NP-MRD: Showing NP-Card for (3s,4ar,6ar,7s,8s,10ar,10bs,12as)-7-(2-carboxyethyl)-3,7,10a,10b,12a-pentamethyl-8-(prop-1-en-2-yl)-2,4,4a,6,6a,8,9,10,11,12-decahydro-1h-chrysene-3-carboxylic acid (NP0267295)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-08 12:02:09 UTC

Updated at

2022-09-08 12:02:09 UTC

NP-MRD ID

NP0267295

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3s,4ar,6ar,7s,8s,10ar,10bs,12as)-7-(2-carboxyethyl)-3,7,10a,10b,12a-pentamethyl-8-(prop-1-en-2-yl)-2,4,4a,6,6a,8,9,10,11,12-decahydro-1h-chrysene-3-carboxylic acid

Description

Koetjapic acid, also known as koetjapate, belongs to the class of organic compounds known as steroid acids. Steroid acids are compounds containing a carboxyl group attached to a steroid backbone. (3s,4ar,6ar,7s,8s,10ar,10bs,12as)-7-(2-carboxyethyl)-3,7,10a,10b,12a-pentamethyl-8-(prop-1-en-2-yl)-2,4,4a,6,6a,8,9,10,11,12-decahydro-1h-chrysene-3-carboxylic acid is found in Maytenus undata and Sandoricum koetjape. (3s,4ar,6ar,7s,8s,10ar,10bs,12as)-7-(2-carboxyethyl)-3,7,10a,10b,12a-pentamethyl-8-(prop-1-en-2-yl)-2,4,4a,6,6a,8,9,10,11,12-decahydro-1h-chrysene-3-carboxylic acid was first documented in 2011 (PMID: 21524294). Based on a literature review a significant number of articles have been published on Koetjapic acid (PMID: 35315091) (PMID: 33860206) (PMID: 32771894) (PMID: 30653753) (PMID: 25690285) (PMID: 25039905).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082214022D          

 34 37  0  0  1  0            999 V2000
   -0.4614   -2.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1913   -2.9882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7314   -3.6118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6188   -3.1441    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8889   -3.9236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6990   -4.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2391   -3.4559    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5091   -4.2355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9690   -2.6764    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5091   -2.0527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3193   -2.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5893   -2.9882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3994   -3.1441    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9395   -2.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7497   -2.6764    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7625   -1.8515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5643   -2.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0846   -3.1860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8585   -1.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0197   -3.4559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4796   -4.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6695   -3.9236    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9395   -4.7032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1294   -4.5473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3193   -4.3914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0492   -3.6118    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9788   -4.4338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1589   -2.5204    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2864   -1.7054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5545   -1.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7386   -1.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5271   -0.9120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7112   -0.1079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1315   -1.4736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  1  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  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  1  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 12 26  1  0  0  0  0
  7 26  1  0  0  0  0
 26 27  1  6  0  0  0
  9 28  1  0  0  0  0
  4 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
M  END

