NP-MRD: Showing NP-Card for zizyberanalic acid (NP0213171)

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Record Information

Version

2.0

Created at

2022-09-05 12:04:23 UTC

Updated at

2022-09-05 12:04:23 UTC

NP-MRD ID

NP0213171

Secondary Accession Numbers

None

Natural Product Identification

Common Name

zizyberanalic acid

Description

Zizyberanalic acid, also known as colubrinic acid or colubrinate, belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. zizyberanalic acid is found in Breynia fruticosa, Paliurus hemsleyanus and Ziziphus mauritiana. Zizyberanalic acid is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI

Colubrinic acid
  Mrv1572001071617142D          

 38 42  0  0  0  0            999 V2000
   11.0737  -16.0129    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.7942  -14.7719    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.5063  -14.3596    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.7900  -15.6006    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.8988  -16.8167    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.3657  -15.6006    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.9556  -13.5433    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.9389  -14.3721    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.2268  -14.7844    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.7494  -16.1463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0783  -16.9042    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.7220  -14.6386    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.9556  -12.7520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5063  -13.5308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0737  -14.3554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2393  -13.1227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3616  -14.7719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7427  -13.3018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4980  -16.0129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2185  -15.6048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2258  -13.9806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9551  -15.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4361  -17.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2685  -12.3439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7381  -15.5881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2190  -17.2498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0778  -14.9801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6827  -17.5913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5146  -15.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7609  -13.8807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6470  -12.3481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3579  -15.4591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9789  -16.3586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4137  -15.9921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8025  -16.3087    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.2060  -13.8849    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3949  -16.3752    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.0139  -15.2175    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  1  1  0  0  0  0
  6  1  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 20  1  0  0  0  0
 10  6  1  0  0  0  0
 11  5  1  0  0  0  0
 12  8  1  0  0  0  0
  7 13  1  6  0  0  0
 14  3  1  0  0  0  0
 15 17  1  0  0  0  0
 16 14  1  0  0  0  0
 17  6  1  0  0  0  0
 18  7  1  0  0  0  0
 19  4  1  0  0  0  0
 20 19  1  0  0  0  0
 21 12  1  0  0  0  0
 12 22  1  1  0  0  0
  5 23  1  6  0  0  0
 24 13  2  0  0  0  0
 25 22  2  0  0  0  0
 26 23  2  0  0  0  0
  1 27  1  6  0  0  0
 11 28  1  1  0  0  0
  3 29  1  1  0  0  0
  2 30  1  6  0  0  0
 31 13  1  0  0  0  0
 32 10  1  0  0  0  0
 33 10  1  0  0  0  0
 34 22  1  0  0  0  0
  4 35  1  1  0  0  0
  9 36  1  6  0  0  0
  6 37  1  1  0  0  0
  8 38  1  1  0  0  0
 10 11  1  0  0  0  0
 15  2  1  0  0  0  0
  9  3  1  0  0  0  0
 16  7  1  0  0  0  0
 18 21  1  0  0  0  0
M  END

