NP-MRD: Showing NP-Card for 2,4,8-trimethyl (1r,2s,3s,4s,5s,8r,9r,12r,13s)-5,13-dihydroxy-4,13-dimethyltetracyclo[10.2.1.0¹,⁹.0³,⁸]pentadecane-2,4,8-tricarboxylate (NP0152099)

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Record Information

Version

2.0

Created at

2022-09-02 08:31:04 UTC

Updated at

2022-09-02 08:31:04 UTC

NP-MRD ID

NP0152099

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2,4,8-trimethyl (1r,2s,3s,4s,5s,8r,9r,12r,13s)-5,13-dihydroxy-4,13-dimethyltetracyclo[10.2.1.0¹,⁹.0³,⁸]pentadecane-2,4,8-tricarboxylate

Description

2,4,8-Trimethyl (1R,2S,3S,4S,5S,8R,9R,12R,13S)-5,13-dihydroxy-4,13-dimethyltetracyclo[10.2.1.0¹,⁹.0³,⁸]Pentadecane-2,4,8-tricarboxylate belongs to the class of organic compounds known as c20-gibberellins. These are gibberellins with carboxy groups in positions 7 and 18 and some also in 20, while others have an aldehyde group in the latter position. Based on a literature review very few articles have been published on 2,4,8-trimethyl (1R,2S,3S,4S,5S,8R,9R,12R,13S)-5,13-dihydroxy-4,13-dimethyltetracyclo[10.2.1.0¹,⁹.0³,⁸]Pentadecane-2,4,8-tricarboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022210312D          

 31 34  0  0  1  0            999 V2000
    1.9005    3.4395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0679    2.6316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8513    2.3727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4672    2.9216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0187    1.5649    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7873    1.2450    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5303    1.6035    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0483    2.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1060    2.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9056    1.9915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8819    2.9885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0823    3.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2123    1.1392    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9554    1.4977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1513    0.3165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4082   -0.0420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7262    0.4222    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5849   -0.3906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9360   -0.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2181   -0.9194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0767   -1.7322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9186    0.2132    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5749   -0.5852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7212   -0.6291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2571    0.0972    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8815    0.5036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4292    0.9541    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6706    1.4374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9720    0.9114    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4021    1.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1668    0.7318    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  2  0  0  0  0
  5  3  1  1  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  6  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  6 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 27 26  1  6  0  0  0
  5 27  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 25 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  1  0  0  0
M  END