     RDKit          3D

 80 83  0  0  0  0  0  0  0  0999 V2000
   -4.6251   -0.0024    2.4299 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4664   -0.7355    1.3852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3024   -2.0327    1.4384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6668   -0.5504    0.1761 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0017   -1.8956   -0.0413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5515   -1.9257   -0.2301 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8882   -0.8563    0.5795 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.9651   -1.1391    2.0591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3691    0.4734    0.1591 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8366    1.5079    1.1232 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6679    1.3686    1.0912 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3083    0.2882    0.6999 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7961    0.3190    0.7310 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.2495    1.2518   -0.3532 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7200    1.2891   -0.5828 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9456    1.2706   -2.1017 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3738    2.5299   -0.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2653    2.5026    0.7714 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.9944    3.7634   -0.6041 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4635    0.0981   -0.0372 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5824   -1.1053   -0.2469 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4565   -0.9932    0.7973 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2011   -1.1917    2.1333 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6229   -2.2135    0.6083 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1882   -2.0563    1.0519 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6069   -0.9360    0.2432 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.7693   -1.2305   -1.2023 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8623    0.6206   -0.0973 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.3723    1.8994    0.4868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8855    0.8868   -1.6284 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1756    1.0772   -2.2713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0710    2.1669   -1.8935 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8158    3.3699   -1.9909 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3481    1.8469   -1.3713 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2922   -0.2748    3.2748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1278    0.9244    2.5963 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3270   -1.7907    1.7599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2620   -2.5145    0.4481 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7577   -2.6867    2.1477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4862   -0.5671   -0.6591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4620   -2.4085   -0.9394 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2554   -2.6335    0.7828 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3356   -1.8286   -1.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1870   -2.9439    0.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9054   -0.9278    2.5447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7548   -2.2200    2.2050 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1971   -0.5124    2.5752 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7922    0.7076   -0.7922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1928    1.4176    2.1458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0984    2.5093    0.6820 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2131    2.2507    1.4247 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0464    0.8610    1.6977 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9571    2.2959   -0.0243 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6657    1.1392   -1.3124 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4992    2.2332   -2.4754 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3118    0.4618   -2.5185 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0083    1.1692   -2.3438 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3238    4.1194   -1.4923 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7835    0.1958    0.9989 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3756   -0.0505   -0.6540 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2055   -1.1610   -1.2663 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1746   -1.9975    0.0595 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4498   -0.1634    2.4993 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0690   -1.8453    2.0195 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4583   -1.5766    2.8919 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6091   -2.5868   -0.4367 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0290   -3.0794    1.2040 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6975   -3.0229    0.8345 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2406   -1.8456    2.1428 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6166   -2.3296   -1.3493 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8315   -1.0808   -1.5564 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1723   -0.6354   -1.9027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8766    2.2126    1.4382 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4640    1.9404    0.5075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0652    2.7835   -0.1883 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3281    1.8824   -1.6886 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2288    0.1566   -2.1548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9124    1.3355   -3.3818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7561    0.1236   -2.4462 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6815    2.2974   -0.5298 H   0  0  0  0  0  0  0  0  0  0  0  0
  3  2  1  0
  2  1  2  3
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  1
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  1
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  6
 15 17  1  1
 17 19  1  0
 17 18  2  0
  9 28  1  0
 28 29  1  1
 28 30  1  0
 30 31  1  0
 31 32  1  0
 32 34  1  0
 32 33  2  0
 28  4  1  0
 26  7  1  0
 26 12  1  0
 22 13  1  0
  3 37  1  0
  3 38  1  0
  3 39  1  0
  1 35  1  0
  1 36  1  0
  4 40  1  6
  5 41  1  0
  5 42  1  0
  6 43  1  0
  6 44  1  0
  8 45  1  0
  8 46  1  0
  8 47  1  0
  9 48  1  6
 10 49  1  0
 10 50  1  0
 11 51  1  0
 13 52  1  1
 14 53  1  0
 14 54  1  0
 16 55  1  0
 16 56  1  0
 16 57  1  0
 20 59  1  0
 20 60  1  0
 21 61  1  0
 21 62  1  0
 23 63  1  0
 23 64  1  0
 23 65  1  0
 24 66  1  0
 24 67  1  0
 25 68  1  0
 25 69  1  0
 27 70  1  0
 27 71  1  0
 27 72  1  0
 19 58  1  0
 29 73  1  0
 29 74  1  0
 29 75  1  0
 30 76  1  0
 30 77  1  0
 31 78  1  0
 31 79  1  0
 34 80  1  0
M  END


  Mrv1652309082214022D          

 34 37  0  0  1  0            999 V2000
   -0.4614   -2.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1913   -2.9882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7314   -3.6118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6188   -3.1441    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8889   -3.9236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6990   -4.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2391   -3.4559    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5091   -4.2355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9690   -2.6764    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5091   -2.0527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3193   -2.2086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5893   -2.9882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3994   -3.1441    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.9395   -2.5204    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7497   -2.6764    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.7625   -1.8515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5643   -2.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0846   -3.1860    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8585   -1.7750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0197   -3.4559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4796   -4.0796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6695   -3.9236    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.9395   -4.7032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1294   -4.5473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3193   -4.3914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0492   -3.6118    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.9788   -4.4338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1589   -2.5204    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2864   -1.7054    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5545   -1.9589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7386   -1.1547    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5271   -0.9120    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7112   -0.1079    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1315   -1.4736    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  4  2  1  1  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  1  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 13 12  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  6  0  0  0
 15 17  1  1  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 15 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 13 22  1  0  0  0  0
 22 23  1  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 12 26  1  0  0  0  0
  7 26  1  0  0  0  0
 26 27  1  6  0  0  0
  9 28  1  0  0  0  0
  4 28  1  0  0  0  0
 28 29  1  1  0  0  0
 28 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0267295

