 31  1  0  0  0  0
 31 32  1  1  0  0  0
 11 33  1  6  0  0  0
 33 34  1  0  0  0  0
  7 34  1  0  0  0  0
 11 34  1  0  0  0  0
 34 35  1  1  0  0  0
 35 36  1  0  0  0  0
M  END

     RDKit          3D

 86 89  0  0  0  0  0  0  0  0999 V2000
    6.3166    0.4873    0.4054 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7038   -0.3669   -0.3500 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3377   -1.0357   -1.4932 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7199   -0.8078   -1.7884 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5137   -0.0977   -1.1789 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.2459   -1.4777   -2.9182 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2721   -0.7718   -0.1193 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.6211   -0.7383   -1.4788 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1182   -0.7525   -1.1852 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7979    0.6081   -0.6252 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2454    0.4556    0.8113 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1964   -0.1183    1.6924 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1867   -0.2502    1.0308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4966    1.0171    0.3952 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1742    2.1596    1.3388 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7623    1.3147   -0.2528 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.0329    1.5403    0.3959 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1943    2.6554    1.3806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7390    0.3396    0.9744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0740   -0.6997   -0.0471 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.7126   -1.8979    0.5754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8999   -1.9874    1.0865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8433   -0.8652    1.1325 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3510   -3.3054    1.6685 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9300   -0.1279   -1.0175 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6271   -0.1631   -2.3591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6068    0.4812   -3.3061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5854   -0.7076   -2.7537 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3493    2.5551   -1.0803 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1679    2.5271   -1.1487 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4390    1.0899   -0.8274 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0976    0.3794   -2.0494 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3894    1.2474    1.2504 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5757   -0.1732    0.9997 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.7921   -0.9385    2.3288 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9833   -2.3988    2.1100 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3324    0.8500    0.3361 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7421    0.9286    1.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1504   -2.1620   -1.3834 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6949   -0.8055   -2.4036 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0975   -2.4830   -3.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3730   -1.8915    0.0748 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8650    0.2280   -1.9557 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9002   -1.6243   -2.0874 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0124   -1.5826   -0.4230 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6292   -1.0965   -2.0619 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4857    1.3420   -1.1454 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4127   -1.1943    1.9762 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0644    0.4155    2.6445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1995   -1.0642    0.2705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8338   -0.6222    1.8450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4046    1.8798    2.4021 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7602    3.0787    1.1501 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8535    2.5011    1.3276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9330    0.4463   -0.9596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7571    1.8516   -0.4461 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0579    3.6731    0.9588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3065    2.6507    1.6331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7242    2.4908    2.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7203    0.6667    1.4155 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1049   -0.0812    1.7970 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1620   -1.1000   -0.5888 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0855   -2.8119    0.5997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7274   -0.3881    2.1413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8769   -1.2817    1.0351 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7287   -0.0891    0.3763 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1227   -3.3208    2.7600 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4570   -3.3867    1.5074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8859   -4.1547    1.1568 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6152    1.5597   -3.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2643    0.3393   -4.3436 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5790    0.0296   -3.1003 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8516    2.5986   -2.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7222    3.4938   -0.5693 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6607    3.2695   -0.5398 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4268    2.7641   -2.2162 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7460    0.5332   -2.8025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3511   -0.6624   -1.8932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8984    0.9209   -2.5985 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3121    1.6962    2.2727 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7580    2.0352    0.5269 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0225   -0.6704    3.0772 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7354   -0.5368    2.7398 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0305   -2.6495    1.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8187   -2.8896    3.1129 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2327   -2.8707    1.4471 H   0  0  0  0  0  0  0  0  0  0  0  0
 36 35  1  0
 34 35  1  1
 34 33  1  0
 11 33  1  1
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  1
 14 16  1  0
 16 29  1  0
 29 30  1  0
 30 31  1  0
 31 32  1  6
 31 10  1  0
 10  9  1  0
  9  8  1  0
  8  7  1  0
  7  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  1  0
  4  6  1  0
  4  5  2  0
 16 17  1  0
 17 18  1  0
 17 19  1  0
 19 20  1  0
 20 25  1  0
 25 26  1  0
 26 27  1  0
 26 28  2  0
 20 21  1  0
 21 22  2  3
 22 23  1  0
 22 24  1  0
 11 34  1  0
 10 11  1  0
  7 34  1  0
 31 14  1  0
 36 84  1  0
 36 85  1  0
 36 86  1  0
 35 82  1  0
 35 83  1  0
 33 80  1  0
 33 81  1  0
 12 48  1  0
 12 49  1  0
 13 50  1  0
 13 51  1  0
 15 52  1  0
 15 53  1  0
 15 54  1  0
 16 55  1  6
 29 73  1  0
 29 74  1  0
 30 75  1  0
 30 76  1  0
 32 77  1  0
 32 78  1  0
 32 79  1  0
 10 47  1  6
  9 45  1  0
  9 46  1  0
  8 43  1  0
  8 44  1  0
  7 42  1  1
  1 37  1  0
  1 38  1  0
  3 39  1  0
  3 40  1  0
  6 41  1  0
 17 56  1  6
 18 57  1  0
 18 58  1  0
 18 59  1  0
 19 60  1  0
 19 61  1  0
 20 62  1  6
 27 70  1  0
 27 71  1  0
 27 72  1  0
 21 63  1  0
 23 64  1  0
 23 65  1  0
 23 66  1  0
 24 67  1  0
 24 68  1  0
 24 69  1  0
M  END