     RDKit          3D

 65 68  0  0  0  0  0  0  0  0999 V2000
   -0.3883    3.9139    2.0019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3021    2.6126    1.5090 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2045    2.2496    0.1891 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1964    3.2096   -0.6002 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1225    0.8862   -0.2173 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8843   -0.0464    0.3156 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2925    0.1986    0.4139 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.6928    0.2111    1.9168 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8412    1.4915   -0.0962 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5622    1.5263   -1.1276 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6007    2.7084    0.5137 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1710    3.8666   -0.0575 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2345   -0.8585   -0.1695 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.4129   -0.9558    0.6159 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6952   -2.2155   -0.3024 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -2.4151    0.2043 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4943   -1.3107   -0.4725 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7982   -1.2734   -1.8858 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3210   -0.4002   -2.5819 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4325   -2.4396   -2.5894 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6691   -2.5460   -3.9794 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9511   -1.3795   -0.1721 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8029   -2.0623   -1.1932 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2391   -1.9549   -0.6979 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5744   -0.5354   -0.2922 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.5090    0.3858   -0.8643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3797    0.0536    0.0691 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.9459    0.1284    1.4143 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3967   -0.3125    1.1893 C   0  0  1  0  0  0  0  0  0  0  0  0
   -4.2784    0.8437    1.6155 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7395   -1.4340    1.9006 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1020    4.6145    1.1898 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4261    4.0881    2.3509 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3306    4.1046    2.8324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1382    0.8987   -1.3624 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4724   -0.3237    1.3451 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8342    0.5911    2.5079 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5654    0.8313    2.0957 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8632   -0.8397    2.2634 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0003    3.8285   -1.1667 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2514    3.9481    0.1234 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6830    4.8041    0.3024 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6512   -0.5080   -1.1621 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0435   -1.4799    0.0836 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6847   -2.5314   -1.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3268   -3.0121    0.1909 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2642   -2.3383    1.2908 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9555   -3.4113   -0.1609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1435   -1.9989   -4.5154 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7204   -3.5994   -4.2883 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6553   -2.0610   -4.1682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0499   -2.0079    0.7659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5539   -3.1622   -1.1374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7406   -1.6844   -2.2062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2754   -2.5706    0.2425 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9493   -2.3882   -1.4035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5726   -0.2148   -0.6212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3107    0.2468   -1.9189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8769    1.4164   -0.7136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8800    1.0365    1.9941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5151   -0.6778    2.0859 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3126    0.7218    1.2578 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2366    0.9594    2.7054 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8932    1.7871    1.1554 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6966   -1.2137    2.8598 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  5  6  1  0
  6 17  1  0
 17 16  1  0
 16 15  1  0
 15 13  1  0
 13 14  1  0
 13  7  1  0
  7  8  1  0
  7  9  1  6
  9 10  2  0
  9 11  1  0
 11 12  1  0
 17 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
 27 28  1  1
 28 29  1  0
 29 30  1  0
 29 31  1  1
 17 18  1  6
 18 19  2  0
 18 20  1  0
 20 21  1  0
 27  5  1  0
  7  6  1  0
 27 22  1  0
 29 25  1  0
  1 32  1  0
  1 33  1  0
  1 34  1  0
  5 35  1  6
  6 36  1  1
 16 47  1  0
 16 48  1  0
 15 45  1  0
 15 46  1  0
 13 43  1  6
 14 44  1  0
  8 37  1  0
  8 38  1  0
  8 39  1  0
 12 40  1  0
 12 41  1  0
 12 42  1  0
 22 52  1  1
 23 53  1  0
 23 54  1  0
 24 55  1  0
 24 56  1  0
 25 57  1  6
 26 58  1  0
 26 59  1  0
 28 60  1  0
 28 61  1  0
 30 62  1  0
 30 63  1  0
 30 64  1  0
 31 65  1  0
 21 49  1  0
 21 50  1  0
 21 51  1  0
M  END


  Mrv1652309022210312D          

 31 34  0  0  1  0            999 V2000
    1.9005    3.4395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0679    2.6316    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8513    2.3727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4672    2.9216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0187    1.5649    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.7873    1.2450    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.5303    1.6035    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0483    2.2730    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1060    2.1945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9056    1.9915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8819    2.9885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0823    3.1915    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2123    1.1392    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.9554    1.4977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1513    0.3165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4082   -0.0420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7262    0.4222    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5849   -0.3906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9360   -0.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2181   -0.9194    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0767   -1.7322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9186    0.2132    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5749   -0.5852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7212   -0.6291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2571    0.0972    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.8815    0.5036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4292    0.9541    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.6706    1.4374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9720    0.9114    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4021    1.5079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1668    0.7318    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  2  0  0  0  0
  5  3  1  1  0  0  0
  6  5  1  6  0  0  0
  6  7  1  0  0  0  0
  7  8  1  1  0  0  0
  7  9  1  6  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
  7 13  1  0  0  0  0
 13 14  1  1  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  6 17  1  0  0  0  0
 17 18  1  6  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 17 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 27 26  1  6  0  0  0
  5 27  1  0  0  0  0
 22 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  1  0  0  0  0
 25 29  1  0  0  0  0
 29 30  1  6  0  0  0
 29 31  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0152099

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C23H34O8/c1-20(28)11-22-10-12(20)6-7-13(22)23(19(27)31-5)9-8-14(24)21(2,18(26)30-4)16(23)15(22)17(25)29-3/h12-16,24,28H,6-11H2,1-5H3/t12-,13-,14+,15-,16-,20+,21-,22-,23-/m1/s1