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=C)[C@@H]1CC[C@]2(C)[C@H](CC=C3[C@@H]4C[C@](C)(CC[C@]4(C)CC[C@@]23C)C(O)=O)[C@@]1(C)CCC(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O4/c1-19(2)20-10-13-30(7)23(28(20,5)12-11-24(31)32)9-8-21-22-18-27(4,25(33)34)15-14-26(22,3)16-17-29(21,30)6/h8,20,22-23H,1,9-18H2,2-7H3,(H,31,32)(H,33,34)/t20-,22-,23+,26+,27-,28-,29+,30+/m0/s1

> <INCHI_KEY>
ASOUKQDZWGOCBR-ICSARBIRSA-N

> <FORMULA>
C30H46O4

> <MOLECULAR_WEIGHT>
470.694

> <EXACT_MASS>
470.339609961

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
55.37194880934343

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3S,4aR,6aR,7S,8S,10aR,10bS,12aS)-7-(2-carboxyethyl)-3,7,10a,10b,12a-pentamethyl-8-(prop-1-en-2-yl)-1,2,3,4,4a,6,6a,7,8,9,10,10a,10b,11,12,12a-hexadecahydrochrysene-3-carboxylic acid

> <JCHEM_LOGP>
6.766004372

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
5.062867977056491

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.423693747125916

> <JCHEM_POLAR_SURFACE_AREA>
74.6

> <JCHEM_REFRACTIVITY>
135.48000000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3S,4aR,6aR,7S,8S,10aR,10bS,12aS)-7-(2-carboxyethyl)-3,7,10a,10b,12a-pentamethyl-8-(prop-1-en-2-yl)-2,4,4a,6,6a,8,9,10,11,12-decahydro-1H-chrysene-3-carboxylic acid

> <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      -0.861  -4.123   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.357  -5.578   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.365  -6.742   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.155  -5.869   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.659  -7.324   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.171  -7.615   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.180  -6.451   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.684  -7.906   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.676  -4.996   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.684  -3.832   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.196  -4.123   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.700  -5.578   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.212  -5.869   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.220  -4.705   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.733  -4.996   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.757  -3.456   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.253  -4.752   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      13.225  -5.947   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      12.802  -3.313   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      11.237  -6.451   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.229  -7.615   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.716  -7.324   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.220  -8.779   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.708  -8.488   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       6.196  -8.197   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.692  -6.742   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       5.560  -8.276   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       2.163  -4.705   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.401  -3.183   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.035  -3.657   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.379  -2.155   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.851  -1.702   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       3.194  -0.201   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0       3.979  -2.751   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5   28                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9   26                                             
CONECT    8    7                                                            
CONECT    9    7   10   28                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   26                                                  
CONECT   13   12   14   22                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17   20                                             
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   15   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   13   23   24                                             
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   12    7   27                                             
CONECT   27   26                                                            
CONECT   28    9    4   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32                                                            
MASTER        0    0    0    0    0    0    0    0   34    0   74    0
END

View in JSmol

Synonyms

Value	Source
Koetjapate	Generator

Chemical Formula

C₃₀H₄₆O₄

Average Mass

470.6940 Da

Monoisotopic Mass

470.33961 Da

IUPAC Name

(3S,4aR,6aR,7S,8S,10aR,10bS,12aS)-7-(2-carboxyethyl)-3,7,10a,10b,12a-pentamethyl-8-(prop-1-en-2-yl)-1,2,3,4,4a,6,6a,7,8,9,10,10a,10b,11,12,12a-hexadecahydrochrysene-3-carboxylic acid

Traditional Name

(3S,4aR,6aR,7S,8S,10aR,10bS,12aS)-7-(2-carboxyethyl)-3,7,10a,10b,12a-pentamethyl-8-(prop-1-en-2-yl)-2,4,4a,6,6a,8,9,10,11,12-decahydro-1H-chrysene-3-carboxylic acid

CAS Registry Number

Not Available

SMILES

CC(=C)[C@@H]1CC[C@]2(C)[C@H](CC=C3[C@@H]4C[C@](C)(CC[C@]4(C)CC[C@@]23C)C(O)=O)[C@@]1(C)CCC(O)=O

InChI Identifier

InChI=1S/C30H46O4/c1-19(2)20-10-13-30(7)23(28(20,5)12-11-24(31)32)9-8-21-22-18-27(4,25(33)34)15-14-26(22,3)16-17-29(21,30)6/h8,20,22-23H,1,9-18H2,2-7H3,(H,31,32)(H,33,34)/t20-,22-,23+,26+,27-,28-,29+,30+/m0/s1