     RDKit          3D

 80 84  0  0  0  0  0  0  0  0999 V2000
   -4.2412   -3.3062   -0.4360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3757   -2.0036   -0.6258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8278   -1.4541   -1.9208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0599   -1.0788    0.4976 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.3452   -0.2929    0.8283 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.5115    1.1246    0.9823 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.4012    0.9002    2.4187 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0803   -0.1508    3.0058 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6919    1.9968    3.2421 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7705    2.3502    0.6006 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3036    2.1463    0.7509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8080    0.9093    0.0694 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8614    1.1822   -1.4176 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6464   -0.3137    0.3762 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.1431   -1.4934   -0.4203 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3362   -1.6849   -0.3750 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1287   -0.4265   -0.4608 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5991   -0.6410   -0.4613 C   0  0  1  0  0  0  0  0  0  0  0  0
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    3.1456   -1.0769   -1.8129 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9674   -2.4816   -2.1309 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.6575    0.4997   -0.7301 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5627    0.3368    0.4379 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1727    1.6938   -1.5462 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2402    0.7373   -0.4350 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8953    1.5388    0.7513 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3974    1.8500    0.6093 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6086    0.5705    0.5328 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5403    0.0278    1.9399 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0670   -0.0185    0.1004 C   0  0  1  0  0  0  0  0  0  0  0  0
   -3.9123   -3.7499    0.4938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4714   -3.9780   -1.2527 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5612   -0.6698   -1.7412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3110   -2.2667   -2.4959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9243   -1.0979   -2.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7049   -1.6625    1.3432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5295   -0.4521    1.9244 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1769   -0.6327    0.1986 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5898    1.8041    1.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0620    1.3873   -0.4871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6589    2.3383    3.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0921    2.7595   -0.3792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0647    3.1538    1.3403 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2079   -1.7277    0.3879 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0069   -1.2755    1.6045 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.7258   -0.3771   -2.5642 H   0  0  0  0  0  0  0  0  0  0  0  0
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    5.2478   -1.5247   -1.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0117   -0.1478   -2.9617 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0173    0.2769    1.4253 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2770   -0.5155    0.3206 H   0  0  0  0  0  0  0  0  0  0  0  0
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 29 30  1  0
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 16 15  1  0
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 34  4  1  0
  4  5  1  0
  5  6  1  0
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  7  8  1  1
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  8  9  2  0
  4  2  1  0
  2  3  1  0
  2  1  2  3
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 13 15  1  0
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 15 53  1  1
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  4 40  1  1
  5 41  1  0
  5 42  1  0
  6 43  1  0
  6 44  1  0
 11 46  1  0
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 14 50  1  0
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 10 45  1  0
  3 37  1  0
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  1 35  1  0
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 27 66  1  0
 27 67  1  0
 27 68  1  0
 28 69  1  0
 28 70  1  0
 28 71  1  0
M  END

Colubrinic acid
  Mrv1572001071617142D          

 38 42  0  0  0  0            999 V2000
   11.0737  -16.0129    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.7942  -14.7719    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.5063  -14.3596    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   11.7900  -15.6006    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   10.8988  -16.8167    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.3657  -15.6006    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   13.9556  -13.5433    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.9389  -14.3721    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.2268  -14.7844    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    9.7494  -16.1463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0783  -16.9042    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   14.7220  -14.6386    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.9556  -12.7520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5063  -13.5308    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0737  -14.3554    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2393  -13.1227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3616  -14.7719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7427  -13.3018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4980  -16.0129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2185  -15.6048    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2258  -13.9806    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9551  -15.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4361  -17.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2685  -12.3439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.7381  -15.5881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2190  -17.2498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0778  -14.9801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6827  -17.5913    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.5146  -15.1176    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7609  -13.8807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6470  -12.3481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.3579  -15.4591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9789  -16.3586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4137  -15.9921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8025  -16.3087    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.2060  -13.8849    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.3949  -16.3752    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.0139  -15.2175    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0  0  0  0
  3  2  1  0  0  0  0
  4  1  1  0  0  0  0
  5  1  1  0  0  0  0
  6  1  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 20  1  0  0  0  0
 10  6  1  0  0  0  0
 11  5  1  0  0  0  0
 12  8  1  0  0  0  0
  7 13  1  6  0  0  0
 14  3  1  0  0  0  0
 15 17  1  0  0  0  0
 16 14  1  0  0  0  0
 17  6  1  0  0  0  0
 18  7  1  0  0  0  0
 19  4  1  0  0  0  0
 20 19  1  0  0  0  0
 21 12  1  0  0  0  0
 12 22  1  1  0  0  0
  5 23  1  6  0  0  0
 24 13  2  0  0  0  0
 25 22  2  0  0  0  0
 26 23  2  0  0  0  0
  1 27  1  6  0  0  0
 11 28  1  1  0  0  0
  3 29  1  1  0  0  0
  2 30  1  6  0  0  0
 31 13  1  0  0  0  0
 32 10  1  0  0  0  0
 33 10  1  0  0  0  0
 34 22  1  0  0  0  0
  4 35  1  1  0  0  0
  9 36  1  6  0  0  0
  6 37  1  1  0  0  0
  8 38  1  1  0  0  0
 10 11  1  0  0  0  0
 15  2  1  0  0  0  0
  9  3  1  0  0  0  0
 16  7  1  0  0  0  0
 18 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0213171