> <INCHI_KEY>
VXPYUMYVGLKCSB-RDYBRCACSA-N

> <FORMULA>
C23H34O8

> <MOLECULAR_WEIGHT>
438.517

> <EXACT_MASS>
438.225368055

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
45.452655172715694

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,4,8-trimethyl (1R,2S,3S,4S,5S,8R,9R,12R,13S)-5,13-dihydroxy-4,13-dimethyltetracyclo[10.2.1.0^{1,9}.0^{3,8}]pentadecane-2,4,8-tricarboxylate

> <ALOGPS_LOGP>
1.31

> <JCHEM_LOGP>
1.017008898666666

> <ALOGPS_LOGS>
-3.27

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.90198211581831

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.450742878147771

> <JCHEM_PKA_STRONGEST_BASIC>
-0.6546725592284698

> <JCHEM_POLAR_SURFACE_AREA>
119.36000000000001

> <JCHEM_REFRACTIVITY>
108.44709999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.38e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,4,8-trimethyl (1R,2S,3S,4S,5S,8R,9R,12R,13S)-5,13-dihydroxy-4,13-dimethyltetracyclo[10.2.1.0^{1,9}.0^{3,8}]pentadecane-2,4,8-tricarboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       3.548   6.420   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       3.860   4.912   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       5.322   4.429   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       6.472   5.454   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.635   2.921   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.070   2.324   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.457   2.993   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.557   4.243   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.531   4.096   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      11.024   3.717   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       9.113   5.578   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       7.620   5.957   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.730   2.127   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      11.117   2.796   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.616   0.591   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.229  -0.078   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.956   0.788   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.692  -0.729   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.480  -1.680   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       7.874  -1.716   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       7.610  -3.233   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.448   0.398   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.807  -1.092   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.213  -1.174   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.347   0.181   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       3.512   0.940   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.535   1.781   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.118   2.683   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.814   1.701   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.750   2.815   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       0.311   1.366   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6   27                                                  
CONECT    6    5    7   17                                                  
CONECT    7    6    8    9   13                                             
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11                                                            
CONECT   13    7   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16    6   18   22                                             
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20                                                            
CONECT   22   17   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   29                                                  
CONECT   26   25   27                                                       
CONECT   27   26    5   22   28                                             
CONECT   28   27   29                                                       
CONECT   29   28   25   30   31                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   68    0
END

View in JSmol

Synonyms

Value	Source
2,4,8-Trimethyl (1R,2S,3S,4S,5S,8R,9R,12R,13S)-5,13-dihydroxy-4,13-dimethyltetracyclo[10.2.1.0,.0,]pentadecane-2,4,8-tricarboxylic acid	Generator

Chemical Formula

C₂₃H₃₄O₈

Average Mass

438.5170 Da

Monoisotopic Mass

438.22537 Da

IUPAC Name

2,4,8-trimethyl (1R,2S,3S,4S,5S,8R,9R,12R,13S)-5,13-dihydroxy-4,13-dimethyltetracyclo[10.2.1.0^{1,9}.0^{3,8}]pentadecane-2,4,8-tricarboxylate

Traditional Name

2,4,8-trimethyl (1R,2S,3S,4S,5S,8R,9R,12R,13S)-5,13-dihydroxy-4,13-dimethyltetracyclo[10.2.1.0^{1,9}.0^{3,8}]pentadecane-2,4,8-tricarboxylate

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C23H34O8/c1-20(28)11-22-10-12(20)6-7-13(22)23(19(27)31-5)9-8-14(24)21(2,18(26)30-4)16(23)15(22)17(25)29-3/h12-16,24,28H,6-11H2,1-5H3/t12-,13-,14+,15-,16-,20+,21-,22-,23-/m1/s1

InChI Key

VXPYUMYVGLKCSB-RDYBRCACSA-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 c20-gibberellins. These are gibberellins with carboxy groups in positions 7 and 18 and some also in 20, while others have an aldehyde group in the latter position.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