InChI Key

ASOUKQDZWGOCBR-ICSARBIRSA-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
Maytenus undata	LOTUS Database	35616633
Sandoricum koetjape	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroid acids. Steroid acids are compounds containing a carboxyl group attached to a steroid backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid acids

Direct Parent

Steroid acids

Alternative Parents

Substituents

Steroid acid
Diterpenoid
Carbocyclic fatty acid
Fatty acyl
Dicarboxylic acid or derivatives
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	6.77	ChemAxon
pKa (Strongest Acidic)	4.42	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	135.48 m³·mol⁻¹	ChemAxon
Polarizability	55.37 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	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00046065

Chemspider ID

23339075

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15513441

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Bailly C: The health benefits of santol fruits and bioactive products isolated from Sandoricum koetjape Merr.: A scoping review. J Food Biochem. 2022 Jul;46(7):e14152. doi: 10.1111/jfbc.14152. Epub 2022 Mar 21. [PubMed:35315091 ]
Aswathy M, Banik K, Parama D, Sasikumar P, Harsha C, Joseph AG, Sherin DR, Thanathu MK, Kunnumakkara AB, Vasu RK: Exploring the Cytotoxic Effects of the Extracts and Bioactive Triterpenoids from Dillenia indica against Oral Squamous Cell Carcinoma: A Scientific Interpretation and Validation of Indigenous Knowledge. ACS Pharmacol Transl Sci. 2021 Mar 9;4(2):834-847. doi: 10.1021/acsptsci.1c00011. eCollection 2021 Apr 9. [PubMed:33860206 ]
Jafari SF, Al-Suede FSR, Yehya AHS, Ahamed MBK, Shafaei A, Asif M, Tabana YM, Majid AMSA, Baharetha HM: Pharmacokinetics and antiangiogenic studies of potassium koetjapate in rats. Biomed Pharmacother. 2020 Oct;130:110602. doi: 10.1016/j.biopha.2020.110602. Epub 2020 Aug 6. [PubMed:32771894 ]
Abubakar S, Al-Mansoub MA, Murugaiyah V, Chan KL: The phytochemical and anti-inflammatory studies of Dillenia suffruticosa leaves. Phytother Res. 2019 Mar;33(3):660-675. doi: 10.1002/ptr.6255. Epub 2019 Jan 17. [PubMed:30653753 ]
Jalil J, Sabandar CW, Ahmat N, Jamal JA, Jantan I, Aladdin NA, Muhammad K, Buang F, Mohamad HF, Sahidin I: Inhibitory effect of triterpenoids from Dillenia serrata (Dilleniaceae) on prostaglandin E2 production and quantitative HPLC analysis of its koetjapic acid and betulinic acid contents. Molecules. 2015 Feb 16;20(2):3206-20. doi: 10.3390/molecules20023206. [PubMed:25690285 ]
Jafari SF, Khadeer Ahamed MB, Iqbal MA, Al Suede FS, Khalid SH, Haque RA, Nassar ZD, Umar MI, Abdul Majid AM: Increased aqueous solubility and proapoptotic activity of potassium koetjapate against human colorectal cancer cells. J Pharm Pharmacol. 2014 Oct;66(10):1394-409. doi: 10.1111/jphp.12272. Epub 2014 Jul 14. [PubMed:25039905 ]
Nassar ZD, Aisha AF, Al Suede FS, Abdul Majid AS, Abdul Majid AM: In vitro antimetastatic activity of koetjapic acid against breast cancer cells. Biol Pharm Bull. 2012;35(4):503-8. doi: 10.1248/bpb.35.503. [PubMed:22466553 ]
Nassar ZD, Aisha AF, Idris N, Khadeer Ahamed MB, Ismail Z, Abu-Salah KM, Alrokayan SA, Shah Abdul Majid AM: Koetjapic acid, a natural triterpenoid, induces apoptosis in colon cancer cells. Oncol Rep. 2012 Mar;27(3):727-33. doi: 10.3892/or.2011.1569. Epub 2011 Nov 30. [PubMed:22134768 ]
Nassar ZD, Aisha AF, Ahamed MB, Ismail Z, Abu-Salah KM, Alrokayan SA, Abdul Majid AM: Antiangiogenic properties of Koetjapic acid, a natural triterpene isolated from Sandoricum koetjaoe Merr. Cancer Cell Int. 2011 Apr 27;11(1):12. doi: 10.1186/1475-2867-11-12. [PubMed:21524294 ]
He XF, Wang XN, Yin S, Dong L, Yue JM: Ring A-seco triterpenoids with antibacterial activity from Dysoxylum hainanense. Bioorg Med Chem Lett. 2011 Jan 1;21(1):125-9. doi: 10.1016/j.bmcl.2010.11.057. Epub 2010 Nov 19. [PubMed:21131198 ]
LOTUS database [Link]