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]12CC[C@]3(C)[C@]([H])(CC[C@]4([H])[C@@]5([H])[C@@H](CC[C@@]5(CC[C@@]34C)C(O)=O)C(C)=C)[C@@]1(C)[C@H](C=O)[C@@H](O)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C30H46O4/c1-17(2)18-10-13-30(25(33)34)15-14-27(5)19(23(18)30)8-9-22-28(27,6)12-11-21-26(3,4)24(32)20(16-31)29(21,22)7/h16,18-24,32H,1,8-15H2,2-7H3,(H,33,34)/t18-,19+,20+,21-,22-,23+,24+,27+,28+,29-,30-/m0/s1

> <INCHI_KEY>
SLWJVQQNDGLXTK-IMBMMKFRSA-N

> <FORMULA>
C30H46O4

> <MOLECULAR_WEIGHT>
470.694

> <EXACT_MASS>
470.339609961

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
80

> <JCHEM_AVERAGE_POLARIZABILITY>
54.60873742774857

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,5S,8R,9R,10R,13R,14R,15S,16R,18R)-15-formyl-16-hydroxy-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icosane-5-carboxylic acid

> <ALOGPS_LOGP>
5.08

> <JCHEM_LOGP>
5.415206136000002

> <ALOGPS_LOGS>
-5.90

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
14.305622276358314

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.6824656389747865

> <JCHEM_PKA_STRONGEST_BASIC>
-3.1018548035078792

> <JCHEM_POLAR_SURFACE_AREA>
74.60000000000001

> <JCHEM_REFRACTIVITY>
133.18499999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.96e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5S,8R,9R,10R,13R,14R,15S,16R,18R)-15-formyl-16-hydroxy-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icosane-5-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Colubrinic acid                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  C   UNK     0      20.671 -29.891   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      22.016 -27.574   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      23.345 -26.805   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      22.008 -29.121   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      20.344 -31.391   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      19.349 -29.121   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      26.050 -25.281   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      26.019 -26.828   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      24.690 -27.598   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      18.199 -30.140   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      18.813 -31.555   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      27.481 -27.325   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      26.050 -23.804   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      23.345 -25.257   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      20.671 -26.797   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      24.713 -24.496   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      19.342 -27.574   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      27.520 -24.830   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      23.330 -29.891   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      24.675 -29.129   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      28.421 -26.097   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      27.916 -28.764   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      21.347 -32.503   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      24.768 -23.042   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      29.378 -29.098   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      22.809 -32.200   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      20.679 -27.963   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      18.074 -32.837   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      23.361 -28.220   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      21.954 -25.911   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      27.341 -23.050   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      17.468 -28.857   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      16.761 -30.536   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      26.906 -29.852   0.000  0.00  0.00           C+0
HETATM   35  H   UNK     0      22.031 -30.443   0.000  0.00  0.00           H+0
HETATM   36  H   UNK     0      24.651 -25.918   0.000  0.00  0.00           H+0
HETATM   37  H   UNK     0      19.404 -30.567   0.000  0.00  0.00           H+0
HETATM   38  H   UNK     0      26.159 -28.406   0.000  0.00  0.00           H+0
CONECT    1    4    5    6   27                                             
CONECT    2    4    3   30   15                                             
CONECT    3    2   14   29    9                                             
CONECT    4    2    1   19   35                                             
CONECT    5    1   11   23                                                  
CONECT    6    1   10   17   37                                             
CONECT    7    8   13   18   16                                             
CONECT    8    7    9   12   38                                             
CONECT    9    8   20   36    3                                             
CONECT   10    6   32   33   11                                             
CONECT   11    5   28   10                                                  
CONECT   12    8   21   22                                                  
CONECT   13    7   24   31                                                  
CONECT   14    3   16                                                       
CONECT   15   17    2                                                       
CONECT   16   14    7                                                       
CONECT   17   15    6                                                       
CONECT   18    7   21                                                       
CONECT   19    4   20                                                       
CONECT   20    9   19                                                       
CONECT   21   12   18                                                       
CONECT   22   12   25   34                                                  
CONECT   23    5   26                                                       
CONECT   24   13                                                            
CONECT   25   22                                                            
CONECT   26   23                                                            
CONECT   27    1                                                            
CONECT   28   11                                                            
CONECT   29    3                                                            
CONECT   30    2                                                            
CONECT   31   13                                                            
CONECT   32   10                                                            
CONECT   33   10                                                            
CONECT   34   22                                                            
CONECT   35    4                                                            
CONECT   36    9                                                            
CONECT   37    6                                                            
CONECT   38    8                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   84    0
END