C20-gibberellins

Alternative Parents

Substituents

Gibberellane diterpenoid
Tricarboxylic acid or derivatives
Beta-hydroxy acid
Hydroxy acid
Tertiary alcohol
Cyclic alcohol
Methyl ester
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Hydrocarbon derivative
Organooxygen compound
Alcohol
Carbonyl group
Organic oxide
Organic oxygen compound
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.31	ALOGPS
logP	1.02	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	14.45	ChemAxon
pKa (Strongest Basic)	-0.65	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	119.36 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	108.45 m³·mol⁻¹	ChemAxon
Polarizability	45.45 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

162953990

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2,4,8-trimethyl (1r,2s,3s,4s,5s,8r,9r,12r,13s)-5,13-dihydroxy-4,13-dimethyltetracyclo[10.2.1.0¹,⁹.0³,⁸]pentadecane-2,4,8-tricarboxylate (NP0152099)

MOL for NP0152099 (2,4,8-trimethyl (1r,2s,3s,4s,5s,8r,9r,12r,13s)-5,13-dihydroxy-4,13-dimethyltetracyclo[10.2.1.0¹,⁹.0³,⁸]pentadecane-2,4,8-tricarboxylate)

3D MOL for NP0152099 (2,4,8-trimethyl (1r,2s,3s,4s,5s,8r,9r,12r,13s)-5,13-dihydroxy-4,13-dimethyltetracyclo[10.2.1.0¹,⁹.0³,⁸]pentadecane-2,4,8-tricarboxylate)

3D SDF for NP0152099 (2,4,8-trimethyl (1r,2s,3s,4s,5s,8r,9r,12r,13s)-5,13-dihydroxy-4,13-dimethyltetracyclo[10.2.1.0¹,⁹.0³,⁸]pentadecane-2,4,8-tricarboxylate)

3D-SDF for NP0152099 (2,4,8-trimethyl (1r,2s,3s,4s,5s,8r,9r,12r,13s)-5,13-dihydroxy-4,13-dimethyltetracyclo[10.2.1.0¹,⁹.0³,⁸]pentadecane-2,4,8-tricarboxylate)

PDB for NP0152099 (2,4,8-trimethyl (1r,2s,3s,4s,5s,8r,9r,12r,13s)-5,13-dihydroxy-4,13-dimethyltetracyclo[10.2.1.0¹,⁹.0³,⁸]pentadecane-2,4,8-tricarboxylate)

3D PDB for NP0152099 (2,4,8-trimethyl (1r,2s,3s,4s,5s,8r,9r,12r,13s)-5,13-dihydroxy-4,13-dimethyltetracyclo[10.2.1.0¹,⁹.0³,⁸]pentadecane-2,4,8-tricarboxylate)

SMILES for NP0152099 (2,4,8-trimethyl (1r,2s,3s,4s,5s,8r,9r,12r,13s)-5,13-dihydroxy-4,13-dimethyltetracyclo[10.2.1.0¹,⁹.0³,⁸]pentadecane-2,4,8-tricarboxylate)

INCHI for NP0152099 (2,4,8-trimethyl (1r,2s,3s,4s,5s,8r,9r,12r,13s)-5,13-dihydroxy-4,13-dimethyltetracyclo[10.2.1.0¹,⁹.0³,⁸]pentadecane-2,4,8-tricarboxylate)

Structure for NP0152099 (2,4,8-trimethyl (1r,2s,3s,4s,5s,8r,9r,12r,13s)-5,13-dihydroxy-4,13-dimethyltetracyclo[10.2.1.0¹,⁹.0³,⁸]pentadecane-2,4,8-tricarboxylate)

3D Structure for NP0152099 (2,4,8-trimethyl (1r,2s,3s,4s,5s,8r,9r,12r,13s)-5,13-dihydroxy-4,13-dimethyltetracyclo[10.2.1.0¹,⁹.0³,⁸]pentadecane-2,4,8-tricarboxylate)