Showing NP-Card for (3s,4ar,6ar,7s,8s,10ar,10bs,12as)-7-(2-carboxyethyl)-3,7,10a,10b,12a-pentamethyl-8-(prop-1-en-2-yl)-2,4,4a,6,6a,8,9,10,11,12-decahydro-1h-chrysene-3-carboxylic acid (NP0267295)

MOL for NP0267295 ((3s,4ar,6ar,7s,8s,10ar,10bs,12as)-7-(2-carboxyethyl)-3,7,10a,10b,12a-pentamethyl-8-(prop-1-en-2-yl)-2,4,4a,6,6a,8,9,10,11,12-decahydro-1h-chrysene-3-carboxylic acid)

3D MOL for NP0267295 ((3s,4ar,6ar,7s,8s,10ar,10bs,12as)-7-(2-carboxyethyl)-3,7,10a,10b,12a-pentamethyl-8-(prop-1-en-2-yl)-2,4,4a,6,6a,8,9,10,11,12-decahydro-1h-chrysene-3-carboxylic acid)

3D SDF for NP0267295 ((3s,4ar,6ar,7s,8s,10ar,10bs,12as)-7-(2-carboxyethyl)-3,7,10a,10b,12a-pentamethyl-8-(prop-1-en-2-yl)-2,4,4a,6,6a,8,9,10,11,12-decahydro-1h-chrysene-3-carboxylic acid)

3D-SDF for NP0267295 ((3s,4ar,6ar,7s,8s,10ar,10bs,12as)-7-(2-carboxyethyl)-3,7,10a,10b,12a-pentamethyl-8-(prop-1-en-2-yl)-2,4,4a,6,6a,8,9,10,11,12-decahydro-1h-chrysene-3-carboxylic acid)

PDB for NP0267295 ((3s,4ar,6ar,7s,8s,10ar,10bs,12as)-7-(2-carboxyethyl)-3,7,10a,10b,12a-pentamethyl-8-(prop-1-en-2-yl)-2,4,4a,6,6a,8,9,10,11,12-decahydro-1h-chrysene-3-carboxylic acid)

3D PDB for NP0267295 ((3s,4ar,6ar,7s,8s,10ar,10bs,12as)-7-(2-carboxyethyl)-3,7,10a,10b,12a-pentamethyl-8-(prop-1-en-2-yl)-2,4,4a,6,6a,8,9,10,11,12-decahydro-1h-chrysene-3-carboxylic acid)

SMILES for NP0267295 ((3s,4ar,6ar,7s,8s,10ar,10bs,12as)-7-(2-carboxyethyl)-3,7,10a,10b,12a-pentamethyl-8-(prop-1-en-2-yl)-2,4,4a,6,6a,8,9,10,11,12-decahydro-1h-chrysene-3-carboxylic acid)

INCHI for NP0267295 ((3s,4ar,6ar,7s,8s,10ar,10bs,12as)-7-(2-carboxyethyl)-3,7,10a,10b,12a-pentamethyl-8-(prop-1-en-2-yl)-2,4,4a,6,6a,8,9,10,11,12-decahydro-1h-chrysene-3-carboxylic acid)

Structure for NP0267295 ((3s,4ar,6ar,7s,8s,10ar,10bs,12as)-7-(2-carboxyethyl)-3,7,10a,10b,12a-pentamethyl-8-(prop-1-en-2-yl)-2,4,4a,6,6a,8,9,10,11,12-decahydro-1h-chrysene-3-carboxylic acid)

3D Structure for NP0267295 ((3s,4ar,6ar,7s,8s,10ar,10bs,12as)-7-(2-carboxyethyl)-3,7,10a,10b,12a-pentamethyl-8-(prop-1-en-2-yl)-2,4,4a,6,6a,8,9,10,11,12-decahydro-1h-chrysene-3-carboxylic acid)