  Mrv1652309102214352D          

 36 39  0  0  1  0            999 V2000
   -2.5659    0.4675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7375    1.2744    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5221    1.5294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1352    0.9773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9637    0.1704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9198    1.2323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1244    1.8265    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2959    2.6334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6828    3.1855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8982    2.9305    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.7267    2.1236    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0580    1.8686    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6711    2.4207    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4995    3.2276    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3065    3.0561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9844    3.8951    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.8094    3.8951    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2219    3.1806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2219    4.6095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0469    4.6095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4594    5.3240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0469    6.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2219    6.0385    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4594    6.7530    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4594    3.8951    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2844    3.8951    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6969    4.6095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6969    3.1806    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4995    4.5625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2851    4.3076    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2851    3.4826    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0388    3.8181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5551    1.3166    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3398    1.5715    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.5947    0.7869    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0427    0.1738    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  7  2  1  6  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  9  1  1  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  6  0  0  0
 14 16  1  0  0  0  0
 16 17  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  2  0  0  0  0
 22 23  1  0  0  0  0
 22 24  1  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 26 28  2  0  0  0  0
 16 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 10 31  1  0  0  0  0
 14 31  1  0  0  0  0
 31 32  1  1  0  0  0
 11 33  1  6  0  0  0
 33 34  1  0  0  0  0
  7 34  1  0  0  0  0
 11 34  1  0  0  0  0
 34 35  1  1  0  0  0
 35 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0300276

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@]12C[C@]11CC[C@]3(C)[C@H](CC[C@@]3(C)[C@@H]1CC[C@H]2C(=C)CC(O)=O)[C@H](C)CC(OC(C)=O)C=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C32H50O4/c1-9-31-19-32(31)15-14-29(7)25(21(4)17-24(16-20(2)3)36-23(6)33)12-13-30(29,8)27(32)11-10-26(31)22(5)18-28(34)35/h16,21,24-27H,5,9-15,17-19H2,1-4,6-8H3,(H,34,35)/t21-,24?,25-,26+,27+,29-,30+,31-,32+/m1/s1

> <INCHI_KEY>
NSRNUNBSWSULGN-ZGNLUHLMSA-N

> <FORMULA>
C32H50O4

> <MOLECULAR_WEIGHT>
498.748

> <EXACT_MASS>
498.37091009

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
86

> <JCHEM_AVERAGE_POLARIZABILITY>
59.657596222420125

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(1S,4R,5R,8S,9S,12S,13R)-5-[(2R)-4-(acetyloxy)-6-methylhept-5-en-2-yl]-13-ethyl-4,8-dimethyltetracyclo[7.5.0.0^{1,13}.0^{4,8}]tetradecan-12-yl]but-3-enoic acid

> <JCHEM_LOGP>
6.929147661333332

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.58557998612428

> <JCHEM_PKA_STRONGEST_BASIC>
-7.013290364943617

> <JCHEM_POLAR_SURFACE_AREA>
63.6

> <JCHEM_REFRACTIVITY>
144.5557

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
3-[(1S,4R,5R,8S,9S,12S,13R)-5-[(2R)-4-(acetyloxy)-6-methylhept-5-en-2-yl]-13-ethyl-4,8-dimethyltetracyclo[7.5.0.0^{1,13}.0^{4,8}]tetradecan-12-yl]but-3-enoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.790   0.873   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.110   2.379   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.575   2.855   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.719   1.824   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -7.399   0.318   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -9.184   2.300   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -3.966   3.409   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.286   4.916   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.141   5.946   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.677   5.470   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.356   3.964   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.108   3.488   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.253   4.519   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.932   6.025   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.439   5.705   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.838   7.271   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.378   7.271   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.148   5.937   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.148   8.604   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.688   8.604   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.458   9.938   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.688  11.272   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.148  11.272   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.458  12.606   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.458   7.271   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       7.998   7.271   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.768   8.604   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.768   5.937   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.932   8.517   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.532   8.041   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.532   6.501   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.939   7.127   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.036   2.458   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.501   2.934   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -2.977   1.469   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -1.946   0.324   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4                                                            
CONECT    7    2    8   34                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   31                                                  
CONECT   11   10   12   33   34                                             
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16   31                                             
CONECT   15   14                                                            
CONECT   16   14   17   29                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   20   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   16   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   10   14   32                                             
CONECT   32   31                                                            
CONECT   33   11   34                                                       
CONECT   34   33    7   11   35                                             
CONECT   35   34   36                                                       
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₂H₅₀O₄