View in JSmol

Synonyms

Value	Source
Colubrinic acid	ChEBI
Colubrinate	Generator
Zizyberanalate	Generator

Chemical Formula

C₃₀H₄₆O₄

Average Mass

470.6940 Da

Monoisotopic Mass

470.33961 Da

IUPAC Name

(1R,2R,5S,8R,9R,10R,13R,14R,15S,16R,18R)-15-formyl-16-hydroxy-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icosane-5-carboxylic acid

Traditional Name

(1R,2R,5S,8R,9R,10R,13R,14R,15S,16R,18R)-15-formyl-16-hydroxy-1,2,14,17,17-pentamethyl-8-(prop-1-en-2-yl)pentacyclo[11.7.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁸]icosane-5-carboxylic acid

CAS Registry Number

Not Available

SMILES

[H][C@@]12CC[C@]3(C)[C@]([H])(CC[C@]4([H])[C@@]5([H])[C@@H](CC[C@@]5(CC[C@@]34C)C(O)=O)C(C)=C)[C@@]1(C)[C@H](C=O)[C@@H](O)C2(C)C

InChI Identifier

InChI=1S/C30H46O4/c1-17(2)18-10-13-30(25(33)34)15-14-27(5)19(23(18)30)8-9-22-28(27,6)12-11-21-26(3,4)24(32)20(16-31)29(21,22)7/h16,18-24,32H,1,8-15H2,2-7H3,(H,33,34)/t18-,19+,20+,21-,22-,23+,24+,27+,28+,29-,30-/m0/s1

InChI Key

SLWJVQQNDGLXTK-IMBMMKFRSA-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
Breynia fruticosa	LOTUS Database	35616633
Paliurus hemsleyanus	LOTUS Database	35616633
Ziziphus mauritiana	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
Steroid acid
3-carboxy steroid
18-oxosteroid
18-hydroxysteroid
Hydroxysteroid
Oxosteroid
16-alpha-hydroxysteroid
16-hydroxysteroid
Steroid
Cyclic alcohol
Secondary alcohol
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Aldehyde
Organic oxygen compound
Organooxygen compound
Alcohol
Organic oxide
Carbonyl group
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3alpha-hydroxy steroid (CHEBI:67591 )
aldehyde (CHEBI:67591 )
hydroxy monocarboxylic acid (CHEBI:67591 )
steroid acid (CHEBI:67591 )

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	5.08	ALOGPS
logP	5.42	ChemAxon
logS	-5.9	ALOGPS
pKa (Strongest Acidic)	4.68	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	74.6 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	133.18 m³·mol⁻¹	ChemAxon
Polarizability	54.61 Å³	ChemAxon
Number of Rings	5	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

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

21672700

PDB ID

Not Available

ChEBI ID

67591

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for zizyberanalic acid (NP0213171)

MOL for NP0213171 (zizyberanalic acid)

3D MOL for NP0213171 (zizyberanalic acid)

3D SDF for NP0213171 (zizyberanalic acid)

3D-SDF for NP0213171 (zizyberanalic acid)

PDB for NP0213171 (zizyberanalic acid)

3D PDB for NP0213171 (zizyberanalic acid)

SMILES for NP0213171 (zizyberanalic acid)

INCHI for NP0213171 (zizyberanalic acid)

Structure for NP0213171 (zizyberanalic acid)

3D Structure for NP0213171 (zizyberanalic acid)