Average Mass

498.7480 Da

Monoisotopic Mass

498.37091 Da

IUPAC Name

3-[(1S,4R,5R,8S,9S,12S,13R)-5-[(2R)-4-(acetyloxy)-6-methylhept-5-en-2-yl]-13-ethyl-4,8-dimethyltetracyclo[7.5.0.0^{1,13}.0^{4,8}]tetradecan-12-yl]but-3-enoic acid

Traditional Name

3-[(1S,4R,5R,8S,9S,12S,13R)-5-[(2R)-4-(acetyloxy)-6-methylhept-5-en-2-yl]-13-ethyl-4,8-dimethyltetracyclo[7.5.0.0^{1,13}.0^{4,8}]tetradecan-12-yl]but-3-enoic acid

CAS Registry Number

Not Available

SMILES

CC[C@]12C[C@]11CC[C@]3(C)[C@H](CC[C@@]3(C)[C@@H]1CC[C@H]2C(=C)CC(O)=O)[C@H](C)CC(OC(C)=O)C=C(C)C

InChI Identifier

InChI=1S/C32H50O4/c1-9-31-19-32(31)15-14-29(7)25(21(4)17-24(16-20(2)3)36-23(6)33)12-13-30(29,8)27(32)11-10-26(31)22(5)18-28(34)35/h16,21,24-27H,5,9-15,17-19H2,1-4,6-8H3,(H,34,35)/t21-,24?,25-,26+,27+,29-,30+,31-,32+/m1/s1

InChI Key

NSRNUNBSWSULGN-ZGNLUHLMSA-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
Kadsura coccinea	LOTUS Database	35616633

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
Carbocyclic fatty acid
Branched fatty acid
Fatty acyl
Fatty acid
Unsaturated fatty acid
Dicarboxylic acid or derivatives
Carboxylic acid ester
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	6.93	ChemAxon
pKa (Strongest Acidic)	4.59	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	144.56 m³·mol⁻¹	ChemAxon
Polarizability	59.66 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

100923243

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 3-[(1s,4r,5r,8s,9s,12s,13r)-5-[(2r)-4-(acetyloxy)-6-methylhept-5-en-2-yl]-13-ethyl-4,8-dimethyltetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-12-yl]but-3-enoic acid (NP0300276)

MOL for NP0300276 (3-[(1s,4r,5r,8s,9s,12s,13r)-5-[(2r)-4-(acetyloxy)-6-methylhept-5-en-2-yl]-13-ethyl-4,8-dimethyltetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-12-yl]but-3-enoic acid)

3D MOL for NP0300276 (3-[(1s,4r,5r,8s,9s,12s,13r)-5-[(2r)-4-(acetyloxy)-6-methylhept-5-en-2-yl]-13-ethyl-4,8-dimethyltetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-12-yl]but-3-enoic acid)

3D SDF for NP0300276 (3-[(1s,4r,5r,8s,9s,12s,13r)-5-[(2r)-4-(acetyloxy)-6-methylhept-5-en-2-yl]-13-ethyl-4,8-dimethyltetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-12-yl]but-3-enoic acid)

3D-SDF for NP0300276 (3-[(1s,4r,5r,8s,9s,12s,13r)-5-[(2r)-4-(acetyloxy)-6-methylhept-5-en-2-yl]-13-ethyl-4,8-dimethyltetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-12-yl]but-3-enoic acid)

PDB for NP0300276 (3-[(1s,4r,5r,8s,9s,12s,13r)-5-[(2r)-4-(acetyloxy)-6-methylhept-5-en-2-yl]-13-ethyl-4,8-dimethyltetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-12-yl]but-3-enoic acid)

3D PDB for NP0300276 (3-[(1s,4r,5r,8s,9s,12s,13r)-5-[(2r)-4-(acetyloxy)-6-methylhept-5-en-2-yl]-13-ethyl-4,8-dimethyltetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-12-yl]but-3-enoic acid)

SMILES for NP0300276 (3-[(1s,4r,5r,8s,9s,12s,13r)-5-[(2r)-4-(acetyloxy)-6-methylhept-5-en-2-yl]-13-ethyl-4,8-dimethyltetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-12-yl]but-3-enoic acid)

INCHI for NP0300276 (3-[(1s,4r,5r,8s,9s,12s,13r)-5-[(2r)-4-(acetyloxy)-6-methylhept-5-en-2-yl]-13-ethyl-4,8-dimethyltetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-12-yl]but-3-enoic acid)

Structure for NP0300276 (3-[(1s,4r,5r,8s,9s,12s,13r)-5-[(2r)-4-(acetyloxy)-6-methylhept-5-en-2-yl]-13-ethyl-4,8-dimethyltetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-12-yl]but-3-enoic acid)

3D Structure for NP0300276 (3-[(1s,4r,5r,8s,9s,12s,13r)-5-[(2r)-4-(acetyloxy)-6-methylhept-5-en-2-yl]-13-ethyl-4,8-dimethyltetracyclo[7.5.0.0¹,¹³.0⁴,⁸]tetradecan-12-yl]but-3-enoic